What started as a one-off joke in a 2008 T-Pain lyric, rhyming “mansion” with “Wiscansin”, has evolved into one of the Midwest’s most consistently stacked and wildly entertaining hip-hop events of the summer. On Friday night, T-Pain’s Wiscansin Fest returned to The Rave in Milwaukee for its latest installment, and the “Buy U a Drank” hitmaker once again proved he knows how to throw a party, even in a state he has no formal ties to, except in rhyme.

This year’s lineup was easily one of the most eclectic and star-studded yet. The crowd was already buzzing early in the night when viral rapper Armani White, best known for his TikTok hit “Billie Eilish,” opened things up. The energy continued with NLE Choppa, who gave fans both high-octane bangers and a heartwarming moment by bringing his young daughter on stage. Prof followed with a set tailored to the hip-hop purists in the crowd, delivering clever rhymes and offbeat humor with the confidence of an underground king.

The night’s biggest curveball, in the best way, came courtesy of DJ Diesel, a.k.a. Shaquille O’Neal. Towering over his turntables like a living meme, Shaq unleashed an electrifying set that fused hip-hop with EDM drops, shaking the entire ballroom. It wasn’t his first time bringing chaos to The Rave, and based on crowd reaction, it better not be his last.

While the schedule ran about 15 minutes behind throughout the night, it was Glorilla’s delayed set that drew the most attention, and not the good kind. The Memphis rapper, who headlined and sold out The Rave earlier this year, took the stage late and left after performing only one song (“TGIF”), resulting in a wave of boos from disappointed fans. Her brief appearance felt more like a cameo than a performance, especially considering her prominence on the flyer.

Kash Doll got the show back on track with a fan-involved set that included a surprise onstage duet with one lucky audience member, who nailed every word. Wale followed with one of the most engaging performances of the night, jumping into the crowd and spitting bars shoulder-to-shoulder with fans. A regular at The Rave, Wale’s familiarity with the venue shined through, making his set feel like a reunion more than a concert.

The night also included a surprise that didn’t disappoint: Flo Milli. Unbilled until she hit the stage, the rising rap star brought infectious energy and gave fans a teaser of what they can expect when she returns to Milwaukee later this summer to open for Megan Thee Stallion at Summerfest.

Still, all eyes turned to the stage when Pusha T arrived. One-half of the legendary duo Clipse, Pusha tore through his solo catalog with razor-sharp precision, giving Milwaukee fans a preview of what’s to come when he returns with Malice later this year for the Clipse reunion tour.

Just as many fans, however, came for Colombian superstar Feid, who nearly matched T-Pain in crowd size and energy. Donning his signature green shades and delivering hit after hit in Spanish, Feid transformed The Rave into a reggaeton hotspot, proving why he’s become one of Latin music’s most in-demand names.

T-Pain, of course, closed out the night, and as always, he delivered. Backed by a full band and a catalog packed with timeless party anthems, Pain balanced hype and heart as only he can, moving effortlessly from chart-toppers like “Bartender” and “Can’t Believe It” to deeper cuts for the day-one fans. His charisma filled the room, his vocals were sharp, and his genuine joy in hosting Wiscansin Fest was unmistakable.

Despite a couple hiccups, including Keyshia Cole’s unexplained last-minute absence, Wiscansin Fest 2025 was a celebration of music, community, and T-Pain’s ever-growing impact on hip-hop and pop culture. From start to finish, the night reminded us why this fest has become such a staple, even if it all started with a made-up word.

Photos by Dan Garcia/The Early Registration