OsamaSon

Early life Amari Middleton was born on May 20, 2003 and raised in Goose Creek, South Carolina, and Columbus, Ohio. His uncle, a geechee musician, taught him how to produce music using FL Studio. Middleton attended Goose Creek High School, where played football in his freshman year and played on the basketball team until his sophomore year. He graduated from Goose Creek in 2021. By 2021, he adopted his current stage name and released the mixtapes Vengeance and Carnival. On April 7, OsamaSon's breakout single, "Cts-V", was released and began gaining traction online. His music was further popularized by Internet personalities such as BruceDropEmOff, who played OsamaSon's songs on his live streams.

2023–2024: Osama Season and Flex Musix On June 2, 2023, OsamaSon released "Troops", the lead single from his debut mixtape, Osama Season; like "Cts-V", the song saw considerable success online. Osama Season itself was released on July 21, with music critics for Pitchfork and the Fader highlighting the tracks "Werkin", "Kutta", "Summer Sixteen", "Anti", and "X & Sex" as standouts from the album. In October, he embarked on the Next Gen Tour alongside fellow rappers Kankan, Summrs, Highway, and the producer F1lthy. OsamaSon released his debut studio album, Flex Musix, on December 8.

On February 16, 2024, OsamaSon released Flxtra, the six track deluxe edition of Flex Musix. On February 18, he kicked off the Flex Musix Tour, his first as headliner; the tour concluded with a performance at Rolling Loud California on March 16. In May 2024, he released 3vil Reflection, a collaborative album with Glokk40Spaz. The tour concluded at Rolling Loud Thailand on November 22, 2024.

2025–present: Jump Out and Psykotic

On January 24, 2025, OsamaSon would release his third studio album, Jump Out, to critical acclaim from publications like Pitchfork. A deluxe version of Jump Out featuring two extra songs would be released 4 days later on the 28th, and the album would be his first to chart on the Billboard 200, peaking at number 151 on February 8th. OsamaSon would embark on a tour in support of the album from March to May. Later in the year, he would begin teasing a new project titled Psykotic, which would become his third studio album. On August 20, 2025, OsamaSon announced The Psykotic Tour, accompanying the album. Following the tour announcement, OsamaSon would go on to reveal the official track list for Psykotic on October 2. Five days later, on October 7, 2025, RapCaviar collaborated with Osama’s alternate Instagram account on a post featuring a picture of a CD announcing the release date to be on Friday, October 10. On that date, OsamaSon released the album, which features seventeen tracks and one feature from the rapper, Che. In May 2026, LiveNation announced Osamason's Psykturnal Tour, with nine dates across Europe and three dates in Australia. On May 20, 2026, his 23rd birthday, OsamaSon released "Off That!", rumored to be the lead single of his rumoured upcoming album Nocturnal. On August 26, 2026, OsamaSon was featured on the track "Vamp City" alongside Ken Carson off his reissue Cartunez.

Artistry OsamaSon has been compared to a number of his contemporaries, including Chief Keef, Playboi Carti, Destroy Lonely, Ken Carson, Future, and the late Speaker Knockerz. He is known for his experimental sound—dubbed "maximalist rage" by the Faders Vivian Medithi—which is characterized by a heavy usage of bass and synths; his musical style was described as "woozy, discombobulating, and sometimes suffocatingly layered" by Leor Galil of the Chicago Reader. OsamaSon has said the biggest influences on his music are Duwap Kaine, Speaker Knockerz, and Lil B. OsamaSon has also dabbled in the modeling industry, with Osama landing an official Balenciaga campaign for the summer of 2026. Jump Out Tour (2025) Psykotic Tour (2025)

Co-headlining Next Gen Tour (2023) (Cancelled)