[3] He began a long-running collaboration with the auteur filmmaker Wes Anderson at age seven when he was cast as a young camper in Moonrise Kingdom (2012), partly because he could play piano.

[4][5] In March 2012, an eight-year-old Ryan narrated, and got a writing credit on, a one-minute stop motion advertisement for Sony Mobile that was directed by Anderson.

[3][5] In Bo Burnham's Eighth Grade (2018), he played a "scene-stealing" boy who takes the main character, Kayla, on a date over chicken nuggets and imitates Rick and Morty; the young actor found watching himself in the film cringeworthy.

[2][4][7] He began co-starring with Nasim Pedrad in the TBS sitcom Chad in April 2021.

[2][7] He took improvisational comedy classes with the Upright Citizens Brigade in New York from age 15.