Best movies like 1999
Last updated March 2024
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Plot Summary:
The century is coming to an end, and New York City is freaking out. "1999" takes place at a New Year's Eve party on December 31, 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. The partygoers are astonished and reawakened as passions flare and ignite, gunshots are fired, battling lovers reunite, and as the new century dawns, all are joined in the curious sense that the best is yet to come.
IMDB Rating: 4.7
IMDB Votes: 319
Genere: Comedy, Drama
Country: USA
Duration: 92 min
Plot tags: neurotic, independent film, humorous, realistic, semi serious, sexual, sexy
Best tv shows and movies like 1999 (1997):
Similar in 83%
The Photographer (2000)
Plot Summary:
A year after becoming the toast of New York City's art scene, photographer Max Martin has lost his ability to take a decent picture. On the night before his make-or-break gallery opening, surrounded by the trappings of success but devoid of inspiration, Max embarks on a bizarre trek through the city in search of ten mysterious photographs that could save his career. Shot in brilliant color and dramatic black and white, first-time director Jeremy Stein's industrial New York City is a wonderland, roamed by witches and magical creatures, where survival hinges on the completion of a simple quest. Accompanied by an unlikely crew of strangers he meets along the way, Max trips through a modern-day Oz and rediscovers the easily forgotten value of seeing magic reflected in everyday life.
IMDB Rating: 4.9
IMDB Votes: 355
Genere: Comedy, Drama
Country: USA
Duration: 91 min
Plot tags: humorous, realistic, witty, semi serious, offbeat
Similar in 86%
Advice from a Caterpillar (1999)
Plot Summary:
When it comes to romance, Missy's attitude has always been whatever. After all, her artistic career is flourishing...her spacious New York City loft is fabulous...and her relationship with a married man is totally uncomplicated-what more could a modern girl want? But then Missy meets Brat, who's sweet, genuine and shares her fondness for 70's sitcoms. Unfortunately, he's also dating her pal Spaz. When Missy and Brat unexpectedly fall for each other, will she lose her identity...and her best friend? No matter how far you run, true love always finds you.
IMDB Rating: 5.3
IMDB Votes: 403
Genere: Comedy, Drama, Romance
Country: USA
Duration: 90 min
Plot tags: sexy, independent film, touching, humorous, realistic, semi serious, sexual, lgbt cinema, gay cinema
Similar in 84%
Hollywood Palms (2001)
Plot Summary:
Set entirely in the Hollywood Palms apartment building and its yard, this movie shows how people there live and interact with each other.
IMDB Rating: 5.4
IMDB Votes: 174
Genere: Comedy
Country: USA
Duration: 86 min
Plot tags: humorous, witty, semi serious, realistic, biting, suspense
Similar in 78%
Watch It (1993)
Plot Summary:
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.
IMDB Rating: 6.2
IMDB Votes: 638
Genere: Comedy
Country: USA
Duration: 102 min
Plot tags: independent film, humorous, realistic, witty, semi serious
Similar in 86%
Fish Without a Bicycle (2003)
Plot Summary:
Comedy - Julianna (Jenna Mattison) is a struggling actress in a dead end relationship with Danny (Brad Rowe), 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 (Bryan Callen), who can barely fit her in between Pilates classes.
IMDB Rating: 4.3
IMDB Votes: 256
Genere: Comedy, Drama, Romance
Country: USA
Duration: 97 min
Plot tags: humorous, captivating, light, emotional, clever, realistic, witty, talky, semi serious, sexual
Similar in 90%
200 Cigarettes (1999)
Plot Summary:
A collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses.
IMDB Rating: 5.9
IMDB Votes: 16000
Genere: Comedy, Drama, Romance
Country: USA
Duration: 101 min
Plot tags: talky, witty, melancholic, feel good, semi serious, humorous, funny, entertaining, offbeat, realistic
Similar in 88%
Mama's Boy (2007)
Plot Summary:
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.
IMDB Rating: 5.1
IMDB Votes: 6000
Genere: Comedy, Drama
Country: USA
Duration: 93 min
Plot tags: humorous, semi serious, realistic, light
Similar in 90%
Jack & Jill (1999)
Plot Summary:
A lighthearted romantic comedy about post-collegiate life, love and career in New York City.
IMDB Rating: 7.2
IMDB Votes: 2000
Genere: Comedy, Drama
Country: USA
Duration: 60 min
Plot tags: touching, humorous, realistic, semi serious, sitcom, talky, sexual
Similar in 85%
Queens Logic (1991)
Plot Summary:
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.
IMDB Rating: 5.8
IMDB Votes: 2000
Genere: Comedy, Drama
Country: USA
Duration: 100 min
Plot tags: sentimental, clever, humorous, realistic, talky, semi serious, independent film, philosophical, sexy, thought provoking
Similar in 85%
Chance (2002)
Plot Summary:
'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".
IMDB Rating: 6.8
IMDB Votes: 1000
Genere: Comedy, Drama
Country: USA
Duration: 75 min
Plot tags: touching, humorous, realistic, semi serious, independent film, non-linear
Similar in 90%
Lily & Kat (2015)
Plot Summary:
Set in New York City, the film follows a naive fashion school graduate named Lily who finds her world turned upside down when her reckless best friend Kat announces she’s moving away to London in a matter of days. At a Lower East Side art opening the next night, they meet the enigmatic rising artist Henri, who Lily quickly takes a liking for. With less than seven days left and a new attractor between them, Lily and Kat will find their “unbreakable” friendship put to the test.
IMDB Rating: 4.7
IMDB Votes: 656
Genere: Comedy, Drama
Country: USA
Duration: 89 min
Plot tags: realistic, semi serious, light, feel good, independent film
Similar in 76%
City Baby (2013)
Plot Summary:
Sexy. Style-conscious. Extreme love affairs. Complicated friendships. Life happens all too quickly when Cloey is reluctantly plucked from her comfort zone and complete reliance on others is overturned – a secure relationship with her boyfriend unravels, her childhood best friend is moving away and daddy’s (Daniel Baldwin) checkbook closes. City Baby comments on the ladder-climbing mentality of always reaching for the next bigger, better thing – relationship, city, job – when sometimes what's right in front of us is just fine. Scattered with cameos from Portland musicians like Stephen Malkmus of Pavement, live musical performances by Glass Candy and Starfucker, and a thoughtful soundtrack featuring all Portland bands and musicians, City Baby depicts a playground for semi-adults, revolving through the lives of cool kids.
IMDB Rating: 4.7
IMDB Votes: 225
Genere: Comedy, Drama
Country: USA
Duration: 88 min
Plot tags: humorous, realistic, captivating, psychological, sexy, independent film, sincere, semi serious, sexual
Similar in 90%
Quarter Life Crisis (2006)
Plot Summary:
A Hindu, and a believer in Astrology, Neil Desai is a second-generation East Indian-American, who is 27 years of age, works for an ad company, and has been in a relationship for over 6 years with Angel Matthews, and lives with her in a small apartment in New York. Before that could happen, misunderstandings crop up, and Neil moves out. He gets a ride from Limo driver, Dilip Kumar, who tells him that since he is his 100th customer, he will get a week of free rides. Neil and his friends decide to take good use of Dilip's offer, and Neil, desperate to get into another relationship, dates a wide assortment of girls, and takes them to a variety of destinations in the limo. A week later, he still misses Angel, and returns to her, little knowing that Dilip is a the producer of a TV serial 'Love In The Backseat' and has a hidden camera that has been recording Neil, his interactions with various women, and is all set to telecast this on TV.
IMDB Rating: 3.6
IMDB Votes: 275
Genere: Comedy, Drama, Romance
Country: USA
Duration: 90 min
Plot tags: semi serious, humorous, realistic
Similar in 90%
Dish Dogs (2000)
Plot Summary:
Two friends travel from town to town taking jobs as dishwashers until they both find love and must choose separate paths.
IMDB Rating: 4.6
IMDB Votes: 730
Genere: Comedy, Drama, Romance
Country: USA
Duration: 97 min
Plot tags: humorous, semi serious, captivating, entertaining, sex comedy, realistic, talky, independent film, hot
Similar in 76%
Highball (1997)
Plot Summary:
A newly-married couple tries to build their social life.
IMDB Rating: 5.6
IMDB Votes: 915
Genere: Comedy, Drama
Country: USA
Duration: 110 min
Plot tags: independent film, clever, humorous, realistic, witty, talky, cynical, semi serious
Similar in 83%
The Private Public (2001)
Plot Summary:
Two college seniors on the cusp of graduation meet after being mistakenly thrown in jail after a bar fight. They team up to make a documentary short that exposes a famous professor as a sexual offender, and their lives are soon thrown into turmoil.
IMDB Rating: 4.2
IMDB Votes: 78
Genere: Comedy, Drama
Country: USA
Duration: 90 min
Plot tags: sexy, serious, realistic, suspenseful, independent film, sexual
Similar in 80%
Mona (2008)
Plot Summary:
Two 35 year old men going backwards in life meet a vibrant 23 year woman, bounding unselfconsciously forward.
IMDB Rating: 4.3
IMDB Votes: 139
Genere: Comedy, Romance
Country: USA
Duration: 87 min
Plot tags: humorous, semi serious, captivating, emotional, independent film, touching, realistic
Similar in 83%
Should've Put a Ring On It (2011)
Plot Summary:
Robin Givens, Miguel Nunez, and Bobby Valentino star in this faith-based romantic drama about Thea Johnson, terribly desperate to be married to her longtime boyfriend Jamar. When he takes too long to propose, she decides to propose to him instead. Thea creates an elaborate proposal, but is thwarted by his reluctance. An obsessed ex-boyfriend, married & single friends, and Thea s father & pastor all take part in the tug of war for her heart.
IMDB Rating: 3.6
IMDB Votes: 92
Genere: Comedy
Country: USA
Duration: 82 min
Plot tags: humorous, realistic, semi serious, sexy, independent film, sexual
Similar in 75%
The Lather Effect (2006)
Plot Summary:
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.
IMDB Rating: 5.9
IMDB Votes: 712
Genere: Comedy, Drama
Country: USA
Duration: 95 min
Plot tags: humorous, talky, semi serious, realistic
Similar in 87%
LOL (2006)
Plot Summary:
The relationships of three men are examined through their use of technology.
IMDB Rating: 4.7
IMDB Votes: 910
Genere: Comedy, Drama
Country: USA
Duration: 81 min
Plot tags: mumblecore, sincere, humorous, talky, clever, touching, offbeat, realistic, witty, semi serious
Similar in 80%
2 B Perfectly Honest (2004)
Plot Summary:
Business partners Frank and Josh go bankrupt after their dot-com start-up collapses before it goes online. Frank, a bachelor and broke, reluctantly moves back home to live with his parents while Josh, a hippie computer wiz who's married and has a son, is forced to consider the unthinkable - getting a real job.
IMDB Rating: 4.5
IMDB Votes: 271
Genere: Comedy, Drama
Country: USA
Duration: 88 min
Plot tags: clever, humorous, realistic, semi serious
Similar in 83%
Mind the Gap (2004)
Plot Summary:
Five seemingly unrelated people decide to take huge risks in their personal lives in an effort to find happiness.
IMDB Rating: 7.0
IMDB Votes: 997
Genere: Comedy, Drama
Country: USA
Duration: 134 min
Plot tags: humorous, talky, semi serious, captivating, sincere, sentimental, clever, touching, offbeat, realistic
Similar in 88%
Just a Kiss (2002)
Plot Summary:
A group of thirtysomethings having problems with fidelity gets an opportunity to turn back the clock.
IMDB Rating: 4.9
IMDB Votes: 2000
Genere: Comedy, Drama, Romance
Country: USA
Duration: 89 min
Plot tags: humorous, realistic, semi serious, clever, offbeat, talky, independent film
Similar in 88%
30 Years to Life (2001)
Plot Summary:
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.
IMDB Rating: 5.9
IMDB Votes: 292
Genere: Comedy, Drama, Romance
Country: USA
Duration: 110 min
Plot tags: sincere, touching, humorous, witty, psychological, romantic, captivating, clever, offbeat, realistic
Similar in 76%
The Last International Playboy (2008)
Plot Summary:
When playboy and one-hit-wonder novelist Jack Frost (Jason Behr) learns that his childhood sweetheart is getting married, he tries to drown his sorrows by dramatically escalating his self-destructive drinking and womanizing. Frost's pals try to coax him back from the brink, but only a precocious youngster (India Ennenga) in his apartment building finds a way around his defenses. Monet Mazur co-stars in this drama from director Steve Clark.
IMDB Rating: 5.6
IMDB Votes: 599
Genere: Comedy, Drama, Romance
Country: USA, South Africa
Duration: 92 min
Plot tags: humorous, realistic, semi serious, sexy, sex comedy
Similar in 90%
Lovelife (1997)
Plot Summary:
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.
IMDB Rating: 5.6
IMDB Votes: 481
Genere: Comedy, Drama
Country: USA
Duration: 96 min
Plot tags: sex comedy, independent film, sentimental, clever, touching, humorous, realistic, witty, talky, semi serious
Similar in 84%
Seven Days of Grace (2006)
Plot Summary:
Four women - a blonde, a hippie, a lesbian and a barmaid - are looking for love, money and success. When one inherits an Italian restaurant from her father, they see this as a chance to fulfil their dreams. Then the restaurant is in danger of closing down - and the girls pull out all the stops to save it.
IMDB Rating: 3.4
IMDB Votes: 125
Genere: Comedy, Drama
Country: USA
Duration: 88 min
Plot tags: semi serious, humorous, realistic, light, feel good, offbeat, independent film
Similar in 81%
Watching TV with the Red Chinese (2012)
Plot Summary:
In New York City in 1980, Dexter Mitchell plays half-willing big brother to his neighbors, a trio of exchange students from the People's Republic of China.
IMDB Rating: 5.8
IMDB Votes: 112
Genere: Comedy, Drama
Country: USA
Duration: 105 min
Plot tags: touching, humorous, realistic, semi serious, offbeat, non-linear, independent film
Similar in 79%
Winter Break (2003)
Plot Summary:
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.
IMDB Rating: 5.0
IMDB Votes: 1000
Genere: Comedy, Drama
Country: USA
Duration: 92 min
Plot tags: humorous, semi serious, realistic, independent film
Similar in 85%
Motherhood (2009)
Plot Summary:
Motherhood is a comedy written and directed by Katherine Dieckmann, and stars Uma Thurman, Anthony Edwards and Minnie Driver. Shot on location in New York’s West Village, focuses on the dilemmas of motherhood, such as marriage, work, and self, shown in the trials and tribulations of one pivotal day.
IMDB Rating: 4.6
IMDB Votes: 5000
Genere: Comedy, Drama
Country: USA
Duration: 90 min
Plot tags: feel good, humorous, realistic, touching, semi serious, independent film, neurotic