The Ladies Man (2000)

Yet another recurring character from Saturday Night Live makes the jump to the big screen in this comedy. Leon Phelps (Tim Meadows) is the host of a radio call-in show in which he dispenses advice on the fine art of seduction, for which he seems to have quite a talent - rather surprising, seeing that he's usually broke, nearly everything he says sounds crass and obvious, and he possesses a fashion sense that would have been gauche in the mid-1970s but seems just plain freakish today. After finally going too far during a broadcast, Leon is fired, but he receives a note from one of his former flames who wants him to come back to her - and is willing to support him in high style. This sounds just fine with Leon, except she hasn't signed her name, and now Leon has to backtrack through his numerous conquests of the past and figure out who wants him to work his love magic. Meanwhile, a group of husbands who've been cuckolded by Leon, led by Barney (Lee Evans) and Lance (Will Ferrell), are hot on his trail, eager to get revenge. The Ladies' Man also stars Tiffani Thiessen and Karyn Parsons as two of the ladies in Leon's life and Billy Dee Williams as the ultra-smooth proprietor of Lester's Straight-Up Lounge.