Sarah Silverman appears before an audience in Los Angeles with several sketches, taped outside the theater, intercut into the stand-up performance. Themes include race, sex, and religion. Her comic persona is a self-centered hipster, brash and clueless about her political incorrectness. A handful of musical numbers punctuate the performance.

College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer!