T-Pain is a bit of a polarizing performer to put it mildly. In 2009, the Tallahassee-bred, self-proclaimed “Rappa Ternt Sanga” purchased a seven-and-a-half pound, 197 carat medallion that read “Big Ass Chain.” For his Thr33 Ringz album campaign, T-Pain donned a haberdashery-style top hat and a formal tuxedo jacket with a tail. None of this undermines the fact that T-Pain appeared on a record 14 Billboard #1 singles in 2008. The man most infamously associated with Auto-tune pitch-correcting software has also worked with the likes of E-40, Lil Jon, Snoop Dogg, Lil Wayne and Kanye West to name just a few. And then there was that one time the President of the United States played a song T-Pain helped create.

“I don’t want to say that’s the highest honor, but at this point in my knowledge, that’s the highest honor I’ve ever had,” T-Pain explained, while exclusively telling HipHopDX about some of his biggest hits. “I mean, the Grammy’s and everything… but that’s the President of the United States. You can’t really say that about the President of the Board on the Grammys that nominates people.”

Add in the fact that one of Hip Hop’s top artists proclaimed Auto-tune dead, and it all makes for an interesting dynamic. How can someone who has been so commercially successful receive so much critical backlash? We asked T-Pain to take a brief break from promoting his latest single and weekly video series to detail the stories behind some of his biggest and/or most recognizable hits. T-Pain obliged, with tales about everything from eating tortilla chips (sans salsa) with Michael Jackson to E-40’s unorthodox practice of lying down before recording his vocals. Pull up a chair, T-Pain has a few stories to tell.

T-Pain’s “Change” Was Originally Meant For Michael Jackson

Song: “Change” (feat. Akon, Mary J. Blige & Diddy)
Album: Thr33 Ringz
Top Charting Position: N/A

T-Pain Says: “It’s a genius song. It’s a beautiful song. [Eric Clapton] wrote it for his daughter and shit like that. At first, I made it for Michael Jackson, ‘cause we was gonna be working together. And, you know, Michael Jackson was like, ‘I don’t do samples or remixes or anything.’ So I had to throw that out, but I still used it.

“Dude, his guest house is bigger than my regular house [laughs]. That was the most amazing shit! It was the craziest shit in the world. He just wanted to tell me that “Bartender” was the only CD he sent someone to go buy in the last four years. I was on my way to the studio, and they said, ‘Michael Jackson wants to meet you.’ So I immediately turned around. I don’t give a fuck if that nigga wanted to meet me in a God damn meat factory. I would’ve fuckin’ went there. So he told me “Bartender” was the only physical CD that he wanted in the last four years, and that was the most amazing shit.

“And then we ate tortilla chips without any kind of salsa or anything, and then I left [laughs]. He didn’t have salsa…we had to go to the store for some salsa. You’d think he’d have salsa. He just had the chips. He didn’t even ask for them! The dude came in there—I’m talking about top-notch—with the white gloves and the shit over his arm. But he only had a bowl of tortilla chips, and I’m like, ‘What the fuck? You got a waiter from a God damn restaurant coming to give you tortilla chips, and he didn’t bring no salsa.’ That shit was good though.”

“5 O’Clock” Happened Because T-Pain Broke One Of His iPhones

Song: “5 O’Clock”
Album: Revolver
Top Charting Position: #10

T-Pain Says: “I called the Apple store because my phone was fuckin’ up, and I had them on speakerphone. I had my other iPhone, and I had to Shazam the song that was playing [while I was on hold]. Once I Shazammed that, I went to the studio and didn’t even finish the call with Apple about the phone. I just threw that phone away and bought another phone. I went to the studio and sampled that, so [Lily Allen] was automatically on the song. I couldn’t lose that feel, and nobody would’ve been able to ever re-sing it as well as she did. She had so much emotion, and it was just so dope.

“With Wiz Khalifa, I just liked Wiz Khalifa at the time. I was a big fan, and I still am a fan. He was just super different.

“My iPhone broke, and if I wouldn’t have called at that exact moment, the hold music would’ve been different. Man, when I heard that shit, I was just like, ‘Oh my God!’ The song changes [sings ‘Who’d Have Known’], and then it goes to this big rock ‘n roll thing. The whole feel of that song changed right there, so the fact that I caught it during the exact moment of those four bars… If I would’ve come on after that, I never would’ve thought that part of the song existed. But yeah, that whole thing came because I called the Apple store at the right time. They put me on hold right when they needed to. Good fuckin’ job. [Points to the sky] That’s for you, Steve Jobs!”

Lil Wayne Beat Pitbull & Paul Wall In A Bidding War For “Got Money”

Song: “Got Money”
Album: Tha Carter III [Lil Wayne]
Top Charting Position: #10

T-Pain Says: “Ahh, man. Oh, God… That one hook went to a lot of people, and it caused a fight. It wasn’t a fist-fight. I made it for Pitbull, but that was right in his transition when he started doing a lot of house music. His label was fighting for it, because they wanted him to at least do one more of them kind of songs. Then it went to Paul Wall for some reason. That ain’t even Paul Wall’s kind of music, so I don’t even know that how that went there. But he recorded a song to it, and then they was fighting for it over there. Then Wayne had it. And of course, ain’t nobody got as much money as Wayne, so that’s why he won. Play N Skillz—the producers of the song—they had the hook, and they took it to a bunch of people. So Rap niggas had it, and Reggaeton niggas had it, and it turned into so much shit! The fucked up thing was, everybody that knew me personally was calling me like, ‘Yo bro, can you please tell them to give me this record?’ It was at least three people that called me personally wanting me to vouch for them. I was like, ‘Look man, y’all can take my hook off the shit. I don’t even want nothing to do with it no more.’ But of course, ‘Cash Money Records for the 99 and 2000, ya heard me?’ That boy came through with that hundred million for real. Yeah…you think you gonna beat Lil Wayne out of a song?”

Lil Wayne Also Took “How To Hate” Off T-Pain’s Album

Song: “How To Hate”
Album: Tha Carter IV [Lil Wayne]
Top Charting Position: #84

T-Pain Says: “That man took a song off my album [laughs]. I took that nigga a song…I took him “How to Hate a Bitch” for him to put a verse on it for my album. The nigga kept the song and put it on his album [laughs]. That’s why I go first, because it was my song. I’m asking him, ‘Dog, can you put a verse on this?’ And I guess he was like, ‘Yes, I can…and another one, and it’s going on my album also. So, yes.’ That mothafucka took the song quick. It was like, ‘Yeah, I got a “How To Love,” so “How To Hate” would go right with it.’ So I basically said, ‘Hey man, I ain’t got as much money as you. Go ahead and keep the Goddamn song.’ I ain’t even want to fight that nigga for that. He got too much God damn money. That would be dumb, and that’s a lose-lose situation.”

Chris Brown Had To Rewrite The NSFW Chorus For “Kiss Kiss”

Song: “Kiss Kiss”
Album: Exclusive [Chris Brown]
Top Charting Position: #1

T-Pain Says: “That’s an interesting one. “Kiss Kiss” was a completely different song, because we recorded it… The hook now goes, ‘She want that lovey dovey / That kiss kiss / In her mind she fantisize ‘bout getting with me.’ But at first, when I was writing it, Chris had just turned 18 at the time. I was like, ‘Oh, OK. You can actually sing the songs that I write now.’ So the first hook to the shit was, ‘My shawty chunky, chunky / She think, thick / She got them thighs, she fuckin’ with me.’ So it was a completely different song [laughs]. We recorded that, and his management came in like, ‘Are you niggas crazy? What do y’all think is going on? No, he’s 18! He can’t fuckin’ rent a car, and he can barely just buy a pack of cigarettes. Stop, and redo all that shit.’

“I let Chris go back and write the shit, because all I could come up with was chunky, thick thighs and fuckin’. I couldn’t think of nothing else, and then I turned it into some drinking shit, and that was just totally out of the question. So I was like, ‘Chris, you just think of some words you can say.’”

Kanye West & T-Pain Spent Five Weeks On “Good Life”

Song: “Good Life”
Album: Graduation [Kanye West]
Top Charting Position: #13

T-Pain Says: “Kanye definitely called me. That would have been the last place I would have thought of going—friggin’ Hawaii. It’s hot, and all I’ve got is a bunch of sweaters [laughs]. But yeah, he called me and he definitely said we need to work on something. That was…oh boy, that took a long time. It started in L.A.; that was like three sessions, and after that, he was like, ‘Maybe we need to get a change of scenery. Let’s go to Hawaii.’ It was good though. It worked out, and I got to go to Hawaii, so that was fun.

““Good Life” took me and Kanye five weeks to finish. It was seven different hooks. So people don’t know that it took us that long to do just that simple of a song. So these people, they see Kanye, that he’s a quote-un-quote asshole and think, ‘If Kanye can do it, then I can do it too.’ And they do it, and they hear their shit, and say, ‘Oh this sounds just like “Good Life!”” and it’s so fuckin’ terrible. But you know, people like a trash hit, so to each his own, if you think it’s good.”

B.o.B. & T-Pain Got Normal For “Up Down (Do This All Day)”

Song: “Up Down (Do This All Day)”
Album: Stoicville: The Phoenix
Top Charting Position: #84 (as of January 20, 2014)

T-Pain Says: “I’ve been working with B.o.B. since he was in Tallahassee, man. We always was looking for a record, and he’s so weird and I’m so weird, that we would always get together and make the weirdest songs possible. We always try to out-weird each other, and it always made the songs so weird that we didn’t understand it at the end of the day [laughs]. So I was like, ‘Yo, we just need to find a normal song that we can do. Let’s just do a normal thing, man; let’s not try to out-Outkast each other.’

“This is actually the most uninteresting one, it was literally just me and my homeboy J-Lyric. We were sitting in Panama City one day, and DJ Mustard sent me a whole folder of beats. I liked that one, and I was like, ‘Dude, you wanna write to this one? Uhh, how should we start it? Umm, up, down…’ I was like, ‘That’s dope. Let’s put that in the middle…’ Maybe if I put in, ‘I don’t even know it, I don’t even know it.’ Maybe I should say that twice.’ It literally just went like that, and in an hour the song was done. It’s literally like that… little pieces, and the song was done in an hour.”

T-Pain Says He Almost Peed His Pants Meeting E-40

Song: “U And Dat”
Album: My Ghetto Report Card [E-40]
Top Charting Position: #13

T-Pain Says: “I had “I’m Sprung” and “I’m N Luv (With A Stripper),” and Lil Jon wanted to fuck with me. I went in there, and E-40 walked in, and I left because I peed a little bit [laughs]. I really fuckin’ love E-40, so I had to go leave and finish peeing all the way. Lil Jon was like, ‘Man, I got this beat. I wanna see if you can do something.’ He played the beat, and I immediately went into the booth. I sat there for a second in amazement because E-40 was there, and I just wanted that moment to last for a second. But then I went right in the booth, and first thing that came in my head was that same hook. Thank God we didn’t have to work on that for more than one day.

“It was that one hook. It was, ‘Bam!’ we put it down right then. E-40 went in the booth and laid down for some reason. He just like laid on his side and sat there for a long time. Then he got up like, ‘Alright, let’s go!’ And he just got up and recorded the shit. It was amazing [laughs]. He was just literally fuckin’ sitting there for a long ass time. Then he got up and recorded the whole song. He showed out on my ass with that song. I should’ve laid down before I went in the booth.

Several Other Rappers Turned Down “I’m On A Boat”

Song: “I’m On A Boat”
Album: Incredibad [The Lonely Island]
Top Charting Position: #56

T-Pain Says: “[The Lonely Island] are crazy as hell, and I think they saw that I had a sense of humor too, and that’s what… people lack that, man. I think people take themselves too seriously and think of themselves too highly. It’s not that they don’t deserve to think of themselves that way, but once you start doing that, you lose focus of your humbleness, and you can’t ever step back from it. You get so deep into how important you are to yourself that you forget how small of a fish you are in this big pond. And once people can see that through your music, and they can see, ‘Hey, maybe this guy likes to have fun. We should check,’ then they check. When we did the “I’m On A Boat” shit, they saw I was down with it. I’m not one of those people who’s like, ‘Nah, that shit’s stupid, bruh. They trying to make fun of Rap music or something?’ They stepped to a few people who said that. When I accepted it, and actually took the challenge, and it sounded good on the song, it made it funnier than they wanted me to make it. And then they came back for another one, the “I Fucked My Aunt” thing. They know when an artist likes to have fun, and you can tell when an artist likes to have fun in his career. I don’t ever want to stop having fun. Then it’ll become a job, and I ain’t doing this for the money. I mean, the money is very good, but I’d be a fool to say that this wasn’t my passion.”

Omar Burgess is a Long Beach, California native who has contributed to various magazines, newspapers and has been an editor at HipHopDX since 2008. Follow him on Twitter @OmarBurgess.