15 chaotic throwback rom-coms, ranked

Who knew your comfort watches were so goddamn deranged?

by Erica Russell
31 March 2020, 7:00am

Don’t let the sweeping soundtracks and starry-eyed romantic gestures fool you: rom-coms are pure chaos. There’s always some convoluted misunderstanding (like in 1999’s She’s All That --Am I a fucking bet?”) or over-the-top dance numbers (it’s preposterous to suggest a group of posh fashion glossy editors would know all the moves to “Thriller” à la 13 Going on 30) to give viewers the impression that love is best served with a big dose of drama.

Whether it’s the result of a topsy-turvy case of mistaken identity, a slapstick honeymoon from hell or a wildly out-of-control house party, people in rom-coms are always falling in love, breaking up and making up in the strangest, most anarchic conditions. But why should romance be simple or straightforward when we’ve got Hollywood A-listers and ensemble teen casts to shake things up on screen and show us all a different way to express our longing, anyway? Don’t swipe right on us! Crash our expensive wedding and proclaim your years-long secretly harboured crush, instead!

And so, here are 15 rom-coms from the 90s and 2000s ranked from least to most chaotic.

15. 13 Going on 30

Unintentional time travel may seem inherently chaotic, but the concept actually fits quite seamlessly within the charming fantasy framework of this sweet lil rom-com from 2004. Sure, there’s an expertly choreographed Michael Jackson dance break in a hip New York City club and yes, there’s a magical dollhouse that somehow grants wishes and transports 80s teens through time, but the only truly chaotic moment of this film is the revelation that adult Jenna Rink -- a.k.a. hot as hell Jennifer Garner -- has been fucking her co-worker’s creepy, super gross husband; a man who also uses pet names like “Pookie”.

14. The Wedding Planner

Rom-com queen Jennifer Lopez is a wedding planner who falls in love with her client’s fiancé in this cozy 2001 flick your mum probably loves. (Okay, fine, we love it too.) Both J.Lo and Matthew McConaughey actually play kinda awful people in this: the former stealing her client’s man and the latter flirting shamelessly with the woman planning his nuptials. The movie’s not too chaotic by traditional rom-com standards (mistaken identities and grand declarations of love are par for the course, after all), but the glamorous Jenny From the Block does almost die after nearly getting flattened by a rogue dumpster on the hills of San Francisco, and that certainly counts for something.

13. Never Been Kissed

This movie is, in retrospect, problematic as hell considering an adult male teacher falls in love with someone who he believes is his teenage student -- Drew Barrymore -- but who is actually an adult undercover journalist writing an exposé about modern high school pupils. As far as 90s teen rom-coms go, this classic flick plays it pretty straight-forward, and is obviously a feel-good fan-favourite. But Jessica Alba (yes, she’s in this!) does get doused in chunky dog food at the school dance while dressed as Disco Barbie. That’s pretty damn chaotic.

12. Sweet Home Alabama

Country-girl-turned-chic-city-fashion-designer Melanie Carmichael, played by Reese Witherspoon, calls things off with her rich, hot, super-sweet McDreamy boyfriend right before their wedding after falling back in love with her ornery small town ex-husband. (Erm, current husband, since he never did quite sign those divorce papers.) Deep South shenanigans ensue. This movie is a total guilty pleasure for many, but it’s also off its Cracker Barrel rocker. No one would leave Patrick Dempsey hanging at the altar like that!

11. 27 Dresses

Katherine Heigl plays a bridesmaid who is obsessively devoted to her friends’ nuptials in this 2008 romantic comedy. This movie is stacked with ridiculous broken engagements, breakups, makeups, and liar-revealed moments; but the true absurdity is how much closet space Heigl’s character’s Manhattan apartment boasts. Or the fact that she hoards all her heinous themed bridesmaid dresses.

10. She’s All That

This 1999 teen cult classic includes a fully choreographed high school prom dance off set to Fatboy Slim, which is the true mark of madness. Someone eats a slice of pube pizza. Shaggy from the live-action Scooby Doo movies plays a predatory reality star. Also, the implication that Rachael Leigh Cook’s peers can’t see that she’s a total babe just because she wears glasses is some Superman/Clark Kent-level bullshit. This movie also features a lot of frosted eyeshadow.

9. How to Lose a Guy in 10 Days

Diabolical bets are waged, love ferns are nurtured and Matthew McConaughey perilously chases Kate Hudson through Manhattan traffic on his motorcycle in this 2003 fan favourite about two hotshot magazine editors who fall in love after initially courting each other for their own selfish career gains. Antics ensue as the pair get more and more tangled in their own web of lies and romantic feelings, but the true madness of this film is revealed when Hudson’s Andie flees a corporate jewellery gala while “frosted” with a borrowed 84-carat yellow diamond necklace -- and isn’t immediately tackled or arrested on sight.

8. Can’t Hardly Wait

This hormone-driven 1998 teen comedy is about as chaotic as the raging house party it takes place at, which is to say, very. Featuring an ensemble 90s cast -- including teen queen Jennifer Love Hewitt, human puppy Ethan Embry and Seth Green, who dresses like Tai from Digimon -- a million things happen at once in this movie, and each moment is as melodramatic as a high school breakup-makeup. Also: wearing an angel costume, Jenna Fisher makes an inspired turn as an aggressive, chain-smoking, wisdom-spewing erotic dancer, while an ultra-peppy Melissa Joan Hart, dressed like Baby Spice, spends the duration of the film in an obsessed frenzy to get her peers to sign her goddamn yearbook.

7. Bridget Jones’s Diary

Bridget Jones, played by a pitch-perfect Renée Zellweger, faces every sort of humiliation imaginable in this 2001 British classic, from a mortifying knickers-baring live TV mishap to a miscommunication about a party that finds Bridget dressed quite inappropriately, in Playboy Bunny garb, at an otherwise buttoned-up Sunday gathering. This movie puts its charmingly imperfect heroine through the emotional, romantic and professional ringer, and even features a street brawl between Hugh Grant and Colin Firth. Yes, Bridget Jones’s Diary is cinematic chaos at its best, but it’s also perfect.

6. Just Friends

Ryan Reynolds wears a super problematic fat suit and hates the state of New Jersey in this wacky 2005 Christmas time rom-com about the mythic friend zone. Also, Anna Faris plays an unhinged, horny pop star who sets a private jet on fire, which is... sort of chaotic good? Anyway, this movie features a lot of bodily injury.

5. Made of Honor

Patrick Dempsey plays a suave Manhattan playboy who finally realises he’s in love with his longtime best friend, Hannah, after she gets engaged to a Prince Charming-esque Scottish Duke and asks him to be her maid of honour. A lot of crazy shit goes down in this 2008 romantic comedy, but all you really need to know is that our fateful friends-turned-lovers’ meet-cute involves a creepy plastic Bill Clinton mask and pepper spray.

4. New York Minute

Admittedly leaning more towards zany coming-of-age flick than romantic darling on the comedy spectrum, there's enough uncomfortable teen sexual tension and nonsensical encounters in this 2004 Olsen Twins vehicle to warrant it an honorary rom-com badge. But like, what even is this movie, really?

New York Minute is unrestrained cinematic insanity, that’s what: Mary-Kate and Ashley are almost naked for the entirety of this film for some reason; Eugene Levy stalks an underage girl across Manhattan; a woman threatens to murder a dog if it doesn’t poop out a microchip; a white dude who drives a limo but is also a Chinatown mobster speaks with a wildly offensive Asian accent that would make even Mickey Rooney recoil. There’s SO MUCH CULTURAL APPROPRIATION and fat-shaming yet so little plot. There are cameos from Simple Plan, Bob Saget and Jack Osbourne. Jack Osbourne!

3. Just My Luck

This 2006 movie is WILD. Lindsay Lohan plays Ashley Albright, a popular working girl in New York City who basically gets everything she wants when she wants, thanks to her inherent luck. Ashley even accidentally receives Sarah Jessica Parker’s dry cleaning at one point -- “and look, it’s Dolce!” -- just before a big date.

She later loses her mojo, however, during a make out session with Chris Pine at a masquerade party. His unlucky-in-life character quite literally steals her luck during the smooch, and the rest of the movie sees her trying to navigate the hardships of everyday life, like… not being able to hail a taxi, or having to work in the service industry. Well, that and getting punched square in the face by a jail cellmate -- then almost getting electrocuted to death during a freak bowling alley accident. She also develops conjunctivitis from a dirty litter box. Don’t ask.

2. The Sweetest Thing

Cameron Diaz, Selma Blair and Christina Applegate are BFF bachelorettes in this delightfully crass 2002 rom-com gag-a-rama. Featuring clichés like crashed weddings and vintage dress up montages, you might be tempted to write this one off as just another feel-good romantic flick, but this movie is actually bonkers. Like, a proto-Bridesmaids or Dumb and Dumber but with a better wardrobe and more sex. Yet in a way, The Sweetest Thing is really just a movie about penises: there’s a choreographed song and dance scene about complimenting dudes for their members’ sizes (a phallic “Bend and Snap” if you will), lots of dick chasing, and even a near-fatal blowjob. No, we’re not kidding.

1. Just Married

Ashton Kutcher and the late, great Brittany Murphy share wonderful chemistry in this hilarious 2003 film about a pair of starry-eyed newlyweds who, through a series of misunderstandings, interferences from exes and revelations about each other, fall apart spectacularly while on their doomed, surprisingly violent European honeymoon. This slapstick-y rom-com is off the walls and features a dog leaping to its death out a window (funnier than it sounds, we promise) away from its farting pensioner owner, dildo-induced arson in the French Alps, a failed Mile High tryst and a stint in an Italian jail cell. If pratfalls really do it for you, you’ll love this.

Jennifer Lopez
lindsay lohan
romantic comedy
Olsen Twins