Nichols and May met as students at the University of Chicago in the early 1950s. They began their career together at The Compass Players, a predecessor to Chicago's Second City which included Paul Sills, Del Close, Loretta Chiljian, and Nancy Ponder.

Nichols dropped out of college in 1953 and moved to New York in 1954 to study acting with Lee Strasberg. May remained in Chicago at Compass, and Nichols returned in 1955. For a short time they worked as a trio with Shelley Berman, but Nichols felt a duo worked better for their style.

Both Nichols and May held various jobs and pursued their craft until 1957, when Compass began an expansion to St. Louis, Missouri. Nichols rejoined the company but was fired in 1958, because May objected to Nichols's treatment of Close, and because the producer suspected Nichols and May were honing an act they planned to take with them.

They soon auditioned for agent Jack Rollins in New York, and within weeks they were booked on The Steve Allen Show and Omnibus. Soon they were touring the country and doing voice over work for ads, most notably a cartoon campaign for Jackson Brewing Company and Narragansett Brewing Company.

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