Movies Like Harold and Maude (1971)

Watch these movies if you like Harold and Maude (1971).

28 items, 920 votes
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Benny & Joon (1993)

Starring: Johnny Depp, Mary Stuart Masterson, Aidan Quinn, Julianne Moore
Duration: 1h 38mins
Genres: Comedy, Drama, Romance

Benjamin "Benny" Pearl and his mentally ill sister Juniper "Joon" Pearl live together following the accidental death of their parents.
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Wilbur Wants to Kill Himself (2002)

Starring: Jamie Sives, Adrian Rawlins, Shirley Henderson, Lisa McKinlay
Duration: 1h 49mins
Genres: Comedy, Drama, Romance

When Wilbur leaves the hospital after having tried once more to kill himself, the staff ask his brother Harbour to let Wilbur move in with him.
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About a Boy (2002)

Starring: Hugh Grant, Nicholas Hoult, Toni Collette, Sharon Small
Duration: 1h 41mins
Genres: Comedy, Drama, Romance

Will Freeman lives a serene and luxurious lifestyle devoid of responsibility in London thanks to substantial royalties left to him from a successful Christmas song composed by his father.
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Prime (2005)

Starring: Uma Thurman, Meryl Streep, Bryan Greenberg, Jon Abrahams
Duration: 1h 45mins
Genres: Comedy, Drama, Romance

Rafi is a recently divorced, 37-year-old career woman from Manhattan who becomes romantically involved with David, a talented 23-year-old painter from the Upper West Side.
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Trust (1990)

Starring: Adrienne Shelly, Martin Donovan, Rebecca Nelson, John MacKay
Duration: 1h 47mins
Genres: Comedy, Drama

Trust concerns the unusual romance between two young misfits wandering the same Long Island town.
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My First Mister (2001)

Starring: Albert Brooks, Leelee Sobieski, Rutanya Alda, Natasha Braisewell
Duration: 1h 49mins
Genres: Comedy, Drama, Romance

In an effort to secure employment at the upscale Century City Mall in Los Angeles, Jennifer (Sobieski), a 17-year-old "goth-punk" girl who just graduated from high school, makes a nuisance of herself at a clothing store run by 49-year-old Randall Harris (Brooks), who eventually hires her on a trial basis as a stockroom clerk.
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Rushmore (1998)

Starring: Jason Schwartzman, Bill Murray, Olivia Williams, Seymour Cassel
Duration: 1h 33mins
Genres: Comedy, Drama, Romance

Rushmore is a 1998 American coming-of-age comedy-drama film directed by Wes Anderson about an eccentric teenager named Max Fischer (Jason Schwartzman in his film debut), his friendship with rich industrialist Herman Blume (Bill Murray), and their love in common for elementary school teacher Rosemary Cross (Olivia Williams).
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How Stella Got Her Groove Back (1998)

Starring: Angela Bassett, Taye Diggs, Whoopi Goldberg, Regina King
Duration: 2h 4mins
Genres: Comedy, Drama, Romance

Stella Payne is a very successful 40-year-old stockbroker raising her son, Quincy, and living in Marin County, California, who is persuaded by her best friend from college, Delilah Abraham, to take a well-deserved, first-class vacation to Montego Bay, Jamaica.
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It's Kind of a Funny Story (2010)

Starring: Keir Gilchrist, Zach Galifianakis, Emma Roberts, Dana DeVestern
Duration: 1h 41mins
Genres: Comedy, Drama, Romance

After contemplating suicide by jumping off the Brooklyn Bridge, 15-year-old Craig Gilner decides to go to the hospital to seek help. Craig tells Dr.
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Gigantic (2008)

Starring: Paul Dano, Zooey Deschanel, John Goodman, Edward Asner
Duration: 1h 38mins
Genres: Comedy, Drama, Romance

see also List of unproduced Disney animated shorts and feature films#2017 Gigantic is a 2008 independent comedy film directed by Matt Aselton and starring Paul Dano, Zooey Deschanel, John Goodman, Edward Asner and Jane Alexander.
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Liberal Arts (2012)

Starring: Josh Radnor, Elizabeth Olsen, Zac Efron, Elizabeth Reaser
Duration: 1h 37mins
Genres: Comedy, Drama, Romance

Thirty-five year old Jesse Fisher, an admissions officer at a New York City post-secondary institution he who loves English and literature, has somewhat lost his passion in life, which includes recently being unceremoniously dumped by his latest girlfriend, who could no longer be the person to prop him up emotionally.
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Tadpole (2002)

Starring: Sigourney Weaver, Aaron Stanford, Kate Mara, Robert Iler
Duration: 1h 18mins
Genres: Comedy, Drama, Romance

Oscar Grubman (Aaron Stanford) is a 15-year-old boy, portrayed as mature beyond his years, traveling home from school for Thanksgiving.
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A Night in the Life of Jimmy Reardon (1988)

Starring: River Phoenix, Ann Magnuson, Meredith Salenger, Ione Skye
Duration: 1h 30mins
Genres: Comedy, Drama, Romance

A Night in the Life of Jimmy Reardon, also known as Aren't You Even Gonna Kiss Me Goodbye?, is a 1988 American coming of age drama film written and directed by William Richert and starring River Phoenix, Ann Magnuson, Meredith Salenger, Matthew Perry, Ione Skye, and Louanne.
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Minnie and Moskowitz (1971)

Starring: Gena Rowlands, Seymour Cassel, Val Avery, Timothy Carey
Duration: 1h 54mins
Genres: Comedy, Drama, Romance

Following a break-up, Minnie Moore, a museum curator, becomes disillusioned by love and meaningful relationships.
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Cannery Row (1982)

Starring: Nick Nolte, Debra Winger, Audra Lindley, Frank McRae
Duration: 2h 0mins
Genres: Comedy, Drama, Romance

The story is about the skid row denizens of Monterey, California, during World War II.
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The Wackness (2008)

Starring: Josh Peck, Ben Kingsley, Olivia Thirlby, Famke Janssen
Duration: 1h 39mins
Genres: Comedy, Drama, Romance

In the summer of 1994 in New York City, Luke Shapiro (Peck) is trading marijuana in exchange for therapy from his psychiatrist, Dr. Jeffery Squires (Kingsley).
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Garden State (2004)

Starring: Zach Braff, Peter Sarsgaard, Natalie Portman, Ian Holm
Duration: 1h 42mins
Genres: Comedy, Drama, Romance

Struggling actor Andrew Largeman wakes up from a dream—in which he apathetically sits on a crashing plane—to a telephone message from his father, telling Andrew that he needs to return home because his mother has died.
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The Other Sister (1999)

Starring: Juliette Lewis, Diane Keaton, Giovanni Ribisi, Tom Skerritt
Duration: 2h 9mins
Genres: Comedy, Drama, Romance

After receiving a well-earned certification from a sheltered boarding school, Carla Tate (Juliette Lewis), an ambitious and mildly mentally disabled young woman, returns home to her overprotective and slightly snobby mother Elizabeth (Diane Keaton).
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How to Make an American Quilt (1995)

Starring: Winona Ryder, Ellen Burstyn, Anne Bancroft, Kaelynn Craddick
Duration: 1h 57mins
Genres: Comedy, Drama, Romance

How to Make an American Quilt is a 1995 American drama film based on the 1991 novel of the same name by Whitney Otto.
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New York Stories (1989)

Starring: Woody Allen, Nick Nolte, Rosanna Arquette, Marvin Chatinover
Duration: 2h 4mins
Genres: Comedy, Drama, Romance

A middle-aged artist obsessed with his pretty young assistant, a precocious 12 year old living in a hotel, and a neurotic lawyer with a possessive mother make up three Gotham tales.
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