We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

Tom Breihan’s The Number Ones column is currently working its way through the latter half of the 2000s, which means the T-Pain era is in full swing. From his debut in 2005 until the end of 2009, the Tallahassee-born rapper-turned-singer notched 33 Hot 100 entries, 13 top-10 hits, and three Number Ones, a dominant run that made his Auto-Tuned pipes the signature sound of the late aughts. A decade-and-a-half removed from the peak of that historic streak, T-Pain is still a beloved cultural fixture, but he’s never seemed too motivated to recapture those glory days.

Maybe it was the Auto-Tune backlash, most famously manifested in Jay-Z’s 2009 single “D.O.A.” and disparaging comments from Usher that sent T-Pain spiraling into a “four-year depression.” Maybe it was the management team he fired in 2019. Whatever the cause, right now T-Pain is content doing anything but chasing hits. Especially compared to his breakneck work schedule in the 2000s, he’s releasing music at a snail’s pace, dropping just two albums in the past four years. Last month’s On Top Of The Covers, featuring his take on an eclectic list of classics from Sam Cooke’s “A Change Is Gonna Come” to Black Sabbath’s “War Pigs,” is T-Pain’s most brazen embrace of his elder statesman status yet.

But mostly, he’s been busying himself with other ventures. He’s podcasting, he’s voice acting, he’s Twitch streaming, he’s winning the first season of The Masked Singer. After a tumultuous stretch of his career, T-Pain seems happy and fulfilled. In a conversation over Zoom, he was very much opposed to the idea of relitigating decade-old music industry dramas, but extraordinarily willing to open up about chasing his many passions, showing up completely unprepared for his Tiny Desk Concert, and — most importantly — not being an asshole.

On Top Of The Covers (2023)

I’m curious how long ago you initially hatched the idea to do a covers album.

T-PAIN: I was on vacation in 2018 and the idea came across the table, so it’s been a while.

And what made you want to do something like this?

T-PAIN: Man, after doing The Masked Singer [in 2019] I started heavily pursuing it because people were just real persistent about hearing me do different songs. I started the idea in 2018, and then The Masked Singer happened, and then it just became, “Yeah, maybe I should do this.” And then just piece by piece it started coming together. I started hanging out with different bands, finally found a great band that can pretty much run the whole thing, and I got all my ideas out.

More and more people kept asking for cover songs, and nobody knew I was actually doing the album. So it actually worked out right on time, right when people were asking for it the most.

And how’d you go about choosing songs to cover for this? I know you’d done Sam Smith’s “Stay With Me” and “A Change Is Gonna Come” in the past.

T-PAIN: They’re all songs that had something to do with a big part of my life, or or songs that I’d listen to back with no problem, just those special songs in my life. Like, “War Pigs” — I would always go to a clip of Jack Black singing it on a talk show. Anytime Jack Black comes up in conversation, I always go to that clip and just show people that he did “War Pigs.” I grew a liking to the song from that.

“Sharing The Night,” the Dr. Hook song, was on an episode of The Cleveland Show, and I’ve always wanted to be on The Cleveland Show. And then I was on The Cleveland Show, I was a recurring character. So I picked a song from that because that’s one of my favorite songs from the show.

Sam Smith’s “Stay With Me” was the song that won The Masked Singer for me, so I had to do that. I had to put that on there.

That’s quite a range of styles. Did you have a desire to showcase a wide variety of stuff?

T-PAIN: Not really. I actually didn’t realize the range of it while I was doing it. I always tell people don’t pass me the aux in the car, ‘cause you’re gonna hear some weird shit.

I try not to keep myself held down to any [one] genre or anything like that. It’s normal to me, but when other people see my playlists, they’re like, “Dude what, where were you? What were you doing when you made this playlist?” It’s normal to me though.

https://twitter.com/TPAIN/status/1639685131962134531

I saw you tweet about people mistaking every vocal effect you use on the album for Auto-Tune. How often do you still get that?

T-PAIN: All the time, 100% of the time, and it’s never gonna stop. That’s just what people know of me. It’s always expected, even when I walk into a room of people and then I talk and they’re like, “Oh, you sound like you do on your songs.” And I’m like, “How did you expect me to sound?” Like, why doesn’t anybody else get that? You know what I mean? If Jamie Foxx walks into a room and speaks, you’re not gonna say, “Oh, you just sound like that.” Nobody else gets that. It’s really fucking strange. But that’s just the nature of the beast. I welcome it with open arms.

NPR Tiny Desk Concert (2014)

That’s a decent segue into the Tiny Desk Concert. Whose idea was it to do that without Auto-Tune?

T-PAIN: I had no idea what the hell I was doing. I walked in there, I thought I was going in for an interview. I didn’t even know what I was doing that day.

Wow. How receptive were you to the idea of performing like, right off the cuff?

T-PAIN: Not really at all. At the time I was smoking cigarettes, and I had just smoked a cigarette before I walked in there, and that’s not good for singing. I was also very hoarse ‘cause I just had a show the night before in a club, and it was also smoky as hell. So my voice was at, like, 60% during that whole thing. I didn’t know what to do and I couldn’t back out while I was there.

But your band was there. Were they just coming along for the interview?

T-PAIN: No! I didn’t even know. I saw my keyboardist there and I was like, “What are you here for?” I thought he was just in town, just chilling. And then they walked us into a room with a keyboard and a stool, and I was like, “Oh, okay. What’s that? What’s going on?”

How long after that did you realize, oh, it was actually a good idea for me to do this?

T-PAIN: Once it became the highest viewed Tiny Desk Concert. Yeah, it took me a little while. The whole time before it came out, I was like, “Man, this is gonna end my career, I sounded like shit.” It was pretty surprising that people were like, “Oh, this is good.” I just knew I wasn’t a hundred percent during that. I was pretty afraid until it became the highest viewed Tiny Desk Concert.

Nappy Boy Gaming, Radio, And Automotive (2019-present)

In the past few years, you’ve expanded the Nappy Boy umbrella, which used to just be your label, into podcasting, gaming, and now even automotive. When did you first start thinking that this could be more of an entrepreneurial thing and less just a label?

T-PAIN: 2005, so a long goddamn time. But in the beginning, I had management, and it wasn’t really their concern. They didn’t really give a shit about what I’d like to do. It was never a pursuant thing for them, they just wanted to just sit back and make me make music, and they wanted their cut of that.

None of my passions were really important to anybody that I ever worked with, which is why I’m doing it now, because [as of 2019] I don’t have any management and I can actually pursue my passions. It’s an easier thing to do once you start realizing what you can do when you’re more hands-on and it’s not a job anymore and it’s actually something you actually wanna do. It’s not “chasing the hits,” and “I gotta be in the studio every night because if I don’t hit the studio every night, then I’m not gonna be able to survive.” Not having to keep my head in the music game and actually do things that I want to do, it’s different now.

But you know, having management over my head, like, “Why are you out there throwing cars at walls? Why are you in the studio playing video games?” When you get all that talk, it makes you not want to do those things anymore. So now that I’m in charge, here we are. All that shit. I get to do everything I want.

Cameo In Furious Seven (2015)

How did this cameo come about?

T-PAIN: I was hanging out with Tyrese and Vin Diesel a lot. I was on set a lot at [Fast & Furious 6], and it just came up a bunch, like, “Hey, you wanna be in the next one?” Hell yeah, I’ll be in the next one. Let’s do it. And then that happened. There’s not a crazy story behind that, I was just hanging around them dudes a lot.

What do T-Pain, Tyrese, and Vin Diesel do when they’re hanging out together?

T-PAIN: Just hanging out whenever they got off set, we would just chill at the house — champagne, talking about weird stuff. Vin Diesel wanted to make a rap album back then, but obviously he didn’t go through with it.

Cartoon Voice Acting (2009-present)

Predating that, you’ve worked with Adult Swim a bunch. You were on The Cleveland Show. You did the singing voice of Tom in the Tom & Jerry movie. It seems you’re a huge fan of cartoons — Is that something you knew you wanted to do early on in your career?

T-PAIN: Not really. I’ve always been into cartoons. I’m still into it; I can’t go to sleep without ’em. I think I just still have my sense of wonder, you know what I mean? I still have a childlike adventurous thing, so cartoons are a big part of that. I don’t think I’m ever gonna let it go.

So you weren’t actively pursuing that?

T-PAIN: Not at all. It came about because I knew so much about the animation world and the cartoon industry, and I would always tweet about it. Adult Swim saw that, and I got invited up there, and I knew everything about everything that was in the building. They were like, “Man, we gotta get you on to some of this.” Even me not being pursuant of it, I still was very knowledgeable of the industry, so it was a pretty easy segue. And I’ve been told I have a distinctive voice, so that probably helps too.

How often are you approached to do extracurricular stuff like this, something you never expected you’d be doing?

T-PAIN: It wasn’t so often in the beginning because I was never put in those positions to pursue anything other than music. It’s happening a lot more often these days than it was back then, because people were withheld from my personality. It was just, music guy, Auto-Tune guy, and that’s the whole of your personality. But now that I’ve gotten to be seen on Twitch and people get to see what kind of person I am, I think people are finding out I’m not an asshole like they thought I was. I guess I’m more approachable these days because people get to see the inner workings of my career and my life.

Were you initially hesitant at all to deviate from music being your main focus?

T-PAIN: No, not at all. I really wanted to get the hell out of there, but you know, how would my managers make money if I didn’t do music? So they kept me in line and kept me on the straight and narrow. I’ve always wanted to do other shit, but I wouldn’t be pursuing it because I would be encouraged not to.

Was it the grind of the music industry that made you want to get out of there?

T-PAIN: No. I’m lazy as shit. I didn’t grind anything. That was never an issue for me. I didn’t have any grind in my body. I was very lazy.

The (Feat. T-Pain) Era (2006-2009)

But look at everything you were putting out, let’s say from 2005 through 2009. You’re on a million songs, there had to be some grind going on there.

T-PAIN: Not really. I didn’t have to do any work. I just had to lay the verse down and whoever’s song it was, they did all the work. I just show up for a video, shoot that shit for two hours, and go back to the hotel room, go to sleep. It was not a lot of work. I’m telling you, it looked like a lot because I was doing the easy parts. All the money getting spent and all the marketing dollars and all that shit that was on whoever’s song it was, I didn’t have to do any of that shit.

So do you just wake up one day and you’re like, oh goddamn, I’m on four of the top 10 songs in the country?

T-PAIN: Yeah. I didn’t plan for it. It was not a lot of work for me. It was easy to be on a lot of songs and easy to be on too many songs. A lot of people could have done that. But for the labels, they didn’t want to work more than two songs at a time. Even when I was on three songs at a time, my management came to me and they’re like, “Dude, you’re on way too many songs.” I was like, “I don’t care, let’s just keep going.” I just kept doing features.

Usually if somebody’s on two songs at the same time that are on the charts, and they would say, “We’re saturating the industry right now, we can’t do any more.” But I was like, “It’s just an hour in the studio. Come on dude, I’ll do it for you, let’s do it.” I wasn’t trying to overload systems and shit like that, but that’s what happens when you’re not a dick and you can lend your capabilities to other people.