Dunnigan was a cast member on the 2002 Fox sketch comedy show Cedric the Entertainer Presents. He had a recurring role as Trudy Weigel’s serial killer boyfriend, Craig Pullin, from 2004 to 2006 on Comedy Central’s Reno 911!, and appeared in the 2007 movie Reno 911!: Miami. He was a cast member on Howie Mandel’s 2009 practical joke reality show Howie Do It. He released the album Wait, There’s More… in 2009.

He appears in stand-up comedy shows on Comedy Central such as Comedy Central Presents Kyle Dunnigan and Premium Blend, and the talk shows Late Night with Conan O’Brien, Jimmy Kimmel Live!, and The Late Late Show with Craig Ferguson. Dunnigan has co-written with Jordan Allen-Dutton and starred as Craig in a pilot, called Brothers Strong. He headlined Laugh-A-Palooza in August 2012, and promised to “high five” the show’s attendees.

In 2013 Kyle released the holiday album Craig’s All Star, Rockin’ Christmas, You Guys! as his alter-ego character “Craig” and his brother Kurt Pullin. He does his impressions of Donald Trump, Bill Maher and Tim Gunn throughout the skits. The album features other artists such as singer-songwriter Jesse Thomas, comedian Amy Schumer and actor Kevin Berntson.

Dunnigan was a writer and performer on all four seasons of the 2013-2016 sketch comedy show Inside Amy Schumer, with recurring roles in various skits. He won the Primetime Emmy Award for Outstanding Original Music and Lyrics for co-writing the song “Girl You Don’t Need Make Up” from that show in 2015.