Best movies like The Last International Playboy

A unique, carefully handpicked, selection of the best movies like The Last International Playboy Starring Jason Behr, Monet Mazur, Krysten Ritter, Lucy Gordon, and more. If you liked The Last International Playboy then you may also like: Yellow, The Wackness, Whiskey Tango Foxtrot, Nola, The Odd Couple 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.

Jack Frost's playboy lifestyle in New York City is rocked by the news that his childhood love is engaged. Amidst his friendships with Scotch Evans, a ribald nightlife correspondent; Ozzy, a troubled but loving heroin addict; and Kate Hardwick, a bewitching, quick-witted reporter, Jack sinks deeper into depression. Haunted by lost-love and his mother's suicide, Jack plunges into whiskey and self-destruction . . . until his eleven-year-old neighbor, Sophie, an unlikely mother figure, leads Jack back into himself, and out of the nostalgia and excess that consumed him.

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Yellow

Amaryllis Campos is a young, classically trained Puerto Rican ballerina, who dreams of leaving her impoverished home in Puerto Rico to pursue fame and fortune as a dancer. Amaryllis heads for New York City, where she is forced to work in a seedy strip club to make ends meet. Setting audiences afire with her erotic moves, Amaryllis quickly becomes the strip club's hottest attraction, but must finally decide between true love and realizing her dream of becoming a star.

The Wackness

Set in New York City in the sweltering summer, The Wackness tells the story of a troubled teenage drug dealer, who trades pot for therapy sessions with a drug-addled psychiatrist. Things get more complicated when he falls for one of his classmates, who just happens to be the doctor's daughter. This is a coming-of-age story about sex, drugs, music and what it takes to be a man.

Whiskey Tango Foxtrot

In 2002, cable news producer Kim Barker decides to shake up her routine by taking a daring new assignment in Kabul, Afghanistan. Dislodged from her comfortable American lifestyle, Barker finds herself in the middle of an out-of-control war zone. Luckily, she meets Tanya Vanderpoel, a fellow journalist who takes the shell-shocked reporter under her wing. Amid the militants, warlords and nighttime partying, Barker discovers the key to becoming a successful correspondent.

Nola

An urban fairy tale-romantic comedy, in which Nola, an aspiring songwriter, leaves an abusive Kansas home and journeys to New York to find her biological father. Once there, she finds more than she expected.

The Odd Couple

In New York, Felix, a neurotic news writer who just broke up with his wife, is urged by his chaotic friend Oscar, a sports journalist, to move in with him, but their lifestyles are as different as night and day are, so Felix's ideas about housekeeping soon begin to irritate Oscar.

Cobain: Montage of Heck

Hailed as one of the most innovative and intimate documentaries of all time, experience Kurt Cobain like never before in the only ever fully authorized portrait of the famed music icon. Academy Award nominated filmmaker Brett Morgen expertly blends Cobain's personal archive of art, music, never seen before movies, animation and revelatory interviews from his family and closest friends.

Basquiat

The brief life of Jean Michel Basquiat, a world renowned New York street artist struggling with fame, drugs and his identity.

Bird

Saxophone player Charlie ‘Bird’ Parker comes to New York in 1940 and is quickly noticed for his remarkable way of playing. He becomes a drug addict but his loving wife Chan tries to help him.

Born to Win

A smart-mouthed junkie and a former hairdresser spends his days looking for just "one more fix".

The Brothers

This is the story of four African-American "yuppies" (a banker, a doctor, a lawyer, and a "playboy") who call themselves "The Brothers". When the playboy gets engaged, the other three friends find themselves having to come to terms with their own issues of commitment and honesty...

Taking Woodstock

The story of Elliot Tiber and his family, who inadvertently played a pivotal role in making the famed Woodstock Music and Arts Festival into the happening that it was. When Elliot hears that a neighboring town has pulled the permit on a hippie music festival, he calls the producers thinking he could drum up some much-needed business for his parents' run-down motel. Three weeks later, half a million people are on their way to his neighbor’s farm in White Lake, New York, and Elliot finds himself swept up in a generation-defining experience that would change his life–and American culture–forever.

Trainspotting

Heroin addict Mark Renton stumbles through bad ideas and sobriety attempts with his unreliable friends -- Sick Boy, Begbie, Spud and Tommy. He also has an underage girlfriend, Diane, along for the ride. After cleaning up and moving from Edinburgh to London, Mark finds he can't escape the life he left behind when Begbie shows up at his front door on the lam, and a scheming Sick Boy follows.

Palooka

Joe Palooka is a naive young man whose father Pete was a champion boxer, but his lifestyle caused Joe's mother Mayme to leave him and to take young Joe to the country to raise him.

Heaven Knows What

A young heroin addict roams the streets of New York to panhandle and get her next fix, while her unstable boyfriend drifts in and out of her life at random.

Interview

After falling out with his editor, a fading political journalist is forced to interview America's most popular soap actress.

It Had to Be You

Sparks fly when Anna Penn and Charlie Hudson meet. Unfortunately, they're both engaged to other people. In fact, they're staying at the same New York City hotel in order to work on wrapping up the last details of their nuptials. Over days and evenings of joint wedding planning, the two grow closer -- and start to wonder if they're getting married to the right people after all.

The Last Days of Disco

Two young women and their friends spend spare time at an exclusive nightclub in 1980s New York.

London

London is a drug laden adventure that centers on a party in a New York loft where a young man is trying to win back his ex-girlfriend.

September

After a suicide attempt, Lane has moved into her country house to recuperate. Her best friend, Stephanie, has come to join her for the summer. Lane's mother, Diane, has recently arrived with her husband Lloyd, Lane's stepfather. Lane is close to two neighbors: Peter, and Howard. Howard is in love with Lane, Lane is in love with Peter, and Peter is in love with Stephanie.

Sunday in New York

Eileen is 22 and is smarting from her breakup with Russ. She comes to New York to visit her brother, Adam, who is an airline pilot. Eileen confides to her brother that she thinks she may be the only 22 year old virgin left in the world. Adam assures her that sex is not what all men look for and insists he hasn't slept around. Of course, Adam is lying and is in hot pursuit of a tryst with his occasional girlfriend Mona. However, Adam's date with Mona has a series of job related interruptions. Meanwhile, Eileen decides to see if she can have some fun for herself in New York, and seems to find the perfect candidate in Mike, a man she meets on the bus. But things get complicated when Russ pops in with a proposal and a mistaken assumption.

Don't Go Near the Water

Madison Avenue-trained Navy men handle public relations on a South Pacific island during World War II.

Guest Wife

Christopher Price, a small-town bank executive, continues to be loyal to and idolize his boyhood friend, Joseph Jefferson Parker, a famous war correspondent. But Chris's wife, Mary, is none to fond of Joe and tired of her husband's idolizing. On the eve of the Price's second-honeymoon trip to New York City, Joe arrives and tells Chris that he needs someone to pose as his wife in order to fool his boss in NYC, who thinks Joe got married to an overseas woman while on an assignment. Chris pushes Mary into posing as Joe's wife. In New York, this leads to many complications and misunderstandings, with Mary finally deciding to teach Chris and Joe a lesson by making them believe she is in love with Joe.

One Naked Night

After the death of her prostitute mother, a young woman travels to New York City only to find herself in the clutches of lecherous men and deviate women. She tries to avoid the fast nightlife lifestyle, but she finds it more difficult than it sounds.

Fiona

Fiona is abandoned at six months of age, raised in foster and adoptive homes, abused, and, still a teen, hustles on the streets of New York. We watch her use heroine, fall in love with other women, be pursued by men, engage in murderous violence, hide out in a crack house, and decide to leave the city. We see her mother, also a streetwalker and drug user, occasionally talk about her lost daughter. Fiona has a necklace she was clutching when a foundling. Will mother and daughter meet? Is there a silver lining?

The Image

When career-focused journalist's investigation indirectly causes a suicide, he questions his own methods and life in general.

Satan in High Heels

A carnival burlesque dancer robs her junkie ex-husband, goes to New York, gets a job at a high-class club where she becomes the mistress of the wealthy owner. She seduces his son and causes a murder.

Gunn

The madam of a floating bordello hires private eye Peter Gunn to prove a gangster killed a crime boss.

Who Killed Nancy?

On October 12th, 1978, New York Police discovered the lifeless body of a young woman, slumped under the bathroom sink in a hotel room. She was Nancy Spungen, an ex-prostitute, sometimes stripper, heroin addict, and girlfriend of Sex Pistols' bassist Sid Vicious.

Louisa

Architect Hal Norton and wife Meg invite his widowed mother Louisa to move in with them, only to discover the sweet elderly lady is romantically involved with what seems to be every old coot in town.

Assholes

Adah and Aaron are recovering addicts who are struggling to stay sober. After meeting in their psychoanalyst’s waiting room, they fall in love, relapse on poppers, and become the biggest assholes in New York City.

Love Is News

When a crafty reporter uses false pretenses to get a story out of heiress Tony Gateson, she turns the tables on him, telling the press that they are engaged. Suddenly he's front page news, every salesman is at his doorstep, and he loses his job. A series of misadventures ensues with him alternately back on his job and fired and her ex-fiancé showing up.

The Pusher

A detective investigating the murder of a heroin addict discovers that there is a connection between the junkie and his fiance, who is his boss' daughter.

Ben: Diary of a Heroin Addict

Ben Rogers was a bright schoolboy from a loving, middle class family. He played in the orchestra, loved cricket and enjoyed the annual family holiday. But his future promise was halted when he started taking drugs in his teens. Early drinking led to cannabis, harder drugs, and then the revelation to his family, at the age of 21, that he was addicted to heroin. Over the next 13 years Ben and his family battled with his addiction, going through detox, rehab and attempts at 'cold turkey', but his health gradually declined. Whilst attempting another detox aged 34, he died from a brain haemorrhage. But during the last two years of his life, Ben filmed an unflinching video diary showing his final desperate attempts to come off heroin. It's a portrayal of his descent; intimate, raw, and at times difficult to watch, he talks to his glove puppet as he injects into a vein in his groin.

The Beautiful Risk

William, a respected artist who lost everything after his divorce, arrives in Montreal on a job prospect. When the job falls through he then is saved and forms an erotic friendship and exposes his soul with a young woman named Paulette.

Matriarch

Afflicted with a mysterious disease after surviving an overdose, a woman returns to her childhood home to confront her personal demons but instead discovers a real one.

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