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In 2006, Cook headlined for Dave Attell's Insomniac Tour and hosted the 2006 Teen Choice Awards alongside Jessica Simpson.The following year he won the award for Best Comedian.Dave Chappelle would break the record five days later by performing for six hours and seven minutes.
Cook has described himself as having been "pretty quiet, pretty introverted, shy" as a child, although he was a "wild child" at home.
In 2006, Retaliation became the highest charting comedy album in 28 years and went platinum.
He performed an HBO special in the Fall of 2006, Vicious Circle, a straight-to-DVD special titled Rough Around The Edges (which is included in the album of the same name), and a Comedy Central special in 2009 titled Isolated Incident.
On November 12, 2007, Cook became the second comic to sell out Madison Square Garden's large arena space after Andrew Dice Clay accomplished this feat in 1990. The show was filmed and would later be put onto a DVD to be sold on Cook's third comedy album.
Cook won the Big Entertainer Award at the VH1 Big in '06 Awards, 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.