The Ladies Man is a 2000 comedy film directed by Reginald Hudlin, starring Tim Meadows (who co-wrote the screenplay), Karyn Paraons, Billy Dee Williams, Tiffani Thiessen, Lee Evans, and Will Ferrell. It centers around the Leon Phelps character originated by Meadows in a series of Saturday Night Live sketches.
Not to be confused with the 1961 Jerry Lewis film of the same title.
- Angry Mob Song: After finding out that Leon is the one who slept with their wives, The Victims of the Smiling Ass are so glad to have a new goal that they cheerfully dance through the city on their way to his workplace while singing about their plan to castrate & kill him.
- Cool House: Leon's opinion of his house boat, decorated like the 1970's Playboy mansion.
- Gag Penis: Everyone who sees Leon's penis seems both shocked and impressed. It even has glorious light and a choir.
- Hero Antagonist: The Victims of the Smiling Ass.
- Impossibly Tacky Clothing: Leon tends to dress as if it were the mid-1970s, despite it being several decades later.
- Interactive Narrator: Lester the bartender. Leon even calls him out on it. Especially for apparently doing it every time he goes to the bar, despite it being the same few barflies.
- I Take Offense to That Last One!: While Leon is trying to sneak past the VSA in the bar, due to them being there to kill him, he speaks up when they say he has a small penis. Cue chase scene and Lester's Face Palm.
- Julie's aforementioned ex.
- The mailman who ridicules Leon's style.
- Given that he enjoys sleeping with married women and mocking their husbands by leaving naked and showing them his ass tattoo, Leon qualifies too.
- Jerk with a Heart of Gold: Leon is very protective of Julie, even if he is a complete womanizer.
- Mood Whiplash: Leon's Valentine's Day poem, which starts out sweet and romantic and ends with "do it in the butt".
- Strange Minds Think Alike: The mob of angry husbands think that Leon's horribly tacky houseboat is "tasteful".
- Transparent Closet: Lance. Also his "wrestling partner" Brian.