[3] 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.

Both Nichols and May held various jobs and pursued their craft until 1957, when Compass began an expansion to St. Louis, Missouri.

[6] They soon auditioned for agent Jack Rollins in New York, and within weeks they were booked on The Steve Allen Show and Omnibus.

[10] Their 1960 album An Evening with Mike Nichols and Elaine May was a recording of their Broadway debut and won a Grammy Award for Best Comedy Performance.

Nichols and May grew in fame quickly, and in 1962, for John F. Kennedy's birthday, they performed, alongside Marilyn Monroe.

[15] The documentary features rare clips of their comedy sketches in which their combination of great comic timing and natural improvisational ability is showcased.

The Chicago Tribune critic noted, "Unlike many films of this kind it understands, too, the importance of including full-length routines, rather than mere snippets.

In an interview with Vanity Fair, Nichols and May said their comic heroes were Sid Caesar, Imogene Coca, Lenny Bruce and Mort Sahl.

[2] In Vanity Fair, Woody Allen declared, "Individually, each one is a genius, and when they worked together, the sum was even greater than the combination of the parts—the two of them came along and elevated comedy to a brand-new level".

In an interview with Pitchfork, standup comedian John Mulaney, described Mike Nichols & Elaine May Examine Doctors (1961) as one of his favorite comedy albums of all time.