The 50 Best Deep Cuts by 21st Century Rap Stars

This week on Billboard, we’re digging for buried gems in the catalogs of our favorite artists across all genres. We’ve already revealed our 100 Best Deep Cuts by 21st Century Pop Stars, and now we’re going deep on hip-hop, unearthing the greatest non-singles by our favorite star rappers from this century — the best album and mixtape cuts, bonus tracks and compilation appearances.

In other words, the best songs you might not know from the MCs that you definitely do. From Missy Elliott to The Massacre, check out our top 50 deep cuts from 21st-century hip-hop titans below.

50. The Game, “Church for Thugs” (The Documentary, 2005)

A highlight from The Game’s debut LP, but more importantly, an upper-echelon Just Blaze deep cut: blaring horns, crashing cymbals, a quivering vocal sample and a smattering of drums so potent that Game simply had to arrive and not mess anything up. The first 15 seconds of “Church For Thugs” is like a roller coaster ratcheting upward before a big drop; you need time to prepare for the rush. — JASON LIPSHUTZ

49. Kid Cudi, “Kitchen” (Passion, Pain & Demon Slayin’, 2016)

2016’s Passion, Pain & Demon Slayin’ stands as Kid Cudi’s return to the space-bound sounds of his Man on the Moon days with a refined command on his more experimental tendencies. “Kitchen” — which arrives at the end of Act III of Passion — is peak Cudi, from its soaring orchestral intro, to the Cleveland rapper-singer’s vocal mix of familiar, hushed bite and deep bellows, to the production led by longtime collaborators Plain Pat and Dot Da Genius. Although “Kitchen” didn’t get its day in the sun, at least it had its moment on late night when Cudi performed the track on The Tonight Show. — BRYAN KRESS

48. Juelz Santana, “Squalie” (From Me to U, 2003)

A Heatmakerz beat you want to wake up to. A hook with a strong point of emphasis made to shout along to. Peak Juelz comparing himself to both Mick Jagger and former New York mayor David Dinkins. A reminder to keep Dipset lieutenant J.R. Writer in your thoughts. Everything about “Squalie” works. — ROSS SCARANO

47. Jadakiss, “Things I’ve Been Through” (The Last Kiss, 2009)

Known for running over his detractors with his Tonka-like delivery, Jadakiss switched gears on “Things I’ve Been Through,” as he spoke about his label mishaps, his partnership with The LOX, and the passing of The Notorious B.I.G. While he ruminated on his shortcomings, he also provided ample advice to aspiring MCs clawing their way up the totem pole of rap: “You can find bullshit in any contract you sign/ If you from the streets though, there’s plenty of loopholes to eat, yo.” — CARL LAMARRE

46. 21 Savage & Metro Boomin, “Ocean Drive” (Savage Mode, 2016)

Prefiguring the multi-faceted experience of 21 Savage’s 2017 release Issa Album, “Ocean Drive” is the meditative moment on the otherwise unrelenting Savage Mode. Metro Boomin wants some relief, and gives 21 a genuinely pretty beat to skate on, spinning a literal rags-to-riches story. From “take out trash for some school clothes” to “bitch I be covered in Bape,” 21 Savage came up. — R.S.

45. Big Sean feat. Kanye West, “All Your Fault” (Dark Sky Paradise, 2015)

Dark Sky Paradise is arguably the creative high point of Big Sean’s career to date, and “All Your Fault” features not only some of the best and most dexterous rapping of his career, but also a classic verse from Kanye and a closing back-and-forth between the two, a move becoming more rare as time goes on. The alternating Sean-‘Ye bars in the third verse — “I ain’t satisfied bein’ on that top five list/I ain’t satisfied until I’m on that all time list/’Til everything I spit is all timeless/My girl on that all fine list/My life a little luck, a lotta grind” — are some of the best on the album. — DAN RYS

44. Lupe Fiasco, “Paris, Tokyo” (Lupe Fiasco’s The Cool, 2007)

There are a few moments when listeners get a reprieve from the deeper, heady musings of Lupe Fiasco on his classic 2007 concept album The Cool, but no greater escape than “Paris, Tokyo.” With a laid-back, elastic delivery, Lupe takes a measured look at the wear and tear of touring life with a globetrotting optimism. Despite the lack of conceptual threads that typically set Lupe songs apart from his peers, it’s refreshing to hear the Chicago MC take a positive spin on something as routinely demanding as touring, “with a bunch of souvenirs and a smile for your mouth.” — B.K.

43. Wiz Khalifa feat. Big Sean and Trae the Truth, “Phone Numbers” (Cabin Fever, 2011)

With Wiz Khalifa coming off an incredible high due to the Billboard Hot 100-topping crossover success of “Black & Yellow,” the Pittsburgh rapper used the Drumma Boy-produced track (and key assists from Big Sean and Trae the Truth) to boast about his accolades, women, and massive bank account. “Now when I get paid, my checks be lookin’ like phone numbers,” states Khalifa matter-of-factly at the start of the hook. Fortunately for Wiz, after the success of Rolling Papers, his checking account was indeed looking pretty nice in the seven-digit range.  — C.L.

42. Kanye West, “Late” (Late Registration, 2005)

The final track on Kanye West’s 2005 sophomore release Late Registration is quintessential ‘Ye, built on a dreamlike sample from The Whatnauts’ “I’ll Erase Away Your Pain.” Playful, jocular rhymes strung on the collegiate theme propel the narrative, while Yeezy also plays on his aptitude for punctuality (“I’ll be there in five minutes/ Five hours later?/ I’ll be there in five minutes”) and unleashes one of the strangest, greatest fake laughs in hip-hop history. — S.J.H.

41. Eminem feat. Kobe, “Talkin’ 2 Myself” (Recovery, 2010)

Acceptance is the first step to Recovery, and on “Talkin’ 2 Myself,” Eminem was brutally honest with himself and his fans — for what certainly felt like the first time in a long time — about how far he’d fallen off, openly admitting that his drug use had tanked his past two albums, and that he’d focused his attention on calling out rappers who’d lapped him while he was struggling to “write a decent punchline even.” Ironic maybe that Em would sound his most inspired in years writing about his own longtime lack of inspiration, but it just proved that oldest of literary axioms: Write what you know, even if you just know that you don’t really know anything. — ANDREW UNTERBERGER

40. Cam’ron feat. Jaheim, “More Reasons” (Purple Haze, 2004)

There’s virtue in crate digging, in the tireless search for a soul loop no one’s heard before, the dusty 45 from a forgotten label turned into a rap beat to begin life anew. And then there’s the gusto in grabbing something famous and flashy, and peeling back to the right part in a gambit that’s as satisfying as it is on the nose. This is Chad Hamilton’s flip of Earth, Wind & Fire’s timeless classic “Reasons.” This is Cam’ron’s one-of-a-kind swagger and wordplay linking up with R&B history. Get them boogies. — R.S.

39. T.I. feat. Kanye West, “Welcome to the World” (No Mercy, 2010)

Originally titled King Uncaged, T.I. changed things up and ran with No Mercy as the name for his 2010 effort. After being released from jail, the rapper made a swift return to the studio and recruited several powerhouses for his new endeavor. For the intro track “Welcome to the World,” he called on Kanye West and Kid Cudi to help propel his comeback. West, of course, stole the show with his guest appearance: “People ask me shit about Illuminati/First off, fuck that mean?!” — C.L.

38. Travis Scott feat. Young Thug & Justin Bieber, “Maria I’m Drunk” (Rodeo, 2015)

A six-minute, star-studded ode to getting fucked up on Don Ju-l-io in the stu-d-io — Bieber’s rhyme, natch. As tipsy as Travis, Thugger and Bieb sound in this one, they’ve still got nothing on that piano hook, so clouded and woozy it sounds like it’s going to trip over the beat at any point. It works, mostly because things aren’t lit so much as they’re seductively dim, with 90-proof-scrambled come-ons like “Let’s lose each other’s mind” making for a surprisingly enticing invitation. And “Call your friends and let’s get dru-unk!” is basically “Friends in Low Places” for the post-post-tailgate. — A.U.

37. YG feat. Kendrick Lamar, “Really Be (Smokin N Drinkin)” (My Krazy Life, 2014)

“I woke up this morning; I had a boner”: Thus begins YG’s stress-ridden bildungsroman of a song. Laugh if you want, but the same level of detail the L.A. rapper brings to his morning informs the rest of the dense track. Kendrick Lamar, another great coming-of-age chronicler, chips in a perfect verse that climaxes with synths that sound like choppy sirens, making for an instant-classic West Coast tale. — R.S.

36. A$AP Rocky, “Suddenly” (LONG.LIVE.A$AP, 2013)

A$AP Rocky’s 2013 debut LONG.LIVE.A$AP covers every corner of the hip-hop landscape by the time it gets to the album closer “Suddenly,” and it wraps like a whirlwind as the versatile Harlem MC takes stock of his meteoric rise. With a subdued beat that unfolds with deliberate timing, “Suddenly” allows Rocky to take center stage and deliver one of his most sincere, visceral verses. Definitely less accessible than singles like the Skrillex-assisted “Wild For The Night” or the feature-heavy “Fuckin’ Problems,” “Suddenly” has the type of career-spanning bars that stand the test of time as Rocky pays homage to his upbringing while reveling in his current, continued fortunes. — B.K.

35. Nas, “Rewind” (Stillmatic, 2003)

“I spit a story backwards, it starts at the ending.” No one’s gonna confuse Nas for Christopher Nolan exactly, but his parlor trick of a Stilmatic deep cut — a gang hit story told in reverse, one line (and sometimes one word) at a time — remains captivating even after you figure out the unremarkable plot, largely because few MCs besides Nas would have the ingenuity to attempt it and fewer still have the command and discipline to pull it of convincingly. Even the hilariously unnecessary reverse-blowjob sequence feels justified when it’s God’s Son on the mic. — A.U.

34. 2 Chainz feat. Lil Wayne, “Yuck!” (Based on a T.R.U. Story, 2012)

Wayne and Chainz, as Tity’s song “Dedication” explains, are real friends and brothers in rhyme. This collaboration from 2 Chainz’s first album is punchline-heavy and weirdly melodramatic, sonically. The strings on the beat make it sound like these two guys trading verses is the most urgent thing in the world — and for the near five-minute runtime, it is. — R.S.

33. Ludacris, “Hip Hop Quotables” (Chicken and Beer, 2003)

A Luda song consisting of nothing but punchlines almost sounds like it should be too much of a good thing, like a Hershey’s Miniatures pack consisting solely of Krackels. But no, for three hookless minutes, Luda piles puns on witticisms on veritable knock-knock jokes, inspiring more yuks than an issue of MAD Magazine, and at no point are you not hanging on his every word. Meanwhile, the beat — produced by Erick Sermon of EPMD, also a co-writer — is practically a gag into itself, bleating and booming like a clown car on hydraulics. — A.U.

32. Nicki Minaj, “Itty Bitty Piggy” (Beam Me Up Scotty, 2009)

Nicki Minaj’s 2009 mixtape, Beam Me Up Scotty, put her at the top of the food chain among new rappers, and the track “Itty Bitty Piggy” was one of the biggest reasons why. Over a sample from Soulja Boy’s “Donk,” Minaj maintained a casual, taunting flow and, most memorably, wrote her own pig-referencing rhyme best kept out of the nursery: “I don’t fuck with pigs, like As-Salaam-Alaikum / I put ’em in a field. I let Oscar Meyer bake ’em.” — CHRISTINE WERTHMAN

31. Drake, “10 Bands” (If You’re Reading This It’s Too Late, 2015)

If You’re Reading This, It’s Too Late was released on a frigid Thursday night in February, and holy hell did it sound like it — the sparse, creaky atmosphere of the “commercial mixtape” was so frosty you could practically see Drake’s breath on every bar. “10 Bands” was one of the set’s anthems, and still so muted and insular-sounding that it’s no surprise those nights in Calabasas were being spent inside the safe house. The cold winter might all be in Drake’s head, anyway: “Haven’t left the condo for a week now,” he croons with eerie calm, suffering from the world’s most expansive case of cabin fever. — A.U.

30. Chance the Rapper, “Smoke Again” (Acid Rap, 2012)

One of several odes to weed in Chano’s catalog, this one stands out among the rest of Acid Rap largely for its warped production, helmed by Blended Babies, a trudging beat with a borderline-comatose hook that plays around with layered vocal distortions. Chance’s delivery weaves between deliberate, drawn-out sing-rap and quicker, slick rhymes, peaking with one of his most clever and droll metaphors — “Lean all on the square/ That’s a fuckin’ rhombus” — that would almost be cringe-worthy if he wasn’t laughing along with it. — D.R.

29. 50 Cent, “What Up Gangsta” (Get Rich or Die Tryin’, 2003)

As the proper opener to his classic debut album, “What Up Gangsta” had to serve as the thesis statement for those who thought 50 Cent was little more than “In Da Club.” The bruising beat with drums that managed to fill any room provided the platform for Fif to go to work — “I walk around like I got a S on my chest/Nah, that’s a semi-auto and a vest on my chest” — and set out his bombastic street vision, showcasing his bona fides and his unrelenting confidence in equal measure. At its core, “What Up Gangsta” also showed off 50’s greatest strength at that point in his career: no matter what the subject matter or what the scenario, he could make any track effortlessly catchy. — D.R.

28. Meek Mill, “Tony Story” (Dreamchasers, 2011)

Meek Mill’s street demeanor and rugged lyricism helped build a strong foundation for the Philly artist when he first joined Rick Ross’ Maybach Music. With “I’ma Boss” blaring through the speakers of every radio station and house party, Meek knew he was on the cusp of success. In 2011, he released mixtape Dreamchasers, with the personal tale “Tony Story” serving as a highlight. The Jahlil Beats-produced track found Meek writing about two close friends who later became foes. Because of the song’s popularity, Meek expanded the series into three installments with “Tony Story 2” and “Tony Story 3,” sequels worthy of the original. — C.L.

27. Kendrick Lamar, “Hol’ Up” (Section.80, 2011)

Count me among those who consider Section.80 to be their favorite Kendrick Lamar project beginning to end; there’s something about the sly, youthful energy in his delivery — at the time, he had just turned 24 — that mark the album and set it apart from his subsequent discography. “Hol’ Up” encapsulates the complexity that has come to define K.Dot, covering a range of topics and contradictions with a flow that isn’t the same in any two verses, yet still feels cohesive as a full statement. — D.R.

26. Gucci Mane feat. 50 Cent, “Recently” (Writing on the Wall 2, 2011)

One could make a credible hip-hop deep cuts list composed entirely of Gucci Mane mixtape tracks; “Recently” is just an example of his baseline greatness, although it stands out due to 50’s lyrical gameness and the brilliant decision for the beat to fall back when he steps in. “Where it at? Where it at? Where it at? Where it at? HERE IT IS!” he exclaims at the song’s climax, making up for the fact that he refers to himself as “King Cha-Ching” a few seconds later. — J. Lipshutz

25. Missy Elliott, “Let It Bump” (This Is Not a Test!, 2003)

Elliott is no stranger to the party — cuts from her 2003’s This Is Not a Test! featured some of her most breathless fare, including singles “I’m Really Hot” and “Pass That Dutch,” as well as the sadly overlooked “Let It Bump.” The latter stands tall with its siren sample and record scratching, as Missy hopscotches: “Sucka MCs come new in the game/ Swear ya hip-hop but don’t know Daddy Kane.” — S.J.H.

24. Young Jeezy, “Circulate” (The Recession, 2008)

Take the street anthems from Young Jeezy’s Thug Motivation series and surround them with a financial crisis; the result is a song like “Circulate,” from Jeezy’s aptly named 2008 album The Recession. “Looking at my stash, like where the fuck is the rest at?/ Looking at my watch like it’s a bad investment,” Jeezy laments over Don Cannon’s luxurious production, a big spender reckoning with the socioeconomic climate head-on. — J. Lipshutz

23. Kanye West & JAY-Z feat. Curtis Mayfield, “The Joy” (Watch the Throne Deluxe Edition, 2011)

Watch The Throne was defined by riches and excess, but that’s what sets Deluxe bonus cut “The Joy” apart — it captures Jay and ‘Ye in introspective moods, reflecting on both fatherhood (Jay’s daughter would be born five months later), their respective upbringings and the issues weighing on their own minds, all over a fantastic Curtis Mayfield-sampling Pete Rock beat. But it’s also got some of the most enjoyable Kanye lines of his career and some inspired cleverness from Jay; it’s hard to choose between Kanye’s “I never understood Planned Parenthood/’Cause I never met nobody planned to be a parent in the hood” and “This beat deserves Hennessy/A bad bitch and a bag of weed, the Holy Trinity,” while Jay’s lyrical double-meaning, “Pete Rock, let the needle drop/I seen so much as a kid, they surprised I don’t [need a pop/needle pop]” has kept fans guessing as to what he actually said for years. — D.R.

22. Rick Ross, “Rich Off Cocaine” (Deeper Than Rap, 2009)

As a rapper, Rick Ross has always been adept at combining his war stories with soulful production. On his acclaimed 2009 album Deeper Than Rap, one of Ross’ best such records was “Rich Off Cocaine,” with Avery Storm sitting comfortably on the hook and Ross bragging about his rags-to-riches story, courtesy of the drug game. “My women imported, I’m never extorted/I’m very important, 20 grand for the mortgage.”  — C.L.

21. J. Cole, “A Tale of Two Citiez” (2014 Forest Hills Drive, 2014)

If there’s one thing to know about J. Cole, it’s that every word and observation is entirely his own. On this deep cut from his famously feature-free opus 2014 Forest Hills Drive, the Fayetteville, N.C. rapper waxes poetic on the economic disparity in his hometown, and the conflicting dreams and unifying desire to experience life on the other side. It’s a pivotal moment on the album where Cole shares some of his most impactful insights on a fittingly gritty beat, and its direct, aggressive honesty may be what kept it from taking hold in the mainstream. However, the song lives on as one of the wildest moments in Cole’s live show — with its crowd-stirring “hands in the air” refrain — and also as part of Cole and Kendrick Lamar’s “Black Friday” beat swap release. — B.K.

20. Future, “Blood on the Money” (DS2, 2015)

Much of Future’s DS2 project exists in a murkiness borne of the rapper correctly retreating from the pop songwriting of his Honest album, but “Blood On The Money” sounds especially haunted — “I know the devil is real,” Future intones, then repeats himself — as he recounts stories of pills, heartbreak and his drug-dealing history. With Zaytoven, Metro Boomin and Cassius Jay providing an atmospheric, pan-flute-laden terrain, “Blood On The Money” is DS2’s longest and most vulnerable moment, an extended confession that serves as the project’s linchpin. — J. Lipshutz

19. Lil Wayne, “La La La” (Tha Carter III Mixtape, 2007)

Weezy has an overwhelming back catalog rife with hidden gems, one of the strongest being “La La La” (not to be confused with “La La” off his classic Tha Carter III, which “La La La” was originally intended for). He sounds comfortable and animated over this fluffy New Birth sample, doling out rhymes against it in peak form (“Tell the cops I can buy my own bracelets/ Imma keep the paper running like a pair of ASICS.”) — S.J.H.

18. Rae Sremmurd feat. Jace, “Unlock the Swag” (SremmLife, 2015)

“This might be [the next single],” Swae Lee said in 2015 about “Unlock the Swag,” from Rae Sremmurd’s infectious debut studio album, SremmLife. It ultimately wasn’t — perhaps because the crawling tempo, the video-game-like bloops, and the ghostly choir voices didn’t exactly spell “hit.” The subterranean sounds made it one of the album’s weirder, more fascinating cuts, and showed that the Pixy Stix raps of Swae Lee and Slim Jxmmi and the Midas touch of executive producer Mike WiLL Made-It could thrive in any environment. — C.W.

17. Young Thug feat. Maceo, “Picacho” (1017 Thug, 2013)

It would be another year before Thugger really broke out with loosies “Stoner” and “Danny Glover,” which is what makes 1017 Thug such an enjoyable listen: It’s raw, unfettered Thug, having a great time experimenting with flow and melody without caring too much about what he’s even talking about. (Not that he ever really developed nuance or metaphor, or that we ever expected or wanted him to.) But that carefree attitude makes “Picacho” such an enduring track; it has a “who cares?” feel to it that makes it endlessly re-playable, and alongside other 1017 Thug cuts like “2 Cups Stuffed” and “Nigeria,” it’s an early-career gem. — D.R.

16. Migos, “China Town” (Y.R.N. [Young Rich N—as], 2013)

The three Migos work so prolifically, it’s hard to pick just one great deep cut. “China Town,” from the group’s second mixtape, the breakout release Y.R.N., remains an early fan favorite. The chorus is vivid and stubbornly Mortal Kombat-indebted, and Quavo’s verse is as dexterous as it is silly: “I got the birds singing like I’m Richie Lionel, I mean Lionel Richie,” he raps, just a few bars before leaving the listener with the image of dope so strong it triggers a heart attack when railed straight off the plate. — R.S.

15. Eminem, “Who Knew” (The Marshall Mathers LP, 2000)

The snotty young punk who still can’t believe anyone gives a shit about what he has to say grabs the megaphone and screams his sexist, homophobic, nihilistic worldview as loudly as possible. But of course, it’s only as serious as we’re willing to take it, and considering the song riffs on controversial topics so wildly that one lyric is literally “Fuck shit ass bitch c–t, shooby-de-doo-wop,” that level of serious should rate as “not very.” The song’s shit-eating mischievousness is evident enough from the Dr. Dre-co-produced beat anyway, a jaunty little shimmy that all but cackles over how everyone keeps getting madder while Em keeps getting richer. It’s such expert trolling that it truly frightens you to think about what mass destruction Marshall could’ve accomplished if he came up during the Twitter era. — A.U.

14. JAY-Z, “Takeover” (Blueprint, 2001)

Pretty obvious why this was never released as a single; radio play, at least the mainstream kind, was never its intended purpose (though it was always destined to be a Hot 97 staple). But for anyone who pays attention to the hip-hop world — or who was there when this was released — “Takeover” is essential in Hov’s discography for its significance at the center of his lyrical battle with Nas (and Prodigy of Mobb Deep), one of the great beefs in rap history. The track was the first large-scale volley in a war of words that escalated with Nas’ infamous response record, “Ether,” with the two songs standing shoulder to shoulder in the debate about the greatest diss track of all time. Which is better depends on your point of view; that both are scathing, intimate and vital does not. — D.R.

13. Nas, “Doo Rags” (The Lost Tapes, 2002)

While Nas has also been touted as a lyrical icon, at times, his lackluster choice in beat has held him back. On The Lost Tapes, he made sure that wasn’t the case, as the Precision-helmed “Doo Rags” proved to be the perfect balance of witty lyricism and flawless production. On the piano-laden record, Nas floats over the keys with X-Acto-knife acuity, providing one of his greatest nostalgic hooks: “The doo rags are back, fitted hats, snorkels and furs/ Rikers Island buses still packed, what’s the word?/ The drinkers stay drinkin’, or puffin’ they herb/ And I’m still enjoyin’ life’s ride; one mo’ time…”  — C.L.

12. Lil’ Kim, “Shut Up Bitch” (The Naked Truth, 2005)

“Shut Up Bitch” never got its own music video, but the gossipmonger tell-off from the song’s hook was too good not to slap on the start of the video for “Lighters Up,” The Naked Truth’s lead single. Kim used “Shut Up” to acknowledge all of the rumors that surrounded her and her career — plastic surgery, ghostwritten rhymes from the Notorious B.I.G., drug use, jail time — and respond to them with one swift kick. Some of the references (Star Jones) sound a little dated now, but nearly a decade after she put out Hard Core, Kim showed that she still carried that weight in her voice, and her rhymes remained tough as hell with one-liners to spare: “You know your mouth’s a cage for your tongue if you just close your teeth.” — A.U.

11. Common, “Be (Intro)” (Be, 2005)

Not only is “Be (Intro)” one of the best songs on 2005’s Be, but it also holds its own among Common’s best material. Kanye West contributes an instrumental that’s instantly inviting, its optimism infectious, as Common sets the tone for the LP with apt cultural surveillance (“Bush pushing lies, killers immortalized/ We got arms but won’t reach for the skies”). — S.J.H.

10. Clipse, “Trill” (Hell Hath No Fury, 2006)

Over 11 years after its release, “Trill” still sounds alien. The Neptunes have a lot of hall-of-fame beats, and “Trill” is nowhere near the Top 20 of their most well-known productions, but there’s an argument that this is among their crowning achievements — a space-horror epic full of ear-zapping synths and percussion that snaps just enough for Pusha T and Malice to spit over. Clipse’s Hell Hath No Fury is rightly considered a classic rap album from the 2000s, and “Trill” encapsulates its icy stare; like its parent LP, the song is unaffected, knows it’s white-hot, and grinds you into dust. “Trill” dares you to get onto its level, and over the past decade, few have done so. — J. Lipshutz

9. OutKast feat. Erykah Badu, “Humble Mumble” (Stankonia, 2000)

“All aboard the Stankonia Express!” Andre 3000 calls before “Humble Mumble” kicks in. Perhaps even more so than the album’s singles, which effectively brought OutKast to the mainstream, “Humble Mumble” captures the heart of Stankonia, a project bursting with spirit and wisdom beyond the years of the duo that created it. Although it’s got an extended intro and outro, a beat change midway through and an Erykah Badu feature, “Humble Mumble” is hardly overstuffed; Big Boi and Andre are nimble with their wordplay, yet can also toss out a line like “Fuck wishing, you missing the ambition on your mission” that can deeply resonate with a listener. Like the best OutKast songs, there are seeds of beauty within “Humble Mumble” that take a few listens to fully bloom. It’s worth the extra effort. — J. Lipshutz

8. Chance the Rapper, “Blessings 2” (Coloring Book, 2016)

“Are you ready for your miracle?” It’s the central question of Chance’s generous Coloring Book, though no one asks it until the end. The chorus of voices singing the question, made up of Ty Dolla $ign, Anderson .Paak, Raury, BJ the Chicago Kid, Nico Segal, Lolah Brown, and HaHa Davis, create the sweetest, most beautiful moment on an album that’s already so earnest and sentimental it shouldn’t work. But, as Chance says, “The people’s champ must be everything the people can’t be.” It’s a lofty challenge he’s given himself. So far, so good. — R.S.

7. 50 Cent, “Ski Mask Way” (The Massacre, 2005)

After supplying hip-hop with the hard-nosed masterpiece Get Rich or Die Tryin’ in 2003, many purists wondered if 50 Cent would be able to duplicate his success on The Massacre. Unfazed by the daunting task at-hand, 50 masterfully scripted a project that had both club bangers (“Just a Lil Bit,” “Disco Inferno,” “Outta Control”) and soulful tunes (“God Gave Me Style,” “Position of Power” and “Baltimore Love Thing”). Despite those monstrous records, it was Fif’s robbery-themed “Ski Mask Way” that stole the show. “This the flow right here that fucked up Jeffrey’s career,” was one of the most poignant lines on the record, because somewhere, Ja Rule was still desperately trying to find his second wind.  — C.L.

6. Drake feat. Rick Ross, “Lord Knows” (Take Care, 2011)

It’s no secret that Drake has a strong ear for beats, and as far back as his mixtape days, he always seemed to land on the right ones. And it’s partly why “Lord Knows” is such a behemoth: The Canadian rapper sounds invigorated over the salient Just Blaze production, replete with gospel choirs and crashing percussion — as, of course, does his ink-fucking guest from Miami. Emotional Drake is what gave the parent LP Take Care its trademark vulnerability, but heavens-scraping tracks like “Lord Knows” reinforced his abilities as a personality-driven lyricist. — S.J.H.

5. Nicki Minaj feat. Eminem, “Roman’s Revenge” (Pink Friday, 2010)

In which Nicki Minaj takes a classic nonsense lyric from Busta Rhymes’ “Scenario” guest verse and builds the definitive fire-breather of her early years out of it. Some of the song’s hashtagginess shows its years, but otherwise, Nicki’s schizophrenic spitting remains among the decade’s most visceral hip-hop thrills, unpredictable and unforgettable. Of course, Eminem shows up too, to provide a very long wind-up of sexual violence to a “Look, two pees and a tripod!” ba-dum-ching, but what’s mostly notable here is that even at his guest-verse screamiest, he was already no match for a possessed Onika: “IS THIS THE THANKS I GET FOR PUTTING YOU BITCHES ON?!?” After all, she wasn’t Jasmine, she was Aladdin. Jafar, too. — A.U.

4. Kendrick Lamar, “Sing to Me, I’m Dying of Thirst” (good kid, m.A.A.d city, 2012)

“Sing About Me, I’m Drying of Thirst” is a complex portrayal of the weight of blame. After two verses of Kendrick rapping in character, he raps as himself on the third verse and he feels guilty — guilty for obsessing over his own death, knowing it’s a gross way of chasing glory. Guilty for taking the stories of others, like the ones you hear in the first two verses, and using them to make his music. Guilty because maybe he’s not good enough to justify his career. Is he working hard enough? Is this bloody business of art worth it?

If the back-half of the 12-minute-long track is the answer, then no. The only thing that’s worth it in this broken world is the righteous path to Jesus. The Lord’s Prayer ends the song, not Kendrick — and I don’t doubt that he believes it, but for many of us his art does more work than any holy text. Thankfully, Kendrick keeps using his words to reach us, rather than going door to door. — R.S.

3. Kanye West feat. Rick Ross, “Devil in a New Dress” (My Beautiful Dark Twisted Fantasy, 2010)

The back-end of the deep cut two-fer that provides the fulcrum of one of the most acclaimed rap albums of the ’10s, following the peerless subterranean posse cut “So Appalled” with one of the most gorgeous and hellish productions in recent hip-hop history. Shoutout to the great Bink!, critical-but-forgotten producer on arguably the only other rap album this century with a rep on Fantasy‘s level, who (along with Mike Dean) twists an innocuous Smokey Robinson sample into a guttural howl here, laying demonic six-string over it that makes Voodoo sound like John Mayer. Kanye rises to the occasion on the mic, juxtaposing moments of personal devastation with cheap punchlines and wisely letting the beat fill everything in between, while a tagged-in, arsenal-emptying Rozay all but collapses over the song’s finish line, with the closing couplet of a lifetime: “I’m makin’ love to the angel of death/ Catchin’ feelings never stumble retracin’ my steps.” — A.U.

2. Lil Wayne, “I Feel Like Dying” (The Drought Is Over 2: The Carter 3 Sessions, 2007)

Maybe the song that converted the most Lil Wayne fans into outright fanatics, “I Feel Like Dying” is a strange song to build a rapper’s gospel around: There’s barely verses or a chorus, and certainly little of the rock-star charisma that helped Mr. Carter take over the world in the late ’00s — just a swirling beat, a disembodied sample and a rapper floating in the ether. But the Cult of Weezy still derives their rawest connection with the Best Rapper Alive through captured moments like this: stream-of-consciousness bad trips and extended stays in substance-abuse purgatory, in which Wayne seems to lose himself in another dimension, but still manages to extend a hand to those on other side. “I Feel Like Dying” is terrifying, beautiful, sublime and sickening, cementing Weezy F. Baby as the gonzo journalist of our time — and he looks way better with a bucket hat and cigarette holder, too. — A.U.

1. JAY-Z, “U Don’t Know” (The Blueprint, 2001)

In 2001, Hov dropped an atomic bomb on the hip-hop game when he unveiled his soulful opus The Blueprint. With Just Blaze and Kanye West providing the soundscapes, JAY-Z pounced on his adversaries with reckless abandon. “Takeover” and “U Don’t Know” conveyed Hov’s bulletproof swagger and demonstrated why his lyrical prowess should never be underestimated. On the latter, Just Blaze’s bombastic production allowed JAY-Z to get into his groove and rap about his success in not only the rap game, but the drug game, as well. “Was clappin’ them flamers before I became famous/For playin’ me, y’all should forever remain nameless,” rapped Hova. To this day, “U Don’t Know” remains an instantly inflammable live staple and enduring fan favorite, and serves as one of the most potent tracks from JAY’s truly unparalleled catalog. — C.L.