20 Iconic Good Girl/Bad Boy Movie Couples

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As Tom Petty once crowed, a “good girl” and a “bad boy” coming together is enough to make you free fall out into nothin’. Growing up, most of us have dreamed of breaking the rules and risking it all to embrace our rebellious side. While actually doing that is never an option, what’s possible is to be swept off your feet by the exciting depiction of the same desire in cinema. The teenage fantasy finds the perfect home in the classic good girl/bad boy romance that has lured audiences for generations now.

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There is an undeniable charm to the dark and brooding outsider who has a heart of gold. Who wouldn’t want to escape their boring everyday routine and seek a thrilling romantic adventure with a rebel — and if along the way the girl says at some point “I can fix him,” you’re in the right place. The unlikely couples in the movies on this list allow us to live vicariously through the good girl’s transformation into a renegade, and through the bad boy shedding his tough exterior and finally revealing his softer side in romance.

Because filmmakers know their audiences root for that spark, the undeniable chemistry, and the feelings rather than common sense when two opposites attract, there is a mine of movies that capture this trope perfectly. As adults, the nostalgia for these iconic on-screen couples runs deep no matter how unrealistic it is, because they introduced us to love’s dizzying heights. Here are the 20 best movies that endure and thrive on the good girl/bad boy fantasy.

20 Katie and Andy — Wet Hot American Summer (2001)

Katie and Andy in Wet Hot American Summer Andy holding her face
Focus Features

Wet Hot American Summer is a parody of summer flicks and the experiences director David Wain had while attending camp as a kid. Set during the crazy last day at Camp Firewood in 1981, the movie throws us in the middle of all the tension — sexual and otherwise — between the counselors. Katie is a shy counselor who’s there with her obnoxious and unfaithful boyfriend Andy, brought vibrantly to life by Paul Rudd.

This cult comedy classic deserves the first spot on the list as it not only kicked off the whole genre of summer camp mockery in cinema but also gave us an endearing but flawed couple in Katie and Andy. They were sweet and cool and awkward and toxic, but we wanted them to work it out somehow anyway.

Rent Wet Hot American Summer on Apple TV

19 Tyler and Nora — Step Up (2006)

Step Up
Step Up

Release Date
August 11, 2006

Rating
PG-13

In Step Up, Nora is a privileged modern dancer and the pride of Maryland School of Arts, where she’s preparing for her senior showcase when she meets Tyler, a delinquent. Apparently, Tyler committed small crimes like breaking-and-entering and destroying the art theater with his brothers, which is what landed him with 200 hours of community service. But he’s great when it comes to hip-hop. After reluctantly pairing up with Nora, he inspires her to get out of her comfort zone and loosen up a little.

Directed by Anne Fletcher, the movie was a breakout hit that launched the careers of Channing Tatum and Jenna Dewan. Beyond their steamy chemistry in their climactic showcase, the film also brought to the screen the actors’ capacity for performing freely and fully. In a way, Step Up became a blueprint for that sizzling dynamic that makes a good girl/bad boy couple so rewarding.

Rent Step Up on Apple TV

18 Jason and Veronica — Heathers (1989)

heathers
Heathers

Release Date
March 31, 1989

Director
Michael Lehmann

Rating
R

Christian Slater and Winona Ryder play Jason Dean and Veronica Sawyer in this dark teen comedy. Veronica is the new girl simply trying to fit in with the popular clique of her high school, led by Heather Chandler. But after meeting outcast and straight-up psychopath Jason, she finds herself mesmerized by his nihilistic pranks that spiral into murdering fellow classmates. In a twist, Veronica realizes that she must stop him before it’s too late.

Related: These Are 5 Comedies Which Got Way Darker Than Expected

Heathers is a biting satire of high school hierarchies and dysfunctional relationships. The movie not only helped welcome a new era of edgier and bolder teen films, but also introduced us to a compelling and darkly charismatic bad boy who knew just how to woo the good girl and fulfill his own whims.

Stream Heathers on Prime Video

17 Tessa and Hardin — After (2019)

after
After

Release Date
April 11, 2019

Rating
PG-13

Based on Anna Todd’s popular Wattpad stories, After the first installment in the series. It follows Tessa Young, a dedicated student who never experienced a reckless rule-breaking lifestyle until she met Hardin Scott, a rebellious friend of a friend. Hardin is the textbook bad guy with the messy hair and tattoos peeking out of his black tee, and successfully seduces Tessa away from her boyfriend.

The movie brought Todd’s beloved fictional pairing to life, and also introduced Josephine Langford and Hero Fiennes Tiffin to audiences. Their intense chemistry had fans glued to the turbulent and raw journey of Tessa and Hardin.

Stream After on Netflix

16 Sandy and Danny — Grease (1978)

Grease
Grease

Release Date
July 7, 1978

Rating
PG-13

Grease was the highest-grossing musical film of the entire 20th century, so it’s only fitting that the film has an iconic romance going for itself. It tells the story of good girl Sandy and bad boy Danny, who meet at a beach over summer vacation, and then see each other again at the same high school. While Sandy tries adjusting to the social scene at Rydell High School, Danny eases into his responsibilities of the T-Birds gang dynamics. Torn between their past and present and their conflicting social statuses, their affection eventually rekindles.

As a classical musical adventure and the perfect summer romance, Grease has inspired a generation of audiences and filmmakers. Through its two opposing characters, it shone a light on teenage identity crises and the trend of playing it cool. Needless to say, John Travolta and Olivia Newton-John are the ideal good girl/bad boy couple. This is also one of thsoe stories where the girl becomes more “bad” instead of the bad boy being “fixed.”

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15 Leilana and Troy — Reality Bites (1994)

Reality Bites Ethan Hawle and Winona Ryder as Troy and Leilana sitting together outside
Universal Pictures

Highlighting the many challenges and struggles of figuring out life as an adult, Reality Bites follows a bunch of college graduates in early 1990s Houston. Among them are Lelaina Pierce, who dreams of changing the world through documentaries, and Troy Dyer, a poetic and aimless coffee-house guitarist. The two have always had a thing for each other, but their easy bond is tested when ambition and uncertainty pulls them down.

Reality Bites is a hilarious and heartfelt rom-com that delivers a subtle yet impactful will-they-won’t-they courtship, where Lelaina and Troy wander the line between love and lust. Ethan Hawle and Winona Ryder carved out a memorable dynamic, capturing the precarious relationship with care.

Rent Reality Bites on Apple TV

14 Noah and Elle — The Kissing Booth (2018)

The Kissing Booth Elle kisses Noah for the first time 
Netflix

Elle Evans is the goody-two-shoes who has never been kissed. Mainly because she spends most of her time goofing around with her childhood best friend Lee. When Elle decides to run a kissing booth at her high school’s Spring Festival, she finds herself face to face with her longtime crush and Lee’s older brother, bad boy Noah Flynn. As their chemistry skyrockets, Elle must either resist her red-hot desires or risk sabotaging her tight bond with Lee.

The Kissing Booth is a Netflix original film based on Beth Reekles’ popular teen novel. It launched Joey King and Jacob Elordi into the scene by sparking a frenzy of emotions into their characters, proving that a fresh and younger cast can revive classic tropes in a more exciting and thrilling fashion.

Stream The Kissing Booth on Netflix

13 Randy and Julie — Valley Girl (1983)

Martha Coolidge presents a brilliant teen romantic comedy about Julie Richman, a type-A, pink-clad cheerleader who leads the perfect life with her arrogant boyfriend, Tommy. At a party, however, Julie falls hard for Randy, a punk rocker from Hollywood. Openly disregarding social norms, Julie dives headfirst into Randy’s freewheeling world of concerts and radical thought. She finds passion but is cautious of the judgment presented by her San Fernando Valley friends.

Related: 10 ’80s Rom-Coms That Aged Well

Valley Girl is an all-time classic but also highly underappreciated. From its funky style and portrayal of ‘80s LA to the new wave soundtrack, the film was a breath of fresh air. Especially the way it handled the “good girl gone rogue” formula. That said, Deborah Foreman and Nicolas Cage are absolutely ideal in their roles.

Stream Valley Girl on Fubo

12 Dogfight (1991)

On the night before being shipped off to Okinawa in the year 1963, Eddie Birdlace and three other Marines set out for one final night of drinking in San Francisco, where they’re on leave for 24 hours. They end up participating in a cruel bet where each soldier must bring the ugliest date to a party. Eddie encounters Rose, a waitress who may not be very attractive but is wise beyond her years. Even though their romance is doomed from the start, it manages to bloom.

Starring River Phoenix and Lili Taylor in breakout roles, Dogfight is a period coming-of-age romance that stays true to its time by taking characters who judge one another by their face value. Eddie and Rose weren’t the perfect couple and Rose wasn’t always treated well, but they left an indelible mark on the genre with their chemistry.

Rent Dogfight on Apple TV

11 Anastasia and Christian — Fifty Shades of Grey (2015)

The first in a series of films adapted from E.L. James’ best-selling erotic novels, Fifty Shades of Grey received mixed reviews from critics and audiences for being creative in picture but lacking substance. The premise, much like the book, sees literature major Anastasia Steele agreeing to fill in for an interview that her sick friend was supposed to conduct. After meeting the billionaire entrepreneur Christian Grey for the first time, she’s appalled by his dominating ways and excessive methods.

After a series of back and forth between the characters, the movie ends with them parting, only for their layered narrative to continue in the sequels. Despite being silly and debatable, the movie catapulted Dakota Johnson and Jamie Dornan into stardom and created a cultural phenomenon. The adaptation stirred fans endlessly, and the couple was nothing if not magnetic.

Stream Fifty Shades of Grey on Max

10 Rapunzel and Flynn — Tangled (2010)

Tangled
Tangled

Release Date
November 24, 2010

Rating
PG

Tangled tells the story of the sheltered Rapunzel and Disney’s self-proclaimed bad boy Flynn. After spending her entire life locked away in a tall tower and yearning to see the floating lights in the distance that happen on her birthday, when Rapunzel finally meets the thief Flynn Rider, she makes a bargain with him to get out of her remote tower and go on an adventure. Though Flynn only cares about saving his own skin at first, their thrilling journey and heartfelt moments lead to something more.

Tangled is Disney’s 50th animated feature and the movie’s fanbase is enormous, a major part of which is known to swoon over the romance shared by Rapunzel and Flynn. The two are voiced by Mandy Moore and Zachary Levi, who instill pure magic, kindness, and delight into the narrative. Overall, Rapunzel and Flynn are the most wholesome bad-boy-good-girl couple on screen.

Stream Tangled on Disney+

9 Keith and Natalie — Keith (2008)

Tremendous, joyful, and resonant are three words that describe Todd Kessler’s Keith perfectly well. The criminally underrated love story follows Natalie Anderson, the academically focused student and tennis enthusiast who always manages to avoid drama with her big dreams and bigger brains. When the rebellious and carefree Keith becomes her lab partner, he drags her into his life of trespassing and breaking rules. Despite opposing each other at first, their playful spirit of youth brings them closer, and they ultimately fall in love.

Perhaps the most damaged and toxic bad boy on the list, Keith is played wonderfully by Jesse McCartney alongside Elisabeth Harnois. His influence on Natalie gets her into trouble, only for him to dismiss her feelings. However, the presentation of the trope as well as the shocking background gives you the feeling of unwrapping a present — one you least expected.

Stream Keith on Tubi

8 Wade and Allison — Cry-Baby (1990)

cry-baby
Cry-Baby

Release Date
April 5, 1990

Rating
PG-13

Working both as a comedy and a musical with a touch of romance, Cry-Baby is set in 1950s Baltimore, where Allison Vernon-Williams is a straight-laced girl from a wealthy and snobbish family, and Wade “Cry Baby” Walker is a leader of a gang of “drapes,” a band of misfits that are total opposites of Allison and her friends. When Allison is drawn to Wade and his complicated edgy world, they realize that they have more in common than they thought.

Related: Why the ’90s is the Greatest Decade in Movie History

Cry-Baby is a rollercoaster ride from start to finish. It packs an abundant amount of emotion. With the flawless pairing of Johnny Depp and Kim McGuire, superb musical numbers, and lavish sets, this campy classic written and directed by John Waters succeeds in giving us another inseparable duo in Allison and Wade.

Rent Cry-Baby on Apple TV

7 Kat and Patrick — 10 Things I Hate About You (1999)

10 Things I Hate About You Kat and Patrick looking at each other after paintball
Touchstone Pictures

10 Things I Hate About You is a Shakespeare-inspired modern iteration that follows two sisters, Bianca and Kat Stratford, who are polar opposites. Bianca is a popular girl ready to have all the classic teenage experiences — including having a boyfriend — and Kat is a stubborn and opinionated feminist who refuses to date.

Their father’s ultimatum for Bianca is that she can only date when her sister does, which leads new student Cameron to bribe the school’s bad boy Patrick to woo Kat and take her to prom.

Filled with teenage angst, iconic music numbers, and phenomenal dialogue delivery, this teen classic revived the good-girl-bad-boy genre with humor and edge. Julia Stiles and Heath Ledger have certainly become a memorable match with their larger-than-life personalities and jagged exteriors on both sides, but it is Patrick’s charming change of heart that makes us squeal in delight.

Stream 10 Things I Hate About You on Disney+

6 Baby and Johnny — Dirty Dancing (1987)

Dirt Dancing - 2023 Placeholder
Dirty Dancing

Madge flies to Peru for a vacation, and meets alpaca farmer Jorge. While their romance blossoms so too does their love for the dance.

As one of the highest-grossing films of its release year, it’s no surprise that Dirty Dancing has earned a loyal following and plenty of appreciation from critics. As far as its winsome narrative goes, the film takes us to the 1960s in the Catskills, where Frances “Baby” Houseman is vacationing with her family.

As a sheltered girl, her eyes are opened to risqué fun when she meets dance instructorJohnny Castle, a bad boy from the wrong side of the tracks. Drawn into his life, their steamy dance sessions guarantee that something deeper and forbidden will blossom.

The movie is an ode to young love, one that transcends expectations and limitations posed by society. Patrick Swayze and Jennifer Grey shared a magical chemistry on screen. And even though Swayze’s character was only a ‘bad boy’ because of some pre-established definition of the term (and his salacious dancing) and not because he was actually problematic, the movie manages to dance to its own renegade beat and cements itself as a passionate romance.

Stream Dirty Dancing on Hulu

5 Annette and Sebastian — Cruel Intentions (1999)

Annette and Sebastian in Cruel Intentions standing outside
Columbia Pictures

Set against the backdrop of their upscale New York City mansion, Cruel Intentions follows step-siblings Kathryn Merteui and Sebastian Valmont. The former is a malicious and cunning queen bee, while the latter is the crown prince of debauchery, always preying on girls he never intends to date.

When a bet leads him to Annette Hargrove, the righteous good girl and headmaster’s daughter, Sebastian transforms into someone with a capacity for genuine care.

Cruel Intentions is an indie classic directed by Roger Kumble and starring Sarah Michelle Geller, Ryan Phillippe and Reese Witherspoon. Each of the characters delivers flawed and fiery performances, with Phillippe and Witherspoon carrying the enemies-turned-lovers trope with their lustful and electric chemistry. The ending made for one of the most memorable needle drops of all time.

Stream Cruel Intentions on Prime Video

4 John and Claire — The Breakfast Club (1985)

The Breakfast Club John and Claire after detention
Universal Pictures

An ‘80s representation of every teenager’s struggle with identity and the great, big world, The Breakfast Club follows five high schoolers, stereotyped into certain cliques, thrown together in detention for eight long hours on a Saturday. There’s the jock, the rebel, the princess, the nerd, and the weirdo outcast. Even though there are tensions between them initially, once the kids get talking, their honest exchanges allow their mutual struggles to surface and turn the afternoon into a transformative one.

The most unexpected part is the coupling between John and Claire. Starting with antagonism and eventually turning to flirtation, their relationship reaches a point where they’ve come to know each other’s true selves by the time detention ends. Many moments from John Hughes’ generation-defining classic live in our head rent-free, but Judd Nelson pumping his fist in the air after Molly Ringwald kisses him is among the best.

Stream The Breakfast Club on Max

3 Hannah and Jacob — Crazy, Stupid, Love (2011)

Emma Stone as Hannah and Ryan Gosling as Jacob in Crazy, Stupid, Love
Warner Bros.

Before they broke our hearts in La La Land with that devastating ending, Ryan Gosling and Emma Stone found rare chemistry and delivered laughs-a-plenty in Crazy, Stupid, Love. The funny thing is, the movie isn’t even about them. It’s about a Cal, a man tackling a midlife crisis and a divorce at the same time.

Determined to change things, he decides to go pick up girls in a bar, and that’s where he meets bad boy Jacob. Jacob is a looker who can sweet talk any woman and bring them home, and Hannah is, well, Cal’s daughter.

Related: These Are the Most Iconic Moments in Crazy, Stupid, Love

Together, Jacob and Hannah’s chemistry is off the charts. Hannah sees past Jacob’s flashy techniques to the sensitive and kind man he is, and teaches him the meaning of real partnership. Gosling and Stone embody the roles of two unconventional soulmates with signature charm and pathos.

Stream Crazy, Stupid, Love on Tru TV

2 Jamie and Landon — A Walk To Remember (2002)

A Walk to Remember Jamie and Landon sitting together
Netflix

Based on Nicholas Sparks’ 1999 novel of the same name, A Walk To Remember is a coming-of-age story about rebellious teen Landon Carter who couldn’t care less about school. In the first five minutes of the movie itself, he gets in trouble and ends up in community service. Part of his punishment requires him to participate in the school play, where he meets Jaime Sullivan, played by Mandy Moore, the pastor’s daughter, who is shy and reserved and your typical good girl.

As they spend time together running lines, Jamie and Landon fall in love, but a heartbreaking secret changes their lives forever. There’s no denying that A Walk To Remember is a certified tearjerker. But what’s more ethereal is the transformation of Shane West’s Landon from a troublemaker to a genuine heartfelt man who would go to extreme lengths for the girl he loves.

Stream A Walk To Remember on Netflix

1 Sutter Keely and Aimee Finicky — The Spectacular Now (2013)

An A24 production, The Spectacular Now centers around Sutter Keely, a charming high school senior who seems to love his life of partying every night without much regard for the future. One day, he gets so drunk that he finds himself waking up on a stranger’s lawn and meets Aimee Finicky.

Aimee is the studious girl who sees beyond the surface and simply wants to get out of town. When the two fall in love, they benefit from each other’s perspectives. Aimee learns to stand up to her overbearing mother, and Sutter finally sees hope for a better tomorrow.

Tender, humorous, and truthful, the movie unfolds slowly and intimately. Miles Teller and Shailene Woodley infuse their characters with a subtle soulfulness. Sutter has personal demons weighing down on him and the more Aimee challenges him just by being herself, the nicer he becomes. In a way, Sutter and Aimee challenge viewers to question their preconceived views about life.

Stream The Spectacular Now on Max

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