Before pursuing a career as a comedian, Giraldo worked as a lawyer, spending less than a year as an associate for Skadden, Arps, Slate, Meagher & Flom. Giraldo very rarely discussed his days as a lawyer. However, in an interview with Ben Kharakh in October of 2007, Giraldo referred to being a lawyer as a 'soul-deadening' profession.
Giraldo toured the country as a headliner at many clubs. He performed more than a dozen times on ''The Late Show With David Letterman'' and ''Late Night With Conan O'Brien'' and was a radio regular on ''The Howard Stern Show.''
His regular appearances on Comedy Central's roast series - one of the network's most successful shows - drew particular attention. Mr. Giraldo was a mainstay on that series, taking the stage in more than a half-dozen shows to mercilessly ridicule pop-culture figures like Pamela Anderson, William Shatner, and Chevy Chase. ''I could only dream,'' he told Mr. Chase, of making ''three good movies'' and ''40 horrible ones.''
In his stand up act, Giraldo sometimes referred to the fact he'd been a heavy drinker, but in recent years he'd been sober, with occasional slip ups.
Mr. Giraldo was born in New York in 1965, the oldest son of immigrant parents. He earned a bachelor's degree from Columbia and a law degree from Harvard. He was divorced with three children.