23 Creepiest Movie Boyfriends

Annie Hall (1977)

The Boyfriend: Alvy Singer

The Creepy: They say write what you know and all that, but Alvy takes it one step too far when his relationship with Annie falls to pieces. Instead of jumping into the sack with a bit of totty for some angry ‘I’m so over her’ sex, he decides to write a play about their relationship.

Recycling dialogue from their actual courtship, he reimagines their time together so that they end up happily ever after. Both tragical and creepy.

Bridget Joness Diary (2001)

The Boyfriend: Mark Darcy

The Creepy: When Bridget first lays eyes on Darcy, he’s wearing a hideous jumper that his mother has knitted for him as a Christmas present. It’s like something a five year old would wear, and makes him look like a serial killer.

Bridget’s initial reaction – that Darcy’s a spineless toff who really should tell his dopey mother to stop knitting such abominations – is correct. Who needs Anthony Perkins 2.0 for a boyfriend?

Theres Something About Mary (1998)

The Boyfriend: Ted Stroehmann

The Creepy: Ted screwed up his chance to date adorable Mary Jensen when he was a teenager. Having successfully asked if he could escort her to the prom, an unfortunate incident with a trouser zip meant he spent the night in ER instead of getting to first base with Mary.

That thought has haunted him ever since, so Ted decides to hire a private investigator to track Mary down, with a view to wooing her all over again. Yeah, there’s stalker, and then there’s Ted Stroehmann.

The Seven Year Itch (1955)

The Boyfriend: Richard Sherman

The Creepy: Husband, actually, as Richard is happily married with a wife and kid. But then Marilyn Monroe crosses his path and - as is wont to happen with any man caught in Monroe’s high beams - he goes, well, a tiny bit loopy-loo.

Richard starts suffering imaginative hallucinations, including one in which Monroe is a femme fatale – and ends up in his arms. Smarmy and psycho, then.

Never Been Kissed (1999)

The Boyfriend: Sam Coulson

The Creepy: Sam’s a put together guy. He’s an English teacher. He eats his greens (we assume). He has lovely, flicky hair. But then he gets a massive giant crush on one of his students.

Okay, so said student is really Drew Barrymore’s undercover reporter. But Sam doesn’t know that when he starts falling for her…

P.S. I Love You (2007)

The Boyfriend: Gerry Kennedy

The Creepy: Dearly departed Gerry tragically died of a brain tumour, leaving his wife Holly grieving her loss. Except Gerry doesn’t want her to forget him. Ever.

Concocting a sinister plan in the months before his death, he makes sure that after he’s gone, Holly receives numerous letters from him that won’t let her move on with her life. Instead, he insidiously encourages her to cling to the past. Devilish bastard.

Pretty Woman (1990)

The Boyfriend: Edward Lewis

The Creepy: Ed meets his leggy, big-gobbed beau Vivian when he hires her company for a week. And by 'company', we mean 'body'. See, Viv’s a prostitute, so he pays her $3,000 (and gives her access to his credit cards) to be his girlfriend.

Which is not only morally bankrupt, but also ten shades of icky. The fact that Vivian then falls for this ‘money buys happiness’ letch is the biggest tragedy of all.

Somethings Gotta Give (2003)

The Boyfriend: Harry Sanborn

The Creepy: Harry’s old enough to get one of those blue disabled parking badges. He’s dating a spritely young thing who wasn’t even born when he hit 40. No wonder he suffers a bed-based heart attack.

In short: he’s that creepy old guy lusting after young girls who most dismiss as either slimy or adorably nutso. Mostly, he’s the former.

The 40-Year-Old Virgin (2005)

The Boyfriend: Andy Stitzer

The Creepy: It’s no surprise Andy’s yet to lose his V plates, despite being about to enter into the ‘mid-life crisis’ phase of his life.

Basically, he lives on his own with only a bunch of action figures for company. If that doesn’t scream out ‘potential loony tunes’, we don’t know what does.

Say Anything (1989)

The Boyfriend: Lloyd Dobler

The Creepy: Lloyd has a crush on valedictorian Diane, and will do anything to get her to notice him.

Yes, including skulking around outside her house blasting love songs from his boom box. Not only is that a criminal offence (noise pollution), but also restraining-order needy.

Overboard (1987)

The Boyfriend: Dean Proffitt

The Creepy: How does a man find a nice woman to take care of him and his four young sprogs? Why, simply hop down to the local hospital, claim an amnesiac woman as your confused other half, and install her in your log cabin.

Dean does just that in order to exact revenge on the newly memory-less Joanna, who once hired then fired him. Taking advantage of a woman in crisis? Nice, Dean. Very nice.

The Switch (2010)

The Boyfriend: Wally Mars

The Creepy: He accidentally knocked the sperm you’re about to impregnate yourself with down the sink, and decided that instead of telling you, it’d be a good idea to replace it with his own. Without telling you.

Sure, Wally was drunk when he did it, but years down the line, when you find out, you’re justified in being mad. Stab-him-in-the-eye mad. It’s not cute, and you certainly shouldn’t date him. (So, of course, Jennifer Aniston does.)

10 Things I Hate About You (1999)

The Boyfriend: Patrick Verona

The Creepy: Aside from having a weird surname, Patrick’s the kind of loose cannon you spend the whole of your high school years hoping never explodes near you. Just look at him in DT class – he’s a destructive vagabond.

Bad-tempered and unpredictable, he even manages to take it one step further by agreeing to woo fellow teen Kat for money. Then publically serenades her on the football field by singing ‘Can’t Take My Eyes Off Of You’. Cringe.

10 Things I Hate About You (1999)

Good Luck Chuck (2007)

The Boyfriend: Chuck

The Creepy: What would you do if hundreds of women wanted to sleep with you, just because they believed that if they did, they’d meet their true love?

You give them all the number of a good psychiatrist and wish them the very best. Not Chuck, who uses it to his advantage and sleeps his way through swathes of the poor, mindless fools. Wrong.

The Wedding Planner (2001)

The Boyfriend: Dr Steve Edison

The Creepy: Duplicitous and conniving, Steve goes on a romantic evening date with wedding planner Mary after having saved her from a nasty encounter with a runaway dustbin.

Only after they’ve danced romantically and nearly smooched does Mary discover he’s married. Not that Steve even has the decency to tell her himself – his fiancée has hired Mary to plan their wedding. Forget creepy, this guy’s just a creep.

Love Actually (2003)

The Boyfriend: Mark

The Creepy: More of a wannabe boyfriend, Mark wouldn’t look out of place in a line-up of Hitchcock villains - though he probably has most in common with the voyeur-tastic star of Peeping Tom.

See, Mark’s holding a (big, giant) candle for his best mate’s new bride, and spent their entire wedding filming her smiling, happy face. If there had been a blade fitted to his camera, we imagine he'd have speared the groom.

Failure To Launch (2006)

The Boyfriend: Tripp

The Creepy: Tripp is 35 years old and still lives with his parents. While that might be the dream scenario of some guys (free food, dry cleaning and housekeeping), there’s no getting away from the fact it’s just plain weird.

Making it worse, Tripp treats his parents’ home as a bachelor pad, bringing unwitting women back for ‘night caps’. When mommy dearest walks in the next morning, he barely bats an eyelid. Screw. Loose.

Knocked Up (2007)

The Boyfriend: Ben Stone

The Creepy: ‘Stone’ is apt, because that’s what Ben spends most of his time doing: getting stoned and wasting his life hanging around with similar-minded wasters.

He’s also the brains behind a naked celebrity website. Which successfully tips him into creepy territory. Would you really want to raise a child with this Neanderthal? (Yeah, yeah, that’s Apatow’s point, but STILL.)

Roman Holiday (1953)

The Boyfriend: Joe Bradley

The Creepy: Opportunism is an ugly trait, and Joe has it in spades. He’s an American reporter working in Rome for the Daily American . When a princess lands in his lap, he decides to use the situation to his advantage and get a story out of it.

Without betraying his true intentions, he poses as a potential beau and gives the princess a guided tour of Rome, making sure that she’s nicely placed for his tailing photographer to get some decent snaps. Deceitful pig.

Moonstruck (1987)

The Boyfriend: Ronny

The Creepy: You take my hand, I take your girl. That’s Ronny’s philosophy, anyway. After Ronny loses his hand in an accident involving a bread slicer, he blames his brother Johnny for distracting him and causing the calamity.

As a result of that bloody incident, Ronny’s fiancée leaves him. Then he meets Johnny’s new fiancée… and beds her. A hand for a hand, and all that. Family politics never were more messed up.

The Perfect Catch (2005)

The Boyfriend: Ben Wrightman

The Creepy: When Lindsey Meeks hooks up with Ben, she thinks she’s finally found the perfect man. Little does she knows he’s got an unhealthy fixation with baseball team the Red Sox.

But Ben isn’t just any old fan, he plans his entire life around the sport. The Red Sox ARE his life: just about everything he owns is emblazoned with their emblem. And that’s just plain wrong.

High School Musical (2006)

The Boyfriend: Troy Bolton

The Creepy: Troy just can’t stop singing. He sings while playing basketball. He sings while courting tween temptress Gabriella. He even sings on the loo (we’re guessing).

Which, really, is just far too much singing. The low point is a saccharine duet with Gabriella, which would turn even the hardiest of stomachs. Scary stuff.

His Girl Friday (1940)

The Boyfriend: Walter Burns

The Creepy: Another ex, Walter used to be married to Hildy Johnson before things turned sour and they filed for divorce.

But when Walter learns that Hildy’s going to get remarried to an unforgivably dull insurance man, he makes it his mission to usurp the nuptials any way he can. Ever heard of therapy, Walt?

Josh Winning has worn a lot of hats over the years. Contributing Editor at Total Film, writer for SFX, and senior film writer at the Radio Times. Josh has also penned a novel about mysteries and monsters, is the co-host of a movie podcast, and has a library of pretty phenomenal stories from visiting some of the biggest TV and film sets in the world. He would also like you to know that he "lives for cat videos..." Don't we all, Josh. Don't we all.