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''The Ladies Man'' is a 2000 comedy film directed by Reginald Hudlin, starring Creator/TimMeadows (who co-wrote the screenplay), Creator/KarynParsons, Creator/BillyDeeWilliams, Creator/TiffaniThiessen, Creator/LeeEvans, and Creator/WillFerrell. It centers around the Leon Phelps character originated by Meadows in a series of ''Series/SaturdayNightLive'' sketches.

Not to be confused with the 1961 Creator/JerryLewis film of the same title.

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!!Tropes include:

* AngryMobSong: 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.
%%* TheCasanova: Leon.
%%* ChickMagnet: Leon, again.
* CoolHouse: Leon's opinion of his house boat, decorated like the 1970's Playboy mansion.
* GagPenis: Everyone who sees Leon's penis seems both shocked and impressed. It even has glorious light and a choir.
%%* HaveIMentionedIAmHeterosexualToday: The obviously gay Lance.
%%* HereWeGoAgain:
* HeroAntagonist: The Victims of the Smiling Ass, the husbands of the various women that Leon's slept with. (And to a point their relatives, but it's mostly the husbands who get focused on.)
* IAteWhat: Leon pushes Julie's ex-fiancee Lester to eat the bar food with him as a display of his street cred. So they dine together on pickled pigs' feet, pickled eggs, prairie oysters, and spicy hog balls. As a finale, Leon tricks Lester into eating something called "back bottom gristle lumps", which turns out to be [[spoiler:pickled human shit]].
* ImpossiblyTackyClothing: Leon tends to dress as if it were the mid-1970s, despite it being several decades later.
* InteractiveNarrator: Lester the bartender. [[LeaningOnTheFourthWall 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.
* ITakeOffenseToThatLastOne: 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 FacePalm.
* JerkAss:
** 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.
* JerkWithAHeartOfGold: Leon is very protective of Julie, even if he is a complete womanizer.
* MoodWhiplash: Leon's Valentine's Day poem, which starts out sweet and romantic and ends with "do it in the butt".
* StrangeMindsThinkAlike: The mob of angry husbands think that Leon's horribly tacky houseboat is "tasteful".
* TooDumbToLive: Leon overhears the VSA threaten his life and is successfully sneaking out of the bar... until he hears them claim he has a tiny penis and loudly objects, leading to a chase.
* TransparentCloset: Lance, whom absolutely everyone gets the vibe off but no one quite has the heart to talk to him about. Also his "wrestling partner" Brian.

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