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.
- Biggus Dickus: Everyone who sees Leon's penis seems both shocked and impressed. It even has glorious light and a choir.
- Cool House: Leon's opinion of his house boat, decorated like the 1970's Playboy mansion.
- Cuckold: A whole gang of them who want to castrate and/or kill Leon for screwing their wives.
- Hero Antagonist: The Victims of the Smiling Ass.
- I Ate WHAT?!:
- Julie's Jerkass ex is tricked into eating human feces at a bar.
- Leon knows exactly what he ate. And goes to puke it up because of that.
- 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.
- You Keep Using That Word: When the group arrives at the radio station to kill Leon, Lance says they are there to declare their "supreme manliness". Cue jazz song and dance number that begins with Lance and Hal nuzzling noses.