The 40 Best Rappers of the 1990s

The 1990s was the peak golden age of hip hop music. Don’t get it twisted, each rap decade since the ’80s has been special in its own way, and I’m certainly not one of those hip hop heads arguing that things were better back in the day.

But if you’re talking the greatest decade for hip hop music, it’s really hard to look past the ’90s. Just have a think about all the incredible rappers that debuted during that decade: Nas, Big, 2Pac, Jay-Z, Snoop Dogg, Lauryn Hill, Ice Cube, Wu-Tang, DMX, UGK, OutKast, Tribe, DJ Quik, Master P, Bone Thugs, Missy Elliott, Eminem, we could go on for days. Is it any surprise that our list for the greatest rappers of all time is mainly comprised of rappers from the ’90s?

So let’s get into it. From Nas, 2Pac and Jay-Z, to Biggie, Andre 3000 and Lauryn Hill, here are the 40 best rappers of the 1990s.

40. Ras Kass

Albums: Soul on Ice (1996) , Rasassination (1998)

Best Ras Kass guest verses of the ‘90s:

• Coolio – “Get Up, Get Down”
• Chino XL – “Riiiot!”
• Xzibit – “Plastic Surgery”
• O.C. – “Action Guaranteed”
• RZA – “Handwriting On the Wall”

Ras Kass may not be mentioned in the same breath as other ’90s West Coast greats like Ice Cube or Snoop Dogg, but that’s never been a problem for the super lyrical talent hailing from Carson, California. Making his debut in 1991 on Wild West Corral’s “Trick or Treat”, Ras Kass went on to drop just two solo albums during the decade, as well as a slew of feature appearances.

That being said, with the level of complex lyricism and dense metaphorical wordplay featured in his albums – just peep “Nature of the Threat” – it was equivalent to any other rapper releasing twice as many projects. Underrated yet consistent as hell, Ras Kass was absolutely one of the best rappers of the ’90s.

39. E-40

Albums: Down and Dirty (with the Click) (1992), Federal (1993), In a Major Way (1995), Game Related (with the Click) (1995), Tha Hall of Game (1996), The Element of Surprise (1998), Charlie Hustle: The Blueprint of a Self-Made Millionaire (1999)

Best E-40 guest verses of the ‘90s:

• Suga-T – “Livin’ for the Weekend”
• Spice 1 – “Mo’ Mail”
• Master P – “Get Your Paper”
• Rappin’ 4-Tay – “What’s Wrong Wit The Game”
• 2Pac – “Ain’t Hard to Find”
• Mystikal – “Here We Go”
• Mack 10 – “Can’t Stop”
• Too Short – “You Might Get Gee’d”

Founded by E-40 in 1989, Sick Wid It Records was a pioneer rap label for the independent movement, inspiring both future moguls like Master P and Birdman. Using his independent record label as a platform for his music, the Vallejo rapper-entrepreneur played a key role in building up the Bay Area scene with his flamboyant raps, undeniable slang and hustler spirit.

E-40 had so much success in cultivating an independent, loyal fanbase in the region that it wasn’t long before the majors came calling. With a major label deal signed with Jive Records in 1994, the rapper went on to drop In a Major Way , which peaked at number 2 on the Billboard Top R&B/Hip-Hop Albums, selling 70,000 copies in the first week.

E-40’s independent business savvy, prolific output and innovative sound would go on to set the blueprint for countless rappers for decades to come. The Bay Area hustler wasn’t just one of the best 90s rappers, he was one of the most influential and impactful.

38. Mase

Albums: Harlem World (1997), The Movement (with Harlem World) (1999), Double Up (1999)

Best Mase guest verses of the ’90s:

• Puff Daddy – “Can’t Nobody Hold Me Down”
• Puff Daddy – “Been Around the World”
• The Notorious B.I.G. – “Mo Money Mo Problems”
• Busta Rhymes – “The Body Rock”
• Cam’ron – “Horse & Carriage”
• DMX – “Niggaz Done Started Something”
• Black Rob – “Down The Line Joint”

If there was ever a rapper who has come to represent the excess commercialism, watered down samples and nostalgia of late ’90s Bad Boy era in the public’s mind, it’s Mase (who understandably dropped the Murder from his name). Over the years, the Harlem rapper has been unfairly criticised for his role in the shiny suit era, a lot of which is undeserved.

Let’s just look at the music itself. Harlem World is arguably the best Bad Boy release by a rapper not named The Notorious B.I.G., and even now, decades since his moment in the spotlight, Mase is still being referenced by A-listers. Peep Pusha T’s Mase flow impersonation on “Let Me Love You,” or Kanye name-checking him on “Devil in a New Dress” or Drake interpolating his lines on “Worst Behavior.” So let’s give Mase credit where credit is due because he’s definitely one of the best 90s rappers ever.

37. Bun B

Albums: The Southern Way (1992), Banned (1992), Too Hard to Swallow (1992), Super Tight (1994), Ridin’ Dirty (1996)

Best Bun B guest verses of the ’90s:

• Jay-Z – “Big Pimpin'”
• Scarface – “2-Real”
• Too Short – “It’s Alright”
• C-Murder – “Ackickdoe!”
• Master P – “Playaz from the South”
• Celly Cel – “Pop The Trunk”
• Master P – “Break ‘Em Off Somethin'”

At the beginning the ’90s, Bun B and Pimp C were two up-and-coming rappers from Port Arthur, Texas who had just released their debut album, Too Hard to Swallow , which had barely made a dent on the charts. By the end of the decade, they were featured on the biggest rap record of the year alongside the biggest hip hop at the time.

In between, they dropped Ridin’ Dirty , arguably a top five Southern album of all time, which features Bun B’s verse on “Murder,” one of the greatest rap verses of all time. While Pimp’s syrup-drenched vocals were full of colour and character, it was Bun’s distinctive flow and nimble delivery that grounded the duo and enabled them to be relatable superheroes to the everyday listener. A dangerous combination of technical ability on the mic and unforgettable Southern tales made Bun B one of the best 90s rappers of all time.

36. MC Eiht

Albums: It’s a Compton Thang (as Compton’s Most Wanted) (1990), Straight Checkn ‘Em (as Compton’s Most Wanted) (1991), Music to Driveby (as Compton’s Most Wanted) (1992), We Come Strapped (1994), Death Threatz (1996), Last Man Standing (1997), Section 8 (1999)

Best MC Eiht guest verses of the ’90s:

• Spice 1 – “The Murda Show”
• South Central Cartel – “Gangsta Team”
• Spice 1 – “1990-Sick (Kill ‘Em All)”
• WC and the Maad Circle – “You Don’t Work, U Don’t Eat”
• Daz Dillinger – “The Ultimate Come Up”
• Mack 10 – “Get Yo Ride On”
• Pete Rock – “One Life to Live”
• King Tee – “Straight Outta Compton”

If you’re a West Coast hip hop head, then it shouldn’t have been a surprise to you when you heard MC Eiht’s make his entrance on the second half of Kendrick Lamar’s “m.A.A.d City.” The Compton rapper is the very definition of an OG.

Coming up as part of Compton’s Most Wanted, MC Eiht was a staple voice of the ’90s West Coast scene with a ridiculously consistent catalogue of solo and group albums. And of course, there’s his debut single, the all-time classic “Streiht Up Menace” which featured in the movie Menace II Society which Eiht played a supporting, but critical role in. Bottom line is: MC Eiht isn’t just one of the best West Coast rappers ever, he’s one of the most important rappers of the ’90s.

35. Eminem

Albums: Infinite (1996), Slim Shady EP (1997, The Slim Shady LP (1999)

Best Eminem guest verses of the ‘90s:

• The Notorious B.I.G. – “Dead Wrong”
• Dr. Dre – “What’s the Difference”
• Dr. Dre – “Forgot About Dre”
• Sway & King Tech – “The Anthem”
• Missy Elliott – “Busa Rhyme”
• Kid Rock – “Fuck Off”

It always blows my mind when I remember that Eminem is older than Nas. Both rappers are only a year apart, but it seems like their music is an entire generation apart.

While the Queensbridge prodigy was busy redefining New York hip hop with his seminal Illmatic , Eminem was still grinding away with Proof to make it in the rap game. After competing in the 1997 Rap Olympics ( put on by Wendy Day as a showcase for him ), the Detroit rapper would garner the attention of one Dr. Dre, who at the time was struggling to find his groove.

Eminem would provide Dre with the energy and inspiration he needed to transform Aftermath Entertainment into a juggernaut, and in return, the Compton legend would give him a platform to become the biggest rapper of all time.

While it was in the 2000s that Eminem would make his most significant impact on hip hop , his output during the ’90s was enough to warrant his placement on this list. In between scene-stealing features (“Dead Wrong”, “What’s the Difference”, “Forgot About Dre”, “The Anthem”) and the ground-breaking The Slim Shady LP , Eminem was undoubtedly one of the best rappers of the 1990s.

34. Inspectah Deck

Albums: Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan) (1993), Wu-Tang Forever (with Wu-Tang Clan) (1997), Uncontrolled Substance (1999)

Best Inspectah Deck guest verses of the ’90s:

• Method Man – “Mr. Sandman”
• GZA – “Duel of the Iron Mic”
• GZA – “Cold World”
• Raekwon – “Guillotine (Swordz)”
• Ghostface Killah – “Assassination Day”
• Big Pun – “Tres Leches (Triboro Trilogy)”
• Gang Starr – “Above the Clouds”
• Pete Rock – “Tru Master”

During the ’90s, as the Wu-Tang Clan were making their way up the music industry, RZA’s Staten Island home studio got hit by two flood, destroying over 500 beats meant for Method Man, Raekwon, GZA, Ghostface and Inspectah Deck.

While the other members were able to recreate their albums, Deck’s debut was delayed for years and the final product was very different from what was destroyed in the floods. Uncontrolled Substance is a strong album, especially looking back at it now, but we’ll always wonder what it could have been if the beats weren’t lost, and Deck managed to drop it in 1995, as originally planned.

All of this is to say that Deck’s solo output during the ’90s wasn’t what it could have been due to horrible luck. But the Rebel INS never let that deter him. Whether it was on the Wu’s debut or on other members’ albums, Deck always stood tall as a highlight reel and one of the standout ’90s hip hop artists.

Hip hop heads will never forget the way he slayed the mic on GZA’s “Duel of the Iron Mic,” set it off on Rae’s “Guillotine (Swordz),” went bar for bar on Pun’s “Tres Leches (Triboro Trilogy)” or stole the show from Gang Starr on “Above the Clouds.” And, of course, there’s “Triumph” – a verse that every real rap fan should have committed to memory, and one of the greatest lyrical performances of all time.

33. Pharoahe Monch

Albums: Organized Konfusion (as Organized Konfusion) (1991), Stress: The Extinction Agenda (as Organized Konfusion), The Equinox (as Organized Konfusion), Internal Affairs (1999)

Best Pharoahe Monch guest verses of the ’90s:

• O.C. – “War Games”
• Sway & King Tech – “The Anthem”
• Street Smartz – “Metal Thangz”
• DJ Spooky – “Rekonstruction”
• Saukrates – “Innovations”

I’ll never forget the way rap legend Kool Moe Dee described Pharoahe Monch’s lyrical skills in his book, There’s a God on the Mic , writing: “Pharoahe Monch is like an eloquent linguistics professor moonlighting as a rhyme serial killer terrorist, challenging the listeners’ I.Q. while daring him or her to keep up.” It’s simply one of the best descriptions of the Queens rapper’s extraordinary technical ability on the mic.

While Monch would become a worldwide name at the end of the decade thanks to his smash hit “Simon Says,” he had been grinding away in the underground as part of Organized Konfusion since 1991. With their expansive vocabulary and inventive metaphors, the duo, and especially Monch, won acclaim and built a loyal cult following that continued to carry them forward.

32. AZ

Albums: Doe or Die (1995), The Firm: The Album (with The Firm) (1997), Pieces of a Man (1998)

Best AZ guest verses of the ’90s:

• Nas – “Life’s a Bitch”
• Nas – “Affirmative Action”
• Foxy Brown – “La Familia”
• RZA – “Whatever Happened (The Birth)”

When Nas was on his murderous feature run during the mid-90s, destroying every guest verse he could get his hands on, his partner-in-rhyme was one of the few rappers who managed to keep up with him every step of the way. Which is quite a feat in itself; keeping up with Nas lyrically in 1995 was like keeping up with Lil Wayne in 2006 or Kendrick in 2013, almost impossible.

Off the strength off his phenomenal verse on “Life’s a Bitch” – which also happened to be the first time AZ stepped into the recording booth , the Brooklyn rapper signed with EMI after a fierce label bidding war and dropped his debut album. While Doe or Die is often compared to Illmatic , the album bears more similarities to Jay-Z’s Reasonable Doubt with its glossy production and AZ’s hustling tales delivered tightly wrapped in his butter-smooth flow and ageless voice.

31. GZA

Albums: Words from the Genius (1991), Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan) (1993), Liquid Swords (1995), Wu-Tang Forever (with Wu-Tang Clan) (1997), Beneath the Surface (1999)

Best GZA guest verses of the ’90s:

• Ol’ Dirty Bastard – “Damage”
• Raekwon – “Guillotine (Swordz)”
• DJ Muggs – “Third World”
• Killah Priest – “Cross My Heart”

At the end of “Can It Be All So Simple” on Enter the Wu-Tang (36 Chambers) , the Wu begin discussing the members and their various roles. When it comes to GZA, Raekwon explains “the G is just the Genius, he’s the backbone of the whole shit,” with Method Man adding “We form like Voltron, and GZA happen to be the head.”

It’s understandable that the other Wu members would look at the Genius with so much reverence. After all, not only is he the oldest member of the group, he had also been through the gauntlet of the music industry when he signed with Cold Chillin’ Records and dropped his album Words from the Genius years before the Wu debuted.

But it was over RZA’s chilling production where GZA would find his groove. With his deliberate flow and endless metaphors, the Genius was always able to conjured up vivid imagery with the fewest words. Not to mention, Liquid Swords remains in competition as the greatest Wu-Tang solo album of all time .

30. Common

Albums: Can I Borrow a Dollar? (1992), Resurrection (1994), One Day It’ll All Make Sense (1997)

Best Common guest verses of the ’90s:

• De La Soul – “The Bizness”
• No I.D. – “State to State”
• Brand Nubian – “Maybe One Day”
• Black Star – “Respiration”
• The Roots – “Act Too (The Love of My Life)”
• Jill Scott – “8 Minutes to Sunrise”
• Slick Rick – “Don’t Come My Way”
• The Beatnuts – “Slam Pit”
• Pharoahe Monch – “The Truth”

To watch Common’s evolution from a Chicago b-boy to one of the leading figures of the conscious rap movement was a fascinating sight. Linking up with fellow Chicago artist, No I.D., back in the early ’90s, Common caught some buzz after he was featured in the Unsigned Hype column of The Source magazine and made his debut with “Take It EZ.” The record was cool, and so was the album, Can I Borrow a Dollar? , but it wasn’t until his sophomore album that Common’s career began taking shape.

By the end of the ’90s, in between holding his own in a rap beef with the fearsome Ice Cube, Common had dropped One Day It’ll All Make Sense and collaborated with underground artists like The Roots and Talib Kweli, positioning him at the forefront of the conscious hip hop movement that would later emerge fully-formed in the early 2000s.

29. Black Thought

Albums: Organix (1993), Do You Want More?!!!??! (1995), Illadelph Halflife (1996), Things Fall Apart (1999)

Best Black Thought guest verses of the ’90s:

• DJ Krush – “Meiso”
• Bahamadia – “Da Jawn”
• Jedi Mind Tricks – “Get This Low”
• Common – “Stolen Moments, Pt. 2”
• Pete Rock – “It’s About That Time”
• Big Pun – “Super Lyrical”
• Black Star – “Respiration (Flying High Mix)”

To understand the true brilliance of The Roots’ lead MC, you need to immerse yourself in the group’s second album. Sure, Illadelph Halflife had more success and Things Fall Apart won them a Grammy, but it’s on Do You Want More?!!!??! that captures Thought with his spontaneity and energy that is usually witnessed at their live shows.

Over kaleidoscopic live instrumentation, Thought displays his virtuosic skills on the mic as he bounces and scats his way through songs like “Distortion to Static”, “I Remain Calm” and “Lazy Afternoon.” As one of the best Philly rappers to ever touch a mic, Thought is forever timeless.

28. Guru

Albums: No More Mr. Nice Guy (as Gang Starr) (1989), Step in the Arena (as Gang Starr) (1991), Daily Operation (as Gang Starr) (1992), Guru’s Jazzmatazz, Vol. 1 (1993), Hard to Earn (as Gang Starr) (1994), Guru’s Jazzmatazz, Vol. 2: The New Reality (1995), Moment of Truth (as Gang Starr) (1998)

Best Guru guest verses of the ‘90s:

• The Brand New Heavies – “It’s Gettin’ Hectic”
• Nice & Smooth – “Down the Line”
• De La Soul – “Patti Dooke”
• Heavy D & The Boyz – “A Buncha Niggas”
• Digable Planets – “Borough Check”
• Group Home – “Serious Rap Shit”

Gang Starr’s work during the ’90s was enough to cement their position as one of the greatest rap duos of all time . From the incredibly raw but promising No More Mr. Nice Guy to their magnum opus Moment of Truth , the duo always worked to push the boundaries of hip hop, with Premo digging deep into the crates for the dopest samples while Guru continued to spout old soul wisdom with his timeless voice. As for the rapper’s solo work, Guru’s Jazzmatazz, Vol. 1 and Guru’s Jazzmatazz, Vol. 2: The New Reality are two pinnacles of the jazz-rap subgenre and remain highly influential to this day.

27. Kurupt

Albums: Dogg Food (as Tha Dogg Pound) (1995), Kuruption! (1998), Tha Streetz Iz a Mutha (1999)

Best Kurupt guest verses of the ‘90s:

• Dr. Dre – “Stranded On Death Row”
• Dr. Dre – “Lyrical Gangbang”
• Snoop Dogg – “Serial Killa”
• 2Pac – “Got My Mind Made Up”
• Snoop Dogg – “Ain’t No Fun (If the Homies Can’t Have None)”
• Dr. Dre – “Xxplosive”
• Snoop Dogg – “Doggy Dogg World”
• Pete Rock – “Tru Master”
• Gang Starr – “You Know My Steez (Three Men and a Lady Remix)”

A Philly-born and raised MC who moved to the West Coast when he was 16 years old. How could Kurupt not become one of the dopest ever? Whether it was destroying tracks like “Stranded on Death Row” over Dr. Dre’s funky production; rapping alongside his homies Snoop Doggy Dogg, Nate Dogg and Warren G on Doggystyle ; putting on for the West Coast as part of Tha Dogg Pound; or striking it out as a solo artist, Kurupt’s ’90s run was undeniable cemented him as one of L.A.’s GOATs.

26. Busta Rhymes

Albums: A Future Without a Past (with Leaders of the New School) (1991), T.I.M.E. (The Inner Mind’s Eye) (with Leaders of the New School) (1993), The Coming (1996), When Disaster Strikes… (1997), The Imperial with Flipmode Squad (1998), Extinction Level Event: The Final World Front (1998)

Best Busta Rhymes guest verses of the ‘90s:

• A Tribe Called Quest – “Scenario”
• Craig Mack – “Flava in Ya Ear (Remix)”
• KRS-One – “Build Ya Skillz”
• Rampage – “Wild for da Night”
• Redman – “Da Goodness”
• Mystikal – “Whacha Want Whacha Need”
• Heavy D & the Boyz – “A Buncha Niggas”
• Pharoahe Monch – “Simon Says (Remix)”
• Puff Daddy – “Victory”
• Capone-N-Noreaga – “Driver’s Seat”
• Mase – “Niggaz Wanna Act”

Busta Rhymes came into the rap game as part of four-man group, Leaders of the New School, alongside Charlie Brown, Cut Monitor Milo and Dinco D, but it was clear from the outset that there one member who was emerging as a clear superstar. This fact was made all the more clear when the group jumped on A Tribe Called Quest’s 1991 posse cut “Scenario” and Busta left the mic smoking once he was done with the final verse .

From there, it was only a matter of time that the rapper went solo. No longer shackled to the confines of a group, Busta was free to take full control of his career and he took full advantage of it. From wrecking feature verses (“Flava in Ya Ear”) to creating spectacular visuals (“Woo Hah!! Got You All in Check”) to dropping brilliant concept albums, Busta Rhymes proved that he was a one-in-a-lifetime rapper with his insane energy and dominating flow.

25. Mos Def

Albums: Mos Def & Talib Kweli Are Black Star (with Talib Kweli, as Black Star) (1998), Black on Both Sides (1999)

Best Mos Def guest verses of the ‘90s:

• De La Soul – “Big Brother Beat”
• The Roots – “Double Trouble”
• Funkmaster Flex – “World Famous”
• DJ Krush – “Shinjiro”
• A Tribe Called Quest – “Rock Rock Y’all”

Mos Def, along with fellow Rawkus Records rappers Talib Kweli and Company Fellow, came to define the underground hip hop scene of the late ’90s. The Brooklyn rapper only dropped two albums during the decade – Mos Def & Talib Kweli Are Black Star and Black on Both Sides – but they were certified classics that showcased Mos’ nimble flow and Afrocentric rhymes, and helped position him as one of the figureheads of the conscious rap movement.

24. Treach

Albums: Naughty by Nature (1991), 19 Naughty III (1993), Poverty’s Paradise (1995), Nineteen Naughty Nine: Nature’s Fury (1999)

Best Treach guest verses of the ‘90s:

• 2Pac – “5 Deadly Venomz”
• D-Nice – “Time to Flow””
• Queen Latifah – “Coochie Bang…”
• 2Pac – “Loyal to the Game”
• M.O.P. – “Brooklyn/Jersey Get Wild”
• Aaliyah – “A Girl Like You”
• Krayzie Bone – “Thugz All Over Da World”
• Da Youngstas – “Crewz Pop”

It’s easy these for rap fans to look back at Naughty by Nature and think of only their biggest hits like “O.P.P.” and “Hip Hop Hooray.” After all, those two singles were huge global smashes and transformed the New Jersey rap group into a household name. But aside from the pop hits, Naughty by Nature, and more particularly, Treach, contributed to perfecting the rap album blueprint.

Building on the formula set out by LL Cool J years before, the group made sure they catered to an array of audiences – ranging from the streets and clubs to the radio and live shows. When he wasn’t penning some of the most memorable hooks in rap history, Treach was getting busy on the mic with his spit-fire delivery. At one point in time during the ’90s, Treach was undoubtedly the best and most well-rounded rapper alive.

23. Big L

Albums: Lifestylez ov da Poor & Dangerous (1995)

Best Big L guest verses of the ’90s:

• Lord Finesse – “Yes You May”
• Showbiz and A.G. – “Represent”
• O.C. – “Dangerous”
• Mase – “Uptown Connection”
• Shyheim – “Furious Anger”
• O.C. – “Get Yours”

Like Biggie and 2Pac, Big L was one of the biggest what-ifs in hip hop. Hip hop heads dream of scenarios where the Harlem rapper wasn’t gunned down in his prime and lived to sign with Roc-A-Fella Records to drop more lyrical wizardry. But unlike the former two rappers, Big L didn’t have the chance to put together as full a body of work as they did.

The reason why L ranks so highly in the hearts and minds of rap fans is because of what they heard on his debut album, Lifestylez ov da Poor & Dangerous , and a handful of other songs like the brilliant “Ebonics.”

Whether it was coming up with incredible freestyles off the dome, explaining street slang with style, dropping punchline after punchline or weaving gritty stories into his rhymes, L cemented his position as one of the greatest rappers of all time , in an incredibly short amount of time.

22. Kool G Rap

Albums: Wanted: Dead or Alive (with DJ Polo) (1990), Live and Let Die (with DJ Polo) (1992), 4,5,6 (1995), Roots of Evil (1998)

Best Kool G Rap guest verses of the ‘90s:

• Sway & King Tech – “The Anthem”
• Mobb Deep – “The Realest”
• Brand New Heavies – “Death Threat”
• Papoose – “Thug Connection”
• Marley Marl – “The Symphony, Pt. II”
• Heavy D & the Boyz – “Don’t Curse”
• Roxanne Shanté – “Deadly Rhymes”
• Pete Rock – “Truly Yours ’98”
• Fat Joe – “You Must Be Out of Your Fuckin’ Mind”

The Corona, Queens legend is a product of the ’80s – coming up with the likes of rap gods like Rakim, Big Daddy Kane and KRS-One – but his best work was created in the ’90s. It’s the decade where the legend of Kool G Rap, the alliteration master, the mafioso don, the street god began. After debuting in ’89 with Road to the Riches , G Rap followed up with two more DJ Polo-featured albums – Wanted: Dead or Alive and Live and Let Die – each one building on the gritty New York world that he had created in his raps.

G Rap’s solo work – 4,5,6 and Roots of Evil – featured an even darker, gritty sound that would influence later New York street kings like Nas, Biggie, Jay-Z, Raekwon, Ghostface Killah, and about a dozen other rappers coming up in the ’90s. You can trace a direct lineage from Kool G Rap to rap classics like Reasonable Doubt , Only Built 4 Cuban Linx… , Life After Death and It Was Written .

21. Q-Tip

Albums: People’s Instinctive Travels and the Paths of Rhythm (1990), The Low End Theory (1991), Midnight Marauders (1993), Beats, Rhymes and Life (1996), The Love Movement (1998), Amplified (1999)

Best Q-Tip guest verses of the ’90s:

• Deee-Lite – “Groove Is In The Heart”
• Heavy D – “Don’t Curse”
• Black Sheep – “La Menage”
• De La Soul – “A Roller Skating Jam Named “Saturdays””
• Big Daddy Kane – “Come on Down”
• Run–D.M.C. – “Come on Everybody”
• Tha Alkaholiks – “All the Way Live”
• Mobb Deep – “Drink Away the Pain (Situations)”
• The Roots – “Ital (The Universal Side)”
• Common – “Stolen Moments Pt. 3”
• Janet Jackson – “Got ’til It’s Gone”
• Missy Elliott – “Hot Boyz”

The rise and fall of A Tribe Called Quest, and the subsequent of Q-Tip’s solo career all happened within the span of the 1990s. That’s how busy the Tribe frontman was during the decade. With his conversational, low-key rapping style and jazzy-inspired flow, Q-Tip bounced off perfectly against Phife’s more energetic, high-pitched delivery with a chemistry that has been rarely seen again in later rap groups. Tip was also a master songwriter, disguising a lot of social commentary in his rhymes with catchy hooks and his signature bass-laden production.

20. DMX

Albums: It’s Dark and Hell Is Hot (1998), Flesh of My Flesh, Blood of My Blood (1998), …And Then There Was X (1999)

Best DMX guest verses of the ‘90s:

• LL Cool J – “4, 3, 2, 1”
• Jay-Z – “Money, Cash, Hoes”
• The LOX – “Money, Power & Respect”
• Mase – “24 Hrs. to Live”
• Onyx – “Shut ’em Down”
• DJ Clue – “It’s On”
• Jay-Z – “Murdergram”
• Mic Geronimo – “Time to Build”
• Nas – “Life Is What You Make It”
• Ja Rule – “It’s Murda”
• Eve – “Scenario 2000”

DMX made his official debut at the beginning of 1998, but truthfully, he had been grinding away at his music for years before that – his first single “Born Loser” dropped in 1993. But when X finally hit the rap game, it was like a tidal wave of black hoodies and Timberland-rocking stick-up artists kicking down the door to the Bad Boy mansion.

With his gruff delivery mixed with a keen sense of melody, DMX was the street hero everyone was waiting for while Puffy and his crew were busy popping expensive champagne in the clubs. It’s hard to understand it if you weren’t there, but DMX was absolutely the biggest and most exciting artist in the rap game as we exited the ’90s.

19. Ghostface Killah

Albums: Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan) (1993), Ironman (1996), Wu-Tang Forever (with Wu-Tang Clan) (1997)

Best Ghostface Killah guest verses of the ‘90s:

• Raekwon – “Criminology”
• GZA – “4th Chamber”
• Raekwon – “Glaciers Of Ice”
• Mobb Deep – “Right Back to You”
• Raekwon – “Rainy Dayz”
• Pete Rock – “Tha Game”
• Raekwon – “Guillotine (Swordz)”
• GZA – “Investigative Reports”
• Ol’ Dirty Bastard – “Brooklyn Zoo II (Tiger Crane)”
• Method Man & Redman – “Run 4 Cover”

As dope as his appearances were on Wu-Tang’s debut album, it was on Raekwon’s Only Built 4 Cuban Linx… that Ghostface had his coming out party. Billed as “Chef Raekwon guest starring Tony Starks,” the Purple Tape featured Ghost on 12 of the 17 tracks, including one solo joint, and the high energy rapper made sure to capitalise on every single moment.

From the opening bars of “Criminology” – one of the best feature verse of the ’90s – to his timeless skit on “Glaciers of Ice,” Ghost emerged as Wu’s most exciting rapper in 1995. Then on his own debut album a year later, Starks doubled down on his wide-eyed flow and coke-fuelled delivery, while sprinkling in more elements of his personality and storytelling chops.

18. Big Pun

Albums: Capital Punishment (1998)

Best Big Pun guest verses of the ’90s:

• Showbiz and A.G. – “Drop It Heavy”
• Fat Joe – “Fire Water”
• Pete Rock – “Verbal Murder 2”
• Onyx – “Shut ‘Em Down” (Remix)
• Fat Joe – “John Blaze”
• Noreaga – “Banned from T.V.”
• DJ Clue – “Fantastic 4”
• Ruff Ryders – “Pina Colada”
• Naughty by Nature – “We Could Do It”

When it comes to pure technical skills, there were very few rappers in the ’90s who could touch Big Pun’s prowess on the mic. I mean, every rap fan worth their weight can recite Pun’s famous lines off “Twinz (Deep Cover ’98)” – “Dead in the middle of Little Italy little did we know / That we riddled some middlemen who didn’t do diddly” (just for those of you who don’t know it.

Initially rapping as Big Moon Dawg, after meeting fellow Puerto Rican and Bronx rapper Fat Joe in 1995, Pun changed his name and made his debut on “Watch Out” off Jealous One’s Envy . A few years later, Pun dropped his debut, Capital Punishment , which featured a blend of gritty street cuts like “Tres Leches (Triboro Trilogy)” and “Super Lyrical” with more commercial-sounding hits like “Still Not a Player.” Capital Punishment ended up being nominated for Best Rap Album at the 1999 Grammy Awards and also became the first solo Latin hip hop record to go platinum.

17. LL Cool J

Albums: Mama Said Knock You Out (1990), 14 Shots to the Dome (1993), Mr. Smith (1995), Phenomenon (1997)

Best LL Cool J guest verses of the ‘90s:

• EPMD – “Rampage”
• Craig Mack – “Flava in Ya Ear (Remix)”
• Method Man & Redman – “4 Seasons”
• Keith Murray – “Incredible”
• Babyface – “This Is for the Lover in You”
• Keith Sweat – “Why Me Baby?”

By the start of the ’90s, LL Cool J was a certified veteran in the rap game. Five years removed since the release of Radio , which also happened to be Def Jam’s first full-length rap release, the Queens MC was no longer the 16-year old b-boy making his debut, but rather a rap superstar three albums deep in his recording career.

At the same time, a new crop of innovative, hungry rappers was emerging and threatening to bypass him. From Rakim’s lyrical wizardry to KRS’ booming baritone, LL was being threatened with being left in the dust. Add to that to the fact that his latest album, Walking with a Panther , didn’t receive the best reception when it dropped, although it was a commercial hit, topping the Top R&B/Hip-Hop Albums chart, and hitting platinum status.

All of these factors led to LL dropping the best album of his career, and the greatest hip hop comeback album ever, when he released Mama Said Knock You Out . The renewed energy propelled him through the rest of the ’90s, with LL making sure he stayed in the conversation every year by tapping into up-and-coming talent, whether it was Keith Murray, Prodigy, Fat Joe and Foxy Brown on Mr. Smith or Canibus, DMX, Method Man and Redman on Phenomenon .

16. KRS-One

Albums: Edutainment (with Boogie Down Productions) (1990), Sex and Violence (with Boogie Down Productions) (1992), Return of the Boom Bap (1993), KRS-One (1995), I Got Next (1997)

Best KRS-One guest verses of the ‘90s:

• Ron G – “Stop The Breaks”
• Fat Joe – “Bronx Tale”
• Sway & King Tech – “The Anthem”
• Public Enemy – “Unstoppable”
• Queen Latifah – “Evil That Men Do”
• D-Nice – “Rhymin’ Skills”
• Kool Moe Dee – “Rise ‘N’ Shine”
• Das EFX – “Represent The Real”
• Dr. Dre – “East Coast/West Coast Killas”
• Kurupt – “Live on the Mic”

KRS-One may have changed the game as part of Boogie Down Productions in the ’80s, but in my opinion, the Blastmaster had an even better run in the next decade. After dropping the last two ever Boogie Down albums – Edutainment and Sex and Violence – KRS embarked on his solo career in 1993 with the aptly-named Return of the Boom Bap .

With ’90s production maestro like DJ Premier, Showbiz and Kid Capri lacing him with the toughest, gulliest street bangers, KRS-One sounded more comfortable and self-assured as ever. A couple of years later, Kris would drop KRS-One , which featured his biggest and best record ever, “MC’s Act Like They Don’t Know.”

15. Big Boi

Albums: Southernplayalisticadillacmuzik (1994), ATLiens (1996), Aquemini (1998)

Best Big Boi guest verses of the ‘90s:

• Goodie Mob – “Black Ice (Sky High)”
• 8Ball & MJG – “Throw Your Hands Up”
• Goodie Mob – “Dirty South”
• Slick Rick – “Street Talkin'”
• Missy Elliott – “All n My Grill”
• Cool Breeze – “Gangsta Partna”
• Mystikal – “Neck uv da Woods”

A hugely talented MC on his own, Big Boi could damn near out-spit 95% of all the rappers who came out in the ’90s. It just so happened that he was paired with quite possibly the most original and brilliant hip hop artist ever, so he was always a little underrated. But over the course of their three album run, Big Boi was right there with Andre 3000 every step of the way. For every incredible bar, couplet or line that Stacks spit, Big Boi was right next to him, and at some points, got the better of the two.

14. Rakim

Albums: Let the Rhythm Hit ‘Em (as Eric B. & Rakim) (1990), Don’t Sweat the Technique (as Eric B. & Rakim) (1992), The 18th Letter (1997), The Master (1999)

Best Rakim guest verses of the ‘90s:

• Mobb Deep – “Hoodlum”
• Gang Starr – “Militia II (Remix)”
• Mica Paris – “Contribution”
• Barrington Levy – “Murderer (Jeep Version)”
• Shaquille O’Neal – “Game of Death”

Rakim had already changed the entire rap landscape in the latter half of the ’80s when he dropped the genre-defining Paid in Full and the equally impressive (if not better) Follow the Leader , but he wasn’t satisfied with that. Coming into the ’90s, the Ra released two more albums with Eric B. – Let the Rhythm Hit ‘Em and Don’t Sweat the Technique – before going solo. As the greatest rapper to emerge from the ’80s , Rakim still had a lot to show and prove in the next decade.

Unlike a lot of his peers from the previous decade, Rakim managed to transition smoothly into the ’90s, linking up with younger production greats like DJ Premier, Pete Rock and Clark Kent for his debut album, The 18th Letter . The final product was a rap masterpiece that featured Ra’s incredibly complex lyricism over fresher beats, reaffirming, once again, that he was the one and only God MC.

13. Raekwon

Albums: Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan) (1993), Only Built 4 Cuban Linx… (1995), Wu-Tang Forever (with Wu-Tang Clan) (1997), Immobilarity (1999)

Best Raekwon guest verses of the ‘90s:

• OutKast – “Skew It on the Bar-B”
• Mobb Deep – “Eye For An Eye”
• Ghostface Killah – “Daytona 500”
• Pete Rock – “Tha Game”
• Mobb Deep – “Nighttime Vultures”
• Fat Joe – “Firewater”
• Ghostface Killah – “Iron Maiden”
• Method Man – “Meth vs. Chef”
• Ol’ Dirty Bastard – “Raw Hide”
• Mobb Deep – “Right Back At You”
• Jodeci – “Freek’n You (Remix)”
• Fat Joe – “John Blaze”

With his signature husky voice, indecipherable slang, and mafioso crime tales, Raekwon the Chef was a staple of ’90s hip hop. Since debuting with the Wu in ’93, there wasn’t a year that decade that Chef Raekwon didn’t stand out to represent for the New York rap scene.

In ’94, he went toe-to-toe with his Wu brother on “Meth vs. Chef”, ’95 he dropped arguably the best street rap album ever with Only Built 4 Cuban Linx… , ’96 he was all over Ghost’s Ironman , ’97 was Wu-Tang Forever , in ’98 he became the first New York artist to collaborate with OutKast , and in ’99 he released his second album Immobilarity . One of the best and most consistent rappers to ever do it, no doubt.

12. Prodigy

Albums: Juvenile Hell (1993), The Infamous (1995), Hell on Earth (1996), Murda Muzik (1999)

Best Prodigy guest verses of the ‘90s:

• LL Cool J – “I Shot Ya (Remix)”
• Pete Rock – “Tha Game”
• Big Pun – “Tres Leches (Triboro Trilogy)”
• Nas – “Live Nigga Rap”
• Method Man – “Play IV Keeps”
• Nas – “Family”

Prodigy positioned himself as one of the best rappers of the 1990s with his killer quotables, icy flow and dead-eyed delivery. Blessed with an undeniable voice, P has probably ended up being one of the most sampled rappers of all time , next to Slick Rick. Mobb Deep’s run from The Infamous to Murda Muzik is legendary, and if you throw in Prodigy’s guest verses for Nas, LL and Big Pun, there’s no denying his standing in ’90s rap music.

11. Method Man

Albums: Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan) (1993), Tical (1994), Wu-Tang Forever (with Wu-Tang Clan) (1997), Tical 2000: Judgement Day (1998), Blackout! (with Redman) (1999)

Best Method Man guest verses of the ‘90s:

• GZA – “Shadowboxin'”
• The Notorious B.I.G. – “The What”
• LL Cool J – “4, 3, 2, 1”
• Redman – “Do What Ya Feel”
• DMX – “Grand Finale”
• GZA – “Living In The World Today”
• Raekwon – “Wu-Gambinos”
• Ol’ Dirty Bastard – “Raw Hide”
• 2Pac – “Got My Mind Made Up”
• Pharoahe Monch – “Simon Says” (Remix)
• Ghostface Killah – “Box In Hand”
• Mobb Deep – “Extortion”
• Onyx – “The Worst”
• Pete Rock – “Half Man Half Amazin”

Hip hop heads talk about Busta Rhymes being the features MVP of the ’90s, but honestly I think Method Man dropped hotter guest verses . The only thing holding Meth back from being higher on this list was his solo outpt – his debut album (and also best album) pales in comparison with fellow Wu members like Raekwon, GZA and Ghostface.

But when you factor in his standout performances on the Wu albums as well as highlight reel of feature appearances, there’s no denying Method Man as being of the top rappers of the ’90s. The husky-voiced MC had a unique flow, charisma and delivery that no other rapper has been able to replicate ever since.

There are times when I’m listening to Meth spitting on “Shadowboxin'” or going back-and-forth with Big on “The What” or opening up Rae’s “Wu-Gambinos” that I think he’s simply the greatest rapper to have ever lived , and there’s nobody even close to him

10. Lauryn Hill

Albums: Blunted on Reality (with Fugees) (1994), The Score (with Fugees) (1996), The Miseducation of Lauryn Hill (1998)

Best Lauryn Hill guest verses of the ‘90s:

• Bounty Killer – “Hip-Hopera”
• Common – “Retrospect for Life”
• Nas – “If I Ruled the World (Imagine That)”
• Wyclef Jean – “Guantanamera”
• Mary J. Blige – “All That I Can Say”
• Mary J. Blige – “Be with You (Remix)”
• Young Zee – “Stay Gold”
• Aretha Franklin – “A Rose Is Still a Rose”
• Carlos Santana – “Do You Like the Way”
• Bob Marley – “Turn Your Lights Down Low”

There’s no denying that Lauryn Hill was simply one of the greatest hip hop artists of the ’90s. The Fugees rapper-singer may have only dropped three albums, including one solo project, during the decade, but she made a bigger impact than 90% of the rappers on this list. Propelled by the singles “Killing Me Softly”, “Fu-Gee-La”, and “Ready or Not”, The Score was a one of the most successful albums of 1996 and became only the second rap album in history to be nominated for the Grammy Award for Album of the Year .

But all that would pale in comparison to The Miseducation of Lauryn Hill , a milestone record in the hip hop, neo-soul and R&B genres, whose impact is still rippling out to this day. A certified triple threat, Lauryn Hill was an incredible MC, gifted singer, and dynamic producer, making her one of the top 10 best rappers of the 1990s and arguably best female rapper ever.

9. Jay-Z

Albums: Reasonable Doubt (1996), In My Lifetime, Vol. 1 (1997), Streets Is Watching (1998), Vol. 2… Hard Knock Life (1998), Vol. 3… Life and Times of S. Carter (1999)

Best Jay-Z guest verses of the ‘90s:

• Puff Daddy & the Family – “Young G’s”
• Big Daddy Kane – “Show & Prove”
• Big L – “Da Graveyard”
• DMX – “Blackout”
• Juvenile – “Ha (Remix)”
• Mic Geronimo – “Time to Build”
• Ja Rule – “It’s Murda”
• The Notorious B.I.G. – “I Love the Dough”
• Foxy Brown – “I’ll Be”
• Mariah Carey – “Heartbreaker”

Jay-Z emerged in the ’90s as the underdog; an underground Brooklyn MC who has the taste for the finer things in life and could articulate it immaculately. Within three years of his debut, he had transformed from the independent hustler to the king of rap .

Blessed with an ice-cold flow and confident swagger, Jay’s biggest success during the ‘90s came from his ability to marry relatable street content with a glossy commercial sound required to dominate the charts. The momentum he created with Vol. 2… Hard Knock Life would propel him all the way to future GOAT status.

8. Andre 3000

Albums: Southernplayalisticadillacmuzik (1994), ATLiens (1996), Aquemini (1998)

Best Andre 3000 guest verses of the ‘90s:

• Goodie Mob – “Thought Process”
• TLC – “Sumthin’ Wicked This Way Comes”
• Goodie Mob – “Black Ice (Sky High)”
• Slick Rick – “Street Talkin'”
• Cool Breeze – “Watch for the Hook”
• Mystickal – “Neck uv da Woods”
• Cee Lo Green – “In Due Time”
• Withdoctor – “Dez Only 1”

Andre 3000’s evolution from OutKast’s debut album, Southernplayalisticadillacmuzik , to their last release in the ‘90s, Aquemini , would provide the blueprint for later greats like Kanye West and Kendrick Lamar, rappers who weren’t content to settle for just one particular sound or look. Like the skit on Aquemini said – “Man, first they was some pimps, man. Then they was some aliens, or some genies, or some shit. Then they be talkin’ about that black righteous space, man, whatever, man.”

But through his transformation over the decade, Stacks never lost a step in his rhyming ability. Whether he was keeping it funky on “Git Up, Git Out”, dropping endless quotables on “Elevators (Me & You)” or sparring with Wu’s Raekwon on “Skew It on the Bar-B,” Andre proved that he was one of the dopest MCs to ever touch a mic.

7. Snoop Dogg

Albums: Doggystyle (1993), Tha Doggfather (1996), Da Game Is to Be Sold, Not to Be Told (1998), No Limit Top Dogg (1999)

Best Snoop Dogg guest verses of the ‘90s:

• Dr. Dre – “Deep Cover”
• 2Pac – “2 of Amerikaz Most Wanted”
• Dr. Dre – “Stranded on Death Row”
• Dr. Dre – “Nuthin’ but a ‘G’ Thang”
• The Lady of Rage – “Afro Puffs”
• Dr. Dre – “Fuck wit Dre Day (And Everybody’s Celebratin’)”
• Dr. Dre – “Still D.R.E.”
• Tha Dogg Pound – “Some Bomb Azz Pussy”
• Silkk the Shocker – “Throw Yo Hood Up”
• Kurupt – “Ride On/Caught Up”
• Soulja Slim – “At the Same Time”

Before 2Pac, before DMX, before Eminem, before 50 Cent, it was Snoop Dogg. Using his star-making performances on The Chronic as rocket fuel on his launch pad, Snoop’s debut Doggystyle sold over 800,000 copies in its first week , which was the record for a debuting artist and the fastest-selling hip hop album ever at the time. Snoop was the West Coast version of Slick Rick rapping over the funkiest production in rap history — how could he not be the biggest thing in the world?

To truly understand the magic of the lanky Long Beach rapper, just revisit the opening lines of “Nuthin’ But a “G” Thang” — “One, two, three and to the four / Snoop Doggy Dogg and Dr. Dre is at the door.” As a rap line, it doesn’t get any more simple than that, but in the hands of Snoop Dogg — with his laid-back flow and distinctive voice oozing with personality, it became one of the most iconic lines ever .

6. Redman

Albums: Whut? Thee Album (1992), Dare Iz a Darksi de (1994), Muddy Waters (1996), El Niño (with Def Squad) (1998), Doc’s da Name 2000 (1998), Blackout! (with Method Man) (1999)

Best Redman guest verses of the ‘90s:

• EPMD – “Head Banger”
• 2Pac – “Got My Mind Made Up”
• EPMD – “Hardcore”
• Busta Rhymes – “Flipmode Squad Meets Def Squad”
• EPMD – “Brothers on My Jock”
• MC Eiht – “Nuthin’ But the Gangsta”
• Method Man – “Big Dogs”
• EPMD – “Symphony 2000”
• 8Ball – “Coffee Shop”
• Das EFX – “Rap Scholar”

There wasn’t a rapper alive in the ‘90s who was as ridiculously consistent as Reggie Noble. The funky New Jersey MC stayed putting out flamers the entire decade. From his debut on EPMD’s 1990 album Business as Usual — “Hardcore” and “Brothers on My Jock” — to his 1991 debut to his group album with Def Squad, all the way to his collaboration with Method Man at the end of the decade, every verse that Redman spit was incredibly memorable.

Reggie had one of the best three-album runs of the decade with his first three projects, and if you pair that with all the dope features he also dropped in the ‘90s, there’s no doubt that he was one of the best rappers to come out.

5. Scarface

Albums: We Can’t Be Stopped (with Geto Boys) (1991), Mr. Scarface Is Back (1991), Till Death Do Us Part (with Geto Boys) (1993), The World Is Yours (1993), The Diary (1994), The Resurrection (with Geto Boys) (1996), The Untouchable (1997), My Homies (1998), Da Good da Bad & da Ugly (with Geto Boys) (1998)

Best Scarface guest verses of the ‘90s:

• Compton’s Most Wanted – “N 2 Deep”
• Kool G Rap & DJ Polo – “Two to the Head”
• 5th Ward Boyz – “Studio Gangster”
• Gang Starr – “Betrayal”
• Devin the Dude – “Sticky Green”
• Nas – “Favor for a Favor”
• Too Short – “Longevity”
• CJ Mac – “Friday Night”

One of the most important pioneer rappers to come out of the South, Scarface was a busy artist during the ’90s. Coming into the decade as part of the infamous Geto Boys, Scarface was responsible for the group’s biggest hit and best rap song of 1991 when he penned “Mind Playing Tricks on Me.”

As a solo artist, Face found even greater success as he perfected his world-weary storytelling rap style across albums Mr. Scarface Is Back and The World Is Yours , dropped his best album to date with The Diary and reached the top of the pop charts with The Untouchable . From his output alone in the ’90s, Scarface cemented his position as one of the greatest rappers of all time, and certainly a top five rapper of the decade.

4. Ice Cube

Albums: AmeriKKKa’s Most Wanted (1990), Kill at Will (1990), Death Certificate (1991), The Predator (1992), Lethal Injection (1993), Bow Down (with Westside Connection), War & Peace Vol. 1 (The War Disc) (1998)

Best Ice Cube guest verses of the ‘90s:

• Public Enemy – “Burn Hollywood Burn”
• Kool G Rap & DJ Polo – “Two to the Head”
• King Tee – “Played Like a Piano”
• Too Short – “Ain’t Nuthin’ But a Word to Me”
• 2Pac – “Last Wordz”
• Master P – “Bangin'”
• MC Eiht – “III: Tha Hood Way”
• Scarface – “Game Over”
• Willie D – “Play Witcha Mama”
• Del tha Funkee Homosapien – “Hoodz Come in Dozens”
• Erick Sermon – “The Ill Shit”

It’s actually so ridiculous when you think about it. Between 1990 and 1992, Ice Cube really managed to drop three certified classic albums – AmeriKKKa’s Most Wanted , Death Certificate and The Predator – and a classic EP ( Kill at Will was also the first rap EP to go platinum ). It really is the greatest run by a rapper of all time.

In addition to all that, Cube also managed to find time to singlehandedly shut down N.W.A. with the legendary “No Vaseline,” form his own side group with Westside Connection, get into it with Cypress Hill and Common, drop five platinum albums as well as co-write and star in his own comedy film. One of the best and most prolific rappers of the 1990s? No doubt about it.

3. Nas

Albums: Illmatic (1994), It Was Written (1996), The Album (with the Firm) (1997), I Am… (1999), Nastradamus (1999)

Best Nas guest verses of the ‘90s:

• Raekwon – “Verbal Intercourse”
• Mobb Deep – “Eye for a Eye (Your Beef is Mines)”
• Main Source – “Live at the Barbeque”
• AZ – “Mo Money, Mo Murder Homicide”
• Kool G Rap – “Fast Life”
• Mobb Deep – “Give It Up Fast”
• AZ – “How Ya Livin'”
• Fat Joe – “John Blaze”
• DMX – “Grand Finale”
• Mobb Deep – “It’s Mine”
• Missy Elliott – “Hot Boyz”
• Noreaga – “Body in the Trunk”

When an 18-year old Nas first showed up on Main Source’s “Live At The Barbeque” talking about going to hell for snuffin’ Jesus and kidnapping the president’s wife without a plan, no-one could have foreseen the heights that he would reach in the coming years.

Of course, he displayed a talent with words far beyond his age and a technical rap ability that suggested he pored over the records of Rakim, Kool G Rap and Big Daddy Kane. But to say that rap fans expected something as great, as thought-provoking and deep as Illmatic a few years after “Live At The Barbeque,” would just be insanity.

There’s been enough written about Nas’ seminal 1994 release that we don’t need to rehash it here — we previously named it the best rap debut album as well as the best rap album of the ‘90s . No, Nas’ greatness goes beyond Illmatic . Boosted by the Lauryn Hill-featured “If I Ruled the World (Imagine That)” and bouncy “Street Dreams,” Nas followed up his debut by becoming one of the biggest rappers on the planet with the triple platinum It Was Written , all while lining up a murderers row of guest verses .

While Nas’ trajectory admittedly hit a downward spiral towards the end of the ‘90s with the (deservedly) maligned Nastradamus , his output during the decade established him forever as one of the greatest of all time.

2. The Notorious B.I.G.

Albums: Ready to Die (1994), Conspiracy (with Junior M.A.F.I.A.) (1995), Life After Death (1997), Born Again (1999)

Best Biggie guest verses of the ‘90s:

• Puff Daddy – “Victory”
• Craig Mack – “Flava in Ya Ear (Remix)”
• Puff Daddy – “Young Gs”
• Jay-Z – “Brooklyn’s Finest”
• Puff Daddy – “It’s All About the Benjamins (Remix)”
• Heavy D & the Boyz – “A Buncha Niggas”
• Total – “Can’t You See”
• Ron G – “Stop the Breaks”
• Mary J. Blige – “What’s the 411? (Remix)”
• Sadat X – “Come On”

The Notorious B.I.G.’s debut album was a monumental release of New York hip hop and positioned him as a future great. With Puff Daddy as his executive producer, the Bed–Stuy showcased his cinematic storytelling and pinpoint delivery over West Coast-inspired production, which helped appeal to Big’s hardcore street fanbase, as well as the top 40 charts and clubs.

But Ready to Die wasn’t Biggie’s magnum opus. That may sound like blasphemy but it’s the truth. Big’s debut wasn’t even the best rap album of 1994, that honour goes to Illmatic as we’ve already established earlier. It was actually on his second album, Life After Death , that rap fans had the opportunity to witness the true greatness of The Notorious B.I.G. Like he told The Source in 1997 leading up to the album’s release:

I want people to buy [my new] album and just straight up say, ‘Yo, he’s the best. He’s the best ever. He’s the best that ever did it.’ That’s what I’m looking for. I want my props. ’Cause they slept on me. I read [what people write and say] and they give me my props as being that solo emcee that blew up from the East Coast: But they don’t give me my props like, ‘Yo, Big be straight dicin’ niggas on the mic! On the rhyme side, he’s nice!’ They don’t really look at me like that.

The Source Magazine | 1997

Over a 2-hour runtime and 24 tracks, Big put forth, defended and won the argument that he was the best to ever do it. Whether it was radio hits (“Mo Money Mo Problems”), club bangers (“Hypnotize”), storytelling joints (“Somebody’s Gotta Die”, “Niggas Bleed”, “I Got a Story to Tell”), or concept tracks (“Ten Crack Commandments”), Big could do it all, and he could do it better than all his competition. He went at Nas and Raekwon, he flossed with Jigga, he traded bars with The LOX, and he flowed like Bone Thugs.

The fact that we all talk about Big and his position on the GOAT list on a regular basis nearly 30 years after he passed and based off of just two albums should speak volumes of why he was absolutely one of the greatest rappers of the ’90s.

1. 2Pac

Albums: 2Pacalypse Now (1991), Strictly 4 My N.I.G.G.A.Z… (1993), Thug Life: Volume 1 (with Thug Life) (1994), Me Against the World (1995), All Eyez on Me (1996), The Don Killuminati: The 7 Day Theory (1996) (as Makaveli), Still I Rise (with Outlawz) (1999)

Best 2Pac guest verses of the ‘90s:

• Bone Thugs-n-Harmony – “Thug Luv”
• Scarface – “Smile”
• Above the Law – “Call It What U Want”
• Scarface – “Homies & Thuggs”
• MC Breed – “Comin’ Real Again”
• Eddie F – “Let’s Get It On”
• E-40 – “Dusted ‘n’ Disgusted”
• Too Short – “We Do This”
• MC Hammer – “Too Late Playa”
• Rappin’ 4-Tay – “Playaz Dedication”

You know what the craziest thing about 2Pac’s rap career was? His debut album 2Pacalypse Now , dropped November 12, 1991, and his first posthumous release, The Don Killuminati: The 7 Day Theory , which came out on November 5, 1996, were almost exactly five years apart .

Within those five years, Pac accomplished more than what most rappers could have hoped to achieve over the course of their entire career. Within those five years, Pac created enough music to last a lifetime. Within those five years, he ran through the entire spectrum of emotions – love, anger, paranoia, nostalgia, rage, jealousy, fear, joy, and more.

Pac represented all the sides of a human being – he was an angry, sensitive, tough, vulnerable, caring, vindictive person and he bared it all in his music. The criticism that 2Pac usually receives from traditionalist rap fans is that he wasn’t “lyrical.”

Which, in their mind, usually means from a complex, multisyllabic rhyming standpoint. So he couldn’t deliver punchlines that made you screw up your face like Big L, spit tongue-twisting alliteration like Kool G Rap, flow as masterfully as Big, spit effortless wordplay like Hov, or weave intricate stories like Nas. That’s correct.

But what Pac was able to do better than any other rapper in history was completely pour himself into his words and get the emotion of his raps through to the listener that helped them connect with him on a much deeper level. And it’s for that reason, amongst many, many others, that Tupac Shakur is the greatest rapper of the 1990s.