In 2003, Fleming landed his first full-length feature Jeepers Creepers 2, where he played the young farm boy, Billy, who was abducted in the opening scenes of the film.

[1] Fleming, a childhood friend of the experiment rock duo Foxygen, joined the group as the live drummer, beginning with tours promoting the band's album We Are the 21st Century Ambassadors of Peace & Magic (2012).

In 2012, Fleming left Agoura Hills for New York and while still touring with Foxygen, began writing and recording what would become the debut Diane Coffee LP My Friend Fish.

Though his means were limited (recording a makeshift drum set with his iPhone voice memo app, using detuned guitars in lieu of a bass), he was able to complete the album in just shy of two weeks.

[2] The live band behind the 2013–2014 My Friend Fish tours usually consisted of Joey Lefitz on drums, Jared Walker on guitar, Emily Panic on bass, and Steve Okonski on Keys.