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June 18, 2015 at 12:00 PM EDT

The degree to which auto-tune auteur T-Pain dominated the charts in the late ’00s is a little unreal. Between 2005 and 2010, the Tallahassee-raised star released hit after hit into the collective American consciousness, scoring six Top 10 hits under his own name, and eight more as a featured guest.

T-Pain hasn’t released a studio album since 2011, but he tells EW he’s narrowing down over 40 tracks for Stoicville: The Phoenix, due out later this year. Below, the rapper reveals the stories behind some of his biggest hits, which include a fiery new single featuring Juicy J and an unlikely parody with Taylor Swift.

On “Make That Shit Work,” ft. Juicy J
T-Pain recorded “Make That S–t Work” with Juicy J—one of his childhood idols—and released it earlier this month. “Hopefully it’s a smash, that means money for me and my family,” he says. “But if not, I got plenty more.”

On his 2014 NPR Tiny Desk concert
T-Pain stopped by NPR’s Tiny Desk concert series last year, and after recording stripped-down versions of hits including “Buy U A Drank (Shawty Snappin’),” the clip went viral. “I was nervous, mostly because I didn’t know what the hell I was doing until I got there,” he says. “I thought it was just going to be an interview, because when I think NPR, I think talk radio. I didn’t think any of that stuff was going to be going on—it really was a surprise for me.” The video ended up with over 7.5 million views on YouTube. “The amount of people made me the most nervous—there were probably about 400 people in there, standing on their desks and AC units. It was disturbing, but it worked out great.”

On his 2009 parody video with Taylor Swift
Taylor Swift emerged as a superstar at the height of T-Pain’s popularity. For the 2009 CMTs, Swift recruited him to lend his auto-tune to a parody song, “Thug Story.” “By the time I even got to the studio, she was already done with it,” T-Pain says. “She wrote all that stuff, and all I had to do was add my backgrounds. It was good, which was weird. Knowing that she writes country music I didn’t think that she could [do] a rap song.” The two hit it off, but only after an uncomfortable start. “When I first met her, she was standing in a doorway, and she’s so tall that I thought there was a step up to get into where she was,” he explains. “I did the whole phantom step thing and I fell right into her. That was embarrassing! I was trying to shake her hand at the same time, and it went right into her belly button. It was gross.”

On the inspiration for “I’m ‘n Luv (Wit A Stripper)”
T-Pain didn’t get a No. 1 hit until 2007—when he scored three of them—but “I’m ‘n Luv” hit No. 5 in 2005. As cartoonish as the song gets, it’s based on the true story of a time T-Pain took his friend to a Jacksonville strip club. “He had never been to a strip club before,” he says. “He immediately found a girl he liked. She’s dancing for a little while, and then she’s… not dancing. Things get so weird when a stripper stops stripping and just starts talking.” When T-Pain’s friend told him later that the conversation had been about buying her a house, it became a running joke in their group. “The next day we went to the studio and that was all we talked about. It was an ongoing joke for a while and then I started playing music and just making fun of him.” T-Pain recorded a joke hook that later became the chorus we know and love.

On Kanye’s approach to recording “Good Life”
“I’ve never recorded a song that many times for that long,” T-Pain says of his work on Kanye West’s 2007 smash “Good Life.” “It took us two weeks and seven sessions. The ‘hook’ is comprised of five different hooks I did. At the end he just chopped them all up and put them together.” Notorious for both his perfectionism and his last-minute revisions—this is the guy who called in Rick Rubin for eleventh hour edits on Yeezus—West told T-Pain he needed to relisten to the song when he arrived on set for the music video. “The song sounded completely different,” T-Pain remembers. “Up until the video shoot, the song didn’t have the “P.Y.T.” sample in it. He changed it so much that it was unrecognizable. But it won a Grammy, so I guess it worked out!”

On recording two Top 10 hits in the same night
“I did ‘Low’ and ‘Shawty’ in the same night,” he says. “I was working with Mike Caren, the president of Atlantic Records—he was just A&R at that point. He would bring me a CD full of beats and tell me to pick which ones I liked. That night I picked the beats for ‘Shawty’ and ‘Low’ and I did them back to back. He just took them to who he thought should have it.” That ethic helped T-Pain score seven Top 10 hits in 2007. “You know what’s crazy?” he adds with a laugh. “I didn’t meet Flo Rida ‘til I got to the video shoot. Didn’t even know who he was.”

On the surprising success of “I’m On a Boat”
One of the more peculiar cuts in T-Pain’s extensive catalog is “I’m On a Boat,” the joke song he recorded with The Lonely Island forSaturday Night Live. “They came to me and I didn’t know if they were serious or not, because the song was actually good!” T-Pain says. “It was weird, but it was funny as hell. That was a no-brainer for me, I couldn’t help it.” The track became a viral sensation and even climbed to No. 56 on the Billboard Hot 100, receiving some unexpected acclaim as a result. “The most surprising thing was that it got nominated for a Grammy,” T-Pain says. “It wasn’t nominated for a comedy song, it was nominated for best rap song. It was up against Jay Z!”

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