Amari Deshawn Adham Middleton (born 2003), known professionally as OsamaSon, is an American rapper, songwriter and record producer. He became widely known within the underground rap scene after his breakout hits "Cts-V" and "Troops" gained traction online in early to mid-2023; his debut studio album, Osama Season, was released in July 2023. His second studio album, Flex Musix, was released in December 2023. His third studio album, Jump Out, was released in January 2025, becoming his first album to chart on the Billboard 200. His fourth studio album, Psykotic, was released in October 2025 and debuted at #81 on the Billboard 200, marking it as OsamaSon's second ever album to chart while also placing 50 spots higher than Jump Out.
OsamaSon began making music in 2020 under the name PradaUMari.[4] By 2021, he adopted his current stage name and released his mixtapes Vengeance and Carnival.[3] In early 2023, the collaborative projects Osamavrt and 2 Slime preceded the release of the EP Bad Habits.[5] On April 7, OsamaSon's breakout single, "Cts-V", was released and began gaining traction online.[6] His music was further popularized by Internet personalities such as BruceDropEmOff, who played OsamaSon's songs on his live streams.[5]
2023–2024: Osama Season and Flex Musix
On June 2, 2023, OsamaSon released "Troops", the lead single from his debut studio album, Osama Season; like "Cts-V", the song saw considerable success online.[5]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.[7][8] In October, he embarked on the Next Gen Tour alongside fellow rappers Kankan, Summrs, Highway, and the producer F1lthy.[9] OsamaSon released his second studio album, Flex Musix, on December 8.[6]
On February 16, 2024, OsamaSon released Flxtra, the six track deluxe edition of Flex Musix.[10] 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.[11][12] In May 2024, he released 3vil Reflection, a collaborative album with Glokk40Spaz.[3] On November 5, 2024, OsamaSon embarked on "The Wish You Were Here Tour" spanning across Canada, London, and Thailand.[13] The tour concluded at Rolling Loud Thailand on November 22, 2024.
On January 24, 2025, OsamaSon would release his third commercial mixtape, 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. On August 20, 2025, OsamaSon would announce that he would have a tour for his album, which would begin on October 16, 2025, in St. Louis, and will end on December 20, 2025, in Vancouver.[14][15][16] 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.[17] Following through with his word, at midnight, OsamaSon released his highly anticipated album, which features seventeen new tracks and one hidden feature from the rapper, Che.
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