Greatest Rapper Five Year Runs Of All Time
Search Menu

The 30 Greatest Rapper Five-Year Runs of All Time

For the longest time, hip hop has been viewed as a young man’s sport. Up until recently, with the likes of Nas and Jay-Z dropping classic albums 30 years into their recording career, it was rare to see an older rapper thriving late in the game.

For many up-and-coming rappers, to have one hot year where they dominate is difficult. To continue that streak for more than one year is damn near impossible. But to extend that streak into a five-year run, well, that’s one of the hallmarks of being a GOAT isn’t it.

From Biggie to 2Pac, Future to Lil Wayne, Ice Cube to Jay-Z, Andre 3000 to Rakim, we look at the 30 greatest rapper five-year runs of all time.

Honourable mentions:

Rick Ross: 2008 – 2012

Greatest Rapper Five Year Runs Of All Time Rick Ross 1024X683

Notable releases: Trilla, Deeper Than Rap, Teflon Don, Self Made Vol. 1 (with Maybach Music Group), Rich Forever, Self Made Vol. 2 (with Maybach Music Group), God Forgives, I Don’t

Guest appearances: Freeway – “Lights Get Low”, Ace Hood – “Cash Flow”, DJ Khaled – “Out Here Grindin”, Bun B – “You’re Everything”, DJ Khaled – “All I Do Is Win”, Kanye West – “Monster”, DJ Khaled – “Welcome to My Hood”, Lil Wayne – “John”, DJ Khaled – “I’m on One”, Birdman – “Born Stunna”, French Montana – “Pop That”, DJ Khaled – “I Wish You Would”, Nicki Minaj – “I Am Your Leader”, Kanye West – “Devil in a New Dress”, The Game – “Heavy Artillery”, Wale – “Ambition”, Drake – “Lord Knows”, Meek Mill – “Maybach Curtains”

Ever since his 2006 debut, the stellar Port of Miami , Rick Ross has amassed one of the most enviable catalogues in hip hop today. A consummate professional that doesn’t rely on big hype cycles or huge singles, Ross just keeps it simple – great music packaged into great albums, dropped consistently. 10 solo albums, three group albums, and four mixtapes later, Ross hasn’t missed yet.

Big Daddy Kane: 1987 – 1991

Big Daddy Kane Battle Kool Moe Dee 14 Years Old 1024X683

Notable releases: Long Live the Kane, It’s a Big Daddy Thing, Taste of Chocolate, Prince of Darkness

Guest appearances: Marley Marl – “The Symphony”, Quincy Jones – “Prologue (2Q’s Rap)”, Quincy Jones – “Jazz Corner of the World”, Public Enemy – “Burn Hollywood Burn”, Heavy D & the Boyz – “Don’t Curse”, Freddie Foxxx – “Heal Yourself”

In the same year that Rakim dropped his landmark debut, Paid in Full , and shifted the rapping landscape, Big Daddy Kane released his debut single, the classic 12″ “Raw”, which also contributed to the evolution of rhyming. Between 1987 and 1991, Kane was consistently in the conversation of the best rappers alive, often against peers like Rakim and Kool G Rap, and while he experienced a notable drop-off after It’s a Big Daddy Thing , he still remains one of the greatest rappers of all time .

Kool G Rap: 1988 – 1992

50 Greatest Rappers Of All Time Kool G Rap 1024X683

Notable releases: Road to the Riches (with DJ Polo), Wanted: Dead or Alive (with DJ Polo), Live and Let Die (with DJ Polo)

Guest appearances: Marley Marl – “The Symphony”, Marley Marl – “The Symphony, Pt. II”, Heavy D & the Boyz – “Don’t Curse”, Roxanne Shanté – “Deadly Rhymes”, The Brand New Heavies – “Death Threat”

Off the strength of his verse on “The Symphony” alone, Kool G Rap established himself as one of the most fearsome MCs of the 1980s . While Rakim and Kane are usually touted as the figureheads of lyrical rap from that era, G Rap was always lurking in the shadows, waiting to completely shred a verse apart. During his run in the late ’80s to early ’90s, G Rap transformed from a relentless Queens spitter into one of the most influential rappers of all time. Legends like Nas, Biggie, Jay-Z, Raekwon and Ghostface are all cut from the Kool G Rap mafioso cloth.

30. Young Thug: 2013 – 2017

Greatest Rapper Five Year Runs Of All Time Young Thug 1024X683

Notable releases: 1017 Thug, Black Portland (with Bloody Jay), Young Thugga Mane La Flare (with Gucci Mane), Tha Tour, Pt. 1 (with Birdman and Rich Homie Quan, as Rich Gang), Barter 6, Slime Season, Slime Season 2, I’m Up, Slime Season 3, Jeffery, Beautiful Thugger Girls, Super Slimey (with Future)

Guest appearances: Tyga – “Hookah”, T.I. – “About the Money”, Rae Sremmurd – “Throw Sum Mo”, Travis Scott – “Mamacita”, Jamie xx – “I Know There’s Gonna Be (Good Times)”, Yo Gotti – “Rihanna”, Bankroll Mafia – “Bankrolls on Deck”, Lil Yachty – “Minnesota”, Gucci Mane – “Guwop Home”, Rick Ross – “Trap Trap Trap”, Travis Scott – “Skyfall”, Travis Scott – “Nothing But Net”, Lil Uzi Vert – “Yamborghini Dream”, Travis Scott – “Maria I’m Drunk”, T.I. – “Peanut Butter Jelly”, Chance the Rapper – “Mixtape”, Nipsey Hussle – “Thug Life”, Meek Mill – “Offended”, Drake – “Sacrifices”, Drake – “Ice Melts”, 21 Savage – “Whole Lot”

Young Thug emerged in 2013 as an interesting rapper with seemingly limitless potential under the banner of Gucci Mane’s 1017 Records. By 2017, he had transformed into a fully-fledged artist who was cemented as one of the most creative and daring rappers of his generation.

29. J. Cole: 2014 – 2018

Ranking The 30 Best Rappers Over 30 Cole 1024X683

Notable releases: Revenge of the Dreamers (with Dreamville Records), 2014 Forest Hills Drive, 4 Your Eyez Only, KOD

Guest appearances: Jeremiah – “Planez”, Janet Jackson – “No Sleeep”, Bas – “Night Job”, Spillage Village – “Can’t Call It”, Royce da 5’9″ – “Boblo Boat”, Miguel – “Come Through and Chill”, Rapsody – “Sojourner”, 21 Savage – “A Lot”, Wale – “The Pessimist”, Joey Bada$$ – “Legendary”, Jay Rock – “OSOM”, Bas – “Tribe”, Wale – “My Boy (Freestyle)”, Moneybagg Yo – “Say Na”

During the early 2010s, there were only two names from the new generation that had fully captured hip hop’s attention: Kendrick Lamar and Drake. With the release of his masterpiece major label debut, the Compton rapper quickly propelled himself into best rapper alive status , while the OVO head honcho had just dropped Take Care and built a name for himself as a certified features killer.

J. Cole was in the conversation, but he wasn’t being spoken about like that. It wasn’t really until 2014 Forest Hills Drive that Cole jumped into the top-tier of hip hop, going number one and hitting platinum status with an album that had no features. Since then, he’s continued to run in his own lane, topping the charts whenever he drops and stirring up the rap world into a frenzy with each feature verse.

28. Redman: 1992-1996

50 Greatest Rappers Of All Time Redman 1024X683

Notable releases: Whut? Thee Album, Dare Iz a Darkside, Muddy Waters

Guest appearances: EPMD – “Head Banger”, Erick Sermon – “Swing It Over Here”, Keith Murray – “How’s That”, MC Eiht – “Nuthin’ But the Gangsta”, Lords Of The Underground – “What I’m After”, Montell Jordan – “Somethin’ 4 Da Honeyz (Human Rhythm Remix)”, Kris Kross – “Tonite’s tha Night (Kris Kross Redman Remix)”, Keith Murray – “Yeah”, 2Pac – “Got My Mind Made Up”, Busta Rhymes – “Flipmode Squad Meets Def Squad”

When you talk to rap fans about Redman, it’s a general consensus that he’s a dope MC. But I don’t think most of them know just how dope, dope, dope of a rapper he is. Reggie was low-key the best rapper alive of the ’90s, from his solo work to collaborations with EPMD, he always brought out the funk and destroyed every verse he spit.

27. Method Man: 1993 – 1997

Method Man 1024X683

Notable releases: Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan), Tical , Wu-Tang Forever (with Wu-Tang Clan)

Guest appearances: GZA – “Shadowboxin'”, LL Cool J – “4, 3, 2, 1”, The Notorious B.I.G. – “The What”, Spice 1 – “Hard To Kill”, GZA – “Gold”, Raekwon – “Wu-Gambinos”, Raekwon – “Ice Cream”, Ol’ Dirty Bastard – “Raw Hide”, 2Pac – “Got My Mind Made Up”, Foxy Brown – “Ill Na Na”, Redman – “Do What Ya Feel”, Mobb Deep – “Extortion”

What happened on Enter the Wu-Tang (36 Chambers) will never happen in hip hop again. Nine completely unique and incredible MCs breaking out of Shaolin and lacing killer verses over RZA’s crazy production; it was just unheard of then. Out of the 9 rappers, it was Method Man with the husky voice and butter flow whose star shone the brightest. Between 1993 and 1997, Meth emerged as the biggest star from the Wu, was one of the few rappers who collaborated with both Pac and Big, and dropped one of the best and biggest rap singles of the ’90s.

26. Tyler, the Creator: 2017 – 2021

Top Five Best Rappers Alive Of 2021 Tyler The Creator 1024X683

Notable releases: Flower Boy, Igor, Call Me If You Get Lost

Guest appearances: Frank Ocean – “Biking”, Kali Uchis – “After the Storm”, GoldLink – “U Say”, Lil Yachty – “T.D”, Jaden – “Noize”, Westside Gunn – “327”, Freddie Gibbs – “Something to Rap About”, Snoh Aalegra – “Neon Peach” / “In the Moment”, Westside Gunn – “The Fly who couldn’t Fly straight”

Outside of Kanye West, there hasn’t been a greater artistic evolution than Tyler, the Creator. The Tyler who sat on the stool eating cockroaches in the “Yonkers” video is a completely different rapper from the one who made Igor or Call Me If You Get Lost . But one thing remains consistent, his desire to consistently experiment and push the boundaries of hip hop music.

25. Westside Gunn: 2016 – 2020

Ranking The 30 Best Rappers Over 30 Westside Gunn 1024X683

Notable releases: Flygod, Hitler Wears Hermes IV, Hitler Wears Hermes V, Westside Doom (with MF Doom), Supreme Blientele, Hitler Wears Hermes VI, Flygod is an Awesome God, Hitler Wears Hermes VII, WWCD (with Griselda), Flygod is an Awesome God II, Pray for Paris, Who Made the Sunshine

Guest appearances: Royce da 5’9″ – “Overcomer”, Conway The Machine – “Spurs 3”, Benny the Butcher – “Echo Long”, Benny the Butcher – “War Paint”

In five years, Westside Gunn went from an underground local rapper from Buffalo to doing GQ interviews alongside the late, great Virgil Abloom, receiving co-signs from Jay-Z and appearing on Kanye albums. Off the strength of the immaculate Flygod , Westside and Conway became the first rappers out of Buffalo to sign to a major label when they inked a deal with Shady Records , and it’s just been all uphill from there.

24. Freddie Gibbs: 2016 – 2020

Greatest Rapper Five Year Runs Of All Time Freddie Gibbs 1024X683

Notable releases: You Only Live 2wice, Fetti (with Curren$y and The Alchemist), Bandana (with Madlib), Alfredo (with The Alchemist)

Guest appearances: Curren$y – “Stash House”, Phonte – “Change Of Mind”, Boldy James – “S.N.O.R.T.”, Westside Gunn – “$500 Ounces”, Conway the Machine – “Seen Everything but Jesus”, Benny the Butcher – “One Way Flight”

Freddie Gibbs’ journey to becoming one of the best rappers alive right now was a decade-long process in the making. After establishing himself as a cult hero and underground king with the Madlib-produced Piñata , Gibbs continued to build on his catalogue, steadily grinding it out with quality releases. Then 2019 and 2020 happened. Gibbs dropped two AOTY contenders back-to-back, signed a partnership with Warner Records, murdered every single feature he was on, and suddenly he was in the conversation for being one of the greatest to ever do it.

23. Cam’ron: 2001-2005

Greatest Rapper Five Year Runs Of All Time Camron 1024X683

Notable releases: Come Home with Me , Diplomatic Immunity (with The Diplomats), Diplomatic Immunity 2 (with The Diplomats), Purple Haze

Guest appearances: DJ Clue – “Fantastic 4, Pt. 2”, Birdman – “Ghetto Life”, DMX – “We Go Hard”, Lil’ Flip – “All I Know”, Young Gunz – “Look in Your Eyes”, Beanie Sigel – “Wanted (On the Run)”, Juelz Santana – “Dipset (Santana’s Town)”, Jim Jones – “Certified Gangstas” / “Crunk Muzik”, Kanye West – “Gone”, Juelz Santana – “Shottas” / “Murda Murda”

While Cam’ron never managed to truly capture the King of New York crown during the early to mid-2000s – there was just too much heat at the time from Jay-Z, Nas and 50 – the Harlem legend racked up an incredible run during his time. In 2002 alone, he dropped three classic mixtapes with Dipset, released his biggest album Come Home with Me , and dominated the charts with “Oh Boy” and “Hey Ma.”

22. Chuck D: 1987 – 1991

50 Greatest Rappers Of All Time Chuck D 1024X683

Notable releases: Yo! Bum Rush the Show, It Takes a Nation of Millions to Hold Us Back, Fear of a Black Planet, Apocalypse 91… The Enemy Strikes Black

Guest appearances: Ice Cube – “Endangered Species (Tales from the Darkside)”

As the story goes, after dropping their debut album Yo! Bum Rush the Show in 1987 and hitting the road with LL Cool J and Eric B. & Rakim, Chuck D heard “I Know You Got Soul” and thought it “was the best fuckin’ record I had heard in my fuckin’ life.” The Long Island duo’s revolutionary single inspired Public Enemy to record “Rebel Without a Pause” and the accompanying It Takes a Nation of Millions to Hold Us Back . But it didn’t stop there. Public Enemy’s subsequent releases, Fear of a Black Planet and Apocalypse 91… The Enemy Strikes Black marked quite possibly the greatest album run by a hip hop group ever – right up there with OutKast and A Tribe Called Quest.

21. DMX: 1998 – 2002

Dmx First Artist First Five Albums Debut Number One Billboard 200 1024X683
(Original Caption) : DMX performs at the Hard Knock Life Tour at the Continental Airlines Arena. (Photo by Mitchell Gerber/Corbis/VCG via Getty Images)

Notable releases: It’s Dark and Hell Is Hot, Flesh of My Flesh, Blood of My Blood, …And Then There Was X, The Great Depression

Guest appearances: The LOX – “Money, Power & Respect”, Onyx – “Shut ’em Down”, DJ Clue – “It’s On”, Jay-Z – “Money, Cash, Hoes”, Jay-Z – “Murdergram”, Jermaine Dupri – “Get Your Shit Right”, Cam’ron – “Pull It”, Foxy Brown – “Dog & a Fox”, Nas – “Life Is What You Make It”, The LOX – “Ryde or Die”, Ja Rule – “It’s Murda”, Eve – “Scenario 2000”, Busta Rhymes – “Why We Die”, LL Cool J – “Fuhgidabowdit”, Jadakiss – “Uh-Hunh!”

DMX’s time at the top of the rap game wasn’t long, but boy, did he make the most of it. During a time where Puffy and Boy Boy had the radio charts on lock, DMX came through representing the streets and became a phenomenon. The Yonkers rapper became the second hip hop artist to top the charts twice in one year (the first was 2Pac in 1996), and even more impressive, DMX became the first artist ever to have his first five albums debut at number one on the Billboard 200 .

20. Ghostface Killah: 1996 – 2000

Rza Ghostface Killah Impossible Greatest Wu Verse 1024X683

Notable releases: Ironman , Wu-Tang Forever (with Wu-Tang Clan), Supreme Clientele , The W (with Wu-Tang Clan)

Guest appearances: Babyface – “This Is for the Lover in You (Puffy Combs Remix)”, Jodeci – “Freek’n You (Remix)”, Cappadonna – “97 Mentality”, RZA – “Bobby Did It (Spanish Fly)” / “Holocaust (Silkworm)”, Pete Rock – “Tha Game”, Method Man & Redman – “Run 4 Cover”, Mos Def – “Ms. Fat Booty (Part II)”, Busta Rhymes – “The Heist”

After turning in a star-making performance on Only Built 4 Cuban Linx… , Ghostface followed up with the classic Ironman , spit the greatest Wu-Tang verse of all time on “Impossible” ( according to RZA anyway ), and dropped the first great rap album of the new millennium with Supreme Clientele . Ghost had previously showcased his abstract, off-the-wall rhyming style on earlier records, but on his sophomore album, he took it to a whole new dimension, resulting in one of the greatest Wu albums ever .

19. Future: 2014 – 2018

Ranking Future First Week Album Sales 1024X683

Notable releases: Honest, Monster, Beast Mode (with Zaytoven), 56 Nights (with DJ Esco & 808 Mafia), DS2, What a Time to Be Alive (with Drake), Evol, Future, Hndrxx, Super Slimey (with Young Thug), Beast Mode 2 (with Zaytoven), Wrld on Drugs (with Juice Wrld)

Guest appearances: Young Scooter – “DISFunction”, Travis Scott – “3500”, Ty Dolla Sign – “Blasé”, Jadakiss – “You Can See”, Timbaland – “UFO”, A$AP Ferg – “New Level”, DJ Khaled – “I Got the Keys”, 21 Savage – “X”, Lil Uzi Vert – “Seven Million”, French Montana – “No Pressure”, Rick Ross – “Green Gucci Suit”, Young Jeezy – “No Tears”, Travis Scott – “High Fashion”, A$AP Rocky – “Fine Whine”, Meek Mill – “Jump Out the Face”, Drake – “Grammys”, Chance the Rapper – “Smoke Break”, Fabolous – “Check On Me”, 2 Chainz – “Doors Open”, Rich The Kid – “No Question”, Drake – “Blue Tint”, Nicki Minaj – “Sir”, Lil Durk – “Spin The Block”

“Tried to make me a pop star and they made a monster.” Before we get into it, let’s get one thing clear – Honest is not a bad album. There are some classic Future records on there that have stayed in rotation like “Look Ahead”, “Move That Dope”, “Honest” and “Benz Friendz (Whatchutola).” It just wasn’t what Future wanted to put out. So he regrouped with DJ Esco and Metro Boomin and went on one of the most legendary mixtapes runs of all time, dropping Monster, Beast Mode and 56 Nights within a span of 6 months. Then came the albums. DS2 , a top five trap album ever made, came in July 2015 and his collaboration with Drake, What a Time to Be Alive , came just a few months later.

18. KRS-One: 1987-1991

Best Rappers Alive Of 1987 Krs One

Notable releases: Criminal Minded , By All Means Necessary , Ghetto Music: The Blueprint of Hip Hop , Edutainment

Guest appearances: Just-Ice – “Going Way Back” / “Moshitup”, D-Nice – “The TR 808 Is Coming”, Queen Latifah – “Evil That Men Do”, D-Nice – “Rhymin’ Skills”

You could chop up KRS-One’s career into two distinct stages, and either one of them would be eligible for this list. For instance, you can take his Boogie Down days from 1987 to 1991, or you can pick his solo career from 1993 to 1997 where he dropped three incredible albums – Return of the Boom Bap , KRS-One and I Got Next . The point is, longevity and consistency plays a huge role when you’re talking about the GOAT rappers, and The Blastmaster has certainly made his case time and time again over the last 30 years.

17. MF Doom: 1999 – 2004

30 Greatest Rapper Five Year Runs Of All Time Mf Doom 1024X683

Notable releases: Operation: Doomsday , Black Bastards (as Zev Love X with KMD), Take Me to Your Leader (as King Geedorah), Vaudeville Villain (as Viktor Vaughn), VV:2 (as Viktor Vaughn), Madvillainy (with Madlib as Madvillain), Special Herbs + Spices Volume 1 (with MF Grimm), Mm..Food

Key guest appearances: Prefuse 73 – “Black List”, MF Grimm – “Foolish” / “Voices Pt. 1”, Scienz of Life – “Yikes!” , The Herbaliser – “It Ain’t Nuttin'”, Madlib – “Stepping Into Tomorrow”, De La Soul – “RockCo.Kane Flow”, Prince Po – “Social Distortion”

Honestly, you could just take MF Doom’s output in 2004 and he would be eligible for his list. Madvillainy and Mm..Food are two of the best rap albums ever dropped, but Doom just kept going, and going, and going. Not to mention Operation: Doomsday is one of the greatest hip hop debuts of all time .

16. Andre 3000: 1996 – 2000

Outkast Aquemini First Southern Album Source Five Mics 1024X683

Notable releases: ATLiens, Aquemini, Stankonia

Guest appearances: Goodie Mob – “Black Ice (Sky High)”, Cool Breeze – “Watch for the Hook”, Slick Rick – “Street Talkin'”, Mystikal – “Neck uv da Woods”, 8Ball & MJG – “Throw Your Hands Up”

Andre 3000 is another rapper who has never been satisfied with maintaining the status quo and consistently pushed the boundaries of his craft with each subsequent release. ATLiens, Aquemini and Stankonia is quite possibly the greatest three-album run by a hip hop act of all time , although you’d have to contend with Tribe and Mobb Deep if you want to go there.

15. Scarface: 1990-1994

50 Greatest Rappers Of All Time Scarface 1024X683

Notable releases: We Can’t Be Stopped (with Geto Boys), Mr. Scarface Is Back , Till Death Do Us Part (with Geto Boys), The World Is Yours , The Diary

Guest appearances: Compton’s Most Wanted – “N 2 Deep”, Kool G Rap – “Two to the Head”, Too Much Trouble – “Still on the Run”, 5th Ward Boyz – “Studio Gangster”

Scarface’s run as part of the Geto Boys would be enough to warrant placement on this list. The Houston group’s single “Mind Playing Tricks on Me” – produced and written by Scarface – became one of the biggest and best songs of 1991. But then as a solo artist, Scarface dropped his magnum opus, The Diary , in 1994, almost a decade since debuting as a rapper. Even looking outside of his five-year run, Scarface might be one of the few rappers in history to have dropped three classic albums in three different decades – Grip It! On That Other Level (1989), The Diary (1994), The Fix (2002).

14. Prodigy: 1995 – 1999

Mobb Deep Beef Jay Z Money Cash Hoes 1024X683

Notable releases: The Infamous , Hell on Earth , Murda Muzik

Guest appearances: LL Cool J – “I Shot Ya (Remix)”, Nas – “Live Nigga Rap”, Pete Rock – “Tha Game”, Big Pun – “Tres Leches (Triboro Trilogy)”

There was just something about Prodigy’s voice, his creeping flow, his menacing threats, that made you think whenever you listened to him, “this is the best rapper who has ever lived.” The Infamous , Hell on Earth and Murda Muzik is as perfect a three-album run as you can get, but then there’s the guest verse that he dropped on “I Shot Ya (Remix).” Even surrounded by hungry newcomers – Keith Murray, Fat Joe and Foxy Brown – who all dropped career-high verses, Prodigy’s Illuminati-referencing imagery blew them all out the water.

13. Snoop Dogg: 1992 – 1996

Most Important Moments Events In Rap Hip Hop History Snoop Dogg Death Row 1024X683

Notable releases: Doggystyle, Tha Doggfather

Guest appearances: Dr. Dre – “Deep Cover”, Dr. Dre – “Fuck wit Dre Day (And Everybody’s Celebratin’)” / “Nuthin’ but a ‘G’ Thang” / “Lyrical Gangbang” / “Stranded on Death Row” / “Bitches Ain’t Shit”, The Lady of Rage – “Afro Puffs”, 2Pac – “2 of Amerikaz Most Wanted”, Nate Dogg – “Never Leave Me Alone”

From 1992 to 1994, with the release of The Chronic , Doggystyle and the Murder Was the Case soundtrack, Snoop really was the rapper everyone else wanted to be. Isn’t it saying something when Biggie, after selling 2 million records with Ready to Die , rapped on his sophomore album: “I’m sittin’ in the crib dreamin’ about Lear jets and coupes, the way Salt shoops and how to sell records like Snoop.” At one point in time, there was Snoop, and then there was everyone else.

12. Drake: 2011 – 2015

Best Song Off Every Drake Album Ever 1024X683

Notable releases: Take Care, Nothing Was the Same, If You’re Reading This It’s Too Late, What a Time to Be Alive (with Future)

Guest appearances: DJ Khaled – “I’m on One”, Lil Wayne – “It’s Good”, Waka Flocka Flame – “Round of Applause”, Rick Ross – “Stay Schemin'”, 2 Chainz – “No Lie”, French Montana – “Pop That”, Meek Mill – “Amen”, A$AP Rocky – “Fuckin’ Problems”, Kendrick Lamar – “Poetic Justice”, DJ Khaled – “No New Friends”, YG – “Who Do You Love?”, Lil Wayne – “Believe Me”, Nicki Minaj – “Only”, Big Sean – “Blessings”, The Game – “100”, Meek Mill – “R.I.C.O.”, Future – “Where Ya At”, Migos – “Versace (Remix)”, 2 Chainz – “I Do It”

Drake’s control over the rap game this past decade has been widely documented. There hasn’t been a rapper in history who has been able to sustain his level of success and relevance for as long as he has. Artists like DMX and 50 Cent had arguably higher peaks, but their time was shorter. Jay-Z has been successful for longer, but he never had a 10-year stretch like Drake has.

To really put Drake’s dominance into perspective, you need to look at the years where he didn’t drop an album and still ran shit. The Toronto rapper was one of the best rappers alive in 2012 , based off of guest verses on “Stay Schemin'”, “No Lie”, “Pop That”, “Fuckin’ Problems” and “Poetic Justice” alone. Then in 2014, he drops a SoundCloud loosie, “0 to 100 / The Catch Up”, which goes platinum and gets nominated for a fucking Grammy , all while snapping on tracks like “Trophies”, “Believe Me” and “We Made It (Remix).”

11. Kendrick Lamar: 2013 – 2017

Greatest Rapper Five Year Runs Of All Time Kendrick Lamar 1024X683

Notable releases: To Pimp a Butterfly, Untitled Unmastered, DAMN.

Guest appearances: 50 Cent – “We Up”, T.I. – “Memories Back Then”, Schoolboy Q – “Collard Greens”, Tech N9ne – “Fragile”, Fredo Santana – “Jealous”, Pusha T – “Nosetalgia”, Mike Will Made It – “Buy the World”, Flying Lotus – “Never Catch Me”, Jay Rock – “Pay for It”, Glasses Malone – “Thuggin'”, DJ Khaled – “Holy Key”, Danny Brown – “Really Doe”, Travis Scott – “Goosebumps”, Rich the Kid – “New Freezer”, Ab-Soul – “Kendrick Lamar’s Interlude”, Dr. Dre – “Genocide”, Dr. Dre – “Darkside / Gone”, Dr. Dre – “Deep Water”, Jay Rock – “Vice City”, Kanye West – “No More Parties in LA”, Future – “Mask Off (Remix)”, Big Sean – “Control”

After dropping his major label debut, Good Kid, M.A.A.D City , which shook up the hip hop world, Kendrick went on a victory lap, bodying guest features, left, right and centre. We don’t even have to mention his verse on “Control.” There wasn’t a rapper alive who was safe from the Compton rapper’s bars – not unless you were Nas, Jay-Z, Eminem or Andre 3000.

But the true greatness in Kendrick’s five-year run is that after the monumental success of Good Kid, M.A.A.D City , he took a complete left-turn and dropped a complex, jazz-funk masterpiece that completely pushed back on any expectation you might have had from him. Good Kid, M.A.A.D City was the album that made him the best rapper of 2012, but To Pimp a Butterfly is what put him in the conversation of greatest rappers of all time.

10. Rakim: 1986 – 1990

Best Rappers Alive Of 1987 Rakim

Notable releases: Paid in Full (with Eric B.), Follow the Leader (with Eric B.), Let the Rhythm Hit ‘Em (with Eric B.)

Guest appearances: Jody Watley – “Friends”, Mica Paris – “Contribution”

Rakim’s impact on the rhyming landscape was so profound and influential that you have to separate hip hop history into two eras – before Rakim and after Rakim. With the release of their debut single “Eric B. Is President”, backed by the even-harder “My Melody,” Eric B. & Rakim completely changed rap music.

Seemingly overnight, loud, abrasive rappers like Run-D.M.C. sounded dated and old school, while a crop of new talent, like KRS-One, Big Daddy Kane and Kool G Rap, led by Rakim became the new innovators. The craziest thing is that, as impactful as Paid in Full was, the Long Island duo’s follow-up, Follow the Leader is even better, with the rhyming and production being taken up a notch further.

9. Nas: 1994 – 1998

Most Important Moments Events In Rap Hip Hop History Nas The Message 1024X683

Notable releases: Illmatic, It Was Written, The Firm: The Album (by The Firm)

Guest appearances: Kool G Rap – “Fast Life”, AZ – “Mo Money, Mo Murder Homicide”, Raekwon – “Eye for a Eye (Your Beef is Mines)”, Large Professor – “One Plus One”, Mobb Deep – “Give It Up Fast”, AZ – “How Ya Livin'”, Fat Joe – “John Blaze”, Noreaga – “Body in the Trunk”, DMX – “Grand Finale”

When we were putting together this list, it felt kinda weird to have Nas at number 15, and not in the top 5 or top 10 at least. After all, this is the Queensbridge prodigy who dropped the culture-shifting Illmatic , followed it up with 3x platinum It Was Written and dropped some of the best guest verses throughout the ’90s . But, the truth is, Nas’ greatness is spread out over longer periods, rather than being jam-packed in a few years like a DMX or Eminem. That being said, Nas’ output between ’94 and ’98 alone is enough to vault him into the best rappers of all time.

8. Lil Wayne: 2004 – 2008

Best Rappers Alive Of 2007 Lil Wayne 1024X683

Notable releases: Tha Carter, Tha Carter II, The Suffix, The Dedication, Like Father, Like Son (with Birdman), Dedication 2, Da Drought 3, Tha Carter III, Dedication 3

Guest appearances: Destiny’s Child – “Soldier”, Cam’ron – “Touch It or Not”, Currensy – “Where da Cash At”, Fat Joe – “Make It Rain”, OutKast – “Hollywood Divorce”, Lloyd – “You”, DJ Khaled – “We Takin’ Over”, Playaz Circle – “Duffle Bag Boy”, The Game – “My Life”, T-Pain – “Can’t Believe It”, T.I. – “Swagga like Us”, Jay Rock – “All My Life (In the Ghetto)”

Earlier on, we spoke about Future’s legendary mixtape run where he dropped three classics in just under 6 months. And as incredible as Future was, Lil Wayne’s mixtape run is undisputedly the greatest of all time. After declaring that he was the very best rapper alive on Tha Carter II , he went on to prove the statement. On Like Father, Like Son , on Dedication 2, on Da Drought 3 , all while murdering guest appearances on the side. Then Tha Carter III dropped, and Lil Wayne was officially the best rapper alive, and the biggest rapper alive .

7. Kanye West: 2007 – 2011

Top Five Best Rappers Alive Of 2010 Cover 1024X680

Notable releases: Graduation, 808s & Heartbreak, My Beautiful Dark Twisted Fantasy, Watch the Throne (with Jay-Z)

Guest appearances: The Game – “Wouldn’t Get Far”, T-Pain – “Buy U a Drank (Shawty Snappin’) (Remix)”, Estelle – “American Boy”, Lil Wayne – “Lollipop (Remix)”, Young Jeezy – “Put On”, T.I. – “Swagga Like Us”, DJ Khaled – “Go Hard”, Keri Hilson – “Knock You Down”, Clipse – “Kinda Like a Big Deal”, The-Dream – “Walkin’ on the Moon”, Rick Ross – “Maybach Music 2”, Kid Cudi – “Make Her Say”, Jay-Z – “Run This Town”, Rick Ross – “Live Fast, Die Young”, Lloyd Banks – “Start It Up”, Katy Perry – “E.T.”

At the start of Kanye’s five-year run, he was making an ode to his big brother; by the end of it, he was collaborating on a full album with Jay-Z. For a rapper who grew admiring Hov and watching him afar during the 1999 Hard Knock Life Tour, those Watch the Throne must have been hard to imagine. With each release during his epic run, Kanye shifted culture and pushed hip hop music to its very edges: Graduation was so ahead of its time that it dictated music trends for the next few years, without 808s & Heartbreak you probably don’t get Drake and a number of other rappers today, and My Beautiful Dark Twisted Fantasy , well, it’s the best hip hop album of the 2010s .

6. Jay-Z: 1999 – 2003

Greatest Rapper Five Year Runs Of All Time Jay Z 1024X683

Notable releases: Vol. 3… Life and Times of S. Carter, The Dynasty: Roc La Familia, The Blueprint, The Best of Both Worlds (with R. Kelly), The Blueprint 2: The Gift & The Curse, The Black Album

Guest appearances: Memphis Bleek – “What You Think of That”, Ja Rule – “It’s Murda”, Beanie Sigel – “Raw & Uncut”, Scarface – “Guess Who’s Back”, Cam’ron – “Welcome to New York City”, Talib Kweli – “Get By (Remix)”, OutKast – “Flip Flop Rock”, Pharrell – “Frontin”, Freeway – “What We Do”

Jay-Z’s run from 1998 to 2003 is about as perfect as he could have planned it. Once Vol. 2… Hard Knock Life hit and became the best-selling album of his career, Hov ruled the rap game, dropping consistent multiplatinum number ones and staying on top of new jacks by dropping scene-stealing features. During his five-year run, the Roc-A-Fella boss released two undisputed classic albums, both of which would be considered in the top five of his catalogue, all before announcing his retirement, just in time to hand the torch over to…

5. 50 Cent: 2002 – 2006

50 Cent First New York Rapper Collaborate Ugk 1024X683

Notable releases: Guess Who’s Back? , 50 Cent Is the Future (with G-Unit), No Mercy, No Fear (with G-Unit), God’s Plan (with G-Unit), Get Rich or Die Tryin’ , Beg for Mercy (with G-Unit), The Massacre

Guest appearances: Lil’ Kim – “Magic Stick”, Eminem – “Never Enough” / “Encore”, The Game – “”Westside Story” / “How We Do” / “Hate It or Love It”, Lloyd Banks – “I Get High” / “Warrior, Pt. 2”, Young Buck – “I’m a Soldier”

I don’t think we’re ever going to see another rapper again who was able to capitalise off his position as much as 50 Cent did, in as short a time. After making a name for himself in the streets and industry off a handful of classic mixtapes, 50 quickly captured the attention of Eminem and Dr. Dre. Once Get Rich or Die Tryin’ dropped February 6, 2003 for any other rapper out there.

But it wasn’t that 50 Cent overwhelmed the rap game with his debut. It’s also about the way he leveraged the success into a bunch of other things: starting G-Unit Records, dropping Beg for Mercy at the end of 2003, launching Tony Yayo, Lloyd Banks and Young Buck all into platinum-selling superstars, and plenty more. Everything 50 touched during his five-year run turned into gold. Peep The Game’s debut album, The Documentary . Do you think it would have sold 5 million without 50 contributing the hooks for “Westside Story”, How We Do” and “Hate It or Love It”? I don’t think so.

4. Eminem: 1999 – 2003

Ranking Eminem First Week Album Sales 1 1024X683

Notable releases: The Slim Shady LP, The Marshall Mathers LP, The Eminem Show, 8 Mile soundtrack

Guest appearances: Biggie – “Dead Wrong”, Sway & King Tech – “The Anthem”, DJ Clue – “What the Beat”, Dr. Dre – “What’s the Difference” / “Forgot About Dre”, Jay-Z – “Renegade”, 50 Cent – “Patiently Waiting” / “Don’t Push Me”, DMX – “Go to Sleep”, Obie Trice – “Shit Hits the Fan” / “We All Die One Day”

Eminem was just the perfect combination of talent meets timing. A supremely-gifted lyrical phenomenon from Detroit linking up with the greatest hip hop producer of all time , who also had an uncanny ability to take the controversial and make it commercial. With Em’s five-year run, you can look at it from a few different angles. You can talk sales – The Marshall Mathers LP sold 1.78 million copies in its first week, The Eminem Show sold 1.3 million – or you can talk classic songs – “My Name Is”, “The Way I Am”, “Stan”, “Sing for the Moment”, “‘Till I Collapse” – or you can talk bars – “Renegade”, “Patiently Waiting”, “Forgot About Dre”, “Dead Wrong.” Just take your pick.

3. The Notorious B.I.G: 1993 – 1997

Biggie 2Pac Busta Rhymes J Dilla Ugliest 1024X683

Notable releases: Ready to Die, Conspiracy (with Junior M.A.F.I.A.), Life After Death

Guest appearances: Heavy D & the Boyz – “A Buncha Niggas”, Super Cat – “Dolly My Baby (Extended Bad Boy Remix)”, Mary J. Blige – “What’s the 411? (Remix)”, Eddie F – “Let’s Get It On”, Craig Mack – “Flava in Ya Ear (Remix)”, Ron G – “Stop the Breaks”, Jay-Z – “Brooklyn’s Finest”, Lil’ Kim – “Drugs”, The LOX – “You’ll See”, Puff Daddy – “Young Gs” / “Victory” / “Been Around the World” “It’s All About the Benjamins (Remix)”

What Biggie accomplished in five years is more than what 90% of all rappers have achieved in a 20-year career. Actually, you know what? What Big accomplished on Life After Death alone is more than what 90% of rappers have achieved in their lifetime. If you really want to understand the greatness of The Notorious B.I.G., then you just need to examine his sophomore album. Over the course of 25-tracks, the Brooklyn MC demonstrates his superiority across every facet of rapping.

Want incredible storytelling joints? There’s “Somebody’s Gotta Die”, “Niggas Bleed” and “I Got a Story to Tell.” Want battle raps? Big went at Nas, Rae, Ghost and Jeru on “Kick in the Door.” How about club songs? “Hypnotize” had it on lock. Radio singles? “Mo Money Mo Problems” was a smash. Concept tracks? You can’t go wrong with “Ten Crack Commandments.” Introspective? Big goes deep with “Miss U.” I could go on and on, but the point is, Big proved he was the master rapper on Life After Death .

Plus, you can’t forget the legendary features he did during his time alive. From Jay-Z’s “Brooklyn’s Finest” to Puffy’s “Young Gs”, Biggie locked down his position as one of the greatest guest rappers of all time off just a handful of dope features.

For XXL feature on the making of Life After Death , the legendary DJ Premier recounted a story of when they were creating “Ten Crack Commandments”:

DJ Premier: I think it’s one of the best records he ever made. As soon as he was done with the vocals he goes, “Premier, I did it. I did it. I’m the greatest!” And that was the last time I ever saw him.

Check Out How Biggie’s ‘Life After Death’ Was Made | XXL

2. Tupac: 1992 – 1996

50 Greatest Rappers Of All Time 2Pac 1024X683

Notable releases: Strictly 4 My N.I.G.G.A.Z… , Thug Life: Volume 1 ( with Thug Life) , Me Against the World, All Eyez on Me, The Don Killuminati: The 7 Day Theory (as Makaveli)

Guest appearances: MC Breed – “Gotta Get Mine” / “Comin’ Real Again”, Eddie F – “Let’s Get It On”, Spice 1 – “Jealous Got Me Strapped”, E-40 – “Dusted ‘n’ Disgusted”, Too Short – “We Do This”, E-40 – “Million Dollar Spot”, MC Hammer – “Too Late Playa”, Bone Thugs-n-Harmony – “Thug Luv”, Scarface – “Smile”

It’s actually crazy that Pac’s five-year run was pretty much the bulk of his entire recording career – he made his recording debut on Digital Underground’s 1991 song “Same Song” and passed in September 1996. Before Wayne, Gucci and Future, Pac was the epitome of a prolific artist. Even during his early days, he was known for being restless in the studio and wanting to create music as quickly as possible.

But after he was released on bail from Clinton Correctional Facility on October 12, 1995, he was a man on a mission, obsessed with recording as much material as possible. The first thing he did was hit the studio and record “Ambitionz Az a Ridah” and “I Ain’t Mad at Cha” on the same night . After that, it was a wrap. All Eyez on Me became the biggest album of 1996, and Pac was the unstoppable force turning Death Row Records into an even bigger rap juggernaut.

1. Ice Cube: 1988 – 1992

Ice Cube Wrote Boyz N The Hood For Home Boys Only 1024X683

Notable releases: Straight Outta Compton (with N.W.A.), AmeriKKKa’s Most Wanted, Kill at Will, Death Certificate, The Predator

Guest appearances: The D.O.C. – “The Grand Finale”, Public Enemy – “Burn Hollywood Burn”, King Tee – “Played Like a Piano”, Too $hort – “Ain’t Nuthin’ But a Word to Me”, Del tha Funkee Homosapien – “Hoodz Come in Dozens”, Kool G Rap – “Two to the Head”

To be honest, you could take any of the top five rappers on this list, slide them into the top spot and it would make sense. But for my money, Ice Cube has the strong claim for having the greatest five-year run of all time. Rap fans these days don’t really understand the true greatness of Ice Cube – just peep his position on a lot of these GOAT lists. I think the younger hip hop heads know that he’s a West Coast legen d and one of the most influential icons ever, but they don’t know he’s truly a one-of-a-kind rapper.

Ice Cube really managed to drop four certified classics – Straight Outta Compton (with N.W.A.), 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 ), all within five years. Granted, The Predator may not be on the same level as Cube’s first two albums, but “When Will They Shoot?”, “Wicked”, “It Was a Good Day”, “Check Yo Self”, “Say Hi to the Bad Guy” – come on!

The bottom line is: what Cube managed to achieve between 1988 and 1992 had never been done again in the history of rap music, and the albums he put out during those five years alone are enough to warrant him placement at the very top of the greatest rappers of all time list.

Related Posts