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.

Carey is a supporter of libraries, crediting them for beginning his successful comedy career. On May 2, 2000, in a celebrity edition of Who Wants to Be a Millionaire, he selected the Ohio Library Foundation to receive his $500,000 winnings. He later went on to win an additional $32,000 on the second celebrity Millionaire, making him one of the biggest winning contestants on Millionaire who did not win the top prize. Carey also has played on the World Poker Tour in the Hollywood Home games for the Cleveland Public Library charity. In June 2007, Carey offered to donate up to $100,000 (in $10,000 increments) to the Mooch Myernick Memorial Fund if anybody could beat him at the video game FIFA Soccer 07 for the Xbox 360. He dared five players from both the U.S. Men's and Women's National Teams to compete against him. Carey ended up donating $100,000, plus $60,000 for losing two games out of the six games he played. In October 2009, Carey made a bid of $25,000 in a charity auction for the @drew Twitter account. He later increased his offer to $100,000 if the number of followers of his account @DrewFromTV reached 100,000 by the end of the auction. In an interview with CBS News, he said he would instead donate $1 million to the charity Livestrong Foundation if his follower count reached one million by December 31, 2009. Another of Carey's offers to contribute in helping others came in September 2014 when he promised $10,000 to help find the perpetrators of a faked "ice bucket challenge" involving an autistic 14-year-old Ohio boy who, instead of being doused in ice cubes and water, received a shower of feces, urine, spit and cigarette butts. Shortly thereafter, celebrities Donnie Wahlberg, Jenny McCarthy and Montel Williams matched Carey's offer.

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