Vince, a charismatic gym owner with no ambition lives with his younger brother Michael, a gorgeous idiot. Their simple life of women and working out is put on hold when the teenage son of Vince is dropped off on their doorstep by Priya, one of his old high school flings.

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.

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.