Early in his career, he worked on commercials. He was behind the camera during auditions and callbacks for a 2009
Folgers commercial that later went viral. From 2012 to 2019, Simons played Jonah Ryan on the
HBO series
Veep, for which he received five nominations and one win for the
Screen Actors Guild Award for Outstanding Performance by an Ensemble in a Comedy Series. He also appeared on the series
Candy (2022) as Pat Montgomery and is a series regular on
Nobody Wants This (2024–present). He has also had acting roles in the films
The Interview (2014),
Christine (2016), and
The Boss (2016). In 2024, Simons was cast for the second season of
Percy Jackson and the Olympians as King
Tantalus. ==Personal life==