Best movies like Lost Holiday

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A unique, carefully handpicked, selection of the best movies like Lost Holiday Starring Kate Lyn Sheil, Thomas Matthews, Keith Poulson, William Jackson Harper, and more. If you liked Lost Holiday then you may also like: The Night Before, The Return of Superfly, Jamesy Boy, American Beauty, The Business 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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Margaret Rockland is as depressed as the ubiquitous Christmas carols are cheerful when she returns to the Washington DC suburb of her childhood for a reunion. The wild bunch she grew up with have settled into respectable family life. Adding insult to injury, her former boyfriend is engaged to the most bourgeois blonde on the East Coast. Margaret reacts by diving into a drinking and drugs marathon. With two remaining fellow souls, she roams the suburban no man’s land and ends up in an incomparable adventure with kidnapping, extortion, misunderstandings and clumsy violence as basic ingredients.

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The Night Before

In New York City for their annual tradition of Christmas Eve debauchery, three lifelong best friends set out to find the Holy Grail of Christmas parties since their yearly reunion might be coming to an end.

The Return of Superfly

In this third entry in the Superfly films, Priest returns to New York from Paris to find who is responsible for his friend's murder. With a couple of new friends, he attempts to bring the killers to justice while trying not to get into criminal activity like he did years ago.

Jamesy Boy

Based on the true story of teenager James Burns who goes from a suburban street gang to a maximum-security prison cell surrounded by hardened criminals. He turns his life around in prison thanks to the unexpected friendship he forms with a convicted murderer who becomes his mentor.

American Beauty

Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after developing an infatuation with his daughter's attractive friend.

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.

Cocaine

A decadent tale of drugs and the London underworld the cosseted daughter of a respectable businessman - in fact head of a cocaine racket - succumbs to the pleasures of drink and drugs. Vivid nightlife scenes recreate the interwar world of flappers and hedonists; the dapper club owner and seedy street dealers.

Cocaine Cowboys

In the 1980s, ruthless Colombian cocaine barons invaded Miami with a brand of violence unseen in this country since Prohibition-era Chicago - and it put the city on the map. "Cocaine Cowboys" is the true story of how Miami became the drug, murder and cash capital of the United States, told by the people who made it all happen.

Grosse Pointe Blank

Martin Blank is a hitman for hire. When he starts to develop a conscience, he botches a couple of routine jobs. On the advice of his secretary and his psychiatrist, he decides to attend his ten-year high school reunion in Grosse Pointe, Michigan.

The Horde

A bunch of crooked cops raid a ruined building located in an impoverished suburb of Paris, determined to furiously avenge the death of one of them, murdered by the ruthless criminal gang hidden on top of the dark labyrinth that will become a deathly trap when the living, unexpectedly turned into the undead by a mysterious plague, begin to devour the world.

Dolemite

Dolemite is a pimp who was set up by Willie Greene and the cops, who have planted drugs, stolen furs, and guns in his trunk and got him sentenced to 20 years in jail. One day, Queen B and a warden planned to get him out of Jail and get Willie Green and Mitchell busted for what they did to him.

Houseguest

In hot water with the mob over an unpaid debt, a con man poses as a family friend in an affluent Pennsylvania suburb.

Street Girls

When a middle-aged father searches for his dropout daughter, Angel, his quest takes him into the underworld of prostitutes, pimps, drug addicts and thieves. Angel has become a dancer in a topless bar, and her dealer boyfriend is turning her on to heroin.

Road Dogz

"Boyz N the Hood" meets "Blood In, Blood Out" in this gritty tale of life on the streets of East L.A. Danny (Jacob Vargas), Alfonso (Greg Serano) and Raymo (Clifton Collins Jr.) are lifelong friends who have spent their days hanging out and playing basketball. But everything is about to change...when one of them gets involved with a dangerous drug dealer, all their lives are at risk and they must make some life and death decisions.

Marihuana

A young girl named Burma attends a beach party with her boyfriend and after she smokes marijuana with a bunch of other girls, she gets pregnant and another girl drowns while skinny dipping in the ocean. Burma and her boyfriend go to work for the pusher in order to make money so they can get married. However, during a drug deal her boyfriend is killed leaving Burma to fend for herself. Burma then becomes a major narcotics pusher in her own right after giving up her baby for adoption.

Pixie

To avenge her mother's death, Pixie masterminds a heist but must flee across Ireland from gangsters, take on the patriarchy, and choose her own destiny.

Rent

This rock opera tells the story of one year in the life of a group of bohemians struggling in late 1980s East Village, New York, USA. The film centers around Mark and Roger, two roommates. While a tragedy has made Roger numb to new experiences, Mark begins capturing their world through his attempts to make a personal movie. In the year that follows, they and their friends deal with love, loss, and working together.

Crack House

Rick and Melissa are a pair of young lovers hoping to get out of the slums for good and escape the poverty and crime their families and friends have gotten involved in. All this comes to an end when Rick feels he must rejoin his old gang to avenge the killing of his brother by a rival gang. In the course of getting even, Rick is arrested, leaving Melissa without anyone to protect her. She falls in with a crack dealer and quickly becomes addicted to the drug. When she gets sold to a drug kingpin by a minor dealer to pay off a debt, only Rick can save her.

Surviving Christmas

Drew Latham is an executive leading an empty, shallow life with only wealth on his side. Facing another lonely Christmas ahead, he revisit his old childhood home in the hope of reliving some old holiday memories – but he finds that the house in which he was raised is no longer the home in which he grew up.

Shifty

Shifty, a young crack cocaine dealer in London, sees his life quickly spiral out of control when his best friend returns home. Stalked by a customer desperate to score at all costs, and with his family about to turn their back on him for good, Shifty must out-run and out-smart a rival drug dealer, intent on setting him up for a big fall.

And Then You Die

A drug deal must deal with the mafia, Hells Angels, and police who want to arrest him. -- WorldCat

Paper Boys

A ragtag bunch of teenage door to door salesmen wreak havoc and spread the news of their coming of age in this summer before they begin their college lives. It centers around Sean, a sexually confused and drug afflicted teen who just can't seem to shake off his dysfunctional family history. Paper Boys is an adventure into the psychology of sales as a metaphor for life as these young "Glengarry Glen Ross" wannabes terrorize a suburban neighborhood near everyone!

Donnybrook

An ex-marine who struggles to provide for his family and a violent drug dealer with an undefeated fighting record are determined to compete in the Donnybrook, a legendary, bare-knuckle brawl with a cash prize of $100,000.

'R Xmas

A New York drug dealer is kidnapped, and his wife must try to come up with the money and drugs to free him from his abductors before Christmas.

The UnMiracle

A suburban town is torn apart in the aftermath of an accidental teen drug overdose in this ensemble film exploring the mysteries of modern faith.

Cahoots

Two men who were "best friends" while growing up together and into their 20's, reconnect after years apart. On the surface, their lives have gone in opposite directions, one married, successful, respectful and settled; the other divorced, footloose, unemployed and prowling. The narrative is not linear but vertical as simple get together to "have a drink" leads to a nihilistic descent into macho hell. The only thing that survives their reunion is their love for one another.

The Christmas Consultant

Christmas is just around the corner but suburban workaholics Maya Fletcher and her husband Jack are too busy to get into the holiday spirit. As their Christmas to do list grows and deadlines fast approach, holiday spirit is at an all time low. Maya forgets she promised to host a Christmas Eve party for her and Jack’s whole family. In an effort to impress a potential new client, Maya has also invited him to spend the holidays with the family.

Black Tar Heroin: The Dark End of the Street

The film follows a simple structure, and shows the drug-related degradation of five youths (Jake, Tracey, Jessica, Alice, Oreo) during the course of three years. The film depicts drug-related crimes and diseases: prostitution, male prostitution, AIDS, and lethal overdoses.

At the Sinatra Club

Brutal and celebrated Mafia gangster John Gotti (Danny Nucci) schemes, shoves and murders his way to the top of that world in this gritty biography told from the perspective of Salvatore Polisi (Jason Gedrick), who owns the Sinatra Club, where Gotti's crew hangs out. Determined to make his name, the young Gotti plans a daring armored-car robbery that he expects to get him noticed by the bosses of each of New York's five major crime families.

Love Locks

Lindsey Wilson first found love in the romantic city of Paris when she was a university student studying art there. Now, twenty years later, she is returning to the City of Light to take her daughter on an adventure there. With a little inspiration from the city's famed "love locks" on its scenic bridges, the adventure proves to be a journey of romance and rediscovery for the divorced Lindsey when she reconnects with her college flame in Paris and finds that her first love just might be the lasting love of her life after all.

Homegrown Christmas

After stepping down as CEO of her dream job, Maddie heads home for the holidays to gain perspective. She finds herself running into her old high school sweetheart Carter, and tensions quickly arise. When forced to put together a Christmas dance for the local high school, Carter and Maddie find themselves putting their differences aside and rediscover what made them fall in love all those years ago.

Christmas Crush

Twenty-eight-year-old Georgia is convinced the man of her dreams is "the one that got away" back in high school. When Georgia learns of her high school reunion a week before Christmas, she's ecstatic to finally have her chance to win Craig back. But as she gets to relive high school for a night, she begins to realize it might not be Craig at all who got away, but Ben, an old friend with whom she'd fallen out of touch.

Mr. Untouchable

The true-life story of a Harlem's notorious Nicky Barnes, a junkie turned multimillionaire drug-lord. Follow his life story from his rough childhood to the last days of his life.

The Grind

The Grind is a modern urban drama, set in world of sex, drug dealers, dance nightclubs and loan sharks. Vince is the nightclub manager of The Grind in Hackney, East London and having fought his way to a decent living and respectable lifestyle he is determined to settle down and take life easier. Upon meeting and starting a relationship with Nancy, Vinces dream of running a casino for his Boss and getting married looks set. Bobby, Vinces best friend from school, is released from prison and their friendship soon falls apart, Bobbys addiction to cocaine and gambling spirals out of control and he now owes a huge amount of money to Vinces boss, Dave ; owner of The Grind and an East End loan shark. Vince's life takes a dramatic turn for the worse. Loyalties are tested and friendships are pushed to their limits.

Christmas Bounty

A former bounty hunter turns into an elementary schoolteacher. Determined to have a normal life and keep her bounty hunter past a secret, she reluctantly returns home for Christmas to help save the family business by catching the one bounty that got away. But when her fiancé follows her home for the holiday, she struggles to hide her wild family business and a bounty hunter ex-boyfriend she thought she'd left behind.

Campfire Christmas

Romance rekindles for Peyton and her closest friends when her parents decide to host a holiday themed reunion before selling their family owned summer camp.

When Sparks Fly

A big city journalist is sent back to her small hometown to write a Fourth of July story and discovers the life and love she left behind are exactly what she's been missing.

Turkey Drop

Lucy Jacobs, a freshman university student, returns home to her small town for Thanksgiving break and suspects she's about to get turkey dropped— aka dumped by her high school sweetheart. To avoid a Turkey Day travesty, Lucy gets out of her comfort zone, proving she's not the same play-it-safe girl she once was.

Picture a Perfect Christmas

A Los Angeles extreme-sports photographer returns home for the holiday to take care of her grandmother, only to have a neighbor grab her attention as he needs assistance watching his young nephew.

A Christmas Reunion

A Madison Avenue executive, Amy, discovers an unusual Christmas surprise when she inherits her Aunt’s hometown bakery. The real surprise comes when she learns the other half of the bakery was left to her long-ago boyfriend, Jack. Unresolved personal issues resurface between them, as the exes return home to co-manage the store, along with its traditional holiday cookie bake-off.

A Golden Christmas 3

Heather is a charming free spirit whose self-absorbed fiancé Roger never seems to hear a word that comes out of her mouth. Bobby is a naval officer who comes home from serving overseas, looking to start a new chapter in his life. Both Heather and Bobby long to meet someone who makes them feel like they are at home in this world, but they are starting to doubt that person exists. Thanks to two Golden Retrievers, Bobby's spirited eleven-year-old niece Myra, and a fun-filled theatre production of 'A Christmas Carol,' these two unlucky and unlikely people end up falling in love at Christmas. But can they overcome the issues of their past and present in order to build a future together?

Merry Matrimony

Brie Traverston is up for partner at her firm if she can successfully coordinate a Christmas wedding reshoot and ignore all the feelings that come with working with the one-that-got-away Eddie Chapman and his possibly new girlfriend Isabella.

High Flyers

Two men running a carnival airplane ride are hired to fly to retrieve what they think are photos for a reporter. Actually, they are retrieving diamonds stolen from a noted gem dealer. As it turns out, their plane crashes on the very estate of the dealer. Thinking the duo are police officers, the dealer offers his home for their convalescence from the accident. Meanwhile, the diamonds have been snatched by a kleptomaniac dog and buried on the estate. When the smugglers track down the pair, they try to convince the dealer that they are officials from an institution from which the two have escaped. Before long, the carnival fellows, the crooks, the gem dealer and his family, along with a platoon of cops, are tearing up the grounds to find where the dog has buried the diamonds.

Sunlight Jr.

Quickie-mart employee Melissa and paraplegic Richie are very much in love. Supported only by Melissa’s small hourly wage, they are nevertheless thrilled to learn that Melissa is pregnant. Then their situation deteriorates, and their tenuous financial situation threatens to bring their happy life crashing down.

The Bridge Part 2

The second-half of the movie picks up in the present day, seven years later, with Ryan returning home from being on the road touring as a professional singer and Molly working at her father's corporation.

Christmas on Honeysuckle Lane

Emma Reynolds returns to Oliver's Well to celebrate Christmas for the last time with her siblings in the home they grew up in. After their parents recently passed, the siblings reluctantly agree to sell the family home on Honeysuckle Lane after the New Year, leaving Emma in charge of its belongings. While antiques expert Morgan Shelby appraises Emma's mother's collection, they find a hidden surprise in an antique desk that takes them on a journey to discover the power of love and family during the holidays.

The Wrong High School Sweetheart

When Danielle reunites with her high school boyfriend, she is shocked to learn how far he's willing to go to keep everything alive.

Bobby G. Can't Swim

Bobby G. lives life on the edge in this real, raw New York street drama. Bobby is a small-time coke dealer, always on the hustle but rarely successful. He lives in Hell's Kitchen with his Puerto Rican girlfriend Lucy, who makes ends meet as a prostitute. A typical day finds Bobby selling $20 bags to neighborhood locals and passing cars. A yuppie kid looking to score a kilo of coke approaches him to broker a deal and Bobby sees the opportunity of a lifetime to make some real money. His rough days may just be over. With the tidy profit he could even leave the business. Playing out of his league, Bobby arranges to get the kilo from Astro, a fearsome, high-level drug dealer. Though Lucy announces that she's decided to go back to Puerto Rico and pleads with him to make a fresh start too, Bobby is sticking to his deal and isn't going anywhere now, convinced he'll be 'livin' large in a matter a' days...

A Cheerful Christmas

Lauren and her best friend Colleen think they have landed their dream job – giving people the best and most magical Christmas ever as their personal ‘Christmas Coaches.’ This holiday season promises to be their biggest ever when they land a royal client, the Anderson family, who has moved from England. When Lauren meets James, the eldest son, he wants nothing to do with planning Christmas as he’s busy negotiating a big acquisition for his father’s company. But Lauren won’t be thwarted in helping this royal family embrace the true spirit of Christmas. The more she prods James about their family holiday traditions the more he opens up. Sparks start to fly but she faces competition in the form of an old childhood friend and business colleague of James. Now Lauren must win his heart while giving the Andersons their best Christmas ever.

Christmas Is You

Emma Bloom is given an ultimatum by her boss Rachel at Old Town Records: go home for the holidays and convince former boyfriend and national recording star, Tyler Thorn, to sign with Rachel’s label or find another job.

Holiday Hearts

While planning an annual Christmas party, Peyton is forced together with Ben to care for a friend's daughter. While finding their Christmas spirit, will there be some romance along the way?

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