15 Memorable Womanizers in Movies

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Sometimes it seems that all you need to do to pick up a girl is smile and say something unique and witty. That’s not really the case in real life, but it always seems to work that way in movies. Of course, some guys fail miserably when it comes to getting girls, but others have it down to a science. It may be appealing to a woman’s hopes and dreams, the ability to make her laugh, or quite simply, the promise of a lustful, unforgettable night that enables some men to simply plow through women and thicken a black book to the point that it looks like a phone book. Whatever the reason, these guys are the best: here are 15 memorable womanizers in movies.

Giacomo Cassanova – Cassanova

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The late Heath Ledger played Giacomo Cassanova, a man known as “the world’s greatest lover.” He’s well known for getting it on with dozens of women, so much so that the people of 1753 Venice would exile him from the city should he fail to marry and settle down like his conservative peers. Knee-deep in women, Cassanova was charged with crimes against sexual morality.

James Bond – 007 Movies

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Cassanova may be the most notorious historic womanizer, but in contemporary times, it’s got to be James Bond. Whether played by Connery, Dalton, Brosnan, or Craig, Bond always gets the girl. Sometimes, it’s several girls. In Casino Royale, we see how the somewhat sociopathic Bond became such a womanizer; treating women as disposable objects is a much more efficient means of “love” for a spy than actually having a relationship.

Alfie – Alfie

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Alfie is a limousine driver in Manhattan, which enables him to meet many women. Not only that, but the back of a limousine provides a perfect spot to get down and dirty with any women Alfie manages to seduce. Which, when you look like Jude Law and speak with an English accent, isn’t that tough to do. After a cancer scare, Alfie starts to second guess his lifestyle of bedding random and large amounts of women. Ah, the old, “got it all out of my system” route.

Nick Marshall – What Women Want

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Nick Marshall, as a high-powered ad executive, was pretty good at bagging chicks to begin with. After an accident in which he’s jolted with electricity, though, Nick is able to hear women’s thoughts, making him virtually unstoppable. A woman’s needs juggernaut, if you will. After losing his “power,” though, Nick is humbled, and it goes to strengthen his relationship with his daughter.

Trent Walker – Swingers

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After just one scene with Trent, it’s clear he’s awesome with women. Act too cool for them, make them laugh, and sort of treat them like crap, and they’ll be all over you. No wonder Swingers appeals to so many guys; that’s pretty much how it works in real life, too. Unlike his buddy Mikey, Trent is all about getting beautiful babies for quick, good times. Be it in Vegas or in L.A.’s social scene, Trent Walker is money.

Eric “Otter” Stratton – Animal House

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Otter has certainly made the rounds around Faber College. Even some of the Omegas’ girlfriends have known him in the Biblical sense. Otter really puts his womanizing skills on display when he and some of his fellow Deltas take a road trip and stop along a women’s college on the way. Explaining to some poor, gullible girl that he was dating her recently deceased roommate (killed in a kiln explosion?), Otter is able to not only get in her pants, but convinces her to bring along three girls for his friends, too.

Jack Holden – Three Men and a Baby

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Jack Holden is a successful Manhattan bachelor with the attractive job of being an actor. When we first see Jack, he’s getting a drink thrown in his face, an experience to which many womanizers can relate. And the baby that appears on his and his roommates’ doorstep? It’s allegedly Jack’s, and with all his promiscuity throughout the years, he readily accepts the consequences.

Joseph “Jody” Summers – Baby Boy

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Look, Jody rules. He proudly displays “Nympho” on his bicycle and tells his girl that yes, he loves her, but he likes to sleep with other girls from time to time. That’s some honesty for you, ladies. And you have to respect honesty.

Frank T.J. Mackey – Magnolia

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Words cannot do Frank T.J. Mackey justice, so I’ll let him tell you how much of a womanizer he is in his own words:

Marcus Graham – Boomerang

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Man, remember when Eddie Murphy was either incredibly vulgar and funny or incredibly smooth and funny? It seems like a lifetime ago. Anyway, in Boomerang, Marcus Graham is an advertising executive (like Nick Marshall), and uses his high status job and good looks to bag any woman he wants. In the beginning of the movie, Marcus has his assistant send flowers to nine different women, but by the end of the movie, he only has eyes for one.

Tony Stark – Iron Man

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If you were a single billionaire, would you settle down with one woman? Probably not. Tony Stark doesn’t, and he has the kind of  money to do whatever and whoever he wants. It’s pretty sweet that he’s able to seduce a hostile journalist who wants nothing to do with him, but that’s nothing compared to his feat of sleeping with each and every Maxim cover model for an entire year’s worth of issues…including twins.

John Beckwith & Jeremy Grey – Wedding Crashers

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John and Jeremy are lawyers, but you’d think that they were professional wedding crashers. They each pull out all the stops to impress and sleep with horny women at weddings (and what better place to seduce a woman than at a wedding?), such as making balloon animals, dancing with kids, making up stories about war and baseball, and generally just lying through their teeth. Naturally, this all catches up to John and Jeremy, but fortunately for us, it’s after we’re treated to the “Shout!” montage that features a huge number of their conquests.

Howard Hughes – The Aviator

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Howard Hughes lived fast and dangerously, and that lifestyle coupled with his fortune meant that women couldn’t resist him. And unlike John and Jeremy, Hughes wasn’t slumming it at weddings and picking up women feeling sorry for themselves. No, Hughes was a true stud, bagging the likes of Billie Dove, Bette Davis, Ava Gardner, Olivia de Havilland, Katharine Hepburn, Gene Tierney, and Bessie Love. He was like Brad Pitt, George Clooney, and Johnny Depp all rolled into one.

Charlie Wilson – Charlie Wilson’s War

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Texas politician led Congress into supporting the Afghans in their war against the Soviets, but Charlie Wilson’s War showed us a side of Charlie Wilson outside of politics. In the movie, Wilson’s office is staffed with young, hot women, and he certainly isn’t shy around them or any others. With his Texas charm, Wilson can get what he wants both in the political and sexual realm.

Are there any womanizers in movies you think should be on this list? Let me know. And ladies, what do you think of these 15 guys? Do you see the appeal, or are you mind-boggled at their success with women? I’m curious to know, hit me up!

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