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He is known for his use of observational, often vulgar, and sometimes dark comedy.
He is one of the first comedians to use a personal webpage and My Space to build a large fan base As an actor, Cook has appeared in films since 1997, including Mystery Men, Waiting..., Employee of the Month, Good Luck Chuck, Dan in Real Life, Mr. He also provided the lead voice role in the 2013 family film Planes, and its 2014 sequel Planes: Fire & Rescue.
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.
On December 3, 2005, Cook hosted Saturday Night Live (SNL).
He would then go on to host the premiere of season 32 of SNL a year later.
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.
From May 29-June 4, 2008 the trio went to Iraq to perform for the troops.