Carey is the youngest of Lewis and Beulah Carey's three sons and raised in the Old Brooklyn neighborhood of Cleveland, Ohio. When Drew was eight years old, his father died from a brain tumor. He played the cornet and trumpet in the marching band of James Ford Rhodes High School, from which he graduated in 1975. He continued on to college at Kent State University (KSU) and was a part of Delta Tau Delta Fraternity.

While still starring in The Drew Carey Show, Carey began hosting the American version of the improvisational comedy show Whose Line Is It Anyway? in 1998. He would announce the improv guests, direct the games, and then would usually involve himself in the final game of the episode. The show ran for a total of 220 episodes until the show's cancellation in 2006. In 1998, the New York Friars' Club made Carey the newest inductee of the group's Comedy Central Roast. His friend Ryan Stiles (who costarred in The Drew Carey Show and Whose Line Is It Anyway?) served as the roastmaster. Carey's income from Whose Line Is It Anyway? and The Drew Carey Show led to his inclusion on the Forbes list of highest-paid entertainers of 1998, at 24th with $45.5 million.  For the WB's 2004-2005 prime time schedule, Carey co-produced and starred in Drew Carey's Green Screen Show, a spin-off of Whose Line Is It Anyway?. It was canceled by the WB, but picked up shortly afterward by Comedy Central. The show's premise relied on the use of a green screen for all of the actors' improv interactions. Animation on the screen was inserted during post-production.  In April 2011, Carey began hosting a primetime improv show, called Drew Carey's Improv-A-Ganza. It was filmed at the MGM Grand in Las Vegas, Nevada, and first aired on April 11. The show took on the premise of Whose Line? and Drew Carey's Green Screen Show in that it features many of the same performers from both shows and did improv based on audience-provided suggestions.  Carey is an outspoken libertarian. He has expressed his political philosophy in the following terms: "I believe the answers to all the problems we face as a society won't come from Washington, it will come from us. So the way we decide to live our lives and our decisions about what we buy or don't buy are much more important than who we vote for."  Carey expressed his distaste for the Bush administration's management of the Iraq War, specifically on the September 14, 2007, episode of Real Time with Bill Maher. He made donations to Ron Paul's presidential campaign for the 2008 election. On the September 26, 2008, episode of The Late Late Show with Craig Ferguson, Carey defined "libertarian" to host Craig Ferguson as "a conservative who still gets high." In 2016, he supported Libertarian Party presidential candidate Gary Johnson in his run for office, and was made an Honorary Chair of the campaign for California.  Carey has spoken about his various political beliefs in several interviews, and in 1998, he led a "smoke-in" in defiance of California's newly passed no-smoking ordinance inside bars and restaurants. Carey has hosted a series of mini-documentaries called The Drew Carey Project on Reason.tv, an online project of Reason Foundation, a libertarian-oriented nonprofit think tank (for which Carey sits as a member of the board of trustees). The first episode, "Gridlock", addresses private highway ownership and was released on October 15, 2007. Other episodes discuss topics such as eminent domain, urban traffic congestion, and medical marijuana.  Carey is a devoted fan of the U.S. National Soccer Team, Cleveland Browns, Cleveland Cavaliers, Cleveland Indians, and the Columbus Blue Jackets. In 1999, Carey was part of the pregame ceremonies at the first game of the return of the Cleveland Browns, televised on ESPN. Carey attended the 2006 FIFA World Cup in Germany and the 2010 FIFA World Cup in South Africa. Carey is a minority owner of the Seattle Sounders FC, who began play in Major League Soccer on March 19, 2009, and won the 2016 MLS Cup. Carey is a fan of FC Barcelona and of the Scottish team Rangers. In 2006, he was a season ticketholder for the Los Angeles Galaxy.  Carey has shown his support for the Indians by throwing the first pitch at an August 12, 2006, game against the Kansas City Royals. He was rewarded by the Cleveland Indians for being "the greatest Indians fan alive" with a personal bobblehead doll made in his likeness that was given to fans. Carey responded to his bobblehead likeness by saying "Bobblehead Day, for me, is as big as getting a star in the Hollywood Walk of Fame."  In 2001, Carey was the first television actor to enter World Wrestling Federation's 30-man "Royal Rumble" match, which he did to promote an improv comedy pay-per-view at the time. He appeared in a few backstage segments before his brief participation in the match. Upon entering the ring, Carey stood unopposed for more than half a minute, but after the next entrant, Kane, refused a monetary bribe, Carey eliminated himself from the match by jumping over the top rope and retreating from ringside. On April 2, 2011, Carey was inducted into the WWE Hall of Fame by Kane.  Carey competed against five other celebrities in the first celebrity edition of the 2003 World Poker Tour. He placed fifth, beating out only actor Jack Black. Carey won $2,000 for his charity.  On May 15, 2011, Carey completed the "Marine Corps Historic Half Marathon" in 1:57:02; then, on September 4, 2011, he improved to complete the Disneyland Half Marathon in 1:50:46. And on October 30, 2011, he finished the Marine Corps Marathon with a chip time of 4:37:11, placing 10,149th out of 20,940.

Has he been into any sports outside of poker?
In 2001, Carey was the first television actor to enter World Wrestling Federation's 30-man "Royal Rumble" match,