The Roots’ Best Songs, Ranked

Across more than 30 years, The Roots have cemented themselves as the greatest live instrumental hip-hop act in the world. Led by drummer/bandleader Questlove and leading mic man Black Thought, the Philadelphia-born group seeped even deeper into mainstream consciousness when they also became the house band for The Tonight Show with Jimmy Fallon in 2009. It’s nothing to sneeze at for a hip-hop group and while your average consumer likely just knows them from TV, The Roots’ over a dozen album discography contains some seriously pivotal hip-hop classics.

Fusing hip-hop with a jazz ensemble, R&B vocals, soul breaks, rock, and more, The Roots are in a class all of their own. From seminal albums like Things Fall Apart, How I Got Over, illadelph Halflife, and beyond, we’re taking a look at the best songs by The Roots below. And if you want to see these songs live for yourself, The Roots are performing a pair of New Year’s Eve shows at the Walt Disney Concert Hall in Los Angeles to ring in 2023.

But without further ado, these are The Roots’ best songs, ranked.

30. “Swept Away” (1995)

The opening bassline (by the dearly departed Leonard “Hub” Hubbard) and saxophone swing put down a groovy jazz club feel. Singer Cassandra Wilson’s backing hum throughout the track is hypnotic and Malik B’s (RIP) coy flow elevates one of the first full-on assaults from Black Thought (“Crazy cardiac, my attack on any fat rhythm”) that just made your head turn.

29. “When The People Cheer” (2014)

While The Roots’ last album, …and then you shoot your cousin isn’t generally considered to be among their top works, they still always find ways to tell stories about people trying to rise up from the ills of inner-city life. “When The People Cheer” sees singer Modesty Lycan delivering the play on words hook that became a hallmark of Black Thought’s songwriting in The Roots’ late-career surge.

28. “What You Want” (1999)

Debuting on the crucial live album, The Roots Come Alive, “What You Want” also ended up serving as the opening song from the soundtrack to The Best Man with Taye Diggs and Nia Long. Featuring Jaguar on the hook, the song’s lyrics tell a story in line with the cult-favorite Black romcom’s matrimonial love triangle. And after thriving in the underground, “What You Want” shows The Roots’ ability to pierce through it and become a bigger act.

27. “The OtherSide” (2011)

When James Poyser joined The Roots for good in 2008, the Soulquarian producer sent the group’s keyboard parts soaring. With Questlove, Poyser, and manager Rich Nichols (who died in 2014) orchestrating behind the boards, “The OtherSide” is among the group’s tightest productions. And for additional posterity here, Bilal is on the passionate hook.

26. “Break You Off” (2002)

Phrenology proved to be a deconstruction album of sorts for The Roots. It’s easily their most experimental album and “Break You Off” is sublime R&B featuring Musiq Soulchild’s velvet vocals on the album’s first single. Questo’s drums are tinged with bossanova, while Black Thought’s flow serves as a sinister and meditative lothario over a hard bass line.

25. “Essawhaman?” (1993)

The Roots’ first album Organix, helped them get their first label deal that would eventually lead into Do You Want More?!!!??! being released on DGC. Organix was first only sold on a modest European tour and the recording of “Essawhaman?” featured on the album is from a gig in Slovenia, soon after Hub joined the band. It helped establish the group’s unique lyrical lexicon and later appeared in a different live version (from Philadelphia’s Trocadero) under the title “Eassaywhuman” on Do You Want More?!

24. “Without A Doubt” (1999)

Predicated on an absolutely filthy breakbeat that Questlove borrowed from Philly rapper Schoolly D’s track “Saturday Night,” “Without A Doubt” shows how The Roots didn’t just sample tracks, they recreated them. “Another one of our in-house geniuses, Chaos, suggested that if we were going to ‘go there’ (Hip Hop’s ever so effortless task of ‘creating’ the cover tune) we should keep it ‘ill’ (adelph),” Questlove said in the Things Fall Apart liner notes. “We hope we did the city proud by this one.”

23. “Guns Are Drawn” (2004)

The Tipping Point is probably the most underrated album by The Roots. It didn’t get the same critical praise as their more heralded works, but “Guns Are Drawn” is a prime example of the gems that lay within. It’s a modern funk and soul original that feels instantly vintage. Son Little’s hook gives a retro veneer to exploration outside of hip-hop’s confines.

22. “Lazy Afternoon” (1995)

This jazzy, R&B tune brings together the elements of scat that resided throughout Do You Want More?! but in a far smoother package swathed in Rachel Graham’s backing vocals. “Lazy Afternoon” is the soundtrack to literally that; there’s hardly a better song to throw on when things need to get done and you’ve made the conscious decision to procrastinate happily instead.

21. “Proceed (Live)” (1999)

One of The Roots’ defining live songs, “Proceed” is a standout off of Do What You Want More?!, but its galvanizing power is most evident on The Roots Come Alive. Recorded from a show in France, the chewy keyboard part is unreal while Rahzel sprinkles in his beatboxing in incredibly tasteful fashion. It’s a signature call-and-response track that still manages to come across like a supreme Philadelphia jam session.

20. “Don’t Feel Right” (2006)

Game Theory marked The Roots’ first album released under the Def Jam imprint and they took the opportunity to make a sociopolitical stance. “Don’t Feel Right” proved to be the most well-formed statement from the album, imploring listeners to pay attention to the insidious oppression in America. “The struggle ain’t right up in your face, it’s more subtle,” Black Thought spits, paving the way for more of this type of commentary from the group for years to come.

19. “Radio Daze” (2010)

How I Got Over was a decidedly pop-forward turn for The Roots and they brought an unapologetic group of wordsmiths along for the ride. Blu and P.O.R.N. are featured on “Radio Daze,” with Dice Raw making another return to the group on the hook. Just like how “Don’t Feel Right” did, “Radio Daze,” is a call to pay attention to injustice. But four years later, The Roots surmise that there are multimedia forces clouding our perspectives. A piano rests alongside Questlove’s drums to make it feel like a eulogy that’s about to be written if something isn’t done about the condition.

18. “Not Sayin Nothin’ New” (1999)

Black Thought and Dice Raw are very much challenging each other on this cut off of Things Fall Apart. The melody truly stands out on “Nothing’ New” and it even features a hint of Eve’s vocals underneath the track. But it’s ultimately one of Black Thought’s greatest moments on their best album when he raps: “Yo, I’m overpaid in dues, blood, tears and sweat. When you f*ckin’ with The Roots, that’s as good as it get…Ultramagnet!”

17. “Kool On” (2011)

Questlove produced “Kool On” around a sample of D.J. Rogers’ “Where There’s A Will,” giving it a fresh soul sound. Kirk “Captain Kirk” Douglas’ delivers one of his best guitar riffs with the group to take the track to new heights. Greg Porn and Truck North each drop a verse on the gangster boogie and Black Thought slays a sleek hook, singing “Come get your kool on, stars are made to shine.”

16. “How I Got Over” (2010)

The title track to How I Got Over features one of Questlove’s best drum beats on the album. Dice Raw joins Black Thought once again for a song about rising from the streets and they come across like kids from Philly who got out and want to help others do the same. Raw’s “Out on the streets, where I grew up. First thing they teach you, Is not to give a f*ck,” lyric is sharply honed, articulating the hood mentality and making sense of a senseless life of crime in America in a way that still resonates.

15. “Mellow My Man” (1995)

There’s a unified groove on Do You Want More?! That much is undeniable. And “Mellow My Man” is soaked with the essence of it. It’s the pinnacle of Black Thought and Malik B’s jazz-scat vocals where you get the sense that this album was very much forged with an underground supper club in mind. This is a track meant to be consumed live and direct, and “Mellow My Man’s” jazz sensibilities (the horn section might as well be in your living room) are what made The Roots the incomparable live hip-hop force that they went on to become.

14. “The Next Movement (Live)” (1999)

No respectable Roots fan can ever hear a mention of Switzerland again without their minds going to Black Thought hyping the crowd at Zurich’s Palais X-Tra shouting, “Switzerland!” On the Come Alive version especially, Rahzel’s twitchy beatbox slides in so fluidly with the band and the organ is among the most defining sounds of any song by The Roots. This is an ultimate hype track.

13. “Respond/React” (1996)

The first song on Illadeplh Halflife, “Respond/React” was The Roots’ grand introduction into Golden Age rap greatness. It’s a Philadelphian diatribe that asserts how no matter where The Roots crew goes, their heartbeat will always be in the city of brotherly love. Black Thought puts on a masterclass in syncopation, finding rhyme patterns where they’re not supposed to be and while the album will eventually straddle genres, “Respond/React” is undeniably hip-hop.

12. “Adrenaline!” (1999)

How this collision of rap and jazz manages to even incorporate a full-on beatboxer into the mix and not make it feel frivolous is one of the greatest achievements in hip-hop history. “Adrenaline!” sees Rahzel at his peak, beatboxing in congruence with Questlove’s drums and a keyboard melody to kill, before giving way to verses from Beanie Sigel and Dice Raw. And while Rahzel’s time with The Roots would soon come to end, “Adrenaline!” saw his novelty in its ultimate state.

11. “Silent Treatment” (1995)

The Roots made a lot of great R&B songs and “Silent Treatment” sees them in their early days slaying the genre in pure, unadulterated form. A sexy horn and sensual keys make way for Black Thought lamenting a love that he just can’t harness. It was a song for sad hip-hop kids before that became a thing and it’s still just as evocative today.

10. “Step Into The Relm” (1999)

It’s really unfair how many perfect drum breaks Questlove puts his stamp on throughout Things Fall Apart. He makes incredible complexity come across with utter poise on “Step Into The Relm,” a track that tugs at anticipation with false fades and gambles on a piano loop that never ends. It’s probably the fiercest track on the album, with Malik B and Black Thought delivering the hook in chilling, soldier-like unison.

9. “Star/Pointro” (2004)

When The Roots sample songs, they sample really good ones. And the opening track to The Tipping Point makes excellent use of Sly & The Family Stone’s “Everybody Is A Star.” The way “Star/Pointro” builds into its explosive beginning is such a brilliant way to kick off an album; as if the group is trying to tell us as emphatically as possible to brace yourself, because they are back for another triumphant go at it.

8. “Dear God 2.0” (2010)

No track testifies to the malleability of The Roots and their inevitable longevity quite like “Dear God 2.0.” In a most improbable collaboration, The Roots and Monsters Of Folk (led by My Morning Jacket’s Jim James and Bright Eyes’ Conor Oberst) turn the latter’s psychedelic tune into a haunting plea to the man upstairs. Black Thought’s opening verse might just be his finest post-2010 moment with The Roots and James’ high-pitched hook came across so naturally in a song that blends rap, folk, and pop in amazing ways.

7. “Dynamite!” (1999)

You know those insane drum breaks on Things Fall Apart that I mentioned earlier? This is the one. And maybe it’s because Questlove takes a beat he got from J Dilla and gives it the royal treatment. “I want to be part of the process,” the drummer recalled in the Deluxe album liner notes. Because instead of just using the Dilla beat, he insisted on playing it to the record. And it sounds heavenly alongside yet another stupefying bass line; this combo never gets old.

6. “Section” (1996)

This is how you build a soundscape. And in 1996, hip-hop didn’t sound like this. “Section” takes the brushstrokes that “Respond/React” laid down and adds bursting sounds and layers of senses that constructs the world of illadelph Halflife as it was just beginning to unfold. Black Thought and Malik B are as sharp as can be, flashing their whimsy while not giving up an inch of their edge.

5. “100% Dundee” (1999)

As far as opening bars to rap songs go, Black Thought’s, “On these seventy-three keys, of ivory and ebony, I swear solemnly that I’ll forever rock steadily. People wanna know where Malik? He right next to me, the weaponry, the secret recipe,” should be mentioned in the same breath as Wu-Tang’s “Triumph.” The bass register is pulsating through the roof on “100% Dundee” and it’s quite possibly the best seesaw showing from Thought and Malik B. If anyone ever doubted early on if The Roots needed to always lean on their jazz chops, this sent that notion crashing.

4. “The Seed 2.0” (2002)

The Roots are polymorphous and they found the best way to explain that concept in “The Seed 2.0,” one they valiantly lay out throughout Phrenology. Working with Cody Chestnutt to revamp his original (hence the “2.0”; just like “Dear God 2.0”), the song is a treatise on the shapeshifting nature of hip-hop. Namely, how it’s everything: soul, jazz, rock, etc… If there was ever a song that’s about The Roots and how their music was continuing to evolve into something that might even have a place on The Tonight Show someday, this is it.

3. “You Got Me” (1999)

An autobiographical love song primarily written by Black Thought and Jill Scott, “You Got Me” featured Erykah Badu on Scott’s hook and the rest is history; Badu will do that. But Eve also put down her most well-known verse with The Roots as the foil to Black Thought’s protagonist too. Then Questlove manages to find a place for a drum and bass outro, which tipped a cap to the power of late ’90s UK jungle music that he had an affinity for. This is peak Soulquarians magic and it netted The Roots their first Grammy Award, forever etching “You Got Me” as an essential golden age of hip-hop cut.

2. “What They Do” (1996)

If you want to make one of the greatest hip-hop and R&B crossover tracks of all-time, Raphael Saadiq pretty much has to be involved. So here he is, on the hook of “What They Do,” essentially giving The Roots sage advice on the pitfalls of the music industry that they need to avoid in order to always be originals (“Never do what they do, what they do, what they do.”) Suffice it to say, they listened. The Roots have hardly ever sounded this gorgeous and Saadiq is a huge part of that. Amen.

1. ”Act Too (The Love Of My Life)” (1999)

Probably my favorite live music moment of 2022 was during The Roots’ headlining set at Montréal Jazz Festival, when the unmistakable melody to “Act Too (The Love of My Life)” flowed through tens of thousands of people at the Downtown Place des Festivals. The Roots were headlining a jazz music festival and my entire life’s relationship with hip-hop flashed before my eyes. It was beautiful.

“The Love Of My Life” defines the journey of The Roots; how they’ve transcended hip-hop, but never compromised their core dedication to the culture. “I thought it was important to have that song so that we could personalize and humanize what hip-hop was,” Questlove wrote in the Things Fall Apart Deluxe liner notes, explaining how Dilla and A Tribe Called Quest’s “Electric Relaxation” were touchpoints for them in crafting this beauty (which also features Common.) Few acts have navigated the ins and outs of hip-hop as fluidly and gracefully as The Roots have and “The Love Of My Life” remains a manifesto of sorts that they’ve never wavered from.