The Roots' 50 Best Songs

As far as hip-hop groups go, the Roots are certainly in the top tier. The acclaimed band from Philadelphia has featured a rotating cast of talented musicians throughout its existence, while founding members Questlove, Black Thought, and a core crew of Kamal Gray, Captain Kirk Douglas, Frank "Knuckles" Walker, Damon "Tuba Gooding Jr." Bryson, and James Poyser have upheld the groups legacy over the span of eleven studio albums. That's without even mentioning their collaborative works with John Legend, Betty Wright, Elvis Costello, and their current role as the house band for Jimmy Fallon's late-night talk show on NBC.

With such a deep catalog of material, filtering through and choosing the best songs from the Roots can be a tough task. Monday might be a Things Fall Apart day, while How I Got Over is the soundtrack for Wednesday. Or maybe you want to take it all the way back to Organix. Which goes to show just how consistent the group has been, as well as how nicely the music has aged. In the end, though, the Roots have classic cuts that rise above the rest. These are the Roots' 50 Best Songs.

David Drake is a writer living in New York City. Follow him @somanyshrimp

50. The Roots "Don't Say Nuthin" (2004)

49. The Roots "Pass the Popcorn" (1993)

48. John Legend and the Roots f/ Black Thought "Lil Ghetto Boy" (2010)

47. The Roots f/ Wadud Ahmad "Take It There" (2006)

46. The Roots "Leonard I-V" (1993)

45. The Roots f/ Martin Luther "Stay Cool" (2004)

44. The Roots f/ Greg Porn "When the People Cheer" (2014)

43. The Roots f/ Aaron Livingston "Guns Are Drawn" (2004)

42. The Roots f/ Dice Raw & MARS "Clones" (1996)

41. The Roots "Proceed" (1994)

40. The Roots f/ Dice Raw "Lighthouse" (2011)

39. The Roots f/ Malik B "In the Music" (2006)

38. The Roots f/ Truck North, P.O.R.N., & Dice Raw "Walk Alone" (2010)

37. The Roots f/ Malik B "Game Theory" (2006)

36. The Roots "Concerto of the Desperado" (1996)

35. The Roots "The Next Movement" (1999)

34. The Roots "Water" (2002)

33. The Roots f/ Wale & Chrisette Michele "Rising Up" (2008)

32. The Roots f/ Monsters of Folk "Dear God 2.0" (2010)

31. The Roots f/ P.O.R.N., Talib Kweli, & Dice Raw "I Will Not Apologize" (2008)

30. The Roots f/ Dom "Duck Down!" (2004)

29. The Roots f/ John-John "Baby" (2006)

28. The Roots "100% Dundee (Live Version)" (1999)

27. The Roots "Double Trouble" (1999)

26. The Roots f/ Nelly Furtado "Sacrifice" (2002)

Producer: The Roots, Khari Mateen

Album: Rising Down

Label: Def Jam

Although its laid-back chorus doesn't quite match its passionate verses, “Criminal” captures Black Thought looking back on a life of petty crime with lines accentuating his regret: “I done robbed an odd job and gambled enough/Till I'm put up in handcuffs and pissin' in a cup/If there's a God I don't know if he listenin' or what.” Truck North follows soon after, but it's closer Saigon who steals the show with a densely packed verse that reorients his frustration through rage and potential energy: “Who wanna challenge mine? I'm sick of St. Valentine/I did the violent crimes, that's why I got this style of rhyme.”

Producer: Kamal Gray

Album: Phrenology

Label: MCA/Geffen

The Roots' commercial ambitions could be a hit or miss proposition, but any time they revolved around R&B loverman themes, they were more apt to work than not. “Break You Off,” at the time, was not a major hit, but it's a little tough to see why in retrospect. It's aged exceptionally well. The song isn't too far afield from what was actually popping on the charts at the time, and its slick Musiq Soulchild hook is smoothly seductive, while its slight keyboard lick is incessantly hooky and tough to deny.

Producer: The Grand Wizzards

Album: Things Fall Apart

Label: MCA

It may take a more tasteful tack than similar back-in-the-day celebrations of hip-hop history, but the Roots' “Act Too” belongs up with 2Pac's “Old School” and Ahmad's “Back in the Day” as an example of how to craft nostalgic mash-notes to your artistic inspiration. Black Thought's opening alone is a dynamic burst of action written in compact couplets: “The anticipation arose as time froze/I stared off the stage with my eyes closed and dove/Into the deep cosmos, the impact pushed back the first five rows.” Now that's writing. The beat glimmers, the strings swell, and the song demands rewinds, Black Thought and Common's heartfelt devotion to their craft a moment of earnest transcendence.

Producer: Questlove, Khari Mateen, Ray Angry

Album: Undun

Label: Def Jam

The death scene of the Roots' ambitious concept album Undun was the record's only single, yet it flies by in a blink. Big K.R.I.T. opens with a reflection on the rewards won along the way, while Black Thought raps from the perspective of a person falling into death. Few rappers have narrated from this perspective; there was Biggie's final words on “Suicidal Thoughts,” or Scarface's narration from “Never Seen a Man Cry.” But for Black Thought, it's a cavalcade of imagery evoking darkness and desperation: “I begin to vanish/Feel the pull of the blank canvas.”

Producer: Questlove, Jeremy Grenhart, Dice Raw

Album: How I Got Over

Label: Def Jam

A record about real tipping points, the Roots' “Now or Never” approaches moments of transition not with optimism, but with apprehension; Black Thought's verse is written from a moment of major self-doubt, one that suggests an autobiographical expressionism. Phonte is even less optimistic about his propensity to change: “My role is cast before I even audition for it/So I don't really see an end to my vice/It's just false reformation, no end of my strife.” For Dice Raw, who brings the song to an end, times of personal change can be moments of life or death; the only certainty is that they will come.

Producer: Questlove, James Poyser, Richard Nichols

Album: Undun

Label: Def Jam

The Bilal-assisted “The OtherSide” rides simmering organs while Black Thought and Greg Porn sketch the story of Undun's conceptual centerpiece, Redford Stephens. It's packed with abstract imagery; for Black Thought, the lyrics work in layers like the onion referenced in his second verse, an impressionistic portrait of how easily we can make the wrong decision given certain circumstances: “He never had enough and got confused when they asked why/Life is only a moment in time and then it passed by.” The song closes with Greg Porn's suicidal imagery and an evocative lyric about thoughts “dark as a glass of fucking Guinness.”

Producer: DJ Scratch, the Grand Wizzards

Album: Phrenology

Label: MCA/Geffen

Although Black Thought's rap style has been described as boring, it would be more accurate to call it dry: forceful and rhythmic, it fires with the percussive force of a drum, rather than floating above the fray, or working to melodic ends. It's especially evident on the aggro Phrenology album opener “Rock You.” With production by Scratch and the Grand Wizzards, the song's insistent bombast wouldn't have sounded out of place behind Redman and Method Man on Blackout!. But rather than go for the elastic style of either rapper, Black Thought's approach is thunderous and punchy.

Producer: Questlove

Album: Rising Down

Label: Def Jam

Second only to grown folks Sade raps, Black Thought is at his best rapping with deft intricacy over obstacle course breakbeats and buzzing basslines a la “75 Bars.” Initially released just prior to the wildly unpopular Fall Out Boy collaboration “Birthday Girl,” the song no doubt softened the blow, a purist's fantasy of intricate rhyming delivered with effortless fluency. Plus it has the agitated energy of revolution, with P.E.-ready agit-prop (“I'm a rebel, a renegade, must stay paid”) and boasts worthy of Rakim (“Cold smooth like that dude Sean Connery was playing”) while taunting inferior technical prowess (“I put a rapper in a hole where the dust will sit/For spitting played out patterns that once was hitting”).

Producer: Questlove

Album: How I Got Over

Label: Def Jam

“Doin' It Again” is a Black Thought lyrical workout centered around a strong flip of the vocals and pianos to John Legend's “Again.” Wedded to a thunderous breakbeat, the song is a propulsive banger that primarily serves for Tariq's internal rhymes: “Eat sleep it or bleed it, write it down and then read it/Asphalt to the cement, your trash talk deleted….”

Producer: Questlove, Ritz Reynolds

Album: Undun

Label: Def Jam

Undun was one of the most narratively ambitious projects not just in the Roots catalog, but in hip-hop writ large; the story of the death and life (in that order) of fictive composite character Redford Stephens. His narrators speak abstractly on “One Time,” occasionally lunging into reality to smash and grab or hop over gates in pursuit of a happiness that remains elusive. But mostly, the narrators speak with self-awareness (“We wylin' out of control”) and chest-beating pride (“Feared in the streets so if you ever see me out in y'all streets, find another one to occupy”). The song's rising piano tones have an uplifting inevitability, and shift in a repetitive cycle as if to illustrate musically the message at the end of Dice Raw's verse: “Tales from the streets, a life of high crime/To make it to the bottom, such a high climb.”

Producer: The Grand Negaz

Album: Do You Want More?!!!??!

Label: DGC/Geffen

One of the Roots' most evocative records, “Silent Treatment”'s soft-focus groove was the platonic ideal of how to make maturity sexually appealing. With its saxophone and feather-touch keyboards creating a silky R&B backing for Black Thought's carefully sculpted narrative, adult relationship trouble suddenly gained dynamic power: slinky, sexy, grown folks music in the best possible sense. One of the group's best iterations was as hip-hop's version of Sade, effectively selling wine-and-candlelight romance (and the tumultuous tremors of the heart that came with it) as not a stern, staid sound, but a sleek and sophisticated one worth aspiring to.

Producer: Questlove

Album: Rising Down

Label: Def Jam

The title track and opener from the Roots' 2008 album, Rising Down, rode a ferocious guitar loop (an ingenious sample of Grand Funk Railroad's “Nothing Is the Same” courtesy Questlove) and thumping drum track (also, it's safe to say, courtesy Questlove). Its three verses are well-balanced: Mos Def's writing is elusive and artful, implying hypocrisy through abstract juxtaposition of imagery (“Grapes of wrath in a shapely glass…“). Styles P, who closes the record, is direct, observing the systemic hypocrisy of illegal drugs vs. drug companies. Black Thought's verse takes on the unsexy subject of climate change, which is difficult to rap about effectively (“How you want it bagged, paper or plastic?”), but as protest songs go, the record's lyrical breadth is admirable.

Producer: Chaos, Questlove

Album: Illadelph Halflife

Label: DGC

Little of “Episodes”' street-level realism will remind you that you're listening to a hip-hop band. The song's grimy snapshot of inner city life, so common to rap records of the time, is a lyrical portrait first and foremost, and carries a parallel bleakness that today would sound out of place on a Roots record. Of its darkest moments, Dice Raw's harrowing story of Tauseen, an ambitious kid who ends up murdering his own younger brother, is perhaps the most haunting. In tone, “Episodes” is most reminiscent of records like Lord Finesse's “S.K.I.T.S.” or Big L's “Street Struck,” a stark and unrelenting document of the world's cruelty: “Niggas causin' mayhem, from p.m.'s to a.m.'s/America's worst nightmare—guns in kids' hands.”

Producer: Questlove, Alectrick.Kom

Album: How I Got Over

Label: Def Jam

The use of indie star Joanna Newsom proved to be—perhaps unexpectedly—a stroke of inspiration. Her unusual vocal style is sui generis, its twisted, high-pitched tone a unique flavor reminiscent of Erykah Badu's gentle ambiguity on “U Got Me.” “Right On” proved late in the Roots' career that the group still has a facility for accessible ambition. Black Thought's verse is solid, but Sugar Tongue Slim's guest spot defines the record, playing off the hook's promise: “I'm above and beyond hot, my measurement in watts/Time rate of flow and energy ain't never going to stop” and the cipher-worthy Canibus-isms of: “I flip my incandescents to flourescents/And in essence I can burn 1,000 joules of energy per second.”

Producer: J Dilla

Album: Things Fall Apart

Label: MCA

Things Fall Apart marked not just the Roots' commercial breakthrough, but the beginning of the Soulquarians collective's creative explosion: Soon records by Erykah Badu, D'Angelo, and Common would redefine the sound of underground hip-hop along a new axis, thanks in large part to the brilliance of a Detroit producer named Jay Dee. Although initially derided for his role in the last days of A Tribe Called Quest, history has proven Dilla's contributions as durable as Tribe's own early work. “Dynamite” was archetypal Dilla, an understated sample that rode the drums not quite on the beat, but at a slight angle, a rhythmically prismatic effect that allowed more creative opportunities for rappers to work. On “Dynamite,” a simple guitar figure comes in and out unpredictably, dropping out and entering again only to be pulled back. Black Thought and ELO the Cosmic Eye played off on what Black Thought would later call an “echo style”—where the first line of verse reflects the last line of the verse before it.

Producer: The Grand Negaz

Album: Do You Want More?!!!??!

Label: DGC/Geffen

Before the Roots became known more for their holistic vision, they were a group whose focus was a jazzy, neo-soul bohemianism. “Mellow My Man” captures the more playful lyrical style of early Black Thought and Malik B, who trade off verses that are interested in the resonance of internal rhymes and the artistic possibilities of alliteration as they were the meaning beyond. Partway through, the song breaks into a walking bassline, while Scott Storch's shimmering Rhodes gave the group a particular sonic signature, toying with the possibilities a live band could bring to a hip-hop context. The sound of early Roots was one of freewheeling experimentalism; while they would move in the direction of more focused composition in the future, there was a freedom to the early work that suggests limitless potential.

Producer: The Roots, Richard Nichols

Album: How I Got Over

Label: Def Jam

How I Got Over brought clarity to a group that had embraced a darker sonic template over the past two albums. This new approach was never brighter than the good-day-sunshine vibes of “The Day.” A feature for true school hero Blu and Little Brother/Foreign Exchange's Phonte, the song starts with Blu's damaged depression (“Everyday I wake up I stare into space and don't say much/Peer in the mirror, feeling dead from the face up”), shifts to Black Thought's anxious stasis (“Feeling like I'm checking out a game from the sidelines/I got to try different things in these trying times”) before resolving on Phonte's pragmatic optimism: “My preacher man told me it could always be worse/Even the three-legged dog still got three good legs to lose/So you can stop and refresh the rules/Breathe in, breathe out, let it heal all your exit wounds.” The whole time, the record's backdrop gives the song a hopeful tone that belies its dark context.

Producer: The Grand Wizzards, Scott Storch

Album: Things Fall Apart

Label: MCA

Based around a Scott Storch-composed piano groove, The Roots' “Adrenaline” could have slid easily onto a Big Pun record of the day—only ?uestlove's foregrounded drums suggested this was more of a Roots record. In fact, Big Pun was originally slotted to be on the track, in exchange for Black Thought's appearance on “Super Lyrical.” Alas, Pun was arrested for double parking outside the Tunnel nightclub that night, as Black Thought revealed in a Complex interview, and it was not to be. Luckily, Beanie Sigel was within earshot. Thought had known Sigel since elementary school, and the duo reunited along with Dice Raw and Malik B for one of the hardest rap records in a competitive year. While Beans' verse is economically brutal as always (he opens his verse robbing drug dealers and threatening to bring out the pliers), we gotta give it up to Dice Raw for one of the most memorable openings of all time: “Beans passed the Mac and we held em, like hostages/Rappers see me, hide they face like ostriches.”

Producer: The Roots, Richard Nichols, Owen Biddle, Pedro Martinez, Brook D'Leau

Album: Game Theory

Label: Def Jam

A standout go-for-the-gut banger on The Roots' otherwise labyrinthine Game Theory, “Here I Come” matches the album's remainder only in acidity: an abrasive workout for the full Roots lineup, the song is an adrenaline-packed record strong enough to make both the Superbad soundtrack and Late Night with Jimmy Fallon as entrance music. Aficianados could spend days debating whose verse is the true standout, but the record is stronger for the divergent styles of Black Thought, Dice Raw, and Malik B—especially B, whose “sloppy” flow to close the song recalls RZA's. It's a moment of beat and rhyme colliding efficiently: the production's sizzling synths and serrated guitar work in tandem to give “Here I Come” a tumbling momentum reminiscent of a Hot Boys record as much as the Roots' own uptempo workouts.

Producer: Questlove, Jeremy Grenhart, Dice Raw, Richard Nichols, Rick Friedrich

Album: How I Got Over

Label: Def Jam

Although it does include one rapped Black Thought verse, the Roots' “How I Got Over” is as much a traditional soul record as it is a rap song. With a sung hook courtesy Dice Raw and sung verses from Black Thought himself, the band takes an unconventional strategy that was more common four decades prior. It is at once a lament for the social conditions of the hood and a therapeutic release, an uplifting sonic blanket for the cold chill of the world's social ills. It works in part due to its repetition: a '70s groove whose repeated melodies promise escape. It directly addresses the most limiting myths (“They tried to convince me that I ain't trying/We uninspired, we unadmired”) to fight a rationalized status quo.

Producer: The Roots, Khari Mateen, Brook D'Leau

Album: Game Theory

Label: Def Jam

Game Theory was an unapologetically Roots album—the new Def Jam allegiance, if anything, only reinforced the group's sense of confidence in themselves. That's about the only thing they were certain of, as Game Theory was one of the darkest records the group would record, a reflection of uncertain times. “Clock With No Hands” is perhaps most representative, as well as one of Black Thought's best lyrical performances. Only rarely does he touch on the specific, as with the likely reference to Malik B, who was wrestling with drug addiction: “My brother back in rehab, just had another relapse/Within himself, it's been like he's been fighting an inner Jihad.” The song provides an uncut snapshot of his state of mind: distrustful, ever paranoid, full of regrets framed by furtive suspicions.

Producer: Questlove, Cody ChesnuTT

Album: Phrenology

Label: MCA/Geffen

“The Seed (2.0)” was one of the Roots' most successful crossover moments, an immediate and catchy pop-rap-rock record. Hoisting “The Seed” from Cody ChestnuTT's then-celebrated The Headphone Masterpiece, a bedroom recording of alt-rock records which had garnered some critical traction, The Roots blew the song up to its full-screen potential. Black Thought's verses, rapped through distortion, were somewhat beside the point next to the hook's unapologetically obvious sexual metaphor, which was so absurd that it snuck past the censors. Then, of course, there was the song's scratchy stop-start guitar hook, which was much more direct and shameless than the Roots were typically known for—very rock'n'roll.

Producer: Questlove

Album: The Tipping Point

Label: Geffen/Interscope

Over a steady funk groove and a sample of Sly Stone and the Family's “Everybody Is a Star,” Black Thought opened The Roots' 2004 album The Tipping Point. Over three verses, Black Thought contrasts a violent world with the potential to transcend it. “There's a lot of bullshit filling the scene/Where everybody's a star and hot shit is few and far between/We lose the grip of what garbage mean,” could have been written in pretty much any era of pop culture (certainly it feels more true today, with the Internet's signal-noise issues, than in 2004), and seems to undercut his message. But what follows takes aim at the real strictures of rap stardom at the time: “Shorties wanna be theyself, I know it's hard to be/Don't wanna do the Ruben Studdard and come off less threatening/Keepin it real will killing you if you end up letting it.” The song's best attribute, though, is its slick delayed-handclap groove, which shuffles effectively even at a slow tempo.

Producer: The Grand Wizzards, Scott Storch

Album: Things Fall Apart

Label: MCA

The Roots' peak crossover moment also happened to be one of their best records, a delicately enchanting song that gave standard promises an unspoken depth. The Roots wove a sparse, enigmatic tapestry that suggested sexuality in poised and adult terms. “U Got” Me” sees devotion not as an endpoint, but as the beginning of a more intriguing journey. Seduction, after all, goes well beyond the early stages of the crush; the consummation of love can be as evocative, as mysterious and fully engaging, as its promise. There is coy teasing—Eve pulling a “Psych!” joke on Black Thought partway through, which works in spite of its silly earnestness (and isn't love silly sometimes, anyway?)—but the overarching mood is one that suggests, counter to hip-hop's then-dominant narratives of control, that love is about letting go, about giving oneself up to its larger, inscrutable logic. How else to explain the lifelike absurdity of a couple that lives on the same floor but first come into contact at Élysée Montmartre? Or the way Black Thought's narrative focuses on the circumstances of their love through details, leaving love's story at the song's unspoken center? Famously, a then-unknown Jill Scott wrote the chorus, but the group ended up using Erykah Badu for its official release due to label pressure. It may have worked out in their favor; Badu's vocals have a subtle, honeyed tone that magnifies the song's addictive uncertainty. “U Got Me” ends with a drum'n'bass coda, an effective quickening of the pulse.

Producer: Questlove, the Grand Negaz, Raphael Saadiq

Album: Illadelph Halflife

Label: DGC

It might be tough to put yourself in the mindstate of '96 now—it feels like questions about 'conscious' and 'commercial' hip-hop have, in some ways, been resolved, or those Manichean tensions have shifted. The Roots are, after all, employees of one of the biggest corporations in the world, and pretty much every artist is involved, in some way or another, with corporate entities, whether it be carbonated sugar water sales or even major labels, as inefficient as they may be in 2014. But at the time, hip-hop was well on its way to becoming a true commercial proposition: 2Pac and Biggie were two of hip-hop's biggest stars, and hip-hop's imminent crossover was a constant conversation. The Roots stood up for their truth, a message of rebellion in a financial climate that was sure to encourage capitulation. UGK's Pimp C, who saw the video's parodic tone as an insult to Too $hort, would go on to attack the group directly on “Top Notch Hoes”: “Bitch nigga get some nuts, bitch nigga say my name/We ain't got no time to be guessin and playin no pussy ass games/What they do, what they do, niggas was corny as fuck/You gets no play in that Texas, yo shit don't bump in the trunk.” Time smooths over such concerns. Both acts are highly respected, places in the canon firmly entrenched. What lasts is the song's sincerity and musicality: with Raphael Saadiq providing a sensuous confidence, the record's spare, atmospheric production is enveloping, its slinky atmosphere history's most comfortable strategy to buck conformity.