Leon Phelps (TIM MEADOWS) is self-proclaimed '70s style ladies man and late-night radio show host who dispenses advice about the matters of the heart and loins to his Chicago audience, stemming from his expertise on the matter of having been with thousands of women - most of them married.
When he steps over the lines of on-air decency one too many times, however, he and his producer, Julie Simmons (KARYN PARSONS), find themselves fired and unable to get another radio gig due to his salacious material. As such, they hang out at Lester's Straight Up Lounge, a bar run by none other than Lester (BILLY DEE WILLIAMS), and try to figure out what to do.
Unbeknownst to Leon, Barney (LEE EVANS), the jealous husband of one of his lovers, has joined a militant band of other such jilted men, the "Victims of the Smiling Ass" (so named for the smiley face on Leon's butt cheek which is the last thing seen of him as he flees into the night after any such encounter). Led by Lance (WILL FERRELL), a Greco-Roman wrestling fanatic, the men have set out to find the adulterer.
When Leon gets an anonymous letter from one of his past lovers that says she's rich and wants him back, the ladies man thinks he's hit pay dirt, despite a growing fondness between him and Julie who previously managed to resist his charms. As Leon sets out to find this woman - who turns out to be Honey DeLune (TIFFANI THIESSEN) - he must not only contend with the VSA members, but also his feelings toward Julie.