On August 3, 1995, the Source Awards held their annual event at the Paramount Theater in New York to celebrate the very best in hip hop culture. While the focus at the time were mainly on East Coast and West Coast rappers like Nas, The Notorious B.I.G., Snoop Dogg, Dr. Dre, Method Man, Warren G, and Eazy-E, there was one Atlanta rap duo who managed to win New Artist of the Year, beating out Bone Thugs-n-Harmony, Ill Al Skratch and Smif-N-Wessun. 

As OutKast made their way up the stage to claim their award, they were confronted with boos and jeers from the (mainly) elitist New York audience. Frustrated by the moment, as well as their personal struggles to break into the music industry, the 20-year old Andre 3000 took to the mic and expressed what he felt.

“But it’s like this though: I’m tired of folks — them closed-minded folks,” the OutKast MC began. “It’s like we got a demo tape and don’t nobody wanna hear it. But it’s like this, the South got somethin’ to say. That’s all I got to say.”

The 2000s was a tumultuous time for the rap game. The new decade started with the kings like DMX, Eminem and Jay-Z all staking their claim to the crown. The underground vs. commercial divide, which began in the late ’90s, began to widen even further. While the first half witnessed some of the biggest rap superstars the industry had ever seen, the second half was dominated by the internet and the challenges on how to evolve accordingly or get left in the ’90s. 

More importantly, Andre 3000’s chilling prophecy at the 1995 Source Awards would ring true just a decade later. As the East Coast and West Coast began to lose their steam, the South began their takeover; slowly at first, but by the end of the decade, it was a known fact that they were running the game and there was nothing anyone could do about it. Out of this situation emerged some of the greatest rappers to ever touch a mic.

So let’s get into it. From underground stalwarts like MF DOOM and El-P to Billboard superstars, Eminem and Jay-Z, and Southern rap giants like T.I. and Ludacris, here are the top 50 best 2000s rappers.

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50
Juvenile

Essential listening: Juve the Great (2003)

Juvenile never reached the same legend status as his Hot Boys co-star Lil Wayne, but he still had his shining moments through the 2000s. Embracing the rugged sound of the Dirty South, Juvenile was a monster on the mic whose husky, swaggering delivery made every verse ooze with confidence. That kind of charisma was perfect for bombastic projects like Juve the Great and Reality Check, where the MC narrated his chequered past in the drug trade, dedicating a few raunchy bangers like “Rodeo” to shake up the clubs. A natural performer with a knack for catchy hooks, play any track from Juve the Great and it will be looping in your head for days.

49
Eve

Essential listening: Scorpion (2001)

After her multi-platinum debut in 1999, it was obvious that Eve would be a chart-topping titan of the new decade. She earned that title as early as 2001 with Scorpion, another set of hardcore highlights where the MC’s tight rhyme schemes and vicious delivery were on full show. Hits like “Who’s That Girl?” and “Let Me Blow Ya Mind” still sound fresh today, where Eve mixed a little R&B elegance to her ferocious style, crafting danceable hits but never losing her hard-hitting edge as a Ruff Ryder. 2002’s Eve-Olution was yet another high point for the MC’s career, sharpening her pop rap style and proving her talents as a natural hook-maker. While Eve’s rap career may have petered out by the end of the decade, her work in the 2000s cemented the Philly MC as one of the best female rappers ever.

48
Juelz Santana

Essential listening: What the Game’s Been Missing! (2005)

Dissing his rivals, threatening his enemies, and spitting the occasional raunchy bar, Santana’s pen game followed the standard New York formula, but it’s his delivery where the MC thrived. Whether he’s competing with Cam’ron and Jim Jones for the best verse on Diplomatic Immunity or boasting about his rapping ability on From Me to U, the Harlem rapper always brought the same vicious energy and swaggering presence, rapping with a deliberate, patient flow for every bar to hit hard. Never the sharpest lyricist, Juelz didn’t need to be, with enough fierce flows and memorable hooks to make any track a highlight — he made sure to cement himself as one of the best 2000s rappers.   

47
Fat Joe

Essential listening: Jealous Ones Still Envy (J.O.S.E.) (2001)

Carrying the explosive energy of Terror Squad through to the 2000s, Fat Joe struck that perfect balance between glamorous pop appeal and the hardcore sound of New York. The legendary Bronx rapper could yell into the mic on one track then unleash his romantic side on the next, switching back and forth from party anthems to grimy East Coast bangers. Jealous Ones Still Envy (J.O.S.E) remains one of his strongest projects, where Joe’s tongue-twisting flows and bombastic mic presence were fully unleashed. Reaching his commercial peak with hits like “What’s Luv?” and the high-energy Wayne collab “Make It Rain”, Fat Joe was a force in 2000s hip hop who dominated the mic like he dominated the charts. 

46
Gucci Mane

Essential listening: The State vs. Radric Davis (2009)

The impact of Gucci Mane on the 2000s can’t be defined using traditional methods. You couldn’t look at how many gold and platinum albums he had; you couldn’t check to see which ones of his singles charted on the Billboard Hot 100; you couldn’t turn on the radio to hear his songs playing; you couldn’t even look at his albums to measure his impact. From his deep mixtape catalogue to relentless work ethic to his ability to spot up-and-coming talent, Gucci’s influence on the Atlanta rap game was far deeper than just surface metrics. It was deeper than pure lyrical talent or punchlines or hit singles. Rappers and producers thriving today, including Future, Young Thug, Migos, Metro Boomin, Zaytoven, and Mike Will Made It can all trace some sort of lineage back to the work Guwop did in the 2000s.

45
Snoop Dogg

Essential listening: R&G (Rhythm & Gangsta): The Masterpiece (2004)

There’s no doubt that Snoop reached his peak in the ‘90s, but let’s not forget some of the classic material he dropped through the next decade. “Drop It Like It’s Hot” may have been overplayed, but there’s no denying the greatness of the Neptunes-produced hit, where Snoop proved his buttery smooth flows and hook-making talent would never disappear. His 2006 record, The Blue Carpet Treatment, instantly became one of the MC’s most revered projects: a star-studded compilation of Crip-loving anthems, full of versatile flows and vivid storytelling that had become second nature for Snoopzilla. Going on an elite feature run, supplying verses for everyone from Eminem to Mariah Carey, Snoop’s workaholic attitude kept him in the limelight through the whole decade.

44
Ja Rule

Essential listening: Pain Is Love (2001)

Ja Rule is remembered now as the rapper who lost to 50 Cent, but in his prime, he was a mainstream hit-making titan. Album after album, the Queens-born MC flooded the charts with pop rap hits like “Always On Time” and “Mesmerize”, proving his consistency by dropping a project a year from ’99 to ’04. His raspy voice was instantly recognisable, teaming up with R&B greats from Ashanti to R. Kelly to deliver tracks full of smooth hooks and hard-hitting bars. Spitting melodic rap ballads on Pain Is Love or dropping diss after diss on the hate-filled highlights of Blood In My Eye, there was no limit to Ja’s versatility, hopping back and forth from soft radio hits to hardcore diss tracks without ever losing his commanding presence.

43
Xzibit

Essential listening: Man vs. Machine (2002)

Moving into the new millennium, Xzibit dropped the gritty sound that brought him to fame, instead joining forces with Dr Dre to embrace the head-bopping grooves of G-Funk. Not everyone was happy with the change, but X sure was, taking over the charts and becoming a platinum-selling success with Restless. All the ingredients that made the West Coast rapper special were still there – his distinct, raspy voice, his aggressive delivery, his brutal street talk – but the fresh style brought out a newfound passion in the rapper, commanding every song with smooth flows perfect for the party anthems of Restless and Man vs. Machine. Going bar for bar stars like Eminem, Xzibit was in prime form in the 2000s.

42
Lil’ Kim

Essential listening: The Notorious K.I.M. (2000)

For the doubters who thought Lil’ Kim would be nothing without Biggie Smalls, she spent a whole decade proving them wrong. Inviting the Biggie comparisons when she dropped The Notorious K.I.M. in 2000, her abilities didn’t quite match B.I.G. himself, but her buttery flows and suave mic presence were closer than most would admit. With no shortage of sexual stories and raunchy one-liners, the hip hop queen balanced out her explicit verses with pop appeal, gliding over bright, energetic instrumentals so that even graphic tracks like “How Many Licks?” were accessible. Kim can still dominate a track nowadays, but her seamless blend of rap and pop was never better than in the 2000s. 

41
Rick Ross

Essential listening: Deeper Than Rap (2009)

There’s a reason Rick Ross became a superstar off his first ever single, and that’s because there has never been an MC like him. Taking the Southern formula of hustle-based bars and bombastic production, Teflon Don took it to the next level with projects like Port of Miami, basing every verse around over-the-top brags and cartoonish insults to the competition, hyping himself up in the most entertaining fashion possible. With his deep voice and swaggering delivery, no beat was too loud for the Florida rapper, thriving on glamorous, overproduced instrumentals to suit his money-loving bars. Grinding in the mixtape scene on top of his chart-topping albums, Rick Ross had a relentless work ethic, earning his title as a hustling king.

40
Blu

Essential listening: Below the Heavens (2007)

Breaking onto the scene near the end of the decade, Blu didn’t need long to prove himself one of the most promising MCs in the West Coast. After dropping the classic Below the Heavens with Exile, Blu wasn’t satisfied releasing just one masterpiece, quickly hopping back in the studio to make The Piece Talks with Ta’Raach and Johnson&Jonson with Mainframe. Releasing all three projects in just two years, the Inglewood MC rose from an unknown rookie to hip hop’s next prodigy. Aside from his impressive work ethic, Blu never disappointed with a verse, rapping with a laidback flow for his relatable lyrics to shine, narrating his everyday struggles with a slick sense of rhyme.

39
Killer Mike

Essential listening: Monster (2003)

Featuring on OutKast’s Stankonia and Jay-Z’s The Blueprint 2, Killer Mike was one of the hottest rappers to emerge the South before he had an album to his name. Back when he debuted, a verse from the Atlanta MC was like a lyrical explosion, shouting every bar with a strong Southern drawl that made every track an anthem of Southern pride. Showing off his bombastic mic presence on Monster, it wasn’t until 2006’s I Pledge Allegiance to the Grind where the MC dipped his toes into politics, using his songs like political sermons to fight back against the rich and powerful. While his best work wouldn’t come until the 2010s, few MCs in the South could match the raw energy of Killer Mike.

38
Lloyd Banks

Essential listening: The Hunger for More (2004)

Reigning over the mainstream as part of G-Unit, Banks brought an aggressive demeanour and razor-sharp pen game to every verse. Spitting explosive verses in the G-Unit Radio series or flexing his lyrical prowess on smoothly-produced albums like The Hunger for More, the Punch Line King never disappointed, telling vivid tales of his criminal past with plenty of witty one-liners sprinkled into his hardcore stories. More than simply dropping albums, Banks earned his title as one of the game’s best mixtape rappers with a prolific run through the 2000s, cooking up ten mixtapes across the decade where his unfiltered bars and raw delivery left more of an impact than any album track.

37
Fabolous

Essential listening: Street Dreams (2003)

The slick talking, punchline-spitting Brooklyn MC never broke a sweat his entire run during the 2000s. After showing up with a legendary freestyle performance alongside N.O.R.E. in 1998, the 21-year old was subsequently signed to DJ Clue’s Desert Storm Records and given a chance to shine. Whether it was climbing up the Billboard charts with radios hits (“Into You”, “Make Me Better”), cementing his reputation as a mixtape legend, or holding his own alongside rap greats like Lil Wayne, Jay-Z, Jadakiss and Pusha T, Fabolous made this shit look easy.

36
Beanie Sigel

Essential listening: The Truth (2000)

Dropping verses here and there on Jay-Z projects, it wasn’t until 2000’s The Truth that Beanie Sigel proved he could hold his own without any help from Hova. A gifted storyteller with a knack for intricate rhyme schemes, Beans quickly rose to become one of Philadelphia’s strongest lyricists, delivering unforgettable verses on introspective highlights like “Feel It in the Air” and “Still Got Love For You”. Along with his solo output, Beans kept his name in the mainstream with an elite run of features, borrowing the mic from his Roc-A-Fella labelmates as he stole the show from Freeway and Cam’ron. From gritty East Coast beats to heartfelt West Coast jams, no matter the style, Beanie never brought a bad performance.

35
Jean Grae

Essential listening: Attack of the Attacking Things (2002)

One of the most underrated rappers of all time, Jean Grae crowned herself queen of the underground with Attack of the Attacking Things. Her abstract sense of lyricism was too bizarre for the mainstream, but for underground fans, she was a lyrical genius. Cramming her verses with intricate rhyme schemes and cryptic bars, the Brooklyn native could be rapping about something as simple as female inequality, but her complex pen game turned any verse into a puzzle of rhymes. With a dry sense of humour and arsenal of animated flows, Jean was in her own lane, constantly finding eccentric new ways to pen her thoughts and deliver her bars.

34
Brother Ali

Essential listening: Shadows on the Sun (2003)

What Brother Ali lacked in mainstream hits, he made up for in cult classics. The Rhymesayers MC quickly made a name for himself as one of the sharpest voices in conscious hip hop, treating the recording booth like a lectern to spread his political messages and advocate for change with his speech-like verses. Rapping with an ever-changing flow and hyperanimated delivery, the MC’s serious subject matter always came off as upbeat and accessible, striking the perfect balance between his lyrical depth and an energetic delivery. From the laidback, summery vibes of Shadows on the Sun to the political anthems of The Undisputed Truth, Ali had the clever pen game to tackle any issue, and the charisma to always make it sound entertaining, cementing himself as one of the greatest underground rappers of all time.

33
Nelly

Essential listening: Nellyville (2002)

On “Excuse Me Miss,” Jay-Z rapped “Only dudes movin’ units – Em, Pimp Juice and us.” Rap fans forget, at one point in time, the only rapper who was touching Nelly’s numbers was Eminem, Hov was still a couple hundred thousand units away. While the St. Lunatics leader might not get the same respect on lyrically as a lot of the rappers on the list, the fact is that he was one of the biggest superstars hip hop had ever seen, and played a huge role in the culture’s crossover during the 2000s. But even putting aside his crazy commercial success, Nelly was one of the main rappers responsible for pioneering that melodic, rapping-singing delivery and crafting deniable hooks. Sure, Bone Thugs may have done it first, but no-one was able to perfect combining melodies in their raps as much as Nelly. Not until 50 Cent and, later, Drake came around. Love it or hate it, there’s no denying that Nelly was one of the best rappers of the 2000s.

32
Tech N9ne

Essential listening: K.O.D. (2009)

Tech N9ne flows so fast you would have to play his tracks in slow motion to catch every bar. A veteran of chopper rap and a technical mastermind on the mic, Tech became a Midwestern sensation in the 2000s thanks to his superhuman speed, spitting dozens of syllables in a few short bars without a single stutter to ruin his flow. On lyrical masterclasses like Killer and Anghellic, the chopper rap icon crafted his own unique style, treating the production like background noise while his relentless flows were enough to keep any track engaging. Putting as much effort into his pen game as his delivery, no verse was lacklustre, packing complex metaphors into each one to earn his reputation as a technical wizard and a lyrical genius.

31
The Game

Essential listening: The Documentary (2005)

From the multi-platinum success of The Documentary to his relentless run of mixtapes, The Game was a force who couldn’t be stopped in his prime. From a lyrical standpoint, Game was on top of the West Coast, sprinkling every verse with intricate wordplay to add some technical flare to his hardcore tales of crime and everyday struggle. He tore apart every funk-laced beat on The Documentary, but Jayceon went even harder on his mixtapes, delivering classic tapes like Stop Snitchin’ Stop Lyin’. Devastating songs like “300 Bars N Runnin” showcased his natural ability to spit insults, delivering some of the best diss tracks of all time as he took aim at 50 Cent, G-Unit, and anyone who stood in his way.

30
Cam’ron

Essential listening: Purple Haze (2004)

Ever since he came into the rap game, Cam’ron has been spitting with the same confidence and dismissive attitude. Like he was doing all this shit for fun, like rap was just a hobby, like the whole thing was too easy for him. Just listening to the way Cam strung words together effortlessly on joints like “Down and Out” (“Observe cock and spray / Hit you from a block away / Drinking sake on a Suzuki we in Osaka Bay”) made me wish he continued his hot streak all the way through the 2000s. Even though Cam and the Diplomats movement fizzled out in the second half of the decade, when they were on, they were on. While Dipset didn’t touch the same commercial success as G-Unit, the Harlem group were more memorable, rocked better fashion, took themselves less seriously, and, overall, made better music. Come Home with MePurple HazeDiplomatic Immunity, Cam and Dipset had New York so locked down and smoking hot that even Hov was feeling the heat in the kitchen. 

29
Talib Kweli

Essential listening: Train of Thought (2000)

Talib Kweli entered the new millennium as a critical darling and figurehead of the underground rap movement. Fresh off the release of Mos Def & Talib Kweli Are Black Star, which established him and Mos Def as two Brooklyn spitters championing the Rawkus Records independent era. While his partner-in-rhyme would balance a recording career with his film aspirations, Kweli stuck with a blue-collar approach to his music, dropping quality releases on a consistent basis throughout the 2000s.

28
DMX

Essential listening: The Great Depression (2001)

Although his run of multi-platinum classics in the late ‘90s was unbeatable, there’s no doubt that DMX was still one of the hottest rappers around in the 2000s. With his barking delivery, infectious adlibs, and bombastic choice in production, the Yonkers rapper had a formula that was impossible to get wrong, crafting abrasive banger after banger that took over charts and clubs alike. His seamless blend of hardcore hype tracks and lowkey introspective cuts remains timeless, with hits like “X Gon’ Give It To Ya” and “Where the Hood At” on par with classics like “Party Up” and “What’s My Name”. Never low on charisma and never out of catchy hooks, X always delivered with his explosive style.

27
Twista

Essential listening: Kamikaze (2004)

One of the fastest flowing rappers in history, Twista was king of chopper rap before chopper rap was even a term. His tongue-twisting bars and technically precise verses helped him skyrocket to mainstream acclaim, dominating the charts through his show-stealing verse on “Slow Jamz” and keeping the public’s attention with the fast-paced highlights of Kamikaze. Not only was the Chicago rapper known as a master of flow, but also a god of rhyme, turning each verse into a technical spectacle of multisyllabic and internal rhyme schemes. Thanks to his vast vocabulary, Twista’s style never got old, always finding new ways to pen his lightning-fast bars.

26
Styles P

Essential listening: A Gangster and a Gentleman (2002)

If there’s one thing you can definitely say about Styles P during the 2000s, that man was working! While The LOX rapper didn’t achieve the same mainstream crossover or commercial impact as a lot of his peers during the decade, he made sure he was delivering quality music to his fans on a consistent basis. With Ghost’s solo debut single, “Good Times,” yielding him his biggest hit to date, P continued the momentum with a string of hard-ass mixtapes and equally hard features. A perfect blend of lyrical, street shit and introspective bars, Styles P was definitely one of the best rappers of the 2000s. 

25
Bun B

Essential listening: Trill (2005)

There were few rappers who worked as hard as Bun B during the 2000s. Of course, you had the Lil Waynes, the Gucci Manes, and the Currensys grinding hard as ever. But where they differed from the UGK rapper is that, outside of a strong work ethic and the drive to be the best (artistically and/or commercially), Bun was doing it for Pimp C. After scoring their biggest hit to date with an appearance on Jay-Z’s 2000 single “Big Pimpin’,” UGK were poised to take their careers to the next level. Unfortunately, on August 5, 2002, Pimp was sentenced to 8 years in prison and the duo were forced to go on hiatus. It was up to Bun to put the UGK brand on his back. Whether it was killing feature verses throughout the decade, dropping mixtapes or releasing solo albums, Bun B did everything he could to keep his partner’s name alive.

24
El-P

Essential listening: Fantastic Damage (2002)

While El-P (and Killer Mike) would enter a whole new level of mainstream recognition and accolades in the 2010s with Run the Jewels, the Brooklyn-born MC producer was already a certified underground hero when the 2000s began. As part of the rap trio Company Flow, El-P was signed to Rawkus Records, and together with his label mates, Mos Def and Talib Kweli, helped define the underground sound of the late ’90s, early ’00s. As a solo artist, what El-P lacked in quantity, he made up for it with quality releases. Each one of his albums – Fantastic DamageHigh Water and I’ll Sleep When You’re Dead – featured the claustrophobic funk and dense lyricism that would later endear him to a new audience.

23
Busta Rhymes

Essential listening: The Big Bang (2006)

Busta Rhymes had already made his presence in the rap game known during the ’90s, but it was in the 2000s where he really cemented his legacy as one of the most exciting and energetic hip hop artists of all time. The Brooklyn-born MC also proved his versatility throughout the decade, going from R&B duets with Mariah Carey (“I Know What You Want”), to collaborating with Q-Tip (“You Can’t Hold the Torch”), to making club bangers (“Pass the Courvoisier, Part II”), to rapping off against Jadakiss and Lil Wayne (“Respect My Conglomerate”), to crafting radio smashes with Swizz Beatz (“Touch It”). Busta Rhymes was everywhere, adding his trademark energy and rapid-fire flow to any rapper who needed it. 

22
Aesop Rock

Essential listening: Labor Days (2001)

Listen to any Aesop verse and it shouldn’t need to be explained why he’s become an underground legend. A natural wordsmith, Aesop has the vocabulary of a thesaurus and the limitless imagination to match, rarely repeating a rhyme in projects like Labor Days and None Shall Pass, where he made each verse as cryptic and complex as possible. Whether you’re talking about his vivid storytelling across the classic Labor Days or his multilayered rhyme schemes on Bazooka Tooth, the New York lyricist had the lyrical skills to turn the most outlandish idea into a masterfully rhymed song, proving time and time again that no lyricist was on his level.

21
Jadakiss

Essential listening: Kiss tha Game Goodbye (2001)

If you weren’t around in the 2000s to witness the greatness of Jadakiss’ during that decade, do yourself a favour and watch The LOX’s Verzuz battle against Dipset (why haven’t you already?!). The night was really just a case put forward for Jadakiss’ standing on everyone’s GOAT list. From timeless LOX cuts (“Fuck You”, “Mighty D-Block (2 Guns Up)”) and legendary freestyle bars (“Who Shot Ya”), to worldwide radio smashes (“Jenny from the Block”) and his own classic solo joints (“We Gonna Make It”), Jadakiss covered everything that made him one of the greatest rappers of the 2000s. 

20
Pusha T

Essential listening: Hell Hath No Fury (2006)

2006 was arguably the peak year for the coke rap subgenre. You had Ghostface releasing one of his best albums ever with Fishscale, you had trap music pioneer T.I. claiming the throne with King, Rick Ross breaking down the door with Port of Miami, and Jeezy dropping the follow-up to Let’s Get It: Thug Motivation 101. But one album stood tall amongst these giants, Clipse’s Hell Hath No Fury, the best coke rap album of all time. While label dramas would prevent them from releasing more albums during the 2000s, the Clipse’s legendary We Got It 4 Cheap mixtape series would more than make up for it. As a duo, you had Malice on one hand, balancing out his drug-dealing tales with hints of remorse. Then you had Pusha T, who was all brash and aggressive, a stone-cold coke-dealing machine who survived and lived to rap about it at the highest level possible. Push was also the flashier rapper, intent on going down as one of the greatest to ever do it, with references to Big abound in his lyrics. 

19
Sean Price

Essential listening: Monkey Barz (2005)

Sean Price had always been an undeniable force in the underground hip hop community. First emerging as part of the legendary Brooklyn crew Boot Camp Clik, Price linked up with Jahmal “Rock” Bush to form Heltah Skeltah and drop their debut album, Nocturnal, via Duck Down Records in 1996. But it was really in the 2000s that the rugged Brooklyn MC came into his own, with his two solo albums, Monkey Barzand Jesus Price Supastar being the shining examples. Over slapping, soulful grooves courtesy from the likes of 9th Wonder, Illmind, Ayatollah, and Khrysis, Price verbally punched all rival rappers in their chest with his incredible rhyme schemes and gritty delivery. R.I.P. to one of the greatest to ever hold a mic. 

18
Missy Elliott

Essential listening: Miss E… So Addictive (2001)

I’ve always found it funny how Lauryn Hill has been receiving accolades these past two decades (as she rightly should), and yet someone like Missy Elliott always manages to fly under the radar, even though she’s like a flyer, wilder version of Ms. Hill. The Virginia rapper, singer, songwriter, and producer is a truly one-of-a-kind artist and one of the greatest hip hop talents we’ve ever seen. With her partnership with Timbaland as the jumping off point with 1997’s Supa Dupa Fly, Missy Elliott had one of the most commercially successful and artistically innovative runs in the 2000s. Whether it was putting together full-length, cohesive projects, guest rapping (and producing) smash hits, dropping some of the craziest visuals of all time, Missy was the full package, and she needs her flowers now! That’s what we named her the best female rapper of all time

17
Young Jeezy

Essential listening: Let’s Get It: Thug Motivation 101 (2005)

Freddie Gibbs – who was once signed to Young Jeezy’s CTE label, and now spends his spare time dissing his former boss – once compared the Atlanta rapper to 2Pac. Even though he was dragged on social media not long afterwards for saying that, a part of me understands the point that Gibbs was trying to make with that comparison. During the South’s takeover in the 2000s, Jeezy was just one of many rappers from the region coming up in the game and making a name for themselves. Compared to his peers, the Snowman couldn’t flow liquid hot like Ludacris, he didn’t have T.I.’s charisma on the mic, and he certainly couldn’t touch Lil Wayne’s genius punchlines or wordplay. It was similar to how 2Pac didn’t have Biggie’s undeniable flow, Nas’ natural pen game, or Jay-Z’s cool wit. But Pac and Jeezy both had a few things in common that helped catapult them to the top of the rap game: a one-of-a-kind voice, captivating delivery, and an absolute belief in their every word. So if you take those qualities and combine them with true-to-life trapping tales and production from Shawty Redd, Drumma Boy and Mannie Fresh, suddenly you had Atlanta’s next superstar

16
Black Thought

Essential listening: Game Theory (2006)

The Roots entered the new millennium with something they’d never tasted before – commercial success. Off the back of their 1999 release, Things Fall Apart, the Philadelphia hip hop band scored the first gold album (and later platinum), their first worldwide hit (“You Got Me”), and their first Grammy win (for Best Rap Performance by a Duo or Group). Unfortunately, the momentum didn’t continue. Beset with label changes and member departures, the group’s follow-up, Phrenology, didn’t come out until 2002, and commercial success continued to evade them. I’m saying all this because I’m trying to figure out what it was that’s kept Black Thought such a consistent MC all these decades. All great rappers, especially the ones who have been around for a while, go through lulls in their career where they don’t sound as like they want it anymore. It happened to Nas, it happened to Hov, it happened to Eminem. There’s no surprise really, it’s almost impossible for a rapper to continue rhyming with the same ferocity and hunger as they did on the come-up. Which is what makes Black Thought so special. And maybe one of the reasons why is because he never achieved the same commercial success as the aforementioned rappers. The main point is: Black Thought was the most consistent rapper in the ’90s, the most consistent rapper in the ’00s, the most consistent rapper in the ’10s, and yes, he’s the most consistent rapper doing it right fucking now. There should be not doubt in any rap fans’ mind on who the best Philly rapper of all time is, the only correct answer is Thought. 

15
Ludacris

Essential listening: Chicken-n-Beer (2003)

Ludacris was one of the first rappers outside of OutKast to prove to New York that these Southern artists could really rap their asses off. While he had dropped an independent album, Incognegro, in 1999, it was really with Back for the First Timeand then the double platinum Chicken-n-Beer, that the Atlanta rapper hit his stride and became a superstar. Blessed with a chameleon flow and pinpoint delivery that never sounded out of pocket, Luda’s biggest strength was his versatility. Hard street shit, lyrical bars, club bangers, radio hits, he could do it all. One day he could be all over the radio next to Usher and Lil Jon (“Yeah!”), the next day he might be trading bars with New York’s finest – we can debate who had the best verse between Luda, Jada and Nas on “Made You Look (Remix).” Bottom line is that Ludacris doesn’t get the respect he deserves from rap fans, even though he’s proved over and over again that he was one of the best to do it during the 2000s. 

14
Big Boi

Essential listening: Stankonia (2000)

It’s crazy to think that being one half of the most successful rap duo of all time can still make you underrated. But that’s exactly how I feel about Big Boi. It’s also something that I’ve been guilty of in the past; holding Andre 3000 in the highest of esteems, while largely ignoring Big Boi’s achievements. Am I underrating him right now by putting him at 14? Maybe. 

Andre 3000: Big Boi can rap better than me—I always said that. If somebody said, “Pick who you want from OutKast to go to battle with you,” it wouldn’t be me. ’Cause like, what I’ma do? Say some mind shit? You can’t have thoughts in a battle—nobody gives a shit about that.

Earth to André 3000: The OutKast Icon Talks Life After “Hey Ya!” | GQ

While his partner-in-rhyme spent most of the 2000s trying to push against the boundaries of hip hop and seeing how far he can take the culture, Big Boi stood firmly as the duo’s rap traditionalist. But that doesn’t make him a conservative artist. Compared to anything else going on in hip hop at the time, Big Boi’s half of Speakerboxxx/The Love Below sounded like the future. Case in point: the Andre-produced “Ghetto Musick” is a dizzying spin through rock guitars and electro that Big Boi effortlessly slows over. And while “Hey Ya!” was no doubt the biggest song off Speakerboxxx/The Love Below, Big Boi proved he was equally as dialled in when he dropped “The Way You Move”, which is as perfect a pop record as you can get while still managing to sound like that classic two dope boyz in a Cadillac OutKast.

13
Scarface

Essential listening: The Fix (2002)

In one of the chapters of his 2010 autobiography, Decoded, Jay-Z recounts an incredible story about the making of “This Can’t Be Life” – his Kanye-produced collaboration with Scarface and Beanie Sigel.

Jay-Z: We’re sitting in the front room, talking, and his phone rings, and he’s like, ‘Nah, man,’ and you can see something’s happening on the other line. And then he gets on the phone again, and he calls his wife and checks on his children. And then he got off the phone and he told me that one of his friends’ kid was in a house fire. And I’m like, ‘Aw, man, I’m so sorry to hear that, we can do this another time.” And he says, nah, and he sat in the corner, and he wrote this song about the whole experience. He took this very sad experience and [made] this powerful art. It almost had me embarrassed about my verse.

The Five Best Stories Jay-Z Told Last Night at the New York Public Library | Vulture

That story is the ultimate summation of Scarface’s superpower: being able to take real-life tragedy and pain, and turning that into beautiful music. Over 10 years after writing “Mind Playing Tricks on Me” – one of the best rap songs of the ’90s – the Houston rapper entered the 2000s and dropped one of his best albums to date. The Fix is classic Scarface, the perfect blend of gangsta, nostalgia and sadness, with his world-weary raps and contemplative flow ageing even better in the new decade.

12
Common

Essential listening: Be (2005)

While Common had already dropped a couple of classics during his 90s run (ResurrectionOne Day It’ll All Make Sense) with the legendary Chicago producer, No I.D., it was in the 2000s, where he linked up with J Dilla and Kanye, that would prove to be his most fruitful decade. Common actually went through a few phases during the 2000s. There was the Soulquarians era, when he worked with The Roots, Dilla and D’Angelo, on Like Water for Chocolate, which became his commercial breakout and earned Common his first Grammy nomination for “The Light” (also his biggest hit to date). Then you have the GOOD Music era which yielded the fantastic Be – one of the best rap albums of the decade – and the good-not-great Finding Forever. Finally, you have the experimental phases – first in 2002 with Electric Circus and later in 2008 with Universal Mind Control, where Common pushed the boundaries of hip hop by dabbling into electro and grunge sounds for his albums. While the experimental phase didn’t go over well with his fans, the Chicago rapper showed that he was willing to take risks and push himself creatively. What more could you want from an artist? 

11
Andre 3000

Essential listening: Stankonia (2000)

You could leave out Andre 3000’s work on OutKast albums and he’d still make this list off the strength of his incredible feature appearances alone. There’s a reason why we crowned Stacks the greatest guest rapper of all time. During his 2000s run, Andre proved that he could literally do anything he wanted to do, and it would never feel like he was reaching. Whether it was hardcore street rap (“Royal Flush”), radio smash hits (“Hey Ya!”), remixes (“Throw Some D’s”), a singing album, whatever it was, Stacks went for it. Kanye gets a lot of credit (as he rightly deserves) for shifting hip hop away from the clichéd gangsta rap tropes that was the dominant force at the time with his debut album. But Andre 3000 was already pushing the boundaries of what hip hop could be as far back as 1998, and very much so on The Love Below. Think about some of the best rappers in the game right now, whether it’s Kendrick, Cole and Drake, or Future, Tyler, and Travis Scott, and chances are, they’ve been influenced by Mr. Stacks in one way or the other. 

10
Lupe Fiasco

Essential listening: The Cool (2007)

After Canibus’ recording career took a steep downhill turn, Lupe Fiasco became the new poster child for lyrical rap. Lupe’s name is often rolled out by rap nerds who can’t understand how anyone would put Jay-Z or 2Pac on their greatest rappers of all time list. We all know those types. But unlike Canibus, Lupe Fiasco is a much more well-rounded MC. Combining a nimble flow and unparalleled vocabulary with his superb gift for storytelling and crafting conceptual songs, Lupe also boasted excellent songwriting skills with subtle pop sensibilities. As lyrically dense and complex as his rapping was, Lupe’s rhymes never felt overwhelming, which enabled him to create cohesive albums with high replay value. Label dramas aside, Food & Liquor and The Cool are two of the best rap albums of the 2000s, and Lupe solidified his position as one of the greatest rap lyricists to ever emerge.

9
MF DOOM

Essential listening: Madvillainy (2004)

Here’s another artist that purist hip hop heads like to roll out when they’re talking about lyrical rappers. Coming into the rap game during the late ’80s, Doom previously went by the name Zev Love X, and had formed a rap group KMD with his young brother DJ Subroc and Rodan (and then later Onyx the Birdstone Kid). After releasing their debut album, Mr. Hood, in 1991, Subroc was tragically killed in a car accident. KMD was dropped by their label not long after, leaving Zev Love X to wander “the streets of Manhattan, sleeping on benches.” It wasn’t until 1999 that Zev Love X re-emerged, this time as the masked villain. MF DOOM’s debut album, Operation: Doomsday, is pretty fucking great, but it was his collaboration with Madlib, 2004’s Madvillainy, that really started his legacy as one of the greatest underground rappers of all time. A 2004 interview with Exclaim gave fans some insights into the mind of MF DOOM while constructing Madvillain, especially around the lack of hooks on the album.

MF DOOM: I like to do what other people are not doing, so what I do stands out a little more. I cut out all the unnecessary shit. Hooks is good, y’know, for certain motherfuckers who need ’em. To me, when I write, every lyric is as strong as the hook would be. So, why? The reason people will use a hook is to keep the people interested or give them something to do so they don’t get bored with the verse. I’m like: just don’t bore ’em with the verse. Kill ’em with the verse, and you won’t need a hook. It makes a more intense experience. You feel it. The hook thing is standardized — 16 bars and a hook. The listener is expecting it to come, so I catch them off guard: “What? No hook? This is the end? Rewind that!” But they were able to listen to the whole song.

Mask Off with MF DOOM: A 2004 Face-to-Face Interview | Exclaim

8
Nas

Essential listening: Stillmatic (2001)

Like his time in the ’90s, Nas’ run during the 2000s was a mix of brilliance and inconsistency. For a rapper who was crowned the King of New York upon his arrivaland placed with the hefty burden of being rap’s most talented poet on the mic, there were a lot of disappointing moments throughout the decade, especially during the later half. Lack of thematic cohesiveness and overthinking led to albums like Street’s DiscipleHip Hop Is Dead and Untitled failing to hit their intended target, while generic beat selection continued to plague all his projects, in one way or another. Still, this is Nas we’re talking about. A disappointing decade by his standard would still be better than 90% of other rappers’ careers. This is the same man who went up against Jay-Z and the mighty Roc-A-Fella army and won. The same man who made “Made You Look.” The same man who dropped StillmaticThe Lost Tapes and God’s Son all within a 12 month timespan. This is Nasty Nas, yo. 

7
Ghostface Killah

Essential listening: Supreme Clientele (2000)

During the ’90s, it seemed as though the mighty Wu-Tang Clan was unstoppable. Following a string of non-stop classic albums – from 1993’s Enter the Wu-Tang (36 Chambers) to Only Built 4 Cuban Linx… to Liquid Swords, it was like everything that RZA touched turned to gold. This culminated in the release of Wu-Tang Forever in 1997. With “Triumph” as the lead single (one of the greatest posse cuts in rap history), the sophomore album debuted at number one on the charts with over 600,000 units sold in the first week. Wu-Tang were right up there with Bad Boy. But with every peak comes the decline. Subsequent Wu albums could never touch the magic of their debut, or even the depth of talent showcased on Wu-Tang Forever. Every solo album after the first round was a disappointment. Except for Ghostface Killah. As dope as Ghost was during the ’90s, especially on Only Built 4 Cuban Linx… and his solo debut Ironman, it was his 2000 album Supreme Clientelethat quickly established Ghost as the best rapper in the Wu-Tang Clan. Tony Stark’s abstract stream-of-consciousness rhyme style showcase on the album was a marvel to behold, and would go on to influence a certain masked villain later on. But that wasn’t it. In addition to playing a crucial role in all the Wu albums, Ghost also continued to drop great solo albums, including 2004’s The Pretty Toney Album, 2006’s Fishscale, and the very underrated Ghostdini: Wizard of Poetry in Emerald City

6
T.I.

Essential listening: King (2006)

If the ’80s was the decade of New York, and the ’90s was the decade of the West’s rise, then the ’00s were definitely all about the South. From Atlanta’s OutKast, Young Jeezy and Ludacris, to Lil Wayne representing New Orleans to the fullest, to the Houston takeover of 2005, which saw rappers like Paul Wall, Mike Jones, and Chamillionaire reach platinum stardom, the 2000s was all about the South. So imagine the audacity it takes for a rapper to declare themselves the King of the South. Although, it wasn’t like T.I. didn’t have the rapping chops to back up his claim. Over his first three albums – I’m SeriousTrap Muzik, and Urban Legend – the Atlanta MC showcased that unique blend of East Coast flows with a Southern flavour time and time again. But it was on King that truly cemented T.I. at the top of the Southern rap scene. Leading off with the ultimate coronation anthem, “What You Know”, and supported by a stellar line-up of producers and rappers (UGK, Jamie Foxx, B.G., Young Jeezy, Young Dro, Pharrell, Common, Just Blaze, Mannie Fresh, DJ Toomp, Swizz Beatz), T.I.’s fourth album proved that not only was he the King of the South, he was the best rapper alive. 

5
50 Cent

Essential listening: Get Rich or Die Tryin’ (2003)

It’s really easy to let the incredible commercial impact of 50’s first two albums overshadow everything else he did in the 2000s. After all, Get Rich or Die Tryin’ sold 12 million units worldwide, while The Massacre sold 9 million. Not only that, but 50’s debut is without doubt one of the best rap albums of the 2000s. But take a closer look, and you’ll realise just how prolific and consistent the South Jamaica Queens rapper was with quality bars throughout the decade. Starting with 2002, 50 and his G-Unit crew dropped a handful of classic mixtapes that would go on to influence future greats like Young Jeezy, Lil Wayne and Drake. Taking popular instrumentals from artists like Raphael Saadiq, Mobb Deep, Jay-Z, Wu-Tang, Missy Elliott, LL Cool J and Puffy, 50 added his original spin to the tracks and made them his own. Then there’s Beg for Mercy, a gangsta rap classic dropped the same year as his debut; his features for Lloyd Banks, Tony Yayo and Young Buck; as well as his huge creative input on Game’s The Documentary – 50 co-wrote on the three biggest songs off the album (“Westside Story”, “Hate It or Love It”, “How We Do”). If you take into consideration his impact on the rap game, catalogue of classic songs and domination of the music charts, there’s no way you can deny that 50 Cent was one of the best rappers of the 2000s. 

4
Kanye West

Essential listening: The College Dropout (2004)

Kanye West was the single most influential hip hop artist of the 2000s. He might have even been the most influential musician of the 2000s overall. There’s no denying that the Chicago producer-rapper dropped three straight classics back-to-back (you could even argue four) between 2000 and 2009. During those years, Kanye shifted the rap landscape, not once, not twice, but three fucking times. Firstly, as a producer on The Dynasty: Roc La Familia and The Blueprint, where he helped bring back to the soul to hip hop music, during an era that dominated by the synthetic sounds of The Neptunes and Swizz Beatz. The second time around, on The College Dropout, Kanye was the main driving force pushing back against the overt gangsta rap and opening up the doors for more regular, every day rappers to have their say. Thirdly, with 808s & Heartbreak, he influenced Drake who would go on to become the biggest rapper in the game. Over the past few years, it’s been easy to let Kanye’s antics and extracurricular activities distract us from his music, but make no mistake, when he was on, he was on. There hasn’t been a hip hop artist who has managed to impact the landscape as profoundly as Kanye, and there’s no doubt that he was very much one of the best rappers of the 2000s. 

3
Lil Wayne

Essential listening: Tha Carter II (2005)

If there was any rapper who could make a strong contention against Tip’s claim of being King of the South, it was certainly Lil Wayne. But the truth was, Weezy wasn’t too concerned about claiming King over anything, he was too goddamn busy making the case that he was the best rapper alive. During a now-legendary 2006 interview with Complex’s Toshitaka Kondo, when goaded with a question about Jay-Z (who had retired in 2003 and made his comeback that year), Lil Wayne unloaded the clip. 

Lil Wayne: Am I better? He ain’t gotta do that. You can look out that window and ask that question. He ain’t have to do that—you can stick your head out that window and answer that question.

Interview: Lil Wayne’s 2006 Cover Story Uncut | Complex

Lil Wayne’s confidence was certainly warranted. Just on the purely rapping tip – we’re not talking money or catalogues or business or classic albums – just on a bar-for-bar basis, there was nobody touching Lil Wayne during the 2000s. He had the mixtapes to prove it, he had the albums to prove it, he had the features to prove it, and most importantly, he had the confidence to prove it. Was Lil Wayne better than Jay-Z? At that moment, yes he absolutely was.

2
Eminem

Essential listening: The Marshall Mathers LP (2000)

While Eminem’s run during the 2000s didn’t last as long as he probably intended, I’d argue that his peak was higher than rapper any before him, and any rapper after him. It doesn’t matter if you want to talk about Snoop Dogg in ’93, Pac in ’96, 50 in ’03, or Drake in ’16/’18, no other rapper in history has managed to reach the heights like Em did between ’00 and ’03. Let’s check it off. You want to talk raw lyrical skills on the mic? That’s an easy one. Eminem was, and still is one of the most talented rappers to ever live, and songs like “The Way I Am”, “Remember Me?”, “‘Till I Collapse” and “Bad Meets Evil” are just a few examples of his incredible flow, breath control and perfect delivery. You want to talk commercial success? Let’s not even go there. The Marshall Mathers LP sold 1.78 million copies in the first week (the biggest first week numbers of all time), and The Eminem Show sold 1.3 million. Both those albums would end up selling over 20 million copies worldwide. You want to talk recognition? “Lose Yourself” won an Oscar for Best Original Song, making Eminem the first rapper to receive the award. You want to talk about the ability to craft records? Em wasn’t just an incredible rapper, he was an amazing songwriter. Tracks like “Stan” and “Sing for the Moment” are just a couple of examples from his deep catalogue. You want to talk features? Stop it. We’re talking about the same rapper who dropped legendary guest verses on “Renegade” and “Patiently Waiting”, then later on “Forever” and “Drop the World.” The best thing about Em’s 2000’s narrative is that he managed to shake off his substance abuse problem and make a comeback by the end of the decade. Say what you want about Relapse, but that album features some of the sharpest rhymes and off-the-wall flows of Em’s career; proof that he still had it. 

1
Jay-Z

Essential listening: The Blueprint (2001)

Sure, Lil Wayne was better than Jay-Z, at that precise moment in time. but the greatness of Jay-Z lies in his ability to stay at the top for a sustained amount of time. All of Jay-Z’s competitors throughout the years – whether it’s Nas, DMX, or Lil Wayne – were bigger and hotter than him at one point in time. But none of them were able to maintain the same level of success, commercially and artistically, as long as he did. Towards the end of the ’90s, Hov was already making a strong case of being one of the best rappers alive. Reasonable Doubt established him a critical darling, an authentic mafioso MC who was living what many rappers were dreaming about in their rhymes. Then In My Lifetime, Vol. 1Vol. 2… Hard Knock Life and Vol. 3… Life and Times of S. Carter happened in quick succession, and suddenly, the underground rapper was the biggest (and best) rapper in the world. He might have been one of the best rappers of the 1990s, but he absolutely crushed it in the 2000s. There’s no way I’ll be able to articulate it better than Hov did himself on “What More Can I Say.” These lines rang true when he rapped them on The Black Album, as they did for the rest of the 2000s. Plenty of rappers came in that decade – Eminem, Wayne, Kanye, Cam’ron, 50 Cent, but the fact is: Jay-Z was the best rapper of the 2000s, period.

Pound for pound, I'm the best to ever come around here
Excludin' nobody, look what I embody:
The soul of a hustler, I really ran the street
A CEO's mind, that marketin' plan was me
And no I ain't get shot up a whole bunch of times
Or make up shit in a whole bunch of lines
And I ain't animated like, say, a Busta Rhymes
But the real shit you get when you bust down my lines
Add that to the fact I went plat' a bunch of times
Times that by my influence on pop culture
I'm supposed to be number one on everybody list
We'll see what happens when I no longer exist

Jay-Z - "What More Can I Say" // November 4, 2003