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The Ladies Man stars Tim Meadows as Leon Phelps, a sex machine who was
raised by Hugh Hefner himself, until sleeping with Hef's wife that is. Now Leon has his own talk show in which he basically talks about his own sexual experiences and is constantly in trouble with the radio network execs for doing so.
After one too many obsene remarks, his show is cancelled and he is fired, along with his producer, Julie. He and Julie go out to all the radio stations and try to get a job, but none of the stations want to hire them because of the vulgarity that comes out of his mouth.
After they've gone to every station they can think of, Leon decides to have sex, and then wait for something to randomly happen to help him. Well, right after he has sex, he gets a letter from one of his former lovers, and she says that she wants to be with him and support him. (She also happens to be rich). The only problem is she didn't sign her name, she only left the signature "sweet thing", which doesn't help at all because Leon calls any and everything sweet thing. So, he has to search for her.
As all of this is happening, a society of men who have had their wives boned by Leon are following his actions and planning to confront him and either kill him or "cut off his balls."
He sets out and goes door to door to all of his former lovers. (He has kept track of them all in a giant black address book.) After a long and exhaustive search, he still has no success finding the one who wrote the letter.
The society of men find out where he lives (a houseboat) and they burn it down. Leon sees his burnt out house and bursts into tears. The next morning he wakes up on Julie's porch. She wakes up and goes downstairs to find him talking to her parents and getting along with them very well. Eventually they go up to her room to talk and he tells her about what happened. In the course of their discussion he reveals that he is tired of being "the ladies man", and that he just wants a girl like Julie. She seems to have mutual feelings and they begin kissing when suddenly Leon sees the logo to a company which also happens to be linked to the letter he recieved. He remembers who it was who sent it now, and he simply runs out and over to her house, leaving Julie alone in her room.
He finds the woman (Tiffany Amber Thiessen), and she tells him to come over the next night and they'll leave and go on a trip around the world. He buys a new suit and the next night heads over to her house, only to find that she has a husband, and she wants to have sex right then and there, and that if her husband arrives, she wants Leon to kill him. Needless to say, Leon is very concerned about this, not to mention that he isn't really that happy about having sex with her. He finally stops her and tells her that he is in love with another woman, Julie. Right as he is saying this, the woman's husband (Will Farrell), who also happens to be the leader of the society of men who have been hunting Leon, arrives at home. The entire society of men are with him as he comes home as well. (There are about 20 of them.)
They grab him and take him outside where the leader challenges him to a wrestling match. The leader attacks him wrestling style, but Leon just knees him in the groin a few times and begins to leave when another man pulls a gun. With the gun pointed at him, Leon gives a speech to all the men whose wives he has boned, that he is a changed man, and that he is in love now. As he is giving this speech, Julie and some of Leon's friends show up to help him, but they don't even need to, because he has already won over the society of men with his speech.
So, everyone goes home happy and then we skip to a year or so later as Leon has gotten back onto the radio circuit, and is currently hosting the top rated show in the nation. And as the movie closes, we learn that he and Julie have a son as well now.
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