Remembering Greg Giraldo: 5 years ago comedy lost one of its best

September 29, 2015 Will Fortune Features, Greg Giraldo

If we were to detail the characteristics of a good comedian, words like perceptive, enlightening, and witty might suffice. For the late comedian Greg Giraldo, this description would be a vast understatement, because he was not simply good, but great. Five years ago today, the comedy world lost Giraldo in tragic fashion, but his sharp, insightful, and sometimes-silly humor lives on. Before we highlight some of the comedian’s finest moments, let’s take a look back at what exactly made him so masterful.

For starters, Giraldo was remarkably bright, perhaps too bright for his own good, but that’s what made his comedy so amazing. Graduating from Columbia and Harvard Law School, Giraldo decided to pursue comedy after realizing he didn’t care for the excruciatingly drab world of corporate law. This instinctive intelligence paired with Giraldo’s raw perception of the world around him made for humor that was highbrow, but still accessible to the masses. Only the likes of Trey Parker and Matt Stone of South Park and a handful of other comedians working today have that unique ability. A glaring example of this is Giraldo’s classic “Civil War Letter” bit, which is off his 2006 debut album, Good Day to Cross a River.

Giraldo was also one of the most diverse comedians. After making countless appearances on the popular Comedy Central Roast Series, his fame grew, but he became labeled as “the roast comic.” While he was undoubtedly a fantastic roaster, this label failed to acknowledge Giraldo as a remarkable stand-up. His true ability shines through on his albums and work on Tough Crowd with Colin Quinn. If you explore his work, you’ll find a comedian who can find humor in politics, popular culture, everyday life, and sadly, the painful nature of his own self-indulgences. This comedic diversity is what made Giraldo so brilliant.

These are a few of the shining qualities of the late, great Greg Giraldo on the 5-year anniversary of his death. To honor Giraldo we compiled some of his finest appearances from stand-up, television, and roasts.

Just for Laughs set