Music

18 Rappers to Watch at Rolling Loud

As Rolling Loud consolidates its U.S. festivals, we highlight 18 emerging and established artists you cannot miss in Orlando.

18 Rappers to Watch at Rolling Loud

When Rolling Loud announced the consolidation of its three annual U.S. festivals into one massive weekend, the anticipation was immediate. While the lineup is undeniably stacked, the most striking aspect is its commitment to the underground. The festival’s focus on emerging talent signals a conscious effort to spotlight the next generation of rap, making this year’s event an essential destination for discovering future stars.

Friday, May 8

The weekend kicks off with D.C. wunderkind Nino Paid, whose 2024 single “Money Problems” solidified his status as a rising force. Following his signing with Signal Records, his momentum has been relentless. Joining him is British jerk rapper YT, who brings a refreshing, carefree energy to the stage, drawing inspiration from the late 2000s and early 2010s hip-hop era. We are also looking forward to the dynamic duo Tezzus and diamond*, whose offstage chemistry and collaborative energy promise a standout performance.

The underground scene continues to shine with k3, the Kansas City rapper known for her intense, snarling delivery and diabolical flows. Finally, xaviersobased, fresh off his debut album Riverside, brings his high-energy, cult-favorite sound to the stage for what promises to be a career-defining set.

Saturday, May 9

Saturday’s highlights include Babychiefdoit, whose live shows have become legendary for their chaotic, high-energy atmosphere. Molly Santana is another must-see, particularly as she continues to push boundaries with her unique production choices and recent viral success. Chuckyy, arguably one of the most promising artists out of Chicago, will showcase his lyrical dexterity and ambient-drill fusion, proving why he is a favorite among peers like 21 Savage and his contemporaries.

The day rounds out with untiljapan, whose art-focused approach to rap creates an immersive, cinematic experience. Karrahbooo, having recently regained her creative independence, brings a renewed intensity to her performance, while prettifun continues to impress with her earnest, nu-digicore-inspired sound.

Sunday, May 10

The final day features the undeniable presence of Sexyy Red, whose massive hits continue to dominate the cultural conversation. OsamaSon, known for his relentless work ethic and cult-classic projects, is set to deliver a high-octane performance. Meanwhile, Loe Shimmy brings his signature “groovy trap” sound to his home turf, with the potential for surprise appearances from his extensive network of collaborators.

The weekend concludes with Che, whose live performances have evolved significantly over the past year, and Skrilla, whose meteoric rise following the viral success of his recent work makes his set a true victory lap. Finally, Skaiwater rounds out the weekend, showcasing their growth as a performer and their ability to command a crowd with their infectious energy.

18 rappers we can’t wait to see at Rolling Loud