First breaking through as a cast member and writer for the NBC sketch comedy series Saturday Night Live during the 2013–2014 season,[2][3] Wheelan currently hosts the podcast Entry Level.

He has also released a half-hour special for Comedy Central, acted in various movies and shows including Big Hero 6: The Series, and opened for John Oliver at numerous sets.

Wheelan was a recurring guest on Saturday Night Live's Weekend Update segment, using his stand-up stories as public service announcements against irresponsible behavior.

On the Bruce Willis / Katy Perry episode, the commentary centered on having tattoos that have no meaning, with Wheelan showing off three tattoos he had in his youth: a tribal stamp on his left arm meant to look like the one Anthony Kiedis from Red Hot Chili Peppers has, a nautical star on his right arm, and a weird oceanscape on his side (which came from a doodle he drew in his freshman year of high school, and which does not make sense to him because he grew up in Iowa, which is not a coastal state).

On the Anna Kendrick / Pharrell Williams episode, the commentary centered on the dangers of drinking alcohol, and the story of how his friends put butter down his pants while he was blacked out drunk and Wheelan worrying that he was dying of an undiscovered sexually transmitted disease.