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Before becoming a comedian, he worked as a lawyer. He is known for his distinct delivery and his skill of ranting, never allowing his rhythm to be broken. Giraldo performs regularly at the Comedy Cellar in Manhattan. Giraldo was a regular panelist on Tough Crowd with Colin Quinn. Additionally, he was the star of the short-lived Common Law and also starred in several pilots, including The Greg Giraldo Show and Gone Hollywood for Comedy Central.
Although the series was not picked up in 2005, The Greg Giraldo Show was a similar format to the cancelled Tough Crowd. The regular comics often joked during the run of Tough Crowd that Giraldo would eventually be the host of the show. However, when Giraldo was offered this series, many of the Tough Crowd comedians were rumored to be frustrated that Giraldo was essentially adopting the format used by Colin Quinn.
Giraldo has appeared on The Late Show with David Letterman, Late Night with Conan O'Brien, and The Howard Stern Show. Giraldo was a panelist on Comedy Central's 100 Greatest Stand-ups of All Time special. He also had his own half-hour special on Comedy Central Presents. He has also written segments for Last Call with Carson Daily.