Kevin O’Connor and Drew Feinberg met while Kevin was pledging Delta Psi Upsilon at St. John’s University in New York. In the Fall of 2001, Kevin and Drew were the breakout stars of the series premiere of CBS’ The Amazing Race. Their keen sense of humor – Kevin’s honed with 18 years of Catholic education, Drew’s with more than ten years in law enforcement - coupled with a friendship described by TV Guide as “the best platonic relationship since Butch and Sundance” earned Kevin and Drew an unprecedented 94% popularity rating from viewers voting on CBS.com. In addition, the boys were named “The Best of Reality Television” in Entertainment Weekly’s annual year-end issue.
In July 2004, they returned to primetime with Discovery's Kevin and Drew Unleashed, where they continued their hilarious travels by doing offbeat jobs such as handling alligators, herding cattle, brewing beer and working for a baseball team.
In February 2007, the boys were cast on The Amazing Race: All Stars.