Carey began appearing in commercials for restaurants in Canada with The Great Root Bear, but his two-year contract with A&W Food Services of Canada was cut short in November 1998 after promoting McDonald's in an episode of The Drew Carey Show.
In 1999, Carey made a cameo appearance in Weird Al Yankovic's music video for "It's All About the Pentiums".
In 2004, he made an appearance for Fountains of Wayne's video for "Mexican Wine". He gave an introduction to the video as if it were on a stage.
On May 7, 2000, Carey's made-for-TV film Geppetto debuted for an ABC presentation of the Wonderful World of Disney. The film was an adaptation of Pinocchio, and included actor Wayne Brady who had joined Carey on Whose Line is it Anyway? and a few episodes of The Drew Carey Show. Carey took singing lessons to prepare for the role.
He provided the entertainment for the 2002 Annual White House Correspondents dinner. Once he completed his standup routine for the 1,800 guests, President George W. Bush made a joke of his own, noting Carey's improv work, "Drew? Got any interest in the Middle East?"
In 2003, he joined Jamie Kennedy to host the WB's live special Play for a Billion.
In September 2003, Carey led a group of comedians, including Blake Clark and the Drew Carey Show's Kathy Kinney, on a comedy tour of Iraq.
In 2005, Carey appeared in three different films. He provided a voice-over for the character Crank in the animated film Robots, in The Aristocrats to retell a dirty joke along with other celebrities, and was interviewed in the documentary Fuck.
He is the current host of The Price Is Right
101 Big D##k Jokes
Life Without Football