He is best known for his work as a writer and his roles on actual play anthology web series Dimension 20 and the creator-owned podcast Worlds Beyond Number.

[7] After his graduation in 2014, Wilson moved back to California and joined the Upright Citizens Brigade in Los Angeles.

[6] In 2017, Wilson starred as Frank in The Guest Book[5] and played Lucas Wiley on Netflix's American Vandal.

[4][12] Wilson is known within the tabletop role-playing game community as a primary cast member of Dimension 20, an actual play anthology web series which premiered in 2018; it was created by CollegeHumor for the streaming service Dropout.

[13][14][15] In January 2023, it was announced that Wilson, alongside Erika Ishii, Aabria Iyengar, and Brennan Lee Mulligan, would star in the creator-owned actual play podcast Worlds Beyond Number; the show premiered in March 2023.