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Although they anticipated appearing earlier in the lineup, they were scheduled to perform between popular band Spin Doctors and the final headline act Phish, making them somewhat nervous but determined to do well.
On April 15, 2005, Cook performed his first HBO Special entitled Vicious Circle.Cook described the incident – as well as how dejected he felt and his resulting determination to someday return to the Boston Garden and perform successfully someday – as part of a web series for The Tonight Show entitled "Worst I Ever Bombed".His big break came in 1998 when he appeared on Comedy Central's Premium Blend.Cook won the Big Entertainer Award at the VH1 Big in '06 Awards, and Rolling Stone magazine's Hot Comic of the Year.The following day, November 13, 2007, he released his third CD/DVD entitled Rough Around The Edges, which was filmed live at Madison Square Garden in New York City.During that time, he embarked on his first arena tour.
On April 10, 2007, Cook broke the Laugh Factory's endurance record (previously held by Richard Pryor) by performing on stage for three hours and 50 minutes.
Both were convicted and sentenced to prison for the embezzlement.
On October 30, 1992, Cook and a group of local emerging improv/sketch comedians were scheduled to appear at the Boston Garden as part of local radio station WBCN's "Rock of Boston" music concert.
The following year he won the award for Best Comedian.
On November 12, 2007, Cook became the second comic to sell out Madison Square Garden. The show was filmed and would later be put onto a DVD to be sold on Cook's third comedy album.
He has released five comedy albums: Harmful If Swallowed; Retaliation; Vicious Circle; Rough Around The Edges: Live From Madison Square Garden; and Isolated Incident.