- Moved to Amsterdam to become a member of the esteemed Boom Chicago comedy troupe following his college graduation.
- Obtained his first major acting job when he was hired as a regular cast member on MADtv in 2002.
- Replaced Topher Grace for the final season of That '70s Show.
- Made his Broadway debut in The Pee-wee Herman Show starring Paul Reubens at the Stephen Sondheim Theatre in 2010.
- Collaborated with his older brother, comedian Seth Meyers, on many occasions.