3 Rising Star Rappers To Watch at Summerfest: 1900Rugrat, Nettspend, BossMan Dlow

Nettspend, 1900Rugrat, BossMan Dlow (from left to right)
S

Summerfest’s side stages are where the real magic happens. This year, three up-and-coming rappers are ready to prove they belong in your playlist rotation.

From 1900Rugrat1900Rugrat’s One Take Freestyle hype to  Rapper, singer, and songwriter Nettspend (Gunner Shepardson).Nettspend’s TikTok-fueled rise and Rapper BossMan Dlow (Devante McCreary). BossMan Dlow’s platinum hit Get In With Me, Summerfest’s rap lineup is stacked with breakout energy this year.

1900Rugrat1900Rugrat

Florida rapper 1900Rugrat performs Friday, June 27, 8:45 p.m. on the Miller Lite Oasis stage. He first made waves with One Take Freestyle, which topped Spotify’s US Viral chart in 2024 and later got a remix with Kodak Black. His debut mixtape, Porch 2 The Pent, dropped in February 2025 and includes features from Rapper BossMan Dlow (Devante McCreary). BossMan Dlow and Lil Yachty.

 Rapper, singer, and songwriter Nettspend (Gunner Shepardson).Nettspend

Nettspend takes the American Family Insurance Amphitheater on Thursday, July 4, at 7:00 p.m. The Virginia rapper is known for his experimental production style and tracks like Impact (2025), Say Please, Laughin, Drop The Blunt, Perc Soda, and shine n peace. His debut mixtape Bad Ass F-cking Kid cracked the Billboard 200 in late 2024.

Rapper BossMan Dlow (Devante McCreary). BossMan Dlow

BossMan Dlow plays the Generac Power Stage on Saturday, June 28, at 9:30 p.m. He broke out with the platinum single Get In With Me in 2024, which appeared on his gold-certified mixtape Mr Beat the Road. His album Dlow Curry dropped in December 2024, followed by a deluxe edition in May 2025, with tracks like Hit (featuring Gucci Mane) and Money Talks. In 2025, he’s on a 15-date Dlow Curry Tour across the US and Canada.