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Movies Similar to Playing It Cool (2014)
60 similar titles
Dearest Jane2015 • 99 minDrama, RomanceA young girl learns to accept love and change after being sent to live with her uncle in Indiana.
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Say Yes2021 • 88 minFacing a critical decision – to marry, to separate, to delay the wedding, or to try to make things work – the film explores the complexities of relationships, friendships, and love, with…6.03.4
All I Wish2018 • 94 minComedy, RomanceA woman fights to break free from her controlling, overly involved mother, and slowly develops feelings for a charming and polished lawyer.5.55.217+
Summertime2021 • 95 minOn a sweltering summer day in Los Angeles, the paths of 25 young Angelinos cross. A skateboarding guitarist, a graffiti artist, aspiring rappers, a frustrated fast-food employee, and a limousine driver –…6.46.317+
Divine Intervention2024 • 17 minA playful angel assigned to Earth has a mission: help two former best friends realize they're in love. The angel needs them to finally confess their feelings if they want to earn…0.06.8
Hatchback2019 • 93 minWyatt, a cynical man with narcolepsy living in a rundown apartment, aspires to be a journalist. His ambitions are threatened when he becomes aware of a mysterious girl named Fern who lives…5.54.514+
Love Wedding Repeat2020 • 100 minComedy, RomanceJack's efforts to ensure his sister's wedding are complicated by a demanding ex-girlfriend, a mysterious guest with hidden motives, a lost sedative, and unexpected encounters with a woman from his past –…5.65.617+
Lagan Special2024 • 110 minShekhar and Suman are set to marry tomorrow, and tonight is their pre-wedding celebration. It's an arranged marriage, and Shekhar appears very enthusiastic. However, just before the festivities, Suman discovers that Shekhar…0.06.0
Tall Girl2019 • 101 minComedy, Drama, RomanceJodi, the tallest girl in school, has always struggled with self-consciousness. After years of trying to avoid attention and enduring teasing for her height, she finally resolves to find the courage to…6.35.26+
Paul & Paulette Take a Bath2025 • 109 minA quirky romantic comedy follows a young American photographer and a French woman drawn to the unsettling. Paul and Paulette meet by chance in Paris, and their unusual friendship develops through a…0.06.5
After You2003 • 110 minComedy, RomanceAntoine is a bartender in Paris. Returning home from work one night, he stops a man from taking his own life. He becomes burdened by a strange guilt over saving the man…6.06.417+
Love Object2004 • 88 min • Budget $1MDrama, Horror, RomanceKenneth, a socially awkward technical writer, develops an obsessive relationship with Nikki, an anatomically realistic silicone sex doll he purchases online.5.96.317+
The Last Days of Disco1998 • 113 min • Budget $8M • Box office $3MComedy, Drama, RomanceIn 1980s Manhattan, a group of friends are captivated by a glamorous nightclub offering excitement and opportunity. The film focuses on two young women who are independent and navigating adolescence during a…6.26.717+
Legally Blondes2009 • 86 min • Box office $16MComedyAfter moving from England to California, Elle Woods' younger cousins find themselves targeted by popular students at their new school. The popular girls turn hostile and attempt to frame them for a…5.73.66+
The Boxer1997 • 114 min • Box office $16MDrama, RomanceIn Belfast, 19-year-old Danny Flynn joins the IRA, leading to his imprisonment and separation from his family and girlfriend, Maggie Hamill. After fourteen years, he's released and returns to his old life.…6.77.017+
17 Again2009 • 102 min • Budget $20M • Box office $136MComedy, Fantasy, DramaFeeling lost at 30, Mike O'Donnell dreams of a second chance. He unexpectedly gets one when he wakes up as his 17-year-old self. Now with an adult mind in a teenage body,…6.36.413+
Beverly Hills Cop II1987 • 103 min • Budget $28M • Box office $299MAction, Comedy, CrimeDetective Axel Foley returns to California to investigate the shooting of Police Captain Andrew Bogomil. Joined by Sgt. Taggart and Det. Rosewood, Foley investigates a series of robberies called "alphabet heists," uncovering…6.56.617+
All About My Mother1999 • 101 min • Budget $5M • Box office $67MComedy, DramaManuela travels from Madrid to Barcelona hoping to find her son's father, a man she's never known. During her journey, she meets a variety of people: a bold transgender sex worker, a…7.67.817+
Back to the Future1985 • 116 min • Budget $19M • Box office $381MAdventure, Comedy, Science FictionSex and the City is a lively look at friendships between women and finding love in New York City. The film adapts Candace Bushnell's popular novel, following four independent women in their…8.38.56+
Three Colors: White1994 • 92 min • Box office $1MComedy, Drama, MysteryKarol Karol's life changes dramatically when his French wife, Dominique, divorces him because of his impotence. This unexpected end to their marriage also costs him the business they built together. With no…7.47.617+
Pretty Woman1990 • 120 min • Budget $14M • Box office $463MRomance, ComedyEdward Lewis, a cynical Los Angeles businessman, unexpectedly finds his life changing when he meets Vivian Ward, a resourceful prostitute trying to survive. After a chance encounter where she helps him navigate…7.57.117+
The Big Lebowski1998 • 117 min • Budget $15M • Box office $47MComedy, CrimeJeffrey "The Dude" Lebowski is a relaxed Los Angeles resident who enjoys bowling and White Russians. His life takes a bizarre turn when a group of thugs break into his apartment, mistaking…7.88.117+
Match Point2005 • 124 min • Budget $15M • Box office $85MDrama, Romance, ThrillerChris, a former tennis player now working as an instructor, develops a close relationship with his student, Tom. Following an introduction to Tom's family, Chris becomes engaged to Tom's sister, Chloe. Though…7.47.617+
O Brother, Where Art Thou?2000 • 107 min • Budget $26M • Box office $71MAdventure, Comedy, CrimeThe story unfolds in the American South during the 1930s. Three convicts, having escaped from prison, embark on a quest to find buried treasure. A determined lawman relentlessly hunts them down.7.37.713+
48 Hrs.1982 • 96 min • Budget $12M • Box office $78MCrime, Action, ComedyA jaded police detective is partnered with a sarcastic ex-con released from prison for a special assignment. They must work together to hunt a ruthless killer through the city. The unlikely pair…6.76.917+
Sacramento2025 • 89 minComedy, DramaWhen Rickey, an old friend of Glenn's, unexpectedly shows up, the two former best friends decide to take a spontaneous road trip together, driving from Los Angeles to Sacramento.6.25.917+
Superstars of Yesteryear2003Relive the golden age of professional wrestling with this collection of classic matches. Witness legendary wrestlers like Nick Bockwinkle, Curt Henning, the Fabulous Freebirds, Bob Orton, Jim "The Anvil" Neidhart, and Jerry…0.0—
Contempt1963 • 103 min • Budget $900K • Box office $528KDrama, RomanceThis drama follows Jeremy Prokosch, a practical art film producer, as he works with renowned director Fritz Lang to adapt Homer's "The Odyssey" for the screen. As the ambitious project faces difficulties,…7.07.4
The Edukators2004 • 127 minDrama, ComedyThree activists devise a kidnapping plan after unexpectedly encountering a businessman at his house.7.27.417+
The Apartment1960 • 125 min • Budget $3M • Box office $25MComedy, Drama, RomanceBud Baxter, an ambitious but unassuming worker at a top New York insurance firm, feels overlooked in his career. Frustrated by favoritism, he devises a plan: offering his apartment as a secret…8.28.3
Barton Fink1991 • 117 min • Budget $9M • Box office $6MComedy, Drama, Thriller*The Midnight Special* was a popular American musical variety show on NBC from 1973 to 1981. The ninety-minute program, created and produced by Burt Sugarman, aired Friday nights after *The Tonight Show…7.57.617+
The Science of Sleep2006 • 106 min • Budget $6M • Box office $9MComedy, Drama, FantasyLost in his own vivid dreams, a man falls deeply in love with a French woman and wants to share his unique perspective with her.7.07.217+
Breakfast at Tiffany's1961 • 115 min • Budget $2M • Box office $9MComedy, Romance, DramaHolly Golightly is a charming and unconventional socialite in 1960s New York City, dreaming of marrying a wealthy Brazilian millionaire. Her carefully built world changes when she meets Paul Varjak, a young…7.67.5
Back to the Future Part III1990 • 119 min • Budget $40M • Box office $244MAdventure, Comedy, Science FictionThe final part of the popular series follows Marty McFly and Doctor Emmett Brown as they arrive in 1885, the Wild West. After recovering the DeLorean from a mineshaft, they discover the…7.57.56+
The Tulse Luper Suitcases, Part 1: The Moab Story2003 • 127 minThis is a humorous look at 20th-century history, following the life of Tulse Luper – a writer, artist, and self-proclaimed prisoner. Born in Newport, Wales, in 1911, he was last seen in…5.16.7
Samba2014 • 118 min • Budget $20M • Box office $151KDrama, ComedyTen years ago, Samba moved to France from Senegal and has worked a series of low-paying jobs. Alice, a senior executive, is recently recovering from burnout. Both are struggling to find a…6.46.717+
Rebecca1940 • 130 min • Budget $1M • Box office $7MMystery, Romance, ThrillerA young woman marries the enigmatic widower Max De Winter and finds herself haunted by the memory of his deceased first wife, Rebecca. Rebecca's death was never explained, and her presence seems…7.98.0
The War of the Roses1989 • 116 min • Budget $26M • Box office $160MComedy, DramaClarissa Darling is a teenager figuring out growing up, portrayed with honesty and realism. She deals with typical pre-teen issues: school, friendships, and family. Clarissa also navigates personal moments like her first…6.96.917+
Beverly Hills Cop III1994 • 105 min • Budget $50M • Box office $119MAction, Comedy, CrimeDetroit police officer Axel Foley returns to Beverly Hills when he discovers evidence connecting his boss's murder to Wonder World, a seemingly perfect California amusement park. Working with Detective Billy Rosewood and…5.95.517+
True Romance1993 • 119 min • Budget $12M • Box office $12MAction, Crime, RomanceIn a harsh city, Clarence unexpectedly marries Alabama, a woman working in sex work. Together, they discover a supply of cocaine and decide to sell it in Hollywood, hoping for a better…7.57.917+
Head-On2004 • 117 min • Box office $11MDrama, RomanceTo escape her family, a young woman arranges a marriage with a forty-year-old addict. This arrangement unexpectedly sparks a passionate and jealous love.7.57.817+
Raising Arizona1987 • 94 min • Budget $6M • Box office $29MComedy, CrimeA former convict and retired police officer, longing for a family, makes a rash decision to become parents when quintuplets are born. They plan to adopt one of the children. This seemingly…7.17.313+
Chocolat2000 • 121 min • Budget $25M • Box office $152MComedy, Drama, RomanceIn the winter of 1959, a single mother and her young daughter move to a quiet French town and open a unique chocolate shop. Their arrival challenges the traditional values of the…7.07.213+
Autumn in New York2000 • 103 min • Budget $65M • Box office $90MDrama, RomanceWill Keane, a New York City restaurateur enjoying a carefree life, meets Charlotte Fielding, a spirited young woman. They begin a passionate relationship that challenges both of them to reconsider their life…6.15.613+
Bringing Down the House2003 • 105 min • Budget $20M • Box office $132MComedy, DramaDivorced lawyer Peter Sanderson is eager to start dating again but struggles to find a connection. He tries online dating and connects with another lawyer. They arrange a meeting, but Peter is…6.05.713+
Esperanza H.2024 • 9 minFollowing a minor offense, a young man is surprised by a declaration of love. Intrigued, he begins a city-wide quest to find evidence of this affection.8.0—
27, Memory Lane2014 • 97 minA divorced doctor receives a custom-made door that transports him back in time, 25 years. He uses this opportunity to find the woman he loved and lost.6.07.6
Sahara2005 • 124 min • Budget $130M • Box office $119MAction, Adventure, ComedyVeteran adventurer and treasure hunter Dirk Pitt, a former Navy SEAL, travels to the African desert with his quick-witted friend Al. They are searching for a lost Confederate ironclad battleship, believed to…5.96.113+
Come Early Morning2006 • 97 min • Budget $6M • Box office $161KDrama, RomanceA woman in her thirties living in the South seeks romance while navigating personal challenges.5.46.217+
Wedding Daze2006 • 90 min • Box office $11MComedy, RomanceGrief-stricken after losing his partner, Anderson believes he's incapable of love. Encouraged by his best friend, he impulsively proposes to Katie, a waitress who is unhappy with her life. A simple dare…5.65.617+
Outsourced2007 • 102 min • Box office $690KComedy, Drama, RomanceWhen his department is outsourced, an American salesman of quirky items travels to India to train the person taking over his job.6.47.013+
Side Effects2005 • 90 min • Box office $2KComedy, Drama, RomanceAmerica: Built on a Better Pill. For the past ten years, Karly Hert has worked as a pharmaceutical sales representative, legally selling drugs to doctors and enjoying the perks: a company car…5.64.817+
New York, I Love You2008 • 103 min • Budget $14M • Box office $9MComedy, Drama, RomanceNew York, I Love You explores the personal lives of New Yorkers navigating love in all its forms. The film follows couples across various neighborhoods – from the Diamond District and Chinatown…5.96.217+
Feeling Minnesota1996 • 99 minComedy, Drama, ThrillerIn a society built on favors and protection, Sam Clayton marries Freddie. Freddie, formerly a stripper, owes her safety and work to Red, the club owner who took her in. Despite their…5.45.417+
Someone Like You...2001 • 97 min • Budget $23M • Box office $38MComedy, RomanceJane Goodale appears to have it all: a successful career producing a popular daytime talk show and a passionate romance with the show's executive producer, Ray. However, when the relationship ends badly,…5.96.113+
Amerikana2001 • 95 minPeter and Chris, two friends in their late twenties, journey from South Dakota to California on a scooter. Their cross-country trip offers contrasting perspectives on America: Peter views the landscape with cynical…6.06.1
Where the Buffalo Roam1980 • 99 min • Box office $6MComedyThis semi-biographical film offers an immersive look into the life and work of Hunter S. Thompson, the acclaimed gonzo journalist. Inspired by his own experiences, the story follows the writer's struggles and…5.96.517+
In the Land of Women2007 • 97 min • Budget $10M • Box office $17MRomance, Comedy, DramaFollowing a painful breakup, Carter Webb relocates to Michigan to care for his grandmother. He finds himself drawn into the world of his new neighbors: a mother and her daughters who live…5.96.413+
Critters 31991 • 86 minComedy, Horror, Science FictionA terrifying invasion begins in a Los Angeles apartment building when vicious, fanged creatures with fur attack the residents. The tenants, a diverse group struggling to make ends meet, are suddenly hunted…5.34.513+
That Touch of Mink1962 • 99 minComedy, RomanceCathy Timberlake's life takes an unexpected turn when she bumps into Philip Shayne, a successful businessman with a carefree approach to life. After Philip accidentally soils Cathy on her way to a…6.46.6
