15 Memorable Womanizers in Movies


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


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


Cassanova may be the most notorious historic womanizer, but in contemporary times, it’s got to be James Bond.  Whether played by Connery, Daltin, 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


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


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 poon juggernaut, if you will.  After losing his “power,” though, Nick is humbled, and it goes to strengthen his relationship with his daughter.  Unfortunately, Nick Marshall does not call any women “sugar tits” in this movie.

Trent Walker – Swingers


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 sh*t, 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


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? Ha!), 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


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.  Me?  I would have blamed it on the ghost.

Joseph “Jody” Summers – Baby Boy


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 your ass.  And you have to respect honesty.

Frank T.J. Mackey – Magnolia


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


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


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 “f*ck you” 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


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 their asses off.  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


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


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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  1. I’m surprised Adam Sandler isn’t on here. Most of the movies that he’s produced/starred in has him as a womanizer in the beginning and then settles with 1 girl towards the end.

  2. @ Lagrange

    Is that womanizing? Whatever it is, it’s funny as hell.

    @ Connor P

    I tried watching some of that movie; it was unbearable. But yes, John Tucker was a womanizer. Good call.

  3. “Act too cool for them, make them laugh, and sort of treat them like sh*t, 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”

    Um……what? I want to laugh, sure, but I definitely don’t want to be treated like shit, thanks.

  4. @ Dorkus Malorkus

    That’s good. But, *lots* of girls, whether they admit it or not, are simply drawn to guys that treat them like crap. I think it’s pretty axiomatic, actually.

  5. What about Jack Sparrow from Pirates? We just see him get slapped a lot by interesting looking “ladies of the evening”

    Out of all the guys, I only like about 3 or 4 of them. Otter is the best. He’s a legacy!!!

  6. @ Laura

    Jack Sparrow’s a good one. The slaps mean that the girls actually cared about him at some point, i.e., they fell for his bullshit. Even with rotting teeth, Depp can get whoever he wants.

    I’m guessing most women wouldn’t like Frank TJ Mackey too much.

  7. How about David Larrabee from Sabrina?
    He was chasing after Sabrina although he was engaged!

    By the way, are you going to do a 15 Memorable Manizers in Movies?
    I got one: Holly Golightly from Breakfast From Tiffany’s.

  8. Roger Doger
    The Fall (Cab Driver)
    Cruel Intentions
    Nip Tuck
    Whipped (Amanda Pete)

    All of these are great especially the Fall its fantastic.

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