For the first time in its eleven-year history, worldwide hip-hop festival Rolling Loud is in sunny Orlando, Florida. Held on the Camping World Stadium grounds, where artists like the Weeknd and festivals like EDC have come to life, the sold-out festival is bringing in all types of music lovers, but most importantly, industry underdogs. While this year’s lineup didn’t have as many big names as years past, it showcases the talent that is beginning to rise, such as the U.K.’s Esdeekid and Molly Santana, as well as other well-known names, like Destroy Lonely, Sexyy Red, Chief Keef, Snow Strippers, and more.
Rolling Loud Orlando is also the only U.S. festival the franchise is putting on this year, and Orlando (and the rest of the country) showed out by selling out all three days.
The three-day show spanned May 8-10, with big names Don Toliver, Playboi Carti, and Ken Carson expected to headline, but what drew most attention was day one, considering it was the first day.
Chief Keef Sosa makes waves
People began to show up once Chief Keef Sosa made his appearance on the Under Armour mainstage in the mid-afternoon, performing all of his hits, including quintuple platinum ‘Love Sosa,’ a song that is most definitely heard on the college house party scene. Sosa is considered to be one of the founding fathers of drill music and is highly influential to all starting artists within the hip-hop industry.
Esdeekid brings the U.K. to Florida
If you’ve scrolled on TikTok between now and late 2025, chances are you’ve heard an Esdeekid song. Known for wearing a mask so you could only see his eyes, many fans speculated that he was Timothee Chalamet for the longest time, until Chalamet was promoting his new film ‘Marty Supreme’ and was subsequently featured on a remix of the former’s song ‘4 Raws.’
His set was a castle, complete with support from knights (who at one point had flaming swords) and stunning visuals showcasing the aesthetic of the British rapper.
Esdee used songs like ‘Phantom’ to get fans to mosh and played more fan favorites like ‘Rottweiler’ and opened his set with ‘Century.’ He also brought out friend and frequent collaborator Rico Ace to perform their biggest hits, ‘LV Sandals’, ‘Cali Man’, ‘Mist’, and ‘Dope Boyz.’ Rico’s performance also showcased his own up-and-coming talent as an artist, ensuring that if you didn’t know him before, you would after he left.
Don Toliver shuts down the mainstage
The most heavily anticipated performer for night one, Don Toliver, made his appearance around 10 p.m, and the crowd was fired up, even though it had rained thirty minutes prior.
His setting consisted of trees on the stage, which confused me at first, but it only added to the visual experience of the set and his performance itself. Toliver entered wearing an all-white fit, opening with fan favorite ‘E85,’ and then launching into other hits from his new album OCTANE, which was released in late January after heavy fan anticipation.
The insane pyrotechnics only added to the stunning set, with Don performing hits from the new album like ‘Body’ and ‘GEMSTONE,’ as well as other big songs like ‘TORE UP’ and ‘No Pole.’
The highlight of the night was when he brought out frequent collaborator Yeat to perform their song ‘Rendezvous’ for the first time together on the Rolling Loud stage. The two artists have many songs together, including ‘Griddle’ off the latter’s most recent record, ADL. Yeat also stayed to perform ‘COME N GO.’
Many of the songs Don chose to play were a callback to the artist who found him, Travis Scott, another member of the JACKBOYS team. Although Travis did not make an appearance like many fans speculated he would, his music was still on the setlist, with Don even playing his portion of ‘CAN’T SAY’ off of Travis’ ASTROWORLD album.
Don closed his set with his TikTok hit ‘After Party’ and played ‘E85’ for a second time to allow fans to mosh. He then played a video after he got off stage, showing him driving, ‘E85’ once again playing in the background.
The first rolling loud Orlando off to a generational start
Now that Central Florida has become an even bigger hub for festivals, Orlando is making an even bigger name for itself, moving outside of the theme park industry into bringing in more tourism and attraction through live music, and honestly, the move is paying off. There is a lot of talent here in Florida, with much still to be discovered, especially through performances on a huge platform like Rolling Loud.
There is more to come for the City Beautiful; Orlando is just getting started.