Cherry began taking improv lessons in 2011, and was placed on a house team at the Upright Citizens Brigade Theatre in New York in 2017.

[4] In 2018, he played bookstore clerk Ethan Russell in season one of the Netflix series You.

[5] He played Wolf on FOX's Duncanville, Pete's manager Kevin on Crashing (2017–2019), and Norman on I Feel Bad (2018), and had minor roles on Succession and Living with Yourself.

Cherry also played Klev in two Marvel Studios movies: Shang-Chi and the Legend of the Ten Rings and Spider-Man: Homecoming.

In 2020, Cherry was cast in a lead role as Dylan George in the ongoing Apple TV+ series Severance.