Best movies like Tom Cool

A unique, carefully handpicked, selection of the best movies like Tom Cool Starring Mila Kunis, Clifton Collins Jr., Emmanuelle Chriqui, John Doe, and more. If you liked Tom Cool then you may also like: Nice Guy Johnny, The Business, Double Whoopee, The Fall Guy, Sorry We Missed You and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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After going through 50 jobs, a young man lands a dream gig as a driver for an escort service.

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Nice Guy Johnny

Johnny Rizzo, is about to trade his dream job in talk radio for some snooze-ville gig that'll pay enough to please his fiance. Enter Uncle Terry, a rascally womanizer set on turning a weekend in the Hamptons into an eye-opening fling for his nephew. Nice guy Johnny's not interested, of course, but then he meets the lovely Brooke, who challenges Johnny to make the toughest decision of is life.

The Business

During the '80s, a young man named Frankie dreams of escaping London's South East region, and his mother's thug of a boyfriend gives him just the opportunity. After beating up the abusive beau, Frankie runs off to Spain, where he lands a job delivering a package to the dapper Playboy Charlie, a gangster who takes him under his wing. Working as Charlie's driver, Frankie is immersed in a world of fast cars and pretty women -- but all the excess could be his undoing.

Double Whoopee

Stan and Ollie wreak havoc at an upper class hotel in their jobs as footman (Hardy) and doorman (Laurel). They partially undress blonde bombshell Jean Harlow (in a brief appearance) and repeatedly escort a stuffy nobleman into an empty elevator shaft.

The Fall Guy

Johnny Quinlan is so desperate for a job that he takes a gig as a "bag man" for the mob. Meanwhile, his beleaguered wife has to deal with her bizarre, unemployed, wise-cracking brother and various neighbors while keeping house in their Brooklyn tenement.

Sorry We Missed You

Ricky and his family have been fighting an uphill struggle against debt since the 2008 financial crash. An opportunity to wrestle back some independence appears with a shiny new van and the chance to run a franchise as a self-employed delivery driver. It's hard work, and his wife's job as a carer is no easier. The family unit is strong but when both are pulled in different directions everything comes to breaking point.

Brightest Star

A recent college graduate sets out to win back the girl of his dreams.

The Immaculate Conception of Little Dizzle

After he loses his high-paying job, Dory takes a gig as a night janitor in order to pay rent. Alone late at night inside a market research firm, he soon discovers the company is experimenting on their other janitors ...

Amateur Night

Guy Carter, an insecure expectant father unable to find work in his field, accepts a job driving hookers around Los Angeles. One long and crazy evening proves to our hero that he is, in fact, up to the task of fatherhood.

Illicit Lovers

When Jeff Diamond is unexpectedly laid off from his job, his wife Susan accepts an offer by her best friend Kathy to pay Jeff as an escort to a party. Kathy enjoyed Jeff so much she requests him again at a higher rate which includes sex. After being unsuccessful in locating a new job, Susan decides to continue booking escort appointments to make up the lost income.

Amore!

Saul Schwartz, a married successful businessman, is bored with his life and decides he has had enough. So he gets a divorce, quits his job, and goes off to pursue his dream, in Hollywood to be a movie star. Only becoming a movie star isn't as easy as he thought. Nobody wants an overweight, 50 year old, New Yorker who looks like a lawyer. He's going to have to make a few adjustments.

The Prime Gig

Pendelton "Penny" Wise is a smooth-talking con-artist who makes a living by scamming people with phoney travel comp vacations over the phone when, desperate for more fast cash, he's called to work for a shady, veteran con businessman, named Kelly Grant, in selling property for a gold mine over the phone, which takes a turn when Penny begins a relationship with Grant's mistress Caitlin, where Penny throws common sense and caution to the wind to woo her, while we wonder who is scamming who here. Written by Matthew Patay

Red Haired Alibi

A young woman new to the big city gets a job as a man's companion. What she doesn't know is that the man is a notorious gangster.

Portrait of an Escort

Jordan West is a divorcée who moonlights at a professional dating service to make ends meet. But her secret job causes gossip among her neighbors and trouble at the real estate office where she works in the daytime, while her teenage daughter is the only one who remains oblivious to her mother's night job. When Jordan tries to quit her escort profession, she finds herself harassed by her boss/madam, Mrs. Kennedy, and then stalked by an unknown former client.

Drowning on Dry Land

A taxi driver (Naveen Andrews) picks up a fare (Barbara Hershey) in Manhattan. She offers the driver a large sum to drive her to the desert. While the pair drive across the country, the woman tries various strategies to lure the driver into conversation. Despite his reticence, the pair begins a tumultuous and steamy relationship.

The Land of Steady Habits

After leaving his wife and his job to find happiness, Anders begins a clumsy, heartbreaking quest to reassemble the pieces of his fractured life.

A Wish Come True

On the night of her 30th birthday, Lindsay Corwin, an unlucky environmentalist with a string of bad relationships, decides to make the ultimate wish: for all of her birthday wishes to come true. When her nearly three decades of wishes, including everything from losing weight to meeting Mr. Right, start magically coming true all at once, Lindsay is awestruck—until she realizes the life, and the man, she’s always wished for might not be the one she really wants.

The Sweeter Side of Life

Pampered Manhattan housewife Desiree Harper has it all. That is until her husband unexpectedly dumps her for his acupuncturist. Faced with an airtight prenup, Desiree reluctantly lands a job making cupcakes at her father's bakery in Flemington, NJ. She soon discovers there's more to life than 5th Avenue and true love can be even sweeter in small town America.

Sunset Limousine

Alan O'Black is a comic who wants to hit it big. But his endless attempts at stardom have worn down his relationship with his ex-girlfriend, Julie. Thinking she'll give him another chance if he gets a real job, Alan gets a gig as a limo driver, which promptly lands him in a slew of trouble when he meets and gets involved in the hijinks of a crooked entrepreneur, Bradley Coleman.

The Return of Joe Rich

Joe believed in right and wrong until... His job outsourced to India. His teaser rate spiked. His wife bailed. But Joe has a plan...to get it all back, and more. Joe returns home, to the last place on planet Earth where real men can be found...Chicago. Joe's Uncle Dominic is "connected". Joe wants in...to The Mob, or "The Outfit", as it is called in Chicago. And he'll do anything to make it happen. Can a wanna-be wise guy live a long and happy life ? A way cool element of The Return of Joe Rich is amazing HD documentary footage of 10 real-life "Chicago Guys" ages 73 to 89. These "guys" found themselves in the same predicament, in real life, in the 1930's, 40's, and 50's, that Joe does today. They form a "Greek Chorus" which inter-cuts with the present day narrative of The Return of Joe Rich. Written by Sam Auster

The Work Wife

After a tense few months following a miscarriage and an unemployment spell, things are finally looking up for Sean and Lisa Miller when Sean lands his dream job at an advertising firm. But when Sean’s assistant, Jen, his self-proclaimed “Work Wife,” begins vying for his affection, it soon becomes clear that she will stop at nothing to rip their marriage apart and claim him as her own.

Sex for Sale: American Escort

The world's oldest profession is now a thriving black market economy, with an underground workforce that's just an Internet connection and a phone call away. National Geographic's Mariana van Zeller journeys to the heart of the American escort industry and uncovers the gritty reality behind the supply and demand of high-end sex work.

Burlesque

Ali leaves behind a troubled life and follows her dreams to Los Angeles, where she lands a job as a cocktail waitress at the Burlesque Lounge, a once-majestic theater that houses an inspired musical revue. Vowing to perform there, she makes the leap from bar to stage, helping restore the club's former glory.

Postcards from London

Jim is a young man from Essex who moves to Soho with dreams of fame and fortune. When he joins a group of luxury male escorts, he finds himself embarking on a psychedelic journey of decadence.

Fairfield Road

Noah McManus is leaving his job with the Boston mayor's office for a dream gig in Washington, D.C. But in a single day, he finds out his new boss in Washington can no longer employ him and that his girlfriend has been cheating on him. Devastated, Noah travels to a quaint Cape Cod town and unexpectedly finds himself at home.

50 to 1

A misfit group of New Mexico cowboys find themselves on the journey of a lifetime when they learn their crooked-footed racehorse qualifies to run in the Kentucky Derby. Based on the true story of Mine That Bird, the cowboys must overcome impossible odds even before they reach Churchill Downs and the land of Kentucky's blue bloods.

Our Father's Keeper

On Thanksgiving, a family struggles to properly care for their father with Alzheimer's disease.

Abundant Acreage Available

After their father dies, a middle-aged brother and sister wrestle with legacy and ownership when three brothers, whose family farmed the land for generations, return after 50 years.

Love for Rent

Two small-town sisters go to Hollywood and find themselves seduced by the glamor of the big time and big money as high-priced professional escorts.

Une manière de vivre

Colette's life is shattered when her husband dies in a mysterious road accident. This may bring her closer to her daughter Gabrielle, a young bulimic woman who works as a luxury escort. The latter begins to take a strong interest in Joseph, a Belgian philosophy teacher who is passing through Montreal. She presses him with questions about existence, which scares the specialist from Spinoza, who quickly thinks of going home to find his lover. Except that he is intrigued by this presence and the power it has over him

The Gig

Six amateur musicians accept an offer to play a 2-week gig in the Catskills. When the bass player suddenly falls ill, they recruit a genuine pro to fill in. As they embark on the opportunity of a lifetime, dreams and reality begin to collide.

Monday Night Gig

The French isn't your ordinary band. Their lead guitarist is an accountant obsessed with breath mints. The bassist talks to his leg and lives by the train tracks while the drummer works to smash the state. They have no fans, no fame, and no future, but try telling that to lead singer Christian. Monday Night Gig is a comedy for anyone who's followed their dreams, no matter where they lead. And for anyone who just pulled up their skirts... and played.

Sing While You Dance

Susan Kent, hoping to establish herself as a song-plugger, tries to obtain a second song from a young songwriter, Johnny Crane, after his first song becomes a hit. While pursuing her objective, she falls in love with Johnny, and lands in jail, but she acquires the song, the job, and Johnny.

One Man's Law

In this old-time Western from director George Sherman, peaceable cowpoke Jack Summers takes the job of sheriff to help his adopted town in its bid to beat out a nearby settlement for a lucrative railroad contract. Trailcross is trying to get the new railroad and Stevens wants it to go to Mason City. Jack and sidekick Nevady arrive and when Jack faces down Stevens' men, he is made Marshal. The townspeople raise money for the railroad and entrust it to Jack. But Stevens plants two of his henchmen as Jack's escorts and they rob him. With the Railroad Officials due to arrive, Jack must retrieve the money.

All I've Got & Then Some

Rasheed, a struggling stand-up comedian, tries to make it to his first paid gig in Hollywood while avoiding disastrous mishaps and moonlighting as a ride share driver.

Irish Wish

Maddie's dream guy is days away from marrying her best friend when a wish for true love made on an ancient stone in Ireland magically alters her fate.

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