In 2003, Cook released his first CD/DVD, Harmful If Swallowed.

He signed a contract with

Comedy Central Records. The album is certified platinum. He released his second CD/DVD in
2005, entitled Retaliation. This album went double platinum and made Cook the first comic in
27 years to have an album in the top 5 on the Billboard charts after Steve Martin's A Wild and
Crazy Guy moved as high as #2 in late 1978.[17][18] He performed at the MTV Video Music
Awards, and then afterwards he joined Snoop Dogg in presenting the award for Best New
Artist.[17]

On April 15, 2005, Cook performed his first HBO Special entitled Vicious Circle. Vicious Circle
was filmed "in the round" at the TD Garden. The same year, Cook shot two pilot episodes for his
own sitcom, Cooked. The sitcom was not picked up and the two pilot episodes were later
released on DVD as the Lost Pilot.[19] That same year, he embarked on a 30-day, 20-show
college tour called Tourgasm with his longtime friends Robert Kelly, Gary Gulman, and Jay
Davis. The tour was filmed and was later made into a 9-episode documentary on HBO.[20]

On December 3, 2005, Cook hosted Saturday Night Live (SNL).[21] He would then go on to host
the premiere of season 32 of SNL a year later.[22] The same year Cook launched his own
company, Superfinger Entertainment, in order to produce his own albums and videos.[13]

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. 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. He did two sold-out shows
in one night. 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,[23] and
Rolling Stone magazine's Hot Comic of the Year.[24] 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.

Cook at Comic Con 2007 promoting Good Luck Chuck

On April 10, 2007, Cook broke the Laugh Factory's endurance record (previously held by
Richard Pryor)[25] by performing on stage for three hours and 50 minutes. Dave Chappelle would
break the record five days later by performing for six hours and seven minutes. Chappelle beat
that record on December 3, 2007 by performing for six hours and twelve minutes.[26] On January
1, 2008, Cook broke Chappelle's record, by performing on stage for seven hours.[27]

From May 23, 2008 to May 25, 2008, Cook reunited with Robert Kelly and Al Del Bene for
three shows at The Coliseum in Caesars Palace. From May 29-June 4, 2008 the trio went to Iraq
to perform for the troops.[28] Del Bene was the Emcee, Kelly was the feature, and Cook was the
headliner.

He finished his fourth album, Isolated Incident; a performance which aired on Comedy Central
on May 17, 2009, with the release of the record following two days later. He kicked off that tour
at the Mohegan Sun in Uncasville, Connecticut, on April 25, 2009. This album was the last as
part of Cook's four-record deal with Comedy Central Records. The new album was performed at
Laugh Factory in Hollywood, which is considered to be Cook's home base, where he goes to
work on new material. He released the DVD version of Isolated Incident in November 2009.[29]