Giraldo performed regularly at the Comedy Cellar comedy club in Manhattan, as well as clubs all over the U.S. Additionally, he was the star of the short-lived sitcom "Common Law". Giraldo landed the sitcom after being spotted by Hollywood agents at the 1995 Just for Laughs festival in Montreal. From 2002 to 2004, he was a regular panelist on "Tough Crowd with Colin Quinn". Giraldo also starred in several pilots, including "Drive" for CBS and "The Greg Giraldo Show", "Adult Content" and "Gone Hollywood" for Comedy Central. In 2004, he was featured in the spoken-word Lazyboy song "Underwear Goes Inside the Pants."