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.
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".
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.
Cook won the Big Entertainer Award at the VH1 Big in '06 Awards, and Rolling Stone magazine's Hot Comic of the Year.
His big break came in 1998 when he appeared on Comedy Central's Premium Blend.
In 2000, Cook did a half-hour special on Comedy Central Presents.