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In February 2020, he independently released the song "Rascal", which quickly went viral on YouTube overnight, due to the video's content and portrayal. He signed to Warner Records and Cmnty Rcrds in April 2020. He dropped the single "Dealer", debuting its remix days later. The remix features American rappers Future and Lil Baby.
On June 12, 2020, he released his debut extended play, Drug Dealing is a Lost Art. The eight-track EP contains features from American rappers Future, Lil Baby, Westside Gunn and Young Thug.
On November 12, he released "The Wishing Hour", a reworking of the Matchbox Twenty song "3AM." It was subsequently announced RMR's next project would be called 4th Qtr Medley, a three-part series of re-imagined songs and interconnected videos similar to "Rascal," set to be released on November 24. On November 24, 4th Qtr Medley was released and featured reworkings of songs from Matchbox Twenty, Drake, and The Goo Goo Dolls. As of 2021, the music video for 4th Qtr Medley is no longer on YouTube, having been removed from RMR's channel, although the three individual songs are still accessible online.
On January 8, 2021, RMR released "Her Honeymoon", the first single off of his upcoming debut album, Hotel. The accompanying music video featured three possible endings to the narrative, concluding with RMR encouraging fans to call or text his personal cell-phone to vote for their preferred ending.
On May 21, 2021, RMR released "Vibes" featuring Tyla Yaweh. The song is the second single from RMR's upcoming debut album Hotel.
On June 11, 2021, Billy Strings released a single for "Wargasm" that features RMR.