By Miles Raymer
March 24, 2015 at 07:18 PM EDT
Mary Kang / The FADER FORT Presented by Converse

Every year the Fader magazine’s Fader Fort Presented by Converse compound hosts a range of artists from indie rockers to dance music DJs, and every year they have a couple special guest headliners that are kept secret until they hit the stage. This Friday the resurgent T-Pain was one of them, and EW was invited by his team to tag along the day of the show.

10:10 am: A pair of Chevy Suburbans slide up outside the sneaker emporium Nice Kicks, where Sway in the Morning is taping. Fans bringing their sneaker A game loosely mob the place. Dej Loaf has already slid through in a pair of crispy Jordans. T-Pain’s publicist glides through the crowd searching for a more private entrance than the packed front door. T-Pain jumps out of the truck in jeans and Jordans and shakes my hand. His publicist tells him I’ll be riding shotgun all day. “Enjoy the ride!” he cackles.

10:47: Sway starts the panel discussion off and T-Pain immediately starts cracking up for no reason. Later on he tells Sway, “I definitely understand being held in a box. That’s how I got so many cars. If Khaled calls me up I’ll say I’ll do the hook but you gotta buy me a car.” T-Pain and Elle Varner get into some real talk about appropriation—white artists can explore whatever they want but urban radio won’t let black artists experiment. “It drives you crazy having a song you wanna make that you know your own culture won’t accept,” he says. “People won’t admit it but we’re in this line of work because we want to be liked.”

11:11: We rush out to head to rehearsal. There’s a mob of people outside asking to get a photo. Pain’s game but he’s not going to stop for them. “You gotta keep up!” he yells over his shoulder. Once in the truck he starts scrolling through his Twitter mentions. Unlike a lot of celebrities he doesn’t have a filter set up so he only sees responses from other verified members. T-Pain wants to know what everyone thinks about him.

11:29: We’re at the Fader Fort for rehearsal. Pain can’t not talk to everyone around him. When there’s a break in the action he grabs a Budweiser tall boy out of the green room cooler and starts chatting up the sound guy.

12:20 pm: “Did It Anyway,” a track from T-Pain’s upcoming mixtape The Iron Way—yes, that’s a Game of Thrones reference—leaked yesterday after someone hacked his manager’s email. The team’s pissed, but happy about the positive reaction it’s getting. And after a string of vulnerable confessional songs and intimate performances, the song is a return to form­–catchy and hilariously raunchy.

1:32: Sound check went long, so Pain goes straight from the stage to his day’s second interview and accompanying photo shoot, which he aggressively art directs himself.

1:52: Finally rolling out of Fader Fort for a mini press junket at the hotel where his team’s staying. Pain absentmindedly hums to himself as we pull out. For the record: T-Pain absentmindedly humming to himself is categorically better than most people’s actual finished music.

2:56: The Omni Barton Creek Resort & Spa is a bastion of old school Texan gentility, full of golf knicknacks and grandmotherly furniture, which makes it a funny place to host a press junket for someone who made his career singing about getting f—ed up at strip clubs. T-Pain occupies a massive suite overlooking a sprawling golf course and hills encrusted with mansions and explains to reporters what it’s like to be—in his eyes—only marginally famous, describing the fear that all celebrities have that they’ll eventually stop being famous. In his complaints about the way the hip-hop/R&B industry works he repeatedly references two types of people he envies for their freedom to fail: country singers, and Quentin Tarantino.

3:27: In between interviews Pain retreats into the bedroom with a room service salad and turns on the Cartoon Network for some quiet time.

7:14: Backstage at the Fader Fort, Pain poses for photos with fans and celebrities, including Bay Area rap legend E-40, Migos, and at least part of Migos’s approximately 50-deep crew. But he also just chills, drinking Budweiser out of a VitaminWater cup, nodding along to Big Sean’s set. His body language is casual, but you can see him mentally taking notes on what Sean’s doing and how it’s going over. It’s a professional assessing the competition’s work.

7:34: Migos takes the stage late—they’re going on at exactly the time T-Pain was supposed to start. Considering that he has an ambitious­—possibly even hubristic—plan to play 70 songs in 45 minutes, a whole band to set up, and hard end time for his set thanks to the Fort’s permits, this could be a problem. Pain seems outwardly unfazed, but his usual frenetic energy seems to have turned into a deep inward focus. His team forms a barricade around him to keep people from approaching him. For the first time today he’s not the most outgoing guy on the face of the planet.

8:13: Lights down. The band begins a slow psychedelic vamp on a Hans Zimmer Batman theme that flips into a hard rock jam. T-Pain takes a dozen slow, deliberate steps onto the stage and the crowd loses its mind.

9:08: Against the odds, T-Pain and his band pulled off their goal, playing a mix of hits, deep cuts, some of his more beloved features from other artists’ songs, and a verse of “Smells Like Teen Spirit” in essentially one extended, Vegas-style medley. The set manages to combine his passionate people-pleasing side–which comes through in his choreography with his hype man that’s half dance and half slapstick comedy–and his seemingly incongruous desire to push the envelope that he’s been talking about all day. R&B and hip-hop are the foundation, but he also dips into EDM, hard rock, pop, old school soul, hair metal, and even a little bit of country in the intro to “I’m in Love With a Stripper.” (And no, he doesn’t use Auto-Tune.) The crowd, most of which are young enough to have grown up on his music, returns every bit of the prodigious energy he throws at them. T-Pain may suffer some anxiety about his place in the pop music universe, but tonight proves that he doesn’t need to worry.