Toledo released their first EP in early 2019, titled Hot Stuff.[2] The duo's second EP, Jockeys of Love, was released on February 12, 2021.[3] In June 2022, Toledo released a new song called "L-Train".[4][5] In the fall of 2022, Toledo released their debut full-length album, How It Ends, through Grand Jury Records.[6][7][8] In February 2023, the duo announced "How It Ends [UNRATED EDITION], a deluxe edition of their debut album, due out March 31. Alongside the announcement, they released the song "Oak Hill".[9]