Best movies like 1999

A unique, carefully handpicked, selection of the best movies like 1999 Starring Dan Futterman, Allyson Downey, Jennifer Garner, Matt McGrath, and more. If you liked 1999 then you may also like: 200 Cigarettes, Watch It, Welcome to L.A., What Love Is, Wives and Lovers 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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On New Year's Eve 1999, as a group of neurotic characters gather at a Greenwich Village apartment, everyone struggles to come to terms with their identities, relationships, and self-doubts before the millennium turns.

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200 Cigarettes

In 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.

6.0 / 10 1993 Comedy
suggested by: pureheart

Watch It

Mike, Danny, and Rick are grown men who share a house in Chicago. They take on a fourth house mate, John, who is Mike's estranged first cousin. John's welcome to the house is crowned by his introduction to a game of perpetual pranks called "Watch it!" When not playing pranks on each other, the three men spend their time womanizing, avoiding commitment, treating women badly, and talking about women in the coarsest terms. John, somewhat of a drifter with a fear of commitment, is nonetheless a man apart from this trio of feckless cowards. He takes a shine to Anne, recently jilted by his cousin Mike. Meanwhile, Rick is doing his best to ruin a promising relationship with the fetching and sincere Ellen. How Annie, Ellen, Rick, Mike, and John sort out (or fail to sort out) their social lives becomes the focus of the movie.

Welcome to L.A.

The lives of a group of Hollywood neurotics intersect over the Christmas holidays. Foremost among them, a songwriter visits Los Angeles to work on a singer's album. The gig, unbeknownst to him, is being bankrolled by his estranged father, a dairy magnate, who hopes to reunite with his son. When the songwriter meets an eccentric housewife who fancies herself a modern-day Garbo, his world of illusions comes crashing down.

What Love Is

It's Valentine's Day and Tom has big plans. He's about to get engaged and has a surprise party planned to share the good news with friends. But things take a turn for the worse. Tom returns home only to discover his girlfriend has packed up and left him. Now, instead of a surprise party, the surprise is on Tom. Fortunately, his friends are there to help him make sense of it all.

Wives and Lovers

Husband and wife Bill and Bertie Austin and their daughter live in a low-rent apartment. He's a struggling writer, at least until agent Lucinda Ford breaks the news that she's sold his book to a publisher, including the rights to turn it into a Broadway play. A new house in Connecticut is the first way to celebrate. But during the long hours Bill is away working on the play, Bertie befriends hard-drinking neighbor Fran Cabrell and her boyfriend Wylie, who plant seeds of suspicion in Bertie's mind that Bill and his beautiful agent might be more than just business partners. Bertie jealously retaliates by flirting with Gar Aldrich, an actor who will be in her husband's play. Bill goes to Connecticut for a heart-to-heart talk, finds Gar there and punches him.

Next Stop, Greenwich Village

An aspiring Jewish actor moves out of his parents' Brooklyn apartment to seek his fortune in the bohemian life of Greenwich Village in 1953.

Queens Logic

When childhood friends Al, Dennis and Eliot get together for Ray's wedding, which may or may not happen, they end up on a roller-coaster ride through reality. During one tumultuous, crazy weekend, they face adulthood and each other with new found maturity and discover what Queens Logic is all about. This comedy takes a look at friendship, loyalty, and love.

Kiss Me, Guido

When he discovers his girlfriend having sex with his brother, Frankie decides to head to Manhattan, leaving his Bronx pizza shop forever for the fame and fortune of show business. But before stardom, he needs a place to stay. Looking in the personals, he notices GWM. And thinking it "Guy with Money," he heads to the Village and the apartment of gay actor Warren, who's in desperate need of this month's rent.

Breaking Up

An aloof, struggling food photographer thinks he has found true love with a fiery grade-school teacher. At first, the relationship is all wine and roses, but as they realize they have little in common besides great sex, the romance wanes, and they struggle through a succession of break-ups and reunions as they try to work things out.

6.9 / 10 2002 Comedy Drama
suggested by: user332avuk6818

Chance

'Chance' is a black comedy about how hard it is to find "the one". Mostly told from the point-of-view of a young, sexually aggressive woman, named Chance, whom according to her: "we're all out there looking for true love", which turns out to be a very elusive thing indeed, and Chance is no exception. She's desperately on the prowl for a man, but since she's more mouse than cat, she gets herself into scrape after scrape in her screwball pursuit of love. Surrounded by a bevy of adoring but completely wrong-for-her men (and one dead girl from Manchester, England), Chance has to pick her way through her messy life in order to figure out which guy is "it".

Denial

Couples split up after a comment at an LA dinner party sets up arguments about how truthful partners are in their relationships.

4.7 / 10 2006 Comedy
suggested by: user93aupqchh7

Fifty Pills

Unless Darren can survive New York's largest drug mogul, write a paper on Dante's "Inferno," escape three thugs chasing the wrong guy and sell fifty pills of ecstasy to make his tuition payment, he'll never date the girl of his dreams.

Slaves to the Underground

The grunge girl band "No Exits" is just about to get a record deal. At this time Jimmy is appearing again, the former boy-friend of the band guitarist Shelly. She had left him because his friend had raped her. But he doesn't know that - up to now. Shelly has fallen in love with the band singer Suzy in the meantime. But she still loves Jimmy, too. So she moves to him again, what Suzy doesn't like that all. Especially because she is becoming a feminist.

4.3 / 10 2003 Comedy Drama
suggested by: user6745yfqn5h7

Winter Break

Viscerally experience a "year off" in Aspen, Colorado with a group of recent college grads who have elected to defer graduate school and career opportunities to ski, snow-board, climb, party, fall in love and basically live life to its absolute fullest out in this spectacular mountain town.

Is It Just Me?

A socially shunned columnist finds his romantic match online, but messaging under the wrong account causes his sleazy roommate’s picture to be forwarded, creating an identity mix-up.

Lovelife

Lovelife is a 1997 romantic comedy film written and directed by Jon Harmon Feldman. The ensemble cast includes Matt Letscher, Sherilyn Fenn, Saffron Burrows, Carla Gugino, Bruce Davison, Jon Tenney and Peter Krause. Lovelife was nominated for a Feature Film Award at the 1997 Austin Film Festival, and won an Audience Award at the Los Angeles Independent Film Festival. The film was winner of the screenplay award at the L.A. Indie fest.

Mama's Boy

A twenty-nine year-old slacker who lives with his mom realizes his sweet set-up is threatened when she hears wedding bells with her self-help guru beau.

Motherhood

In Manhattan, a mother of two preparing for her daughter's sixth birthday party has no idea of the challenges she's about to face in order to pull off the event.

30 Years to Life

First of all, the title does not refer to someone sentenced to jail. It is a movie about 6 lifetime friends who are all hitting the big `3-0' together during the same year. Each one looks inside themselves to see where has my life gone and what am I going to do with my future. Actually, what I saw was a black Seinfeld comedy. Tracy Morgan, who is one of the main characters, is a struggling comedian just like Jerry Seinfeld. He gives his opinion of what women want in a man in one of his comedy routines. Melissa De Sousa is looking for a man before time runs out. She is just like Elaine in Seinfeld. I don't remember the big problem with turning thirty, however, all the characters in this movie can show you what they are, such as not having fame, riches, a husband, a thin body, and staying young. Their life stories are probably repeated many times around the world.

The Sex Monster

A neurotic L.A. building contractor (Mike Binder in his best Woody Allen imitation) pushes his wife (Mariel Hemingway) into entering into a three way sexual relationship. Unfortunately for him, his wife gets more out of it than he does and becomes a tigress seducing every female she meets including the contractor's secretary.

Sleep with Me

Six different writers wrote a scene each of this romantic comedy featuring the marriage and turbulent relationship of Joseph and Sarah, with Joseph's best friend Frank trying hard to cope with letting the love of his life marry his best friend.

Two for the Seesaw

Jerry Ryan wanders aimlessly around New York after giving up his Nebraskan law practice. His wife asks for a divorce. He meets Gittel, a struggling dancer from Greenwich Village and they try to sort out their lives. An extended conversation piece with a static camera, but reflects the moral climate of the time.

The Lather Effect

On the eve of selling her mother's house, a thirty-something housewife wakes up to a hangover surrounded by her best friends from high school...

Amy's Orgasm

Amy is a single 29 year old Jewish woman. She wrote a successful self-help book about how women can't truly be in love and experience "mental orgasm." Her parents and acquaintances always try to give her advice. Eventually, she breaks her celibacy and starts dating a radio shock jock, who is known for hitting on his bimbo guests. Of all men, will she find in him the true love she never believed in

Hairshirt

A self-obsessed man runs through one woman after another in this screwball comedy. One of his rejected former lovers decides to take it upon herself to see to it that he never develops another relationship.

Perfect Opposites

The story of two college graduates from the Midwest who move to Los Angeles, where their love is tested for the first time.

Because Why

After five years of travelling abroad, Alex arrives back in Montreal. All he has with him are a back-pack and a slip of paper with an ex-girlfriend's address scrawled on it.

29th and Gay

Following a year in the life of James Sanchez, it's a story about a guy rapidly approaching thirty, who doesn't have a six-pack, full head of hair or a boyfriend. While his best friend Roxy, an actress-turned-activist, struggles with showing him there's life beyond the glitz of the disco ball, his other friend, Brandon, one of those gay boys comfortable in his own gay skin, works on getting James to at least talk to a boy. Feeling out of place in the world of circuit boys, caught between his Hispanic-American heritage and being gay, we watch James find his place in the world, realizing that life is in the journey, not the destination.

Sheila Levine is Dead and Living in New York

Sheila Levine - an innovative, bright, but painfully introverted individual - arrives in New York City to take an apartment with a partygoing roommate. There, she experiences love and heartache in equal measure.

The Four-Faced Liar

A story of love and lies for four twenty-somethings looking to find themselves in New York City. A pair of best friends and a seemingly perfect couple meet at a local Irish pub tucked in the winding streets of the West Village. Through their chance meeting, the four bond and over time all of their relationships with one another morph into love, betrayal and heartbreak for all.

Puccini for Beginners

When her inability to commit leads to a breakup with her girlfriend, opera-loving writer Allegra winds up in the bed of amiable professor Philip. He is so smitten with Allegra that he dumps his lover, Grace, and convinces Allegra to continue their affair. When Allegra meets Grace, sparks fly, and she begins a parallel romance, unaware that her new lover is the woman Philip left to be with her.

Fish Without a Bicycle

Julianna is a struggling actress in a dead end relationship with Danny, a fireman who no longer lights her fire. When she decides to leave him and go "find herself" she ends up falling in love with an egotistical director, Michael, who can barely fit her in between Pilates classes.

The Perfect You

A waiter/writer living with his dad and a neat freak who's just landed a job as a reporter in New York, meet by colliding on the Brooklyn Bridge, and romance ensues.

Finding Me

Faybien Allan has it all going on; he's young, stylish, and knows the importance of being seen with hip friends at NYC's trendiest spots. But beneath the sparkle of his nightlife and his stunning good-looks, is a man buckling under his father's homophobia. Filled with self-loathing and desperate for direction, he meanders through life until meeting Lonnie, a confident activist with a flirtatious smile. However, despite their obvious chemistry and fireworks in bed, Faybien's insecurities have him looking for the door. Can a budding romance and a few good friends keep him from making the biggest mistake of his life?

The Happy Sad

Two young couples in New York-one black and gay, one white and heterosexual-find their lives intertwined as they create new relationship norms, explore sexual identity, and redefine monogamy.

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