When journalist Dennis gets assigned to write about Pretty Woman for Marquee magazine's “Hooray for Hollywood Hookers” issue, he invites five friends over to screen, celebrate and skewer the modern-day Cinderella story. The partiers include his roommate Tony, a burnt-out cruise ship crooner who's desperately looking for a new gig on land; Lauren, a relationship-challenged aspiring stand-up comic; Marcos, a sweet-natured attorney who never met a tangent he couldn't go off on; Ross, an Opera-loving video clerk with multiple tattoos and arsenal of movie fun facts at the ready; and Dr. Beverly Beaverman, the shrink next door who finds Freudian psychological meanings in everything she sees. Together, they do their best to make sense of the 1990 Richard Gere-Julia Roberts romantic comedy classic while discovering that the movie's themes—sex, money, sex for money—resonate in their lives in ways both ridiculous and profound.

A struggling LA actress impersonates Madonna for the day as a birthday gift for her recently dumped gay BFF, musical numbers and all....but things don't go as planned.