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Home/Playing It Cool/Similar Movies

Playing It Cool

Movies Like Playing It Cool (2014)

Playing It Cool is a 2014 comedy, romance film from Justin Reardon with a MovieMagicScore of 5.8/10. Here are 20 similar films, ranked by real viewer ratings — starting with Something Borrowed and Let's Be Cops.

Something Borrowed poster

Something Borrowed

2011

Though Rachel is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy. Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan, Rachel's confidant, harbors a potentially explosive secret of his own.

Let's Be Cops poster

Let's Be Cops

2014

Best pals Ryan and Justin are stalled in their respective careers -- a fact that is painfully driven home when they go to a college reunion. Dressed as police in the mistaken belief that they were to attend a costume party, Ryan and Justin find that the uniforms earn them much respect and attention. Although Justin is uncomfortable with the idea, Ryan decides to continue with the charade, putting them both in increasingly dangerous situations. When these newly-minted “heroes” get tangled in a real life web of mobsters and dirty detectives, they must put their fake badges on the line.

Pillow Talk poster

Pillow Talk

1959

Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a complaint against him, Brad sets about to seduce her in the guise of a sincere and upstanding Texas rancher. When mutual friend Jonathan discovers that his best friend is moving in on the girl he desires, however, sparks fly.

The Wheeler Dealers poster

The Wheeler Dealers

1963

Henry J. Tyroon leaves Texas, where his oil wells are drying up, and arrives in New York with a lot of oil money to play with in the stock market. He meets stock analyst Molly Thatcher, who tries to ignore the lavish attention he spends on her but, in the end, she falls for his charm.

Along Came Polly poster

Along Came Polly

2004

Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.

Kadhalil Sodhappuvadhu Yeppadi poster

Kadhalil Sodhappuvadhu Yeppadi

2012

After Arun and Parvathi's stormy romance ends, he goes to Puducherry where he befriends Cathy, the girlfriend of his buddy John. But their friendship is mistaken for love by John.

(500) Days of Summer poster

(500) Days of Summer

2009

Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.

Hot Frosty poster

Hot Frosty

2024

When a young widow's magic scarf brings a dashing snowman to life, can he help her rediscover romance, laughter and holiday cheer before he melts away?

Boys Don't Cry poster

Boys Don't Cry

1999

A young transgender man explores his gender identity and searches for love in rural Nebraska.

Falling in Love Like in Movies poster

Falling in Love Like in Movies

2023

Bagus, a screenwriter, reunites with his high school friend and crush, Hana, who is still grieving from the loss of her husband. He wants to convince her to fall in love once again, just like in the movies.

Chasing Liberty poster

Chasing Liberty

2004

The President's daughter, unable to experience life like a normal 18 year-old, escapes from her entourage of Secret Service agents while traveling in Europe. She falls in love with a handsome British stranger, who also happens to be working undercover for her father.

First Daughter poster

First Daughter

2004

Samantha MacKenzie, the daughter of the president of the United States, arrives at college with a group of Secret Service agents. Samantha, however, resents their presence and decides she wants to attend school just like a normal student. Her father agrees to recall the agents but secretly assigns James, an undercover agent, to pose as a student.

Anything for Love poster

Anything for Love

2016

Katherine, a high-powered executive who believes men are intimidated by her career, is persuaded by her friend to create an internet dating profile claiming she is an executive assistant.

Failure to Launch poster

Failure to Launch

2006

At 35, Tripp has an interesting job, a hip car, a passion for sailing, an active dating life, and a great house - trouble is, he still lives with his parents, Al and Sue, who are not happy about it. Al and Sue are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to help. In desperation to push Tripp out of the nest once and for all, Al and Sue hatch a plan to hire Paula, an "interventionist," who has a formula in these cases.

The Way We Weren't poster

The Way We Weren't

2019

Charlotte and Brandon meet online just after their previous relationships have imploded; in an effort to make themselves more appealing, they have fudged, exaggerated, re-imagined, and outright lied about their pasts in an attempt to be each other's perfect match. Now that they've said their "I do's" they are about to get a funny, hellish, and eye-opening look at just who they've vowed to spend the rest of their lives with. Will familiarity breed contempt... or bliss?

Bros poster

Bros

2022

Two emotionally unavailable men attempt a relationship.

Midnight in Paris poster

Midnight in Paris

2011

While on a trip to Paris with his fiancée's family, a nostalgic screenwriter finds himself mysteriously going back to the 1920s every day at midnight.

Barton Fink poster

Barton Fink

1991

A renowned New York playwright is enticed to California to write for the movies and discovers the hellish truth of Hollywood.

Leaving Las Vegas poster

Leaving Las Vegas

1995

Ben Sanderson, an alcoholic Hollywood screenwriter who lost everything because of his drinking, arrives in Las Vegas to drink himself to death. There, he meets and forms an uneasy friendship and non-interference pact with prostitute Sera.

Seven Psychopaths poster

Seven Psychopaths

2012

A struggling screenwriter inadvertently becomes entangled in the Los Angeles criminal underworld after his oddball friends kidnap a gangster's beloved Shih Tzu.

Frequently asked

What are the best movies like Playing It Cool?

The top films similar to Playing It Cool by MovieMagicScore are Something Borrowed (6.2), Let's Be Cops (6.5), Pillow Talk (7.1). Each shares comedy/romance themes and is ranked by real viewer ratings, not critics or studios.

Is Playing It Cool worth watching?

Playing It Cool holds a MovieMagicScore of 5.8/10 from 787 viewer ratings.

What kind of movie is Playing It Cool?

Playing It Cool (2014) is a comedy, romance film directed by Justin Reardon, starring Chris Evans, Michelle Monaghan, Topher Grace.

Where can I find more recommendations like Playing It Cool?

Browse the full ranked list above, or explore more comedy recommendations on MovieMagicScore, where every list is ordered by genuine viewer ratings.

Keep exploring

Movies like Something Borrowed Movies like Let's Be Cops Movies like Pillow Talk Movies like The Wheeler Dealers Movies like Along Came Polly Movies like Kadhalil Sodhappuvadhu Yeppadi

About movies like Playing It Cool

This ranked list pairs Playing It Cool (2014), a comedy and romance film from Justin Reardon, with similar titles by genre, theme and cast overlap (fans of Chris Evans take note). Unlike critic-driven sites, every position here is ordered by MovieMagicScore — a rating built only from real viewers, with no studio marketing or paid placement. Scores update as more people rate, so the list stays current.

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