In 2017, he co-starred on the Fox time-travel comedy Making History, playing the role of John Hancock. Gemberling writes for Comedy Central's The President Show, where he also has a recurring role as Steve Bannon. Gemberling also has a recurring role as Bevers on the Comedy Central series Broad City. Gemberling portrayed John Belushi in the Netflix film A Futile and Stupid Gesture, a biopic of National Lampoon co-founder Douglas Kenney.