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T-Pain may not have any direct Wisconsin roots, aside from rhyming “mansion" with "Wiscansin” back in 2008, but the rapper turned cultural phenomenon has made Milwaukee his second home with his now-annual Wiscansin Fest. Returning to The Rave this past weekend for another sold-out celebration of hip-hop, the 2025 edition of Wiscansin Fest delivered big names, big tracks and big moments. From a surprise appearance by Flo Milli to a sea of Feid fans packing The Eagles Ballroom to its brim, here are 10 of our favorite moments from this year’s Wiscansin Fest:
1. Feid had as many fans as T-Pain
One of the biggest acts in Latin music right now, Feid delivered a performance worthy of a headlining slot, and based on the crowd response, you’d be forgiven for thinking he was the main event. Just days after dominating the stage at New York’s Governors Ball (second only to Olivia Rodrigo on the daily lineup), Feid turned The Eagles Ballrom into a reggaeton rave, with sea-green glasses dotting the crowd and fans belting every lyric back in Spanish.
2. Pusha T gave fans a taste of what’s to come
With Clipse officially reuniting and scheduled to bring their tour to Milwaukee later this year, Pusha T’s solo set felt like a sneak preview of the main course. The G.O.O.D. Music alum ripped through fan favorites and deep cuts with surgical delivery, teasing what fans can expect when he returns, this time with brother Malice by his side.
3. Wale Made the Crowd Feel Like Family
Wale has been rocking The Rave’s stages for more than a decade, and his familiarity with the venue shone through. He didn’t just perform to the crowd, he literally rapped with them, jumping into the audience and giving fans up close, face-to-face moments they’ll be bragging about for years. A seasoned vet, Wale’s presence reminded us why he keeps getting invited back.
4. DJ Diesel (Shaq) Was a One-Man Earthquake
Shaquille O’Neal, yes the basketball legend, brought his alter ego DJ Diesel to Wiscansin Fest and nearly blew the roof off The Rave. Towering over his decks, the NBA legend turned festival-favorite unleashed a high-octane EDM/hip-hop hybrid set that had the crowd bouncing (and shaking) like it was the NBA Finals. With past performances at Summerfest and The Rave under his belt, Diesel is no stranger to turning Wisconsin crowds into mosh pits. If you want more, don't worry; he'll be back in Milwaukee at American Family Field later this year.
5. NLE Choppa Had a Father-Daughter Moment
NLE Choppa’s set was packed with energy, fast flows, and one especially sweet moment: when he brought his young daughter on stage. It was an unexpected heartwarmer amid a night of high-tempo hype, a moment of real-life joy that gave fans a reason to smile and cheer even louder, and just a day before Father’s Day.
6. Prof Had the Hip-Hop Heads Locked In
For those in the crowd craving bars over bass, Prof had them covered. His witty wordplay and offbeat humor provided a sharp contrast to some of the more mainstream-heavy acts, showing why he’s earned cult status among hip-hop purists. And he made sure you remembered it, whether through punchlines or pure charisma.
7. Kash Doll Brought a Fan On Stage and Was Blown Away
Kash Doll’s set was already solid, but she leveled up when she invited a fan to join her on stage to rap one of her verses. What could’ve been a brief crowd-pleaser turned into a legit showcase, the fan nailed every bar, impressing even Kash Doll herself and drawing massive cheers from the crowd.
8. Flo Milli Was the Surprise We Didn’t Know We Needed
Though not originally on the lineup, the night’s surprise headliner was none other than Flo Milli, and she did not disappoint. She turned The Rave into a rowdy party in seconds, dropping baddie anthems with effortless swagger. Bonus: she’ll be back in Milwaukee in just a couple weeks, opening for Megan Thee Stallion at Summerfest.
9. Armani White brought his viral TikTok classic
Known most for his viral track, “Billie Eilish”, which exploded on TikTok a couple of years ago, rapper Armani White gave fans a reason to show up early in the day. His energy was unmatched, even amongst some of rap’s biggest veterans.
10. T-Pain Did What He Does Best
And of course, the man of the hour delivered. With a catalog stacked with timeless party-starters, T-Pain brought Wiscansin Fest to a euphoric close, effortlessly moving between auto-tuned anthems, heartfelt vocals, and crowd-hyping banter. Milwaukee has become the unofficial home for this very official holiday, and once again, the self-proclaimed “Wiscansin” native showed why.
And a Few Not-So-Favorite Moments...
Not everything went as planned this year, and a few moments left the crowd confused, disappointed, or downright annoyed.
Jermaine Dupri vs. DJ Mando
Dupri, who performed a DJ set featuring only his own hit songs, seemed irritated that Milwaukee’s DJ Mando played some of those same tracks before his set. Dupri took time during his performance to call out Mando and blame him for the crowd’s energy, an awkward moment that broke the flow.
GloRilla’s Disappearing Act
One of the festival’s biggest names, GloRilla took the stage significantly late and after performing just one song (“TGIF”), she left. Fans booed after realizing that was the entirety of her set. Especially disappointing since she sold out The Rave earlier this year as a headliner.
Keyshia Cole’s Last-Minute No-Show
Listed on the lineup and expected by fans, Keyshia Cole was a last-minute scratch and didn’t appear. No formal announcement was made during the event, leaving many wondering what happened and why. Despite those hiccups, Wiscansin Fest once again delivered on its promise: a one-of-a-kind celebration of hip-hop in the heart of Milwaukee, curated by one of music’s most enduring (and entertaining) voices. Until next year, we’ll be in the mansion, in Wiscansin.
