Prior to SNL, he performed in AT&T's "It's Not Complicated" commercials, in which he interviewed children,[3] and produced sketch videos with the comedy group Good Neighbor.

[9] In 2003, Bennett joined the improv/sketch group Commedus Interruptus along with fellow future SNL cast member Kyle Mooney and Nick Rutherford.

[10] and director Steven Spielberg, who sent Mooney, Bennett, Rutherford, and McCary a personal acknowledgement after being impressed with the Hook parody, Unbelievable Dinner.

In March 2013, he appeared in an episode of Last Man Standing, and that August voiced a character for Axe Cop for Fox's Animation Domination High-Def programming block.

That year, Good Neighbor produced a pilot for Comedy Central with Adam McKay's Gary Sanchez production company, though it was not picked up as a series, due to the move of three of the troupe's four members to New York City to star on Saturday Night Live.

[22] Bennett voiced Launchpad McQuack in the DuckTales reboot which ran from 2017 to 2021,[23] and Eric in the Sony Pictures Animation film The Mitchells vs. the Machines.