When Ahmir Thompson decided to switch to a digital DJ rig several months ago, he knew he faced an uphill battle: The Roots' drummer owns more than 60,000

When Ahmir “?uestlove” Thompson decided to switch to a digital DJ rig several months ago, he knew he faced an uphill battle: The Roots' drummer owns more than 60,000 specimens of vintage and otherwise irreplaceable vinyl, from high school stage-band albums circa the 1970s to jazz gems never issued on CD. Until recently, prepping for a DJ gig meant simply pulling whatever he needed from the library-style shelves in his record room. After watching several of his peers use the Rane/Serato Scratch Live computer interface, which replicates intricate vinyl-scratching maneuvers without the usual MP3 delay, he was convinced that the transition was worth enduring a slow ramp-up period.

“Seemed to me a trade-off of convenience,” Thompson says, sitting at his Apple laptop in The Roots' Philadelphia studio headquarters, probing the far corners of the Apple iTunes music store on the endless search for rarities. “The downside is, I can't just grab stuff off my shelf and go right now — I pay somebody to come in on a weekly basis and transfer the vinyl. Already, I have 17,600 MP3 files. Eventually, it'll be possible to call up almost anything that I'd use on vinyl, which is important to me because during an average three-hour set, I might cram in 200 or 250 pieces of music.”

Thompson brings the same intensity to his DJ work that he does when driving The Roots, the pathfinding band that is one of the rare hip-hop acts to not simply sustain a recording career for more than a decade but actually evolve artistically along the way. He considers himself a music historian: His father, a doo-wop singer, turned him on to all kinds of music growing up, and during Thompson's performing-arts high school years, he played in jazz bands, as well as with the singers who became Boyz II Men, before he explored hip-hop.

While DJing, Thompson juxtaposes unexpected pieces with clever, inventive segues and has been known to connect vintage jazz, spoken-word tirades and heavy-metal guitar riffs with drumbeats and breaks he records himself specifically for his DJ sets. Thompson has a standing Saturday night at Philly's Fluid when he's home, and he travels to spin when he's not on the road with The Roots.

No matter where he is, he thrives on confounding expectations. “There are so many audiences I have to please when I'm spinning, including the manager and the barmaids,” Thompson says. “You got to impress them if you want to be back. So after two hours of hip-hop, I have been known to start playing [Metallica's] “Enter Sandman” or the theme from Family Ties. I'm always thinking about the 1 a.m. moment, the drinking hour. The other night, I was in Chicago, and for some reason, it seemed like a good idea to play gospel. People at first were like, ‘Whaaat?’ But it worked. To me, that's like finding the ultimate wave to surf.” Here are some of the songs that are helping him find those waves.


“Buttercup” (Epic)

Carl Anderson was an actor [The Color Purple, Jesus Christ Superstar] who tried to get a music career going in the 1980s. Somehow, he got aligned with Stevie Wonder. The first time I heard it, I thought it was Stevie — he's got the killer L.A. musicians and an effortless way of singing. When I finally tracked down the album, I learned that the song was written by Stevie, but he never recorded it.


AWB/The Clover Sessions(Sony)

It's the original version of the album with “Pick Up the Pieces” and all those great songs. The story goes that the band was on MCA and got Wilco'd. Atlantic picked 'em up but didn't like the existing versions of these songs, so they rerecorded the whole thing and cleaned 'em up. The band owns the masters to the original, and they put it out last year to mark the 30th anniversary. Maybe I'm weird; I like the grimy-sounding stuff. To me, the original is much more interesting. All the way through, there's more energy. This is a DJ weapon, and now it's available in stores.


“Mother” (Columbia)

That's quintessential, classic Chicago right there: the stop-on-a-dime horns, the melody changing every little while, not to mention all of the tempo changes. And yet it's all crammed into a four-minute pop experience. I sometimes use the acoustic-guitar intro to [Chicago's] “Beginnings” in a club, and it really sets up a mood of anticipation. People know it, but they don't know from where, and it can transition into almost anything. Plus, it has a little bit of cred — try playing “You Make Me Feel Like Dancing” by Leo Sayer for a bunch of black people.


“Are You My Woman? (Tell Me So)” (Brunswick)

To me, one of the most important aspects of playing records is slipping in some background way below the radar so people don't even know it. If I utterly hate a song, I won't play it; I don't care how popular it is. But if there's a hit out there built on a cool sample, I'll do the history-lesson thing. So I grabbed this when Beyonce's “Crazy in Love” was happening, just to connect the dots for people. Or let's go to the jazz pages of iTunes and check out [British jazz pianist] Jamie Cullum's version of that Pharrell track “Frontin.'” People know the song, but they hear this, and it takes 'em sideways a little bit. Play this in a ghetto club, and you're blowing people's minds.


“Darling Nikki” (Vitamin)

I love to throw people off. The other day, I played — just as a joke — Carmen Elektra's first record, the one produced by Prince. People looked at me like I was crazy, and so, naturally, I had to follow that with a half hour's worth of really bad music. I'm a total sucker for these string-quartet tribute records. For club purposes, I like the ones where there's no drums. This, I found the other day, and I put it right into a club set I was doing in Memphis — even fooled my own band. It sounds like The Lion King or something.


“What Have You Done for Me Lately” (Daptone)

There's nothing better than a totally unexpected cover, and this version of the Janet Jackson song — by this wonderful band from Brooklyn — totally qualifies. Lots of cats have sampled this, and, still, there's something about the groove that really holds people. I gravitate toward grooves that I like and would play as a drummer. It helps that it sounds great: The way these guys engineer their records, with tube amps and a lot of live-room feel, has me losing sleep.


“Whole World” (Arista)

Sometimes, I'll give myself certain challenges when I'm working. I hear this, and I go, “Man, what a great beat; let me see where I can take it.” It's a shuffle groove, so I'll try to put together, like, a shuffle set, with four or five other things. From Outkast, I might want to go into Michael Jackson's “The Way You Make Me Feel” or James Brown's “Doin' It to Death,” Luther Vandross' “Bad Boy Having a Party,” maybe end with “Rock and Roll Pt. II” by Gary Glitter. Something like that works like gangbusters right in a row.


“Hurry on Now” (Tru Thoughts)

I know Joss Stone is winning the race for “Ha-ha, fooled you, white-girl soul singer,” but listen, because she's not the only one. Alice Russell's voice is astounding. This is what soul singing is to me — I was starting to think that singing was becoming a lost art, and then I heard this. She's pacing herself; she's not doing runs every 12 seconds. She's really drawing you into the song the way Aretha used to do. This, you can put on early in the evening, and right away, you establish a vibe. It'll probably be in heavy rotation for the next few months when I spin.

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