Kyle Dunnigan won an Emmy Award for the song "Girl You Don't Need Make Up" in 2015. He was a writer and performer for four seasons on Inside Amy Schumer, with recurring roles in various skits. He appears in stand-up comedy shows on Comedy Central such as Comedy Central Presents Kyle Dunnigan, and the talk shows Late Night with Conan O'Brien, Jimmy Kimmel Live!, and The Late Late Show with Craig Ferguson. He had a recurring role as Trudy Weigel's serial killer boyfriend, Craig Pullin, on Comedy Central's Reno 911!, and appears in the movie Reno 911!: Miami. Dunnigan has co-written with Jordan Allen-Dutton and starred as Craig in a pilot, called Brothers Strong. Dunnigan is a cast member on Fox's Cedric the Entertainer Presents. He was a cast member on Howie Mandel's practical joke reality show Howie Do It. He headlined Laugh-A-Palooza in August 2012, and promised to "high five" the show's attendees.

He released an album titled Wait, There's More... in 2009. Dunnigan is internationally known for his appearances on Comedy Central's Premium Blend.

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, along with Tig Notaro and David Huntsberger, co-hosted the podcast Professor Blastoff on the Earwolf network until July 21, 2015. The podcast ended abruptly when co-host Tig decided to leave the show, having earlier given her four month notice.

He was a member of the Groundlings Sunday Company and received his BFA in theater from the University of Connecticut.

He's a regular guest on The Howard Stern Show where he does celebrity impersonations of Caitlyn Jenner, Donald Sterling, Bill Maher, Hashtag Guy, Donald Trump, and Perez Hilton.