The romantic comedy is one of the most beloved and enduring cinematic genres. Although seemingly grounded in reality, it shares more things in common with fantasy than with, say, drama. Indeed, rom-coms tell stories that don't reflect reality and have fairytale endings that would never happen in real life. There's no better example of this than the infamous and beloved opposites attract trope.
It's always exciting for fans to watch the journey of two people who start out disliking each other before learning that love is stronger than their differences. Even though modern, cynical audiences have called these movies out for being unrealistic, movies with good storytelling and magnetic characters like When Harry Met Sally and Grease remain popular despite their detractors. These are the best opposites-attract romantic comedies, proving that some cinematic tropes are genuinely timeless.
10 'Romancing The Stone' (1984)
Directed by Robert Zemeckis
Being stuck in a rainforest with two people who can't stand each other and have lots of sexual tension sounds like a horrible time. However, watching from the safety of home makes this situation absolutely hilarious. Romancing the Stone is the perfect blend of action, comedy, and romance and helped kick-start a whole subgenre of films.
Michael Douglas and Kathleen Turner's chemistry is so strong that it can be felt just as much when they are arguing as when they're flirting, slowly falling head over heels for each other. The plot blends humor and swoon-worthy moments, showcasing the couple's complicated yet undeniable chemistry. Meanwhile, director Robert Zemeckis adds impressive shootouts and car chases, especially for the 80s, that keep things from getting too soapy.
Romancing the Stone
- Release Date
- March 30, 1984
- Cast
- Michael Douglas , Kathleen Turner , Danny DeVito , Zack Norman
- Runtime
- 106 minutes
- Writers
- Diane Thomas , Lem Dobbs , Howard Franklin
9 'She's All That' (1999)
Directed by Robert Iscove
A modern, teen-centric retelling of Bernard Shaw's classic Pygmalion may sound strange now. However, She's All That became a 90s pop culture moment, grossing $103 million worldwide, including debuting with 16 million over Superbowl weekend. This 90s teen gem cleverly leverages its cheesy and exaggerated portrayal of school life in the MTV era.
From the unforgettable prom flash dance to Laney's (Rachel Leigh Cook) iconic slow walk down the stairs post-makeover, this movie revels in its campiness. These scenes, which might have been cringe-inducing in other films, are fun and enduring moments that still resonate today. She's All That's glossy and over-the-top view of high school is peak '90s, including freestyles about prom queens, a school's Disc Jock's between classes, and hallway stare-downs, filling it with fun energy that's impossible to resist.
She's All That
- Release Date
- January 29, 1999
- Cast
- Freddie Prinze Jr. , Rachael Leigh Cook , matthew lillard , Paul Walker , Jodi Lyn O'Keefe , Kevin Pollak
- Runtime
- 95
- Writers
- R. Lee Fleming Jr.
8 'Pretty Woman' (1991)
Directed by Garry Marshall
Julia Roberts and Richard Gere became legends of the romantic comedy genre with their performances in the now-seminal '90s film Pretty Woman. Although its premise has aged somewhat poorly, the film remains a favorite of many; during its original release, it was the fourth highest-grossing film of all time.
This feel-good romance requires viewers to extend their belief and buy into the unlikely pairing of a wealthy businessman and a sex worker with a heart of gold. Even Richard Gere stated, "The film started as a drama, but Disney rewrote the script into a modern fable." Despite its fantastical elements, Pretty Woman is about two people bringing the best out of each other. The film's belief that two vastly different people can bring out the best in each other may be overly optimistic, but that's also why it works.
Pretty Woman
- Release Date
- March 23, 1990
- Cast
- Richard Gere , Julia Roberts , Ralph Bellamy , Jason Alexander , Laura San Giacomo , alex hyde-white
- Runtime
- 119
- Writers
- J.F. Lawton
7 'You Got Mail' (1998)
Directed by Norah Ephron
Norah Ephron's 90s hit about a businessman who falls in love with a quaint owner of a children's bookstore in an internet chat room was one of the first rom-coms to address dating online. In their third romantic comedy together, Meg Ryan and Tom Hanks prove why they are one of Hollywood's greatest onscreen duos. An impressive feat considering their onscreen time is limited, just as it was in the previous collaboration, Sleepless In Seattle.
You've Got Mail's unconventional approach makes the times they share the screen feel unique, leaving viewers wanting more. The duo's magnetism quenches audiences until their next scene together, balancing their opposing personalities and creating an irresistible dynamic. Even though audiences know they'll end together, these two morally opposed characters seem like they'll never overcome their differences, making for a well-earned tear-jerking finale.
You've Got Mail
- Release Date
- February 26, 1998
- Cast
- Tom Hanks , Meg Ryan , Katie Sagona , Greg Kinnear , Parker Posey , Jean Stapleton
- Runtime
- 119
- Writers
- Miklós László , Nora Ephron , Delia Ephron
6 '10 Things I Hate About You' (1999)
Directed by Gil Junger
Set in a modern-day high school, this 90s take on Shakespeare's The Taming the Shrew introduced the masses to talents like Julia Stiles and the late Heath Ledger. Over the years, 10 Things I Hate About You has built a massive fanbase, spawning a spin-off show a decade later, almost unheard of for a rom-com.
Shakespeare is simply not everybody's cup of tea. However, 10 Things I Hate About You has enough witty jokes, charming characters, and '90s ska music to win over the biggest Shakespeare critic. Cat (Stiles) and Patrick's (Ledger) contentious relationship is fun to watch, making it feel more real than most opposites attract stories. Even more surprising is that, despite being a whacky teen comedy, the film has a great deal of sincerity and heart that elevates it past its contemporaries.
10 Things I Hate About You
- Release Date
- March 31, 1999
- Cast
- Heath Ledger , Julia Stiles , Joseph Gordon-Levitt , Larisa Oleynik , Larry Miller , Andrew Keegan
- Runtime
- 97 minutes
- Writers
- Karen McCullah , Kirsten Smith
5 'As Good As It Gets' (1997)
Directed by James L. Brooks
Three-time Oscar winner Jack Nickolson blew fans away with his performance as an obsessive-compulsive who falls for a kind waitress in the Oscar-winning rom-com As Good As It Gets. The film grossed $314 million at the box office, quite an achievement for a mid-budget effort. When it comes to opposites attracting, no onscreen couple is more different than the selfish, brutally honest Melvin and the caring-family-oriented Carol.
This untimely partnership makes for a fascinating study of someone's ability to change if influenced by the right person. Unsurprisingly, Helen Hunt and Nickolson won Best Actor and Actress for their roles. As Good As It Gets also has strong, scene-stealing supporting performances from the electric Cuba Gooding Jr. and Greg Kinnear, who were interesting enough to have had their own movie.
As Good As It Gets
- Release Date
- December 25, 1997
- Cast
- Jack Nicholson , Helen Hunt , Greg Kinnear , Cuba Gooding Jr , Shirley Knight
- Runtime
- 139 minutes
4 'When Harry Met Sally' (1989)
Director by Rob Reiner
This groundbreaking film about two friends whose romantic involvement affects their friendship was based on real-life conversations that director Rob Reiner and writer Nora Ephron had. For many years, When Harry Met Sally... was the blueprint for modern romantic comedies. The film breaks all the typical rom-com rules; for example, the two main characters don't become romantically involved until almost the third act, leaving audiences with this anticipation.
When Harry Met Sally... doesn't romanticize their relationship, showing how messy friendships with the opposite sex can be. Harry and Sally, who are purposely as starkly different as possible, show men's and women's distinct approaches to relationships. Leads Meg Ryan and Billy Crystal also pull off the high-wire act of finding the humor in Harry's depression and Sally's breakdown over her ex while never trivializing it. That said, this movie's true genius is that it establishes a thesis: can men and women be friends?
When Harry Met Sally
- Release Date
- January 12, 1989
- Cast
- Billy Crystal , Meg Ryan , Carrie Fisher , Bruno Kirby , Steven Ford , Lisa Jane Persky
- Runtime
- 96 minutes
- Writers
- Nora Ephron
3 'Grease' (1978)
Directed by Randal Kleiser
Before High School Musical, this classic movie about a rebellious greaser dating a clean-cut cheerleader became a phenomenon. Grease was also behind several iconic movie moments, including Olivia Newton-John and John Travolta's performances of "Summer Nights" and "You're the One That I Want."
Similar to actual high school, Grease simultaneously feels innocent and naughty, and its oddly raunchy dialogue and lyrics give it a refreshing edge. That said, its catchy, feel-good music and hyper-animated characters still evoke warm feelings that make viewers nostalgic for a time they probably never experienced. Grease's ending has become controversial in recent years as Danny and Sandy try to change themselves to please each other. However, these characters learn an essential lesson: relationships require some give and take.
Grease
- Release Date
- June 16, 1978
- Cast
- John Travolta , Olivia Newton-John , Stockard Channing , Jeff Conaway , Barry Pearl , Michael Tucci
- Runtime
- 110
- Writers
- Jim Jacobs , Warren Casey , Bronte Woodard , Allan Carr
2 'My Fair Lady' (1964)
Directed by George Cukor
This best picture winner is about a snobby professor who tries to turn a London flower girl into a lady. While well known for its catchy music, Audrey Hephurn's singing was dubbed over by singer Marni Nixon, who also dubbed Maria's singing in West Side Story.
My Fair Lady's impressive set design and costumes suck viewers into Victorian England. Audrey Hepburn is in rare form, abandoning her usual elegant personality to play a funny, over-the-top commoner. Meanwhile, Rex Harrison's amusingly pompous Henry Higgins struggles to change her cockney accent, leading to lots of hilarity. Their romantic story is sweet but chaotic, showcasing how different they are yet how much they, in the words of the now-iconic song, have grown accustomed to each other's faces.
My Fair Lady
- Release Date
- October 21, 1964
- Cast
- Audrey Hepburn , Rex Harrison , Stanley Holloway , Wilfrid Hyde-White , Gladys Cooper , Jeremy Brett
- Runtime
- 170 minutes
- Writers
- Alan Jay Lerner , George Bernard Shaw
1 'Harold and Maude' (1971)
Directed by Hal Ashby
Harold and Maude is about a sheltered youth pressured by his family to get married when he falls for a free-spirited, much older woman. Although panned by some critics for being creepy, it developed a cult following and placed 45 in the AFI's 100 Funniest Comedies.
This quirky film is full of dark humor and profound moments, making it hard to fit into any category. The May-December romance between Harold and Maude seems very strange, but thanks to the leads' quirky but authentic performances, it is no less believable; despite their age, they're kindred spirits. In fact, their age difference is just a tool to show the film's true message of authenticity and liberation. Harold and Maude is the ultimate romantic comedy for unromantic people, an existentialist yet rewarding experience unlike any other.
Harold and Maude
- Release Date
- December 20, 1971
- Cast
- Ruth Gordon , Bud Cort , Vivian Pickles , Cyril Cusack , Charles Tyner , Ellen Geer
- Runtime
- 91 minutes
- Writers
- Colin Higgins