16 Most Entertaining Age-Lopsided Relationships in Movie History

Cougars do not choose to become cougars, they are decreed so by Simon and Garfunkel songs. Generally, cougars are still in their prime, slender and seductive, and they attract prey by sending complex mating signals out their cleavage. Ben (Dustin Hoffman) falls for Mrs. Robinson's (Anne Bancroft) trickery in the classic, The Graduate. Ben is a recent graduate who is worried about what to do with his future. Enter Mrs. Robinson, the original cougar. The wife of his father's business partner, Mrs. Robinson has Ben drive her home after a party, which leads to Ben becoming the meat in a Mrs. Robinson sandwich. The affair eventually ends, but comes back to haunt him when he finds himself falling for Mrs. Robinson's daughter Elaine (Katharine Ross), who is actually capable of having children at this point in her life. Honorable mention to the original MILF, Stifler's mom.

I know a lot of you can't imagine anything more irresistible than Natalie Portman nestled in your bed with only your gift of grope to guide you. There's just something about Natalie Portman that I can't quite articulate. Oh,wait...I've got it. It's her personality! Usually knowing a girl is in her twelveteens will kill the libido, but we can't undo a great personality, now can we? Portman received a considerable amount of creepy attention after a few roles where she played the confidante to lost, lonely men seeking borderline sexual relationships. In Beautiful Girls, Marty (Natalie Portman), is the Conway family's neighbor. Willie Conway is a semi-successful pianist who she connects with in fleeting moments. Before Beautiful Girls there was Leon aka The Professional a film about an assassin (Jean Reno) who takes Mathilda (Natalie Portman) in after her family is brutally murdered. I liked watching these movies when I was in my teens, but nowadays Natalie's roles seem too much like pedophile wish fulfillment. And just for good measure, Natalie also worked with a director known for casting himself against hot actresses and marrying adopted children, Woody Allen. Not to mention, Natalie was the original choice as Lolita in the 90s remake, but she turned the role down due to her feelings about young girls exposed to sex on film. Honorable mention goes to the original, Lolita (1962).

At a family wedding, young Julio (Gael García Bernal) and Tenoch (Diego Luna) meet Luisa (Maribel Verdú) and try to impress the older woman with an excursion to la Boca del Cielo ("Heaven's Mouth"), also known as young man bullshit. She rejects their advances, but changes her mind so she can even the score with her cheating husband. The three set out for rural Mexico in search of the invented beach. Along the way Luisa suddenly loses her freaking mind and seduces Tenoch without inviting Julio. So, the jealous Julio decides to tell Tenoch that he's bagged Tenoch's girlfriend. The next day Luisa once again loses her freaking mind and sleeps with Julio. Tenoch then admits that he's bagged Julio's girlfriend. Luisa’s lost count of unsettled scores, and since the boys have slept with the same women (their slutty girls and Luisa), Luisa decides they should make an oral alliance…in her mouth. Mexicans follow porn logic just like Americans do, so if one man commits adultery with another man's girlfriend, and the other man reciprocates, then it’s time for a bisexual threesome! Right?

Struggling with a mid-life crisis, jaded movie star Bob Harris (Bill Murray) goes to Tokyo to film a whiskey commercial. Meanwhile, Charlotte (Scarlett Johansson) is a young wife left behind by her husband to explore Japan. Charlotte quietly meets Harris in the bar of the hotel where they are both staying. They strike up an ambiguous relationship based on equal parts birthplace and romantic tension diluted by Bob making funny faces. After Charlotte finds out that Bob has slept with the hotel lounge singer, they split up, but eventually, they reconcile. When Harris leaves at the end, he whispers his age in Charlotte's ear, which is of course 20 years younger than his real age.

The reasoning behind a relationship between a 20-year old and an 80-year old is not hard to imagine for guys who worship in the sacred burial ground of brunettes--the Playboy Mansion. But in this story about an eccentric, horny senior citizen, the gender roles are reversed. Maude (Ruth Gordon) is a life-affirming 80-year-old mentor and Harold (Bud Cort) is the fresh faced 20-year old. The man-child and the senior citizen meet in a cemetery, and then grow close enough to share their methods for getting through this wild world. Even as the morbid Harold endeavors to act out suicide fantasies, Maude encourages him to breathe a little and enjoy life. Harold gets the hots for Maude, and inevitably there's some skin on wrinkle action. The movie is great, but after watching their geriatric love scene, I thought it was missing one suicide attempt. Mine.

There's “mindf*cked,” and then there's “on your quest for vengeance your daughter feeds you a live and very wriggly squid before taking you home where you try and surprise her on the toilet...with your erection.” Oh Dae-Su's (Choi Min-Sik) unwitting and beautiful daughter, Mi-do (Kang Hye-jeong), takes pity on him and promises that there is a time for incest, but she asks him to let it come naturally, like after discovering the important stuff, such as each other’s names, favorite music, and immediate family members you may have almost screwed lately. Hopefully I'll find out that the Korean chick I date is not a father**cker. And by date, I mean take photos of her while she sleeps and post them on my blog. What can I say, besides I hope she's a keeper!

Harry Sanborn (Jack Nicholson) is a music mogul/playboy with a history of dating women half his age. He and his latest trophy girlfriend, Marin Klein (Amanda Peet), drive to her mother's (Diane Keaton) Hamptons beach house. While getting it on with Marin, the awakening of his flaccid parts causes Harry to have a heart attack. Harry is left to recuperate at the beach house under the care of a young doctor (Keanu Reeves) who falls in love with the mom. The mom falls for Harry, and Harry falls in love with Viagra. Now, far be it from us to judge these generation-swapping lovers, but I find one point hard to swallow. How is that Keanu Reeves can be interested in the mother, Erica, or even Marin when a Harry Jack Nicholson is prancing around butt nekkid? If you think Keanu being gay is just a rumor, then I’ve got another rumor for you; you are ignorant.

Directed by Terry Zwigoff and based upon Daniel Clowes’ graphic novel, Ghost World centers on Enid (Thora Birch), an alienated, witty 18-year-old and Seymour (Steve Buscemi), in Buschemi role #846. Actually, let's try and differentiate between the creepy roles that Buschemi takes on. He's either playing a bug eyed loser, a weasel, or a fast talker with bug eyes. Enid initiates contact with Seymour as a sort of prank, but she winds up falling into his bed. The movie ends with Seymour in therapy and Enid in the shower scrubbing the Seymour off.

Lester Burnham (Kevin Spacey) is having a mid-life crisis. He’s trapped in a loveless marriage with a unfaithful real estate agent, and father to a girl who dates their drug dealing neighbor, He keeps his sanity by beefing up to impress his daughter's friend Angela (Mena Suvari), and in his fantasies he plucks rose petals out of her. When Angela's virginity is revealed, Lester the molester makes the correct moral decision, but we're not clear what message the creators of the movie want to send. Is it that only a bullet to the head can prevent the defloweration of a minor? Sorry to be blunt, but I tend to find this logic offensive to my libido. When my tubesocks come off my feet for me to deflower, I'm too eager for relief to get into moral decisions about experience, age, or a hole in my head. But that's just me, and I'm going to hell.

This Holocaust themed flick is not so much about the Holocaust as it is about Kate Winslett stripping for a child. The film pairs a virginal 15-year-old Michael Berg (David Kross) in bad health who is taken home by Hanna (Kate Winslett), a luscious-lipped illiterate 36-year old. Michael recovers from sickness and seeks out Hanna to thank her for bringing him home. The two quickly learn Hanna is more embarrassed about being illiterate than she is about getting it on with a teenager. Hanna becomes enthralled as Michael reads her passages from "Huck Finn" and "Her Vagina." After Hanna mysteriously disappears one day after too many weekends filled with laser tag, fart jokes, and Saturday morning cartoons, Michael is left confused and heartbroken.

Only in the last hundred years or so have our notions of society, social norms, and ickiness deemed finding a mature 14-year-old attractive so taboo. So if you can't make out the difference between the under-aged and the adults of this puritanical world, then my advice to you sickos is don't wait until Dateline starts to investigate. Plan an escape route to wherever Polanski's been hiding NOW. In this film, Andre (Gerad Depardieu) is a divorced Frenchy who takes his neglected teenage daughter, Nicole (Katherine Heigl), on vacation with him. She never acts her age, so in order to convince a local boy she is a woman and not a girl, she lies to him and says André is her lover, not her father. You know, I've heard a lot about how the French consider Americans to be prudes, but I'd rather be a prude than nail my 14 year old daughter...for the most part. I mean, my daughter obviously isn’t Katherine Heigl, so I’ve never had to gouge my eyes out to prevent that from happening.

I always wondered how a guy whose sole charm was his spectacles could end up with gorgeous chicks. I’m awkward and wear glasses myself, so I know that in the real world if you look and act like Woody Allen then the only hope you have when approaching a pretty woman is that she doesn’t beat you up. In the movies, Woody is hooking up with women left and right, like Téa Leoni (31-years younger than him), Julia Roberts (32) and Mariel Hemingway (16 while filming, which wasn’t even legal). There are so many intergenerational relationships in Allen flicks that it was hard to choose one. The Curse of the Jade Scorpion follows CW Briggs (Woody Allen) a veteran insurance investigator and Betty Ann Fitzgerald (Helen Hunt) who is a new employee. During a night out with the officemates, they see a magician who secretly hypnotizes both of them for evil schemes. The next day, Briggs commits a crime that he doesn’t remember. Will Briggs be able to deduce how many child-sex laws Woody Allen movies have broken over the years? Or will Briggs confess that there’s no chance in hell that Helen Hunt, Charlize Theron, and Elizabeth Berkley all find Woody desirable?

Linus (Humphrey Bogart) is nearly a corpse, yet curiously capable of wooing Sabrina (Audrey Hepburn), the chauffeur's daughter who oozes naivety and vivacity. Linus happens to be the "world's only living heart donor." But somewhere inside Linus is a a heart raring for a chance at love. He admits as much by wishing he were his brother, David. However when a million dollar deal starts breaking down due to his younger brother's sudden infatuation with Sabrina, its his unscrupulous business nature that compels Linus to sweep Sabrina away. I have to be honest, there wasn't much chemistry between these great actors. In fact, when cast members went for drinks after filming, Hepburn and co. left without inviting the notorious drinker Bogie. Years later, Bogie developed cancer and, Bogie being Bogie, he cut back on smoking. But he never stopped drinking. Though he did switch from scotch to martinis. His last words were, “I never should have switched from scotch to martinis.”

Travis Bickle (De Niro) is an isolated man desperate to make contact and share his existence. He is of unknown origins, though he sends his parents cards, lying about a government project he is supposedly working on. He likes to take dates to porno movies and defends his actions by calling it sex education. Bickle really wants to be a normal nice guy, but he doesn't comprehend that as a taxi driver, all we want from him is to speed the fuck up. Iris (Jodie Foster) is a 12-year-old child prostitute attempting to escape her pimp. She has breakfast with Bickle, and piques his inner need to be a savior of some sort. Unable to manage social interaction, Bickle pays for Iris' time, and tries to convince her to leave the lowlives and prostitution behind. Bickle becomes obsessed over saving Iris, and slips further into a violent alienation where he judges what is right, what is wrong, and who to kill.

A young boy, Josh Baskin, (Tom Hanks) makes a wish at a carnival to be big. He wakes up the following morning to find that his wish has been granted and his body has grown into adulthood, while his mind has not. On the inside, Josh remains a 12 year old. Now he must learn how to hold down a job and hold Susan Lawrence (Elizabeth Perkins) when she wants to cuddle. Glancing back, I realize I learned a lot from this movie about the importance of experience, and in the years since my first viewing, I've managed to grow nicely in one very important way: as a person. On the other hand, from my first romantic encounter with a tube sock to the only lover I've ever left satisfied, Hayden Patisserie, I've learned that not everybody can be big. Some of us have to learn to live with troll sex.

Max Fischer (Jason Schwartzman), all 15 years of him, is Rushmore's most likely member to join a club and least likely student to receive smiley faces on his homework. Max's character is sort of like Ferris Bueller if Ferris had set his mind to not taking days off from school. And by “like Ferris Bueller” we mean if you added a green velvet suit, spooky geek glasses, and made him an oddball who saved Latin Class. Save Latin from what (possibly the French?), I'm not sure. What I do know is when I tracked down this hot chick posting on Craigslist, she turned out to be a bag of rabbits. Lucky for Max that when he tracks down a writer she turns out to be Rosemary Cross (Olivia Williams), a widowed first grade teacher who quickly becomes the object of Max's obsession. And Max's obsession means you get an aquarium built for you.