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32 Somewhat Obscure Rom-Coms You Should Know — And Popular Ones You Don’t Know As Well As You Think

Ryan Reynolds in a fat suit? Ryan Reynolds in a fat suit

32 Somewhat Obscure Rom-Coms You Should Know — And Popular Ones You Don’t Know As Well As You Think

April 27, 2024

Think you know everything there is to know about romantic comedies? Think again, lover boy…

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32

Forgotten Rom-Coms Chasing Amy The sexual politics of this Kevin Smith classic have aged badly, but it's still hilarious, adorable, and insanely witty. Ben Affleck plays a comic book writer who falls for fellow creator Joey Lauren Adams-who happens to be gay. This film asks for two things: to be rightfully torn apart, and to be enjoyed as an earnest piece of rom-com sweetness. 1997 CRACKED.COM — Source

31

Forgotten Rom-Coms 1988 Working Girl Melanie Griffith plays an ambitious secretary who falls in love with Harrison Ford while trying to climb up the corporate ladder and get back at Sigourney Weaver. This is a classic nobody discusses anymore, even though it was nominated for a bunch of Oscars (we blame the film's dated neoliberal ideology). CRACKED.COM — Source

30

Forgotten Rom-Coms 2002 Brown Sugar This movie is just awesome: killer cast, killer script, and that music. Sanaa Lathan and Taye Diggs play childhood friends in love with rap music, and who grow up to actually work in the industry. Will-they-or-won*t-they misunderstandings ensue. Brown Sugar might well just be called Love & Hip-Hop, like Lathan's previous Love & Basketball. CRACKED.COM — Source

29

Forgotten Rom-Coms 1977 The Man Who Loved Women You didn't expect some classy, high-art Truffaut film, did you? A very French womanizer dies, and during his funeral we get flashbacks of the female trouble and skirt-chasing that led to his death. It's a brilliant movie, but you should ignore the 1983 American remake (and just watch the first seasons of Californication instead). CRACKED.COM — Source

28

Forgotten Rom-Coms Splendor Gritty indie director Gregg Araki turned to quirky fluff territory with this comedy about a girl who ends up in a relationship with two guys. The concept may seem quaint in our time of open relationships, but it hasn't really been explored in actual movies, let alone adorable rom-coms. It's a solid effort (and the soundtrack is awesome). 1999 CRACKED.COM — Source

27

Forgotten Rom-Coms 1998 Sliding Doors Before the Goop, erm, venture, Gwyneth Paltrow used to make interesting movies. This early film shows her talent as a woman who both fails to catch a train and actually does it. The split narration alternates between the two paths her life takes - which we're just gonna say makes this a quantum rom-com. CRACKED.COM — Source

26

Forgotten Rom-Coms 2002 Secretary There are sexy romantic comedies, and then there's Secretary. Maggie Gyllenhaal plays a new secretary to James Spader, who is way too bossy and mean - until they both start getting off on exactly that. Yeah, it's a BDSM rom-com, somewhat like 50 Shades of Grey, except it celebrates authenticity instead of glorifying toxicity (and is, you know, good). CRACKED.COM — Source

25

Forgotten Rom-Coms 1998 The Opposite of Sex This quirky dark comedy had a peak-Friends Lisa Kudrow. indie darling Martin Donovan, and Christina Ricci playing a misanthropic, manipulative weirdo back when she was only known for PG films. It's an interesting story about neurotic people and gender fluidity, stylistically more in line with Election or Ghost World than with mainstream rom-coms. CRACKED.COM — Source

24

Forgotten Rom-Coms 1995 The American President Rob Reiner directed The Princess Bride and When Harry Met Sally, so he knows a thing or two about the genre. This movie boasts a stunning cast and an Aaron Sorkin script, and it's way better than those U.S. President-related rom- coms with his daughter or whatever. The peak-'gos themes and politics are a bit outdated, but the charm is all there. CRACKED.COM — Source

23

Forgotten Rom-Coms 1998 Martha, Meet Frank, Daniel and Laurence Entirely composed of meet cutes, this British film tells the story of a girl who meets her three dream guys on the same day-and they all happen to be best friends. You can see her predicament. Monica Potter and Joseph Fiennes are competent, Rufus Sewell plays a great weirdo as usual, and Tom Hollander is annoying. Still a decent rom-com, though. CRACKED.COM — Source

22

Forgotten Rom-Coms Midnight Challenging the Hays Code, this wacky comedy is way too raunchy for the prudish reputation of old-timey Hollywood. A gold-digging American showgirl is left stranded in Paris, and is romantically pursued by a cabbie while a wealthy man pays her to ruin his wife's love affair. It's pure screwball insanity, and the quick-witted script hasn't aged one bit. 1939 CRACKED.COM — Source

21

Forgotten Rom-Coms 2022 Honor Society An honor student named Honor (get it?) honeypots the only nerd able to ruin her Harvard chances. You won't really guess what happens next - and indeed, the cynical third- act switcheroo might have hurt this flick's chances of actually making a mark. Still, there's the glimmering of an adorable rom-com struggling to get out there somewhere. CRACKED.COM — Source

20

Forgotten Rom-Coms 2003 Down With Love Bring It On might be Peyton Reed's best romantic comedy, but Down With Love is a superior technical effort. An independent writer denounces love, and is seduced by a womanizing journalist in this send-up of the screwball rom-coms of the '60s with a contemporary feminist spin. The set-design, camerawork, and editing are delightful, and the two leads are clearly having fun. CRACKED.COM — Source

19

Forgotten Rom-Coms Celeste and Jesse Forever Before Palm Springs. Andy Samberg had already tried a more serious type of comedy than his usual goofy shtick. This indie film is about a separated couple trying to juggle a new life with their care for each other. It's a sweet, mature movie (and who are we kidding, Samberg's shtick is always hilarious). 2012 CRACKED.COM — Source

18

Forgotten Rom-Coms 1996 The Truth About Cats & Dogs Uma Thurman fans surely know this film, but it still deserves a wider audience. A radio host played by the absolutely underrated Janeane Garofalo begins falling for a listener, and asks her cuter friend to meet him and pretend to be her. Yes, it's the whole Cyrano de Bergerac thing, with a '90s rom-com twist. CRACKED.COM — Source

17

Forgotten Rom-Coms 1953 How to Marry a Millionaire Yes, this is a classic, but it still deserves a whole new audience. Marilyn Monroe, Betty Grable, and Lauren Bacall play three gold diggers focused on marrying three wealthy marks, but this pesky thing called true love interferes. Monroe appeared in even better films in this genre, but this is a wonderful showcase of her impeccable comedic talent. CRACKED.COM — Source

16

Forgotten Rom-Coms 1985 My Beautiful Laundrette Stephen Frears' best rom-com would be High Fidelity, if it weren't for this capital-C Classic from the UK. A young Pakistani man becomes the manager of a crumbling laundromat and begins an affair with a rebellious street punk who works there, played by Daniel Day-Lewis (which means Day-Lewis has been doing awesome films since forever). CRACKED.COM — Source

15

Forgotten Rom-Coms Cry-Baby Yikes-y Johnny Depp leads this musical comedy about Cry-Baby Walker, an emo bad boy who falls for the cutest square in Squaretown. It's watered-down John Waters insanity, but it still works, and the musical numbers are fun. Plus, Traci Lords, Iggy Pop, and Willem Dafoe are here, what more could you ask for? 1990 CRACKED.COM — Source

14

Forgotten Rom-Coms Just Friends This is a tacky, raunchy, stupid Ryan Reynolds comedy, but still a great example of this cursed subgenre. Reynolds plays a womanizing producer who reunites with the girl who back in high school loved him like a friend. The relentless jokes actually land, the soundtrack is surprisingly sweet, and Anna Faris kills it as a deranged popstar. 2005 - GOLGARS CRACKED.COM — Source

13

Forgotten Rom-Coms 1990 Green Card Directed by Dead Poets Society and The Truman Show's Peter Weir, this movie it deals with precisely what the title implies: a convenience marriage. Gérard Depardieu is hilarious, Andy MacDowell is adorable, and the entire third act pulls the usual genre clichés with class and earnest sweetness. CRACKED.COM — Source

12

GROUNDHOG DAY OMNISCIENT MAN HAS UNLIMITED TIME TO LEARN HOW TO TRICK WOMAN INTO LOVING HIM. To her, he has only known her one day. For him, he has learned every detail about her in order to become someone she would want him to be. CRACKED.COM — Source

11

50 FIRST DATES MAN COERCES WOMAN DAILY INTO HAVING A RELATIONSHIP WITH HIM. Womanizer Henry takes advantage of a woman's memory disorder in order to manipulate her into dating him. CRACKED.COM — Source

10

CRAZY RICH ASIANS MAN LIES TO GIRLFRIEND ABOUT ENTIRE CHILDHOOD. How do you date someone for a year without revealing how many butlers you had growing up? Still a great movie, though. CRACKED.COM — Source

9

LOVE ACTUALLY TEN SEPARATE STORIES, ALL OF THEM UNHEALTHY RELATIONSHIPS. So we're supposed to be rooting for a couple that can't communicate, a man who stalks his best friend's wife, and a Prime Minister who fires his subordinate for being too hot... just to name a few. CRACKED.COM — Source

8

THE NOTEBOOK MAN THREATENS SUICIDE TO MANIPULATE A WOMAN TO GO ON DATE WITH HIM. Also, Noah builds his whole life around a woman who he thought rejected him. CRACKED.COM — Source

7

HOW TO LOSE A GUY IN 10 DAYS TWO PEOPLE as UNKNOWINGLY MANIPULATE EACH OTHER INTO A RELATIONSHIP. Two wrongs don't make consent, and both characters are actively deceiving the other one. CRACKED.COM — Source

6

CRUEL INTENTIONS SEXUAL ASSAULTER FINDS NEW VICTIM. This movie is based on the premise that if someone dies, they suddenly become a redeemable person. Incorrect. CRACKED.COM — Source

5

PHANTOM OF THE OPERA MURDERER LIVING IN WALLS GROOMS CHILD TO BE HIS BRIDE. Maybe this one is cheating because Phantom isn't SUPPOSED to be romantic, but people still view him that way. CRACKED.COM — Source

4

THE DEVIL WEARS PRADA A WOMAN QUITS HER JOB TO SPEND MORE TIME WITH HER BOYFRIEND WHO HATES THAT SHE HAS A JOB. Andy's boyfriend is constantly annoyed at her for having a demanding job. They break up when she needs to take a work trip. How dare she. CRACKED.COM — Source

3

CRAZY, STUPID, LOVE BABYSITTER GIVES UNDERAGE CHILD NUDES OF HERSELF. A crazy abuse of power from a 17-year-old to a 14-year-old, that includes a teen giving her own underage pornography to a child. CRACKED.COM — Source

2

SLEEPLESS IN SEATTLE ENGAGED WOMAN STALKS MAN UNTIL HIS CHILD CONVINCES HIM TO DATE HER. Annie hires a private investigator and travels all the way to Seattle to spy on a grieving man and his child. CRACKED.COM — Source

1

NEVER BEEN KISSED TEACHER FALLS IN LOVE WITH STUDENT. Okay, it's less creepy because she's not actually underage, but he fell in love with her while believing she was. Gross. CRACKED.COM — Source

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