Cross was born in Atlanta, Georgia, the son of Barry and Susi, the former of whom emigrated from Leeds, England. Six months after his birth, Cross\'s family moved to Florida. After additional moves to New York and Connecticut, the family settled back in Roswell, Georgia, where Cross remained for nearly a decade. His family was poor and Barry left the family when Cross was 10 years old; the two have not spoken since he was 19, though they both primarily resided in New York City until Cross sold his home there in 2011. Cross and his family were evicted from their home while living in Georgia. He spent some time living in motels and at friends\' homes while growing up. He has two sisters and once bailed his youngest sibling out of jail. \n', '

At age 17, Cross began performing stand-up comedy. The day after he graduated from Northside High School in Atlanta, Cross relocated to New York City. Lacking a plan, he drifted, working briefly for a lawn care company on Long Island. Later, he enrolled at Emerson College in Boston. He would drop out after only a semester, but during his time there, Cross joined This is Pathetic, a college sketch group, where he met John Ennis. In the summer of 1985, the two aspiring actors took a road trip to Los Angeles, although this did not significantly further their acting careers. In Boston, Cross began to perform stand-up more regularly. From the mid-1980s to the early 1990s, Boston had a booming comedy scene, although Cross did not fit the types of acts being booked most of the time. He recalls that it was "a loud-, dumb-, pandering-, racist-, homophobic-type scene".\n', '

In 1990, a new comedy scene began to emerge at the comedy club chain Catch a Rising Star. Alongside Janeane Garofalo, Louis C.K., and other comics, Cross appeared regularly several nights a week. Cross formed the sketch comedy group "Cross Comedy" with 12 other performers, and they put on a new show every week. They were known for playing tricks on the audience, such as introducing fake comics or planting fake hecklers. Cross became increasingly focused on his comedy work.\n', '

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