By Allen Halas OnMilwaukee Staff Writer Published Jun 29, 2025 at 10:01 AM Photography: Dan Garcia

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The second weekend of Summerfest came to a close on Saturday, with near-perfect weather and a huge crowd that flooded the grounds. A big percentage of that crowd made their way to the Generac Power Stage as the sun set, with a stacked lineup of up-and-coming rap artists, including Milwaukee’s own MT Twins and DJ Nic Stokes, as well as Memphis artist YTB Fatt, and headed up by Florida rapper Bossman Dlow. 

With a huge internet following and a larger-than-life presence, Dlow moved like a superstar in a relatively short set that brought plenty of bass. So much, in fact, that it literally rattled the infrastructure of the Generac Power Stage throughout the course of the night. If the heavy beats weren’t enough to do it, the massive crowd that stretched back to the main drag of the festival grounds would play their part as well.

Before Dlow could hit the stage, though, the crowd was already at a boiling point. YTB Fatt’s set featured a trip into the crowd that fired up the fans along the barricade, and in the downtime between sets, Stokes kept the music going, with each song that dropped amping the crowd up even further. It frankly wouldn’t take much for Dlow’s set to be a success, and while his set was  low on flash, it was enough to keep the Power Stage crowd bouncing the whole time.

Unlike Fatt, who had a flurry of photographers and crew onstage with him, Dlow made it known that he was the main attraction. Aided only by his DJ and a pair of background dancers, he’d float through material from the four projects that he’s dropped in only the past two years, with one fan favorite after another with little to no pause in between.

The majority of Dlow’s catalog is full of flex-heavy raps, and his live show matched that energy. He’d move across the stage with confident composure, with his signature flow on tracks like opener “Sportscenter.” Whenever he pulled the mic away from his mouth, thousands of fans could complete every bar for him. That’s a testament to the impact that he’s making currently, and he knows that his star is as bright as the giant chain that he was wearing on Saturday.

Bossman Dlow performs on the Generac Power Stage at Summerfest 2025 in Milwaukee.X

Over the course of 45 minutes, he’d run through track after track, each one not reaching completion. It was all hype with no chance for the crowd to cool down, not that they wanted to anyway.

“Y’all are turnt right now. I didn’t know Milwaukee got like that” he told the crowd before the beat would drop on “Get In With Me.” Three songs in, he would try to take his own walk through the crowd to get closer to the fans. While he was down there, he passed out a couple of $100 bills to fans. However, the track was a short one, and he only made it about halfway through the barricade divider between the pit and the bleachers before reverting back onstage. It was still enough to ignite that section of the stands. He would later make his way onto the speakers at the front of the stage, where fans would lob phones to him to take videos from the stage before tossing them back their way.

Just over a month removed from the release of the deluxe edition of 2024’s “Dlow Curry” project, the set would feature much of the new material. That included tracks like “PJ” with Lil Baby and “Pillsbury Dlow” with Ice Spice, with the crowd filling in for the absent features. The fan reactions, however, paled in comparison to single “Mo Chicken” with French Montana, which saw the whole Generac Stage crowd chanting the hook along with Dlow to essentially shut the show down at the end of the set. Rather than taking the fans up and down in his time onstage, he held the energy high for the duration of his time and went out with a bang. With his DJ still playing music after he walked offstage, he would head down to the front barricade after for pictures with fans before calling it a night.

While it may have been shorter than the average Summerfest set, and there wasn’t much in terms of creating a spectacle, Bossman Dlow didn’t need any extra tricks to keep the crowd hyped up on a Saturday night. He merely maintained the energy of an already excited flock of fans, but as a performer, that’s all that’s required to be a success.