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R. Kelly doesn’t need to throw on a tuxedo and dig into a McRib sandwich—like he did at the photo shoot that accompanies this story—to demonstrate that he is a complicated guy. In fact, the 44-year-old Kelly is the walking, talking embodiment of complicated: Complicated because, as a singer, songwriter, and producer, he has worked with everyone from Quincy Jones and Ronald Isley to Jay-Z and Michael Jackson, and represents so much of what is both good and important and difficult-bordering-on-ridiculous about R&B. Complicated because he is, if not the inventor, the preeminent purveyor of both soul music–as–art rock and the slow-moving sex jam. Complicated because of the scope of his talent, which allows him to move so easily from making a club-ready album like Chocolate Factory (2003) to creating a more introspective one like Happy People/U Saved Me (2004). Complicated because of the near-visionary, bombastic ambition of projects like his 22-part, soap-operatic, audiovisual song cycle epic “Trapped in the Closet” (2005–2007). Complicated because he grew up not terribly well-off on the South Side of Chicago, and started out as a street performer, quite literally singing for his dinner. Complicated because his solo debut, 12 Play (1993), includes songs with titles like “Bump N’ Grind,” “I Like the Crotch On You,” “Freak Dat Body,” and “Sex Me, Pts. 1 & 2.” Complicated because he once referred to himself in a lyric as a “sexasaurus” and included a philandering little-person character in the aforementioned “Closet” epic. Complicated because so much of what he does shouldn’t work. Complicated because so much of it does. Complicated because of the video tape that emerged in 2002 of him allegedly having sex with an underage girl, reawakening questions about the nature of his relationships with a number of young women, and the subsequent child pornography charges. Complicated because of all of the legal wrangling that followed (Kelly was cleared of all charges). And complicated because as the difficulties of Kelly’s personal life have deepened, so has his work, moving beyond the patent uplift of a song like “I Believe I Can Fly”—as considerable a hit as it may have been—to a place of real heart, real soul, and real conflict. But for all of the big songs and bravado, what has really defined Kelly’s work is a certain fearlessness and a willingness, even in his most difficult moments, to do something very uncomplicated by delving head­long into all of the inspiring, disappointing, heroic, and tragic forces that make someone like young Robert Kelly throw his hat on the sidewalk, steady himself, and belt one out for the ladies.

Kelly’s impact on contemporary R&B cannot be overstated: So many of the themes and tropes of the genre, both the outrageous and the outrageously brilliant, are ones he created or developed or helped bring into the modern pop consciousness by adapting or reimagining them. During his tour behind 2009’s Untitled, Kelly began performing two songs by the late soul singer Sam Cooke. That set—as well as a Sam Cooke– themed party that Kelly threw at his Chicago home— inspired his recently released new record Love Letter (Jive), an old-school R&B album that explores, among other things, the subjects of love and forgiveness.

Kelly was in New York City in early December to promote Love Letter and to perform on Late Night With Jimmy Fallon. Singer, songwriter, and actor Will Oldham sat down with Kelly in his dressing room backstage at the show, which is recorded at NBC’s midtown head­quarters at 30 Rockefeller Plaza—the 30 Rock of 30 Rock—to discuss the making of Love Letter and why the long, bumpy road that led Kelly to make the album has him revisiting the past and thinking about the future.

WILL OLDHAM: Do you watch 30 Rock?

R. KELLY: No. What’s that?

OLDHAM: It’s a television show, a comedy, that takes place in all of these hallways. It’s pretty funny. It’s, like, a good sitcom. It’s got Alec Baldwin. You know Alec Baldwin?

KELLY: Alec Baldwin? Yeah! Don’t he have a brother and they all kind of look alike?

OLDHAM: They’re, like, four brothers.

KELLY: Steve Baldwin . . .

OLDHAM: Yeah, exactly. [laughs] So I wanted to start by talking about how you work. For example, is this new album, Love Letter, a set of songs that you were working on constantly, where you were focused completely on this project? Or were you also working on other songs along the way? How do you approach making an album?

KELLY: Well, you know, Love Letter is a concept album, and whenever I do a concept album—and I love doing concept albums more than any other kind of album—it allows me to get dressed, in a way, musically. It’s not just like a freestyle situation. To make an album like Love Letter, everything’s got to be about love. Everything has to have a great feeling when you listen to it. So once I’ve decided that, I’ve geared myself up. I’ve programmed myself musically to come up with love-feeling tracks that are romantic, sexy, but classy, all in one. And that’s the challenge. Once I create that music, then the lyrical content starts to come—you know, the stories and things like that. But I have to say, it was fun doing this Love Letter album because, hey, man, love has never failed. It has won every battle. And today and forever more it will go on undefeated. I’m also a very loving person.

OLDHAM: But do you remember the day when it started? When did you start to think, I’m making a record about love?

KELLY: Well, a party that I gave at my house influenced me. I gave a Christmas party last year—well, two Christmases ago—where I did a Sam Cooke show. I didn’t perform as R. Kelly. I performed the Sam Cooke show from 1964, when he performed at the Copacabana.

OLDHAM: You performed the whole set?

KELLY: I did the whole set. I invited, like, 1,000 people out to my house, and everybody had to be dressed like it was the ’60s. People had the long-stem cigarettes and the zoot suits and all that stuff, man. It was just a good time.

OLDHAM: And that was before doing the Sam Cooke miniset that you did on the tour?

KELLY: Oh, yeah—way before that. It was about a two-and-a-half-hour show that I put together in my living room. Built a stage and catwalk. I had the bulb lights and everything. I had tap dancers. I had a girl with me who sounded just like Billie Holiday. I had a guy who sounded just like Frank Sinatra. And then I did Sam Cooke. We had the marquee on the outside of the door, and I went and got old-school pictures of myself and we put them up like I was born back then and performing back then. We had a sign that said, “One night and one night only.”

Part 2-4 is at http://www.interviewmagazine.com/music/r-kelly/