A comedian in front of the camera as well as behind the scenes, Miles honed his stand-up skills on New York's alternative comedy scene. In the early 2000s, he began landing small TV and film roles and often worked with his old cohorts, including Michael Showalter, who penned him a part in Wet Hot American Summer. Miles then branched out into screenwriting, producing and directing, helming a number of short films such as Ray Has Sex, which featured him as a virginal übernerd. In 2006, he landed his first series-regular role on Comedy Central's small-time newsroom mockumentary Dog Bites Man, and in 2008 he was cast in Paul Rudd's comedy Role Models. Around this time Miles also gravitated toward creative work on the web: He appeared in the satirical online (and eventual TV) series Children's Hospital, and wrote and produced the online series Horrible People and Hot Sluts. 2009 presented him with the biggest opportunity of his career when he signed on to be the head writer for Late Night With Jimmy Fallon.
- Began his career performing stand-up comedy in New York City clubs, while also writing and acting in short films.
- In addition to his comic work, has also appeared in Law & Order: Criminal Intent and indie dramas like Thirteen Conversations About One Thing and The Believer, both released in 2001.
- Made his big-screen debut in 2001's Wet Hot American Summer.
- Has written and produced several online series, including Horrible People and Hot Sluts, as well as acted in the online and TV satirical series Children's Hospital.
- Is the head writer for Late Night With Jimmy Fallon.
- 2014, Emmy — Outstanding Writing for a Variety Series: Nominee
- 2011, Emmy — Outstanding Writing for a Variety, Music or Comedy Series: Nominee
- 2016, Writers Guild Awards — Comedy/Variety (Including Talk) - Series: Nominee