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The Most Uncomfortable Age Gaps In Movies

They say "all you need is love." They also say "age is just a number." But every so often when you're watching a movie, you see a mismatched couple (or at least one lovestruck stalker) taking things a bit too far. When it comes to cinematic relationships, sometimes the number of birthdays really does matter, and we got a little weirded out when we saw these uncomfortable age gaps in movies.

That's My Boy (2012)

Adam Sandler is no stranger to comedy that might be labeled as "questionable." But even if you're a fan, you've got to admit that Sandler didn't just cross the line in That's My Boy—he straight-up pole vaulted over that sucker.

As Geoff Berkshire wrote for HitFix, the premise of this 2012 comedy is "particularly tasteless," as it involves a younger version of Sandler's character (played by Justin Weaver) hooking up with his hot teacher (Eva Amurri Martino). Just to be clear, we're talking about a 12-year-old having sex with an adult, and as Berkshire writes, this is all played as a "naughty joke. However, as That's My Boy only has a 20 percent on Rotten Tomatoes, it seems like critics weren't in the mood to laugh.

Big (1988)

With its famous keyboard scene and great Tom Hanks performance, it's no wonder Big is considered a comedy classic. Directed by Penny Marshall, this 1988 flick follows a young kid named Josh (David Moscow) who morphs into a 30-year-old man. At first, this magical transformation seems pretty cool, especially when Josh is paid big bucks to play with toys for a living. But things get problematic when he starts dating Susan (Elizabeth Perkins), his adult coworker.

True, Hanks and Perkins are about the same age in real life, but in the movie, Josh is just 13. So when the two end up sleeping together, we're witnessing a serious felony offense. This illegal relationship has prompted some people to label Big the "creepiest story ever told" or describe the film as a celebration of "unrepentant pedophilia." While that sounds harsh, you've got to admit it's creepy at the end when Josh reverts to his child form, and Susan waves goodbye to her 13-year-old ex.

American Beauty (1999)

At the 72nd Academy Awards, Kevin Spacey won the Best Actor Oscar for playing Lester Burnham, a middle-aged loser who's inspired to take control of his life after falling head over heels...for a high school student (Mena Suvari). Making things even worse, she's his daughter's best friend, but Lester isn't going to let a little thing like age get in the way of his fantasies.

Sure, Roger Ebert claimed the film wasn't about a "Lolita relationship," instead saying it was really about "yearning after youth, respect, power and, of course, beauty." While that's true, some of those dream sequences still left us feeling icky, and we can't help but sympathize with Kirsten Dunst, who turned down the role of Angela because she "didn't want to kiss Kevin Spacey or be seen lying naked in those rose petals." After all, she was only 15.

Don't worry, Kirsten. We totally get it.

Birth (2004)

Directed by Jonathan Glazer, Birth is a pretty divisive movie that was greeted with an avalanche of jeers and catcalls when it premiered at the Venice Film Festival. Mainstream audiences weren't super happy, either. After all, the film follows an upper-class widow (Nicole Kidman) who's convinced that a 10-year-old boy (Cameron Bright) is actually her husband reincarnated.

At first, she's a little reluctant to believe this kid is her lost love, but as the film goes on, not only do Kidman and the kid share a kiss, they even spend a few minutes sitting in the bath together. Granted, Jonathan Glazer didn't intend for this to be "salacious." Instead, he wanted to make a film about "the idea of eternal love." Still, anytime you've got a full-grown woman making eyes at a prepubescent boy, your film is probably going to bomb big time at the box office.

Captain America: Civil War (2016)

Steve Rogers (Chris Evans) and Peggy Carter (Hayley Atwell) are pretty much the perfect Marvel couple. They're brave, beautiful, and most importantly, age appropriate. But their relationship gets tricky after Steve wakes up from a nearly 70-year-long nap and finds his old flame looking kind of elderly.

Of course, Steve is the exact same age as Peggy (Arctic ice does wonders for the skin), so it's a bit weird when he falls for Agent 13 (Emily VanCamp), an undercover SHIELD operative. Still, at least they both look like they're in their early 30s...but that illusion doesn't last long, as it's later revealed Agent 13 is Peggy's great-niece.

That tiny detail makes their whole smooching scene in Civil War a little uncomfortable, and even Hayley Atwell was perturbed, saying, "I wouldn't want to date my great aunt's guy. It just feels like it crosses an incestuous boundary....You can't tap that!"

Labyrinth (1986)

Widely hailed as a 1980s fantasy classic, Labyrinth is mostly famous for two things: David Bowie and David Bowie's, um, bulge. As The Washington Post put it oh-so delicately, you can make out quite a bit of anatomy thanks to the singer's "over-revelatory spandex." With all that male charisma onscreen, it's easy to see why so many people have said Labyrinth was the movie that kickstarted their sexual awakening.

Now, that's all fine and good...but then you've got to remember that Bowie's character Jareth the Goblin King is actively pursuing a 15-year-old girl (played by a 14-year-old Jennifer Connelly). In fact, he drugs her, tries to seduce her, and begs her to, "Do as I say, and I will be your slave."It's a bit intense for a kid's film, although it's nowhere near as freaky as that cackling junk lady.

Chaplin (1992)

Before donning his Iron Man suit, Robert Downey Jr. earned an Oscar nod for his performance as Charlie Chaplin. As the film reveals, the real-life Chaplin was a complicated guy and something of a ladies' man...who liked his ladies young.

Chaplin's taste for underage girls becomes pretty apparent when he marries a 16-year-old child actress named Mildred Harris (Milla Jovovich), a girl one of Chaplin's friends describes as "jailbait." In both real life and the movie, Chaplin would then go on to marry another 16-year-old and a 22-year-old woman claiming to be 17 before the 50-something comedian finally settled down with an 18-year-old.

It all gets weirder when you realize Jovovich herself was also around 16 years old when she landed the role, increasing the awkwardness of her character's nude scene with the 20-something Downey (it was filmed by a body double, but still).

Leon: The Professional (1994)

Directed by Luc Besson, Leon: The Professional is a movie that'll leave you feeling a little odd. It's an awesome film, but while the relationship between Jean Reno's Leon and Natalie Portman's Mathilda isn't "inappropriate" per se, it is just a tad...disconcerting.

The plot involves a 12-year-old girl (Portman) who asks a hitman (Reno) to get revenge on the psychotic DEA agent (Gary Oldman) who murdered her family. Leon and Mathilda's relationship starts off strange—he's childlike, she's wise for her years—and only gets weirder from there, especially when she starts crushing on Leon, dressing up as Madonna, and telling strangers this full-grown man is her lover.

True, as Jeff Saporito of Screen Prism points out, Leon loves Mathilda—but not like that. The assassin never really deals with the situation in a mature way, but then, he's also training her to become a killer, so maybe he's not the best father figure in the world.

The Diary of Teenage Girl (2015)

Based on the graphic novel by Phoebe Gloeckner, Marielle Heller's The Diary of a Teenage Girl is meant to push boundaries and start conversations. After all, this is a film about a 15-year-old girl discovering her sexuality, a subject that's rarely discussed on the big screen. However, some might argue that Diary takes things a bit far when its teenage protagonist winds up in bed with a 35-year-old man.

The 15-year-old in question is Minnie Goetze (Bel Powley, actually in her 20s here), a wannabe cartoonist in 1976 who loses her virginity to her mom's boyfriend, Monroe (Alexander Skarsgard). Yeah, it's "consensual" (that word gets tricky when you're talking about a kid), but that doesn't make it any less uncomfortable. And sure, as film critic Kate Erbland points out, this is a movie about a girl "making her own decisions, even if they're probably bad ones," but in a film that's all about breaking taboos, perhaps Diary broke one taboo too many.

An Education (2009)

In England, the age of consent is 16, so while the age gap at the center of An Education is technically legal, that doesn't make it any less unsettling. In this film written by Nick Hornby (based on the memoirs of journalist Lynn Barber), 24-year-old Carey Mulligan plays Jenny, a teenage cellist who can't wait to leave her little London neighborhood. And as Jenny grows more and more restless, who should arrive but David (Peter Sarsgaard), a 30-something smooth-talker with no scruples about getting involved with a 16-year-old.

Over the course of the film, David teaches Jenny all about high society, sex, and eventually, deception. As Roger Ebert described him, David is "a rotter, a bounder, a cad, a dirty rotten scoundrel. But you can't get far in any of those trades if you're not also a charmer." Fortunately, Jenny eventually realizes this guy is a wolf in 1960s clothing, and she walks away from David a little older, a little wiser, and—you guessed it—a little more educated.

Harold and Maude (1971)

Perhaps the most famous movie ever made about May/December relationships, Harold and Maude was a box office failure in 1971, but over the years, it's gained a cult following. Today, it's often considered must-watch cinema, although if you're only familiar with the basic premise, you might think this is a film simply about a kid who sleeps with a woman old enough to be his grandma.

Of course, Harold and Maude isn't just about the sex (we don't even see anything happen onscreen). Directed by Hal Ashby, the film follows death-obsessed Harold (Bud Cort), a 20-year-old who fakes suicide and visits random funerals. Eventually, he runs into the larger-than-life Maude, a 79-year-old who teaches Harold how to live. The two gradually fall in love, and while the thought of Harold's "firm young body commingling with withered flesh" might sound unsettling at first, Harold and Maude is really about choosing to say yes or no, to live high or live low.

Venus (2006)

It's a sad fact that Peter O'Toole—one of Hollywood's greatest actors—never won an Academy Award (honorary ones don't really count), even though he was nominated eight times. And his final nomination came for the movie Venus, in which O'Toole plays Maurice Russell, an aging actor in his 70s who looks like death warmed over.

But things take a turn for Maurice when he's introduced to his (brace yourself) friend's niece's teenage daughter (Jodie Whittaker). As critic Seongyong Cho puts it, Maurice is "fabulous dirty old man," and while he's physically incapable of getting it on, that's not going to prevent him from spending time with a pretty girl.

Of course, Whittaker's character isn't sexually interested in Maurice, but as the film progresses, the two do form a sort of bond, regardless of their whopping age gap. It's kind of sweet, kind of skeevy, and proof that O'Toole is one of the greatest actors who never took home an Oscar.

Hello, My Name is Doris (2016)

As Don Solomon of Fast Company points out, movies often pair aging actors like Jack Nicholson with much younger women, so it's kind of refreshing that Hello, My Name Is Doris has Sally Field chasing after a much younger guy. In this comedy directed by Michael Showalter, Field plays a 60-something eccentric who lives the life of a loner until a self-help speaker inspires her to pursue her 30-something co-worker, John (Max Greenfield).

Sadly, things get uncomfortable as we realize that John—who's a good guy—just isn't interested. Unfortunately, Doris is blind to the truth and spends her time dreaming about romantic episodes with her decades-younger love interest. All of this culminates in one of cinema's most cringeworthy confessions of affection, one that'll leave you feeling absolutely awful for both Doris and her unrequited crush.

Mr. Holland's Opus (1995)

You could describe Mr. Holland (Richard Dreyfuss) as a frustrated guy. Sure, deep down in his heart, he loves teaching kids about music, but he only got the gig to make ends meet. His "real" goal in life is to compose classical music, but that's not working out so well. Things at home aren't that great either, as he's growing distant from his wife and struggling with the fact that his son was born deaf. So when a gorgeous student (Jean Louisa Kelly, who also appeared in Uncle Buck) auditions for his upcoming Gershwin revue, well, middle-aged Mr. Holland suddenly gets his groove back. The girl serves as his musical muse, but the situation gets trickier when the clearly twitterpated student asks her gray-haired teacher to run off with her to New York. Being a good dude, Mr. Holland gently turns her down...but you can tell he was totally considering it for just a second.

The Reader (2008)

When asked by the folks at Coming Soon if she ever worried about appearing in movies like The Reader, a film about statutory rape, Kate Winslet replied, "I've got to tell you, I'm so offended by that....To me, that is absolutely not this story at all. That boy knows exactly what he's doing."

With all due respect to the Oscar winner, that excuse wouldn't fly in a court of law. And if we want to get technical, The Reader is totally about statutory rape...and Nazis.

The film follows 15-year-old Michael Berg (David Kross) who gets involved with 36-year-old Hanna Schmitz (Kate Winslet). When the two aren't making love, he's constantly reading to her, thus the title of the movie. But their affair takes a nosedive when Michael discovers Hanna used to work as a concentration camp guard. In other words, this just might be the unhealthiest relationship on this entire list.

Lolita (1962, 1997)

Vladimir Nabokov's Lolita is widely hailed as one of the best novels of the 20th century, but it's not what you'd call light reading. Sure, the writing is beautiful, but the subject matter is a bit on the dark side. Nevertheless, the novel inspired two separate movies, Stanley Kubrick's 1962 version starring James Mason and Sue Lyon and Adrian Lyne's 1997 version featuring Jeremy Irons and Dominique Swain.

Both movies focus on Humbert Humbert (Mason, Irons), a child molester who sets his sights on the titular Lolita (Lyon, Swain). Both Lyon and Swain were in their early teens when cast in their respective roles, and naturally, the subject matter stirred up some controversy. Of course, it's not like Humbert is supposed to be a hero—and don't worry, he eventually figures what the term "jailbait" really means.

The Man Who Wasn't There (2001)

If you've ever seen a Coen brothers movie, you know these guys are masters of the absurd, and in The Man Who Wasn't There, the directors take their zaniness up to 11, filling their film with UFOs, electric chairs, and uncomfortable car rides with teenaged girls.

This black-and-white noir follows Ed Crane (Billy Bob Thornton), a laconic barber who winds up in a murderous blackmail scheme (you've just got to watch it) before running into teenage pianist Rachel "Birdy" Abundas (Scarlett Johansson), and deciding to help her become a world famous musician.

Of course, as Owen Gleiberman points out, their "relationship is tinged with an erotic undercurrent," and while Ed never acts on his illegal impulses, we can't say the same for Birdy. But hey, this is film noir—and she's underage—so this car wreck of an affair doesn't exactly pan out as Birdy planned.

Manhattan (1979)

Manhattan is one of the greatest movies ever made. It's also a film about Woody Allen dating a 17-year-old. Allen plays a 40-something comedy writer involved with a high school girl (Mariel Hemingway)—the guy even finds it amusing when his girlfriend ends a date because she has to study for a test. "I'm dating a girl who does homework," Allen jokes, but it's hard to chuckle along.

Still, the movie is well-made, and Hemingway received an Oscar nomination for her work. However, it seems the events of the film followed her into real life. According to Hemingway, after she turned 18, Allen showed up at her house and allegedly tried to convince her parents to let her accompany him to Paris. Evidently, Allen didn't have quite the same allure he did onscreen, because the teenager shot his plans down and sent him packing.

Raging Bull (1980)

Jake LaMotta (Robert De Niro) is a man who takes what he wants, and if he doesn't get it, he'll probably just beat it to death. A professional boxer with heavy hands and a short temper, this 20-something pugilist is—like the title implies—an angry animal, always on the prowl. So when he spots Vickie, a 15-year-old blonde bombshell (Cathy Moriarty) at the city pool, he decides right then and there that's he going to have her. After all, he's Jake LaMotta, and he's not going to let the law stand in his way. At first, Vickie is only too happy to hook up with the middleweight mauler, until she realizes he doesn't stop swinging once he steps out of the ring.

Sunset Boulevard (1950)

When it comes to May/December relationships, there's no couple quite so eerie as Norma Desmond (Gloria Swanson) and Joe Gillis (William Holden). In this Billy Wilder classic, Joe is a screenwriter who runs into Norma, a fading starlet, completely by accident. But once he steps inside her mansion, there's no getting away. Norma is like a spider, and Joe is the fly. Of course, so long as she's paying for his suits and keeping him comfortable, he can't really complain much.

True, the gap here isn't huge. Norma is about 50, and Joe is half her age. However, the actress is completely lost in the past. Her dusty mansion is a shrine to her faded career, and she spends her evenings watching her own movies from Hollywood's silent era. In other words, Norma might still have a few birthdays left, but she feels absolutely ancient. As Roger Ebert points out, Norma "has aged not in the flesh but in the mind," and when Joe decides it's time to date someone his own age, he discovers you can't walk away from a movie star that easily.