The Wu-Tang Clan had dominated the '90s both as a group and as individual artists -- thanks in no small part to Ghostface Killah, whose 1996 debut album Iroman is among the Wu-Tang's finest work -- but by the end of that decade, there were serious doubts in the hip hop community that the group had anything left to say. Ghostface wasn't giving up that easy, though. He tapped the Wu-Tang's production mastermind RZA to helm about half the tracks on this 21-song album, and he matched the production with some of the best rapping of his career. It's a bolder, richer, more modern-sounding album than Ironman, and it helped the Wu come into the new decade swinging. Would they be the timeless group they are today had this album not saved them from becoming '90s relics? Maybe not.

The first album on this list was still largely rooted in the sound of the '90s, but the second one hit fast forward another 1,030 years. Deltron 3030, the self-titled debut album by the supergroup of Del the Funky Homosapien, Dan the Automator, and Kid Koala, wasn't just lyrically a concept album set in 3030; it still sounds futuristic today. Automator's production is hypnotic and psychedelic and sounds like a trip through outer space, and Del's tongue-twisting rhymes and sci-fi themes make it even more dizzying. Among the album's guests was Blur's Damon Albarn, and he credits the album as a major inspiration on Gorillaz, whose debut single ("Clint Eastwood") the following year featured Del returning the favor. Deltron never became the superstars that Gorillaz did, but this album remains the Iggy Pop to their Ziggy Stardust. If you listen to alternative, psychedelic rap today, there's a good chance it was influenced either directly or indirectly by Deltron 3030. Sometimes the stuff that's meant to be the most futuristic ends up quickly sounding the most dated, but not this album. We very possibly aren't done experiencing its influence and impact.

Lil' Kim got her big break after Biggie took her under his wing, and her instant-classic 1996 debut album Hard Core was met with its fair share of comparisons to Big's work, but Kim also had a clear voice of her own and that came through on the loud, brash album. Big's tragic passing took place the year after Hard Core came out, and Kim paid tribute to him with the title of this album. She said she "felt Biggie's spirit" while making it, and despite (or because of?) that, it was also the album where Kim entirely emerged from Biggie's shadow. The glossier production sounded distinctly like what we now think of as "2000s" compared to the very '90s-sounding Hard Core, and Kim was an even tougher, more compelling rapper on this album than on its predecessor. And while it lacked a Top 40 hit, The Notorious K.I.M. holds your attention even on its deepest cuts. When Kim raps "I guess you know by now who's number one," she practically dares you to suggest it could be anyone else.

OutKast did it all. The production -- which combined sampling with live instrumentation and pulled from psychedelia, soul, funk, and more -- was as musically ambitious as the classic '60s and '70s records that OutKast and other rappers were using as source material, yet OutKast and frequent collaborators Organized Noize still made it sound like ahead-of-its-time rap music. And the rapping itself was just as out of this world as the music. Andre 3000 was still three years away from "Hey Ya!," but he already started flexing his singing muscles on this album, and he was still a razor-sharp rapper too. As always, Andre's out-in-space style is grounded by Big Boi's more down-to-earth style and bulletproof punchlines, and standout verses by Killer Mike and Gangsta Boo add grit to OutKast's increasingly melodic sound too. These days, it's easy to take for granted how fantastic OutKast were in their prime, and forget how they had to release masterpiece after masterpiece just to get accepted by the East and West Coast scenes that thought the South was a joke. But whenever you take the time to really dive back into Stankonia, OutKast sound even better than you remember. The hits ("Ms. Jackson," "B.O.B.," "So Fresh, So Clean") have aged like fine wine and the deeper cuts rival them at just about any moment. It's truly timeless.

OutKast were well-established by 2000, but that year also saw the emergence of another soon-to-be Atlanta rap star, Ludacris. Following Luda's independently-released 1999 debut Incognegro, he inked a major label deal with Def Jam South (the now-defunct Southern branch of Def Jam), re-recorded a lot of Incongegro's songs, added a few very key new ones, and came out with the instant-classic Back for the First Time. OutKast collaborators Organized Noize did produce one track on this album ("Game Got Switched"), but Luda represented a different side of the South than OutKast, and the album's most groundbreaking production came from two rising Virginia artists who hadn't contributed to Incongegro: The Neptunes ("Southern Hospitality") and Timbaland ("Phat Rabbit"). Coming from Virginia, where they were pretty much equidistant from the New York rap scene and the Southern rap scene, The Neptunes and Timbaland absorbed all different kinds of regional sounds and came out with a maximalist, futuristic, genre-defying production style that would define the early 2000s, not just within hip hop but within pop and rock and beyond. Still today, one of the greatest Neptunes beats of all time is "Southern Hospitality," and it was also one of the earliest examples of Luda figuring out how to add real hooks into his music. Later albums would find him getting more and more pop-friendly, but Back for the First Time is overall pretty raw. It's the Ludacris album of choice if you want him at his hardest and least frilly, and it remains a grand introduction to one of the most charismatic rappers of the early 2000s.

Eve came into the 2000s swinging after her breakthrough 1999 debut album Let There Be Eve...Ruff Ryders' First Lady and her standout verses on Ruff Ryders' first two Ryde or Die compilations, but it was 2001's Scorpion that established Eve as a superstar and one of the seminal rappers of her generation. With a Dr. Dre beat and a Gwen Stefani hook on "Let Me Blow Ya Mind," Eve was able to leave her mark on the mainstream (Gwen would return the favor three years later by having Eve guest on the Dre-produced "Rich Girl"), but don't let that song overshadow the rest of Scorpion. Eve loads the album with menacing bars, and the bold, dark production of most of the album only makes her sound more sinister. (Dr. Dre shows up again on "That's What It Is," which goes as hard as any of the Dre-produced hits of the era.) Guest appearances by DMX, The LOX, Da Brat, and Trina add to the intensity, but nobody overshadows Eve.

A good 15 years (at least) before Run The Jewels, El-P was running underground rap as a member of Company Flow, a producer, a solo artist, and the co-owner of the Definitive Jux label. And one of Def Jux's first great albums was The Cold Vein, the El-P-produced debut album by Harlem duo Cannibal Ox. Not a million miles away from the Deltron 3030 album, El's production on The Cold Vein pulled from the boom bap and turntable scratches of the '90s, but in a way that was cinematic and psychedelic and sounded like it was from the future. Vast Aire and Vordul Mega rise to the occasion with wordplay and tongue-twisters that are just as mind-bending as the production, and they always manage to talk about real shit, even when they sound surrealist on the surface.

Jay-Z made a name for himself rapping alongside Jaz-O and then Big Daddy Kane in the late '80s and early '90s, but took his time when it came to making his own album. And while he was watching and waiting, the young Queensbridge rapper Nas released his 1994 debut album Illmatic, an instant-classic that received a now-legendary score of five mics from The Source and changed rap forever. Jay took obvious notes from Illmatic (and sampled a line from it) when he finally released his own debut album, 1996's Reasonable Doubt. Gone was the fast-rapping Jay-Z of the Jaz-O days and in his place was an artist with a smoother, grittier style who told real-life stories of life on the streets in Brooklyn over some of the finest production of the era (courtesy of Ski, Clark Kent, Illmatic contributor DJ Premier, and others). Jay-Z intended for Reasonable Doubt to be a classic, and it was, but it wasn't the instantly-game-changing album that Illmatic was and it couldn't compete with the flashy, pop-crossover "Jiggy Era" that Puff Daddy started to lead after Biggie's tragic death. So Jay-Z went in an increasingly pop direction, and by the time of his 1998 single "Hard Knock Life (Ghetto Anthem)," he wasn't just competing with the "Jiggy Era," he was starting to take over.

Going pop in the late '90s and early 2000s also meant getting dissed by other rappers, among them Prodigy of Mobb Deep and Nas, whose feud with Jay-Z was about to boil over as Jay-Z geared up for his best album since Reasonable Doubt, The Blueprint. Months before its release, Jay made Hot 97 Summer Jam history by debuting "Takeover," a diss track aimed at Prodigy and Nas, during his set, alongside a childhood photo of Prodigy in dance clothes on the big screen. The finished version of "Takeover" ended up on The Blueprint, and the studio version proved it to be not just a brutal diss track but also a genuinely great song, and one of many on The Blueprint. Jay-Z didn't stop being "pop" on The Blueprint -- it still had the radio-friendly "Izzo (H.O.V.A.)," the sentimental balladry of "Song Cry," and other "pop" moments -- but he figured out how to put the accessibility of the "Jiggy Era," the grit of the streets, and the album-oriented structure of Reasonable Doubt into one whole masterpiece of an album. Production came largely from Just Blaze and Kanye West (plus Bink, Timbaland, Eminem, and others), and together they established a rich, soulful production style that would dominate rap for years. There's perhaps never been a better example of the classic Kanye sound than "Heart of the City (Ain't No Love)." Jay's ear for beats on The Blueprint was matched by his most consistently great rapping since Reasonable Doubt, and still some of the very best rapping of his career. Unlike his previous guest-filled albums, Jay carried the album almost entirely by himself, and he never lost steam. The only guest appearance came from Eminem on "Renegade," and look, Nas is right, Em out-rapped Jay on the track, but Jay still packed some of his finest rhyme schemes into that song.

The backpack rap scene that Aesop Rock was one of the leaders of could at times feel more geared towards punk and indie rock audiences than towards hip hop audiences, and when there was a long-overdue corrective throughout the music industry that gave hip hop the chance to deservingly top Coachella lineups and year/decade-end lists, a lot of the backpack rap stuff (and the snobbery associated with it) lost a lot of the credibility it once had. That's mostly a good thing, but like his former collaborator El-P (whose Def Jux label he was signed to in the early 2000s), Aesop Rock was always one of the genuinely good ones. He's always sounded like he has a lot of respect for the hip hop traditions that his music is steeped in, and he's always been a great rapper and producer. He remains prolific and consistently good to this day, but he was nearly unstoppable in the early 2000s, during which time he released a handful of now-classic records, including Labor Days. In hindsight, Labor Days doesn't actually sound like the antithesis to albums like The Blueprint; it feels like it's coming from a similar place as Jay-Z was. The production (largely by Blockhead and Aesop himself) sounds very much inspired by the hazy, head-nodding boom bap of '90s New York rap, and Aesop's word-scrambling delivery falls right into the pocket.

Jay-Z's claim that Nas had a "one hot album every 10 year average" wasn't entirely fair, but by the end of the '90s, it was hard to deny that Jay-Z was enjoying more critical and commercial success than ever and Nas' relevancy was fading. But when Jay-Z brought national attention to their feud on "Takeover," it lit a fire up under Nas' ass and resulted not just in the response track "Ether" but also in the best Nas album since Illmatic. Like "Takeover," "Ether" is brutal but also a great song (though, as was too often the case in early 2000s rap, it's riddled with homophobia). It's the reason "ether" -- as in, to utterly destroy someone -- is now a verb, and it's also the reason that "stan" is a noun. (It comes from Eminem's song, but Nas made it a noun.) Stillmatic is more than "Ether" though, and Nas making such a great album really spoke more volumes against Jay-Z's claims than any line in "Ether." He nabbed a few beats from Illmatic contributors Large Professor, DJ Premier, and L.E.S., and he sounded sharper and more focused than he had two years earlier on Nastradamus. Singles "Got Ur Self A Gun" and especially "One Mic" helped re-establish Nas as a major force and set the tone for the following year's God's Son, which is at least as good as Stillmatic and birthed Nas' biggest hit of the 2000s, "I Can." And the album's deeper cuts saw Nas reclaiming his status as the expert storyteller he was on Illmatic (and "Ether" is not the album's only track aimed at Jay-Z, see also: "You're Da Man"). These days, it doesn't really matter anymore who -- if anyone -- won the Jay-Z/Nas beef, but what does matter is that beef resulted in two of the all-time great rap albums within four months of each other, and nearly 20 years later, both still hold up.

El-P is an artist who never stops inventing himself, and whose old stuff never sounds outdated no matter how many times he pushes his career forward. These days, he's more famous than ever as one half of Run The Jewels, but he was running underground rap two decades ago and his music from that era sounds as forward-thinking today as it did then. After the breakup of his great '90s group Company Flow, El went solo with his 2002 debut album Fantastic Damage, a drastic artistic leap from Co Flow's already-classic Funcrusher Plus. As both the rapper and the producer, El had full creative control over Fantastic Damage and was able to establish himself as a true visionary. More than just a collection of beats and rhymes, Fantastic Damage is full of musical ebbs and flows and really plays out like a much grander statement than any of its individual songs could on their own. The masterful production was matched by El's militant rapping (and that of his guests, which included Aesop Rock, Cannibal Ox's Vast Aire, Mr. Lif, and more), and it's especially thrilling to listen back to El-P's raps on this album now that we're so used to hearing him with Run The Jewels. We've seen so many rappers make one or two classic albums and fall off, but it's less often that we see someone evolve over time like El-P. The place he's at now as an artist really makes you see his classic records in a different light.

If we're picking one album per artist, a lot of people would go with 2000's near-perfect The Marshall Mathers LP for Eminem, but if pressed, I always go with The Eminem Show because it feels like the grand finale to the classic Eminem era. The Marshall Mathers LP is just as essential, but Eminem as we came to know him doesn't exist without The Eminem Show.

An artist who almost always knew how to title an album, Marshall Mathers introduced the world to his massively offensive alter-ego Slim Shady on 1999's The Slim Shady LP, he introduced us to the man behind the madness on The Marshall Mathers LP, and he took a look at the impact Eminem the artist had on the world with The Eminem Show. (He also admitted the show was over with 2004's Encore, and then made a series of failed comeback attempts with Relapse, Recovery, The Marshall Mathers LP 2, and Revival, before finally abandoning this trend on the still-just-okay-sounding Kamikaze and Music to Be Murdered By.) Eminem catapulted to the forefront of rap because of white privilege but also became a scapegoat for everything white suburban conservatives hated about rap, and there's perhaps no better response to all of it than "White America," the first proper song on The Eminem Show. And then there's "Sing for the Moment." The Marshall Mathers LP gave us "Stan," a Dido-sampling ballad about the real-life dangers of toxic fandom and the importance of mental health, and The Eminem Show gave us "Sing for the Moment," an Aerosmith-sampling ballad about the importance of rap music to young kids amidst backlash from the media, the government, and scared parents. You might argue that song ruined white rap forever (and also unfortunately convinced Eminem he needed more and more ballads on later albums), but it also spoke directly to and validated the feelings of a lot of kids who needed to hear it. The Eminem Show also attacked George W. Bush ("Square Dance"), took on personal issues like the toll fame takes on a person ("Say Goodbye Hollywood") and fatherhood ("Hailie's Song"), and also reminded the world Eminem was still better than most people at making straight-up rap songs ("Business"). One of three songs on The Eminem Show produced by the man who made Eminem a star, Dr. Dre, "Business" found Eminem packing so many career-best punchlines over a top-tier Dre beat, reminding us that -- when you put all the baggage associated with Eminem aside -- he was truly one of the greats at the pure art of rapping.

As mentioned in the Ludacris blurb, The Neptunes (Pharrell Williams and Chad Hugo) were crafting a new sound in the early 2000s that changed rap (and pop music overall) forever, and though they produced songs for tons of artists, their closest relationship was with fellow Virginia Beach duo Clipse, aka brothers Pusha T and No Malice. The Neptunes produced all the music on Lord Willin', one of the truly original debut albums of the 2000s. The Neptunes' bright, multi-layered, rhythmic production sounded like a futuristic beach dance party, but Push and Malice's raps were as cold and deadly as anything coming out of New York. As with El-P, there's a different appeal to early Clipse records today than there was at the time because of the revitalized career Pusha T has had ever since hooking up with Kanye West in the 2010s (which so far hit its highest peak with 2018's Daytona). He's one of the best rappers in the world right now, which seems all the more impressive when you remember he was putting out classics two decades ago. These days, he sounds right at home over Kanye beats or on psychedelic Griselda and Freddie Gibbs tracks, but when you wanna hear him over out-of-this-world Neptunes production, there's nothing like Clipse. "When the last time you heard it like this?" they ask on the album's biggest song. 18 years later, the answer is still Lord Willin'.

The Neptunes' core, hometown collaborators were Clipse, and likeminded Virginia producer Timbaland's was Missy Elliott. They'd been making records together since Missy' 1997 debut album Supa Dupa Fly, and they proved to be a dynamic duo. Both were visionaries who were always looking towards the future, and together they were an unstoppable force who made rap and R&B songs that really didn't sound like anyone else in the world. It's hard to pick just one early 2000s Missy Elliott album (a lot of people would've understandably went with 2001's Miss E... So Addictive), but I'm going with Under Construction, and not just because it's "the one with 'Work It.'" "Work It" is probably a top 5 rap single of the early 2000s and there's still never been another song like it, but the rest of Under Construction finds Missy at the top of her game too. It's a little shorter and tighter than the ones that led up to it, and with less guests crowding the album, there's more time for Missy to shine on her own. (And of the six guest appearances it does have, all of them are extremely well-picked and well-executed: Beyonce, Jay-Z, Ludacris, Method Man, TLC, and Ms. Jade.) Missy was far and away one of the best rappers of the early 2000s -- charismatic, innovative, and unmistakable, no one else scratches the itch if you're in the mood for Missy Elliott. She was also a great singer and songwriter, and production wiz Timbaland knew exactly how to craft the kinds of beats she needed for her songs to reach their fullest potential.

The Roots came into the 2000s riding high off the strength of 1999's Things Fall Apart -- widely and deservingly regarded as one of their best albums -- and they just kept pushing forward with their first new album of the new millennium, Phrenology. Having a live band always allowed Questlove & co to push their sound in all kinds of directions that were atypical of most hip hop, and Phrenology did that even more than the group's '90s albums did. With everything from a hardcore punk interlude ("!!!!!!!") to a ten-minute, psychedelic, three-part suite ("Water"), Phrenology had virtually no limits, musically speaking, and Black Thought had only sharpened has rapping skills in the time since Things Fall Apart. (Like Pusha T, Black Thought is a lifer who's now also a regular of the new wave of golden age-inspired rap, and he still manages to get even better.) Some of the albums on this list feel very much like a product of the early 2000s, but not Phrenology. The Roots made great records in the '90s, the '00s, and the '10s, and they always feel like they're transported to our world from a time and place of their own.

Phrenology was a multi-genre, album-oriented masterwork, but Common's Electric Circus -- made in collaboration with The Roots' Questlove, future Roots member James Poyser, and other members of the Soulquarians collective, and released just a few weeks after Phrenology -- took that concept to another level. Down to the album artwork, Electric Circus was modeled more after pop opuses like Sgt. Pepper's then after other rap albums, and it almost entirely eschewed standard hip hop production in favor of a lively, multi-layered mix of psychedelic rock, funk, and soul. It was made with an ensemble cast that not only included Common, Questlove, and James Poyser but also The Neptunes, J Dilla, Prince, Erykah Badu, Jill Scott, Mary J. Blige, Cee Lo Green, Bilal, Stereolab's Lætitia Sadier, P.O.D.'s Sonny Sandoval, and more, and it's rare that the spotlight is on any one individual for too long. It's more that all these extremely talented individuals came together to create this vast piece of work that was unlike anything else coming out at the time, and unlike any Common album before or since. It's an anomaly, and you can still hear its impact echoing in some of the very best modern rap albums like My Beautiful Dark Twisted Fantasy and To Pimp A Butterfly, both of which marched through the doors that Electric Circus kicked open.

In the earlier days of hip hop -- way before the internet blurred the lines between "mixtape" and "album" -- a mixtape was usually something put together by a DJ like DJ Clue or Kid Capri, who would mix together a compilation of songs and often have exclusives of previously-unreleased verses or help popularize new rappers in the process. When 50 Cent came around, he helped turn mixtapes from a DJ-led art form to a rapper-led art form. Instead of acting as compilations, mixtapes basically became "street albums" for aspiring rappers, who put album-worthy bars over other people's beats and used the mixtape as a way to prove themselves without the budget of a major label. 50 and G-Unit's early tapes like Guess Who's Back?, 50 Cent is the Future, No Mercy, No Fear, and God's Plan defined this era, and they contained what are still some of his best songs ("Wanksta," "Your Life's on the Line" - both Ja Rule disses). The Queens native was blacklisted by the music industry in his home city due to his beef with Murder Inc, but after Eminem and Dr. Dre took notice of his buzzed-about mixtapes, they signed him to Shady/Aftermath and executive-produced and contributed to his instant-classic debut album Get Rich or Die Tryin'. "I've been patiently waiting for a track to explode on," 50 rapped on the Eminem-produced "Patiently Waiting," and when he finally got the chance, explode he did. That song has one of Eminem's best verses of the early 2000s and 50 still wasn't overshadowed by him. He was gifted with perhaps the best Dre beat of the early 2000s, and he knew exactly how to turn it into the world-dominating single "In Da Club." With Dre and Em behind him, 50 figured out how to give his songs hooks without losing the ferocity of his street albums, and it resulted in a landmark album that still sounds remarkable today. Like half the songs were huge hits, and the ones that weren't were just about as good. It wasn't constructed as a capital-A Album like Illmatic or The Blueprint, but it was so stacked with quality songs and so void of filler that it became a top-tier hip hop album anyway.

North Carolina has never been the kind of major hip hop hub that New York or LA or Atlanta or Chicago is, but from Petey Pablo to J. Cole, it's a had a long, rich hip hop history, and one of NC's most important groups in the early 2000s was Little Brother, the trio of rappers Phonte and Big Pooh and DJ/producer 9th Wonder. Their soulful sound took some clear inspiration from late '80s / early '90s stuff like A Tribe Called Quest and De La Soul, but it also sounded totally new at the time and fit right in next to artists like The Roots (whose Questlove co-signed them very early on) and the soul-sample-loving Jay-Z (who tapped 9th Wonder to produce a track on The Black Album just months after The Listening came out). It's no surprise that The Listening was received like a classic album by such prominent figures in hip hop off the bat -- 17 years later, i still sounds like one. It's got a rich soundscape meticulously crafted by 9th Wonder, recurring themes and concepts including a running skit involving a fictitious radio station, and life-affirming, in-the-pocket bars by both Phonte and Big Pooh. It's an album that sounded a little more organic and had a little more of an old soul that most of what was going on in mainstream hip hop at the time, but not in a way that felt self-righteously anti-mainstream. It's every bit as accessible and enjoyable as the hit songs of the era, and has held up in a way that's more timeless than a lot of them. It's no surprise that when they reunited (without 9th Wonder) for a new album in 2019, they still sounded as refreshing as ever.

50 Cent is generally regarded as the pioneer of rapper-driven mixtapes, but as the Queens rapper was churning out his early tapes, Dipset were doing a similar thing in Harlem. Group leader Cam'ron then had a major breakthrough with 2002's Come Home with Me -- his first album for Jay-Z and Dame Dash's Roc-A-Fella Records, and home to gigantic singles "Oh Boy" and "Hey Ma" (both of which had originated on early Dipset mixtapes) -- which opened the doors for The Diplomats as a group (Cam, Jim Jones, Juelz Santana, Freekey Zekey, and others) and led to the first proper Diplomats studio album, 2003's Diplomatic Immunity. The double album is home to a remix of "Hey Ma," though songs like "Dipset Anthem" and "I Really Mean It" proved to be this album's fan faves, but Diplomatic Immunity wasn't driven by its hits the way Come Home with Me was. This was an album that was meant to showcase Cam, Jim Jones, and Juelz Santana as some of New York's finest new rappers, and it had no trouble doing just that. Over gorgeous, soul sampled-infused production from frequent collaborators the Heatmakerz as well as Roc-A-Fella associates Just Blaze and Kanye West, The Diplomats cruised through over 100 minutes of gut-punching penmanship. Their time in the mainstream may have been short-lived, but Diplomatic Immunity gave them a diehard fanbase that still hasn't faltered.

One of the strongest and longest-lasting rapper/producer duos of the boom bap era was Gang Starr, aka Guru and DJ Premier, who returned in 2003 with The Ownerz, their first album since 1998's Moment of Truth and last before Guru's 2010 death (and 2019's posthumous One of the Best Yet). A lot changed within rap music between 1998 and 2003, but not much changed for Gang Starr, who did what they did best on The Ownerz and knocked out one more classic before calling it quits. Guru's quiet yet deadly style was in fine form on The Ownerz, and Preemo filled the album with the same kind of jazzy boom bap production he dominated the '90s with. It didn't matter that Gang Starr's style wasn't dominant in the mainstream at the time; it's timeless and The Ownerz holds up today better than a lot of the more "of the moment" albums released that same year. Just like a decade prior, Guru and Preemo were true album artists and they didn't need much help to hold your attention for the length of an entire disc, but The Ownerz gets bonus points for "Rite Where U Stand," home to one of the best Jadakiss verses of all time.

When G-Unit and Dipset were changing mixtape culture in New York, T.I. and his group P$C were doing a very similar thing in Atlanta. Tip's 2001 debut album I'm Serious failed to make good on Pharrell's promise that he was "the Jay-Z of the South," so he took to the streets with his 2002 mixtape In da Streets, which helped Tip earn the reputation he deserved and led to his breakthrough studio album, 2003's Trap Muzik. OutKast were pop stars by 2003 ("Hey Ya!" came out that year) and Ludacris brought his pop-friendly sound to the top of the charts that year with "Stand Up" (and infiltrated Hollywood with 2 Fast 2 Furious), and at the same time, Trap Muzik introduced the world to a grittier side of Atlanta. Today, "trap music" is the dominant subgenre of rap music in Atlanta and hugely dominant on an international level as well, and it's hard to imagine any of that happening without the precedent Trap Muzik set. It established T.I. as the smooth-sounding wordsmith he's known as today and established his collaborator DJ Toomp's trunk-rattling production as a dominant sound of the South (while also boasting production from Kanye West on two songs). It also gave the world an adrenaline rush of great songs, from massive fan faves like "24's" and "Rubber Band Man" to quality deeper cuts like "Long Live Da Game," "Be Better Than Me," and the Kanye-produced "Doin' My Job." T.I. would just get better and better after this album, and by the time he named his career-best 2006 album King he had more than earned the title, but none of it would've happened without Trap Muzik.

It's hard to figure out what exactly is going on with Kanye West these days, but for a while he was the leading visionary in hip hop, reinventing himself at every turn and influencing generation after generation of major rappers in the process. It wasn't always obvious he'd do that though; he proved himself as an era-defining producer through his work with Jay-Z, Cam'ron, Talib Kweli, T.I., Ludacris, and others, but when he tried to embark on a career as a rapper, he was met by hesitation even from his closest collaborators. Against all odds, he released the massive solo single "Through the Wire" in 2003, and his debut album The College Dropout (featuring that song and 20 others) arrived to rave reviews four and a half months later. It utilized the same soul sample-fueled production style that he popularized on The Blueprint, but Kanye took it to a new level with this album, fleshing out the samples with real-life choirs and string arrangements, and putting the whole thing together in a way that played out more like cinema than like a collection of rap songs. (It makes sense that he made his next album with Jon Brion, a film composer.) The "Benz and a backpack" line wasn't just one lyric but an entire mentality. Kanye eschewed the lyrical themes that were typical of mainstream rap in the early 2000s and instead looked at personal introspection, religion, racism, and other topics that were par for the course in underground "conscious" rap, and he did so without the fiercely niche approach of underground rap. He put left-of-center rappers like Mos Def, Talib Kweli, and Common on the same stage as superstars like Jay-Z and Ludacris, and it all felt natural with Kanye in the director's chair. It also helped to have a handful of talented guest rappers because, though Kanye was a better MC than people thought he'd be, he still was a lot better at envisioning masterpiece albums than he was at rapping on them. But even that didn't hurt him -- the contrast between his shortcomings as a performer and his ambitions as an artist became part of his charm. The College Dropout was a maximalist, imperfect musical triumph that forced worlds to collide and could've easily been a disaster in a lesser artist's hands. In Kanye's, it tore down boundaries between scenes and subgenres and changed rap forever, and still, he'd go on to top it several times.

The early 2000s saw producer Madlib release the debut album by his alter-ego Quasimoto, a seminal remix album of Blue Note Records releases called Shades of Blue, a collaborative album with J Dilla and more; and it also saw rapper MF Doom release his classic Mm.. Food, a couple great albums as Viktor Vaughn, and more. Together, Madlib and MF Doom teamed up as Madvillain, and the result was one of the finest experimental rap albums of the era (or probably ever), Madvillainy. Madlib provided psychedelic, jazz and soul sample-infused production, and MF Doom matched it with an equally mind-bending delivery that ignored hooks and traditional rhyme scheme. It's 22 tracks including instrumental interludes and vignettes that play out more like a song cycle than a traditional album. "Guest appearances" come in the form of Madlib and Doom's own alter-egos. The whole thing is a trip, not intended for easily digestible consumption or for throwing one or two songs on a playlist, but a massive treat when given the time and attention it deserves. It's an album where you can never really decide if it sounds vintage or futuristic, and it remains both timeless and influential today. It's hard to imagine Earl Sweatshirt, MIKE, and other psychedelic artists that dominate today's rap underground sounding the way they do without Madvillain.

Like Pusha T and Black Thought, Jadakiss remains a sought-after veteran within the world of golden age-inspired modern rap, the kind of guy who can show up on an Alchemist or Statik Selektah-produced project and steal the show, and he remains a huge influence on gritty, street-smart rappers like the Griselda crew, whose group album WWCD is like the modern-day answer to Jadakiss' group The LOX. Jadakiss is one of the most purely skilled rappers of all time, though he's much better at the art of rapping than he is at the art of making albums. He's never really put out an album that qualifies as a classic the way Illmatic or The Blueprint does, but with Kiss of Death, he came pretty damn close. It's home to his biggest single ever, "Why?", which is also his most perfect fusion of radio-friendly pop and street-cred-worthy bars, and though "Why?" is a tough song to top, Kiss of Death gives it a run for its money numerous times. He roped in a hugely impressive cast of producers -- Kanye, The Neptunes, Swizz Beatz, Eminem, Havoc of Mobb Deep ("Why?"), The Alchemist, Roots member turned hitmaker Scott Storch (who helmed the album's second best song, "Time's Up") -- and the warm, big-budget sound gave Jadakiss' cold, hard raps the backdrop they needed to go from great bars to great songs. Like every Jadakiss album, there's a little bit of filler, but the amount of times he stops you in your tracks with pure greatness outweighs the filler. Jadakiss will probably never be the type to think about album-making the way someone like Kanye West does, but he doesn't need to be. Kiss of Death willed its way into becoming a classic album simply by containing more moments of sheer and utter greatness than most albums ever do.

Sometimes you make a classic album just by being so purely skilled at what you do, and sometimes you make one by immersing yourself so deeply in other classic albums until those albums become so embedded into your brain that your natural instinct is to emulate them. That's what The Game did for his major label debut The Documentary, and he tells you exactly which albums he's emulating on the title track: Ready To Die, Reasonable Doubt, Chronic, Death Certificate, All Eyez On Me, and Illmatic. Game had released a few independent albums and mixtapes before The Documentary, but he knew this would be his chance at making a classic album, and he saved his best ideas and his producers' best beats for this record. Like Eminem and 50 Cent (and Snoop Dogg) before him, the possibility of fame and greatness became very real after Dr. Dre took him under his wing and signed him to Aftermath/Interscope. Dre also got 50 Cent's G-Unit Records involved, and the then-extremely-popular 50 featured on the album's two biggest songs, "Hate It Or Love It" and "How We Do." (Em's on a song too.) Like he did with Em and 50, Dre gave Game some of his hardest beats of the early 2000s, and on top of that, they assembled an all-star team of producers to flesh the album out, including Kanye, Just Blaze, Timbaland, Havoc, Hi-Tek, Buckwild, Cool & Dre, and more. Game didn't have Eminem's natural talent or 50 Cent's effortless starpower, but every producer involved was on their A game, 50 Cent lent him some career-best hooks, and The Game rapped as hard as he ever would. It was the strongest West Coast debut in some time, and one of the last classics to come out of gangsta rap's era of dominance, before The Great Kanye vs 50 Cent Album Sales War of 2007 signaled the rap mainstream's pivot away from that subgenre. It was also Dre's last time getting heavily involved with a new breakthrough artist until Kendrick Lamar in the 2010s. From Straight Outta Compton to good kid, m.A.A.d city, Dre was at least partially responsible for classic albums within four decades of rap, and the next time someone makes a song that rattles off all his achievements, The Documentary would have to be in it.