Best movies like The Rum Diary

Last updated March 2024

Looking for movies similar to The Rum Diary? Offer your knowledge to steer others to tv series and movies you've viewed previously that they might also like. Promote expanding the assembly of people introducing videos to each other. We appreciate your engagement!

Plot Summary:

Tired of the noise and madness of New York and the crushing conventions of late Eisenhower-era America, itinerant journalist Paul Kemp travels to the pristine island of Puerto Rico to write for a local San Juan newspaper run by the downtrodden editor Lotterman. Adopting the rum-soaked lifestyle of the late ‘50s version of Hemingway’s “The Lost Generation,” Paul soon becomes entangled with a very attractive American woman, Chenaults and her fiancée Sanderson, a businessman involved in shady property development deals.  It is within this world that Kemp ultimately discovers his true voice as a writer and integrity as a man.


IMDB Rating: 6.1

IMDB Votes: 107000

Genere: Comedy, Drama

Country: USA, UK

Duration: 119 min

Plot tags: stylized, sexy, light, surreal, humorous, ironic, cult classic, offbeat, talky, scenic

Best tv shows and movies like The Rum Diary (2011):

Similar in 75%

How to Lose Friends & Alienate People (2008)

Plot Summary:

A British writer struggles to fit in at a high-profile magazine in New York. Based on Toby Young's memoir "How to Lose Friends & Alienate People".


IMDB Rating: 6.4

IMDB Votes: 71000

Genere: Biography, Comedy, Drama, Romance

Country: UK

Duration: 110 min

Plot tags: funny, romantic, light, humorous, intellectual, entertaining, hilarious, feel good, romantic comedy, clever

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The Classic (2001)

Plot Summary:

A self-loving fictional autobiography of author Kari Hotakainen.


IMDB Rating: 6.9

IMDB Votes: 854

Genere: Comedy, Drama

Country: Finland

Duration: 80 min

Plot tags: humorous, semi serious, realistic, captivating

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The Front Page (1974)

Plot Summary:

A journalist suffering from burn-out wants to finally say goodbye to his office – but his boss doesn’t like the idea one bit.


IMDB Rating: 7.3

IMDB Votes: 15000

Genere: Comedy, Drama, Romance

Country: USA

Duration: 105 min

Plot tags: talky, light, humorous, hilarious, witty, captivating, period piece, cult classic, independent film, realistic

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Similar in 87%

Factotum (2005)

Plot Summary:

This drama centers on Hank Chinaski, the fictional alter-ego of "Factotum" author Charles Bukowski, who wanders around Los Angeles, CA trying to live off jobs which don't interfere with his primary interest, which is writing. Along the way, he fends off the distractions offered by women, drinking and gambling.


IMDB Rating: 6.6

IMDB Votes: 15000

Genere: Comedy, Drama, Romance

Country: Norway, USA, Germany, France, Italy

Duration: 94 min

Plot tags: dark comedy, philosophical, humorous, serious, realistic, dark, grim, meditative, sad, tense

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Henry Fool (1997)

Plot Summary:

An egocentric bum transforms the lives of a shy New Jersey garbageman and his sister.


IMDB Rating: 7.1

IMDB Votes: 8000

Genere: Comedy, Drama

Country: USA

Duration: 137 min

Plot tags: independent film, philosophical, cult classic, dark comedy, offbeat, humorous, talky, stylized, allegory, black comedy

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Tamara Drewe (2010)

Plot Summary:

A young newspaper writer returns to her hometown in the English countryside, where her childhood home is being prepped for sale.


IMDB Rating: 6.2

IMDB Votes: 22000

Genere: Comedy, Drama, Romance

Country: UK

Duration: 107 min

Plot tags: sexy, witty, romantic, sentimental, humorous, semi serious, entertaining, feel good, realistic, sex comedy

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Barfly (1987)

Plot Summary:

Downtrodden writer Henry and distressed goddess Wanda aren't exactly husband and wife: they're wedded to their bar stools. But they like each other's company- and Barfly captures their giddy, gin-soaked attempts to make a go of life on the skids.


IMDB Rating: 7.1

IMDB Votes: 22000

Genere: Comedy, Drama, Romance

Country: USA

Duration: 100 min

Plot tags: talky, depressing, melancholic, touching, humorous, semi serious, intellectual, dark, stylized, black comedy

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She's Funny That Way (2014)

Plot Summary:

On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.


IMDB Rating: 6.1

IMDB Votes: 28000

Genere: Comedy, Drama

Country: Germany, USA

Duration: 93 min

Plot tags: light, funny, humorous, stylized, melancholic, surreal, feel good, semi serious, clever, talky

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Postcards from the Edge (1990)

Plot Summary:

Substance-addicted Hollywood actress Suzanne Vale is on the skids. After a spell at a detox centre her film company insists as a condition of continuing to employ her that she live with her mother Doris Mann, herself once a star and now a champion drinker. Such a set-up is bad news for Suzanne who has struggled for years to get out of her mother's shadow, and who finds her mother still treats her like a child. Despite these problems - and further ones to do with the men in in her life - Suzanne can begin to see the funny side of her situation, and it also starts to occur to her that not only do daughters have mothers, mothers do too.


IMDB Rating: 6.7

IMDB Votes: 19000

Genere: Comedy, Drama

Country: USA

Duration: 101 min

Plot tags: touching, humorous, melancholic, sentimental, realistic, clever, witty, talky, funny, dark comedy

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Similar in 79%

Heartburn (1986)

Plot Summary:

Rachel is a food writer at a New York magazine who meets Washington columnist Mark at a wedding and ends up falling in love with him despite her reservations about marriage. They buy a house, have a daughter, and Rachel thinks they are living happily ever after until she discovers that Mark is having an affair while she is waddling around with a second pregnancy.


IMDB Rating: 6.1

IMDB Votes: 12000

Genere: Comedy, Drama

Country: USA

Duration: 108 min

Plot tags: melancholic, lyrical, sentimental, humorous, realistic, semi serious, talky, emotional, sex comedy, cult classic

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Similar in 85%

SubUrbia (1996)

Plot Summary:

A group of suburban teenagers try to support each other through the difficult task of becoming adults.


IMDB Rating: 6.7

IMDB Votes: 10000

Genere: Comedy, Drama

Country: USA

Duration: 121 min

Plot tags: grindhouse, teen, independent film, realistic, talky, cerebral, philosophical, art house, indie film, clever

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Broadcast News (1987)

Plot Summary:

Basket-case network news producer Jane Craig falls for new reporter Tom Grunnick, a pretty boy who represents the trend towards entertainment news she despises. Aaron Altman, a talented but plain correspondent, carries an unrequited torch for Jane. Sparks fly between the three as the network prepares for big changes, and both the news and Jane must decide between style and substance.


IMDB Rating: 7.2

IMDB Votes: 33000

Genere: Comedy, Drama, Romance

Country: USA

Duration: 133 min

Plot tags: realistic, talky, funny, romantic, melancholic, sentimental, semi serious, romantic comedy, clever, witty

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Trainwreck: My Life as an Idiot (2007)

Plot Summary:

A dramatic comedy about a self-induced attention-deficit disordered, learning disabled, Tourette's syndrome suffering, balance impaired, ex-alcoholic young man from the Upper East Side of Manhattan and the gold-digging girl who inspires him to try to get it together.


IMDB Rating: 5.4

IMDB Votes: 3000

Genere: Comedy, Drama

Country: USA

Duration: 94 min

Plot tags: tragicomedy, humorous, semi serious, realistic, funny, independent film, offbeat

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My Favorite Year (1982)

Plot Summary:

Benjy Stone is the junior writer on the top rated variety/comedy show, in the mid 50s (the early years). Alan Swann, an Erol Flynn type actor with a drinking problem is to be that weeks guest star.


IMDB Rating: 7.3

IMDB Votes: 10000

Genere: Comedy, Drama

Country: USA

Duration: 92 min

Plot tags: funny, touching, humorous, witty, parody, sincere, offbeat, sentimental, feel good, realistic

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Mistress (1992)

Plot Summary:

A comedy about a screenwriter (Wuhl) whose old movie script is read by a producer (Landau) and the search for financial backers begins. But it seems that each money source (Aiello, DeNiro, Wallach) has his own mistress that he wants put into the film. Gradually, the screenwriter is forced to make changes to his script to accommodate these backers until he finally sees no semblance of his original ideas in the writing.


IMDB Rating: 5.4

IMDB Votes: 2000

Genere: Comedy, Drama

Country: USA

Duration: 110 min

Plot tags: humorous, cynical, light, captivating, cult classic, exciting, independent film, realistic, witty, talky

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Trees Lounge (1996)

Plot Summary:

Tommy has lost his job, his love and his life. He lives in a small apartment above the Trees Lounge, a bar which he frequents along with a few other regulars without lives. He gets a job driving an ice cream truck and ends up getting involved with the seventeen-year-old niece of his ex-girlfriend. This gets him into serious trouble with her father.


IMDB Rating: 7.1

IMDB Votes: 17000

Genere: Comedy, Drama

Country: USA

Duration: 95 min

Plot tags: independent film, grim, cult classic, talky, art house, dark comedy, intellectual, entertaining, black comedy, indie film

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State and Main (2000)

Plot Summary:

A Hollywood Film unit invades a small Vermont town leading to wholesale abandonment of values and virtue. A smart, warm and funny movie - and not just for movie buffs. Tagline: When a film crew came to Waterford, Vermont - They Shot First And Asked Questions Later.


IMDB Rating: 6.7

IMDB Votes: 22000

Genere: Comedy, Drama

Country: USA

Duration: 105 min

Plot tags: feel good, humorous, talky, funny, melancholic, cynical, stylized, realistic, clever, witty

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Similar in 77%

Where the Buffalo Roam (1980)

Plot Summary:

Semi-biographical film based on the experiences of gonzo journalist Hunter S. Thompson.


IMDB Rating: 6.5

IMDB Votes: 13000

Genere: Biography, Comedy

Country: USA

Duration: 99 min

Plot tags: talky, surreal, road movie, humorous, grindhouse, cult classic, witty, psychedelic, light, captivating

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The Paper (1994)

Plot Summary:

Henry Hackett is the editor of a New York City tabloid. He is a workaholic who loves his job, but the long hours and low pay are leading to discontent. Also, publisher Bernie White faces financial straits, and has hatchetman Alicia Clark, Henry's nemesis, impose unpopular cutbacks.


IMDB Rating: 6.7

IMDB Votes: 15000

Genere: Comedy, Drama

Country: USA

Duration: 112 min

Plot tags: talky, clever, sentimental, humorous, black comedy, sincere, realistic, semi serious, intellectual, feel good

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Celebrity (1998)

Plot Summary:

The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of Manhattan, but as he jumps from one lavish party to another and engages in numerous empty romances, he starts to doubt the worth of his work. Meanwhile, top TV producer Tony falls for Robin and introduces her to the world of celebrity.


IMDB Rating: 6.3

IMDB Votes: 28000

Genere: Comedy, Drama

Country: USA

Duration: 113 min

Plot tags: black and white, stylized, satirical, humorous, realistic, semi serious, independent film, clever, art house, motivational

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Adaptation. (2002)

Plot Summary:

A love-lorn script writer grows increasingly desperate in his quest to adapt the book 'The Orchid Thief'.


IMDB Rating: 7.7

IMDB Votes: 200000

Genere: Comedy, Drama

Country: USA

Duration: 115 min

Plot tags: absurd, philosophical, psychological, satirical, black comedy, mind bending, dark comedy, postmodern, surreal, mindfuck

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Living in Oblivion (1995)

Plot Summary:

Nick is the director of a low-budget indie film. He tries to keep everything together as his production is plagued with an insecure actress, a megalomaniac star, a pretentious, beret-wearing director of photography and lousy catering. Divided in three acts, each representing a different scene to shoot, this film is an essential for amateur filmmakers.


IMDB Rating: 7.5

IMDB Votes: 20000

Genere: Comedy, Drama

Country: USA

Duration: 90 min

Plot tags: surreal, independent film, humorous, funny, atmospheric, talky, light, art house, semi serious, cult classic

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Ed Wood (1994)

Plot Summary:

The mostly true story of the legendary "worst director of all time", who, with the help of his strange friends, filmed countless B-movies without ever becoming famous or successful.


IMDB Rating: 7.8

IMDB Votes: 182000

Genere: Biography, Comedy, Drama

Country: USA

Duration: 127 min

Plot tags: black and white, humorous, black comedy, dark comedy, atmospheric, stylized, sentimental, touching, independent film, gothic

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Withnail & I (1987)

Plot Summary:

Two out-of-work actors -- the anxious, luckless Marwood and his acerbic, alcoholic friend, Withnail -- spend their days drifting between their squalid flat, the unemployment office and the pub. When they take a holiday "by mistake" at the country house of Withnail's flamboyantly gay uncle, Monty, they encounter the unpleasant side of the English countryside: tedium, terrifying locals and torrential rain.


IMDB Rating: 7.5

IMDB Votes: 47000

Genere: Comedy, Drama

Country: UK

Duration: 107 min

Plot tags: black comedy, dark comedy, funny, art house, cult classic, offbeat, atmospheric, grim, independent film, clever

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Ready to Wear (1994)

Plot Summary:

Paris Fashion Week draws the usual bunch of people; designers, reporters, models, magazine editors, photographers. Follows the various storylines of these characters, centering around a murder investigation of a prominent fashion figure. Features an all-star cast.


IMDB Rating: 5.2

IMDB Votes: 16000

Genere: Comedy, Drama

Country: USA

Duration: 133 min

Plot tags: satirical, humorous, talky, light, melancholic, artsy, non-linear, realistic, semi serious, erotic

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Wonder Boys (2000)

Plot Summary:

Grady (Michael Douglas) is a 50-ish English professor who hasn't had a thing published in years -- not since he wrote his award winning "Great American Novel" 7 years ago. This weekend proves even worse than he could imagine as he finds himself reeling from one misadventure to another in the company of a new wonder boy author.


IMDB Rating: 7.2

IMDB Votes: 66000

Genere: Comedy, Drama

Country: USA, Germany, UK, Japan

Duration: 107 min

Plot tags: melancholic, humorous, realistic, talky, dark comedy, touching, intellectual, feel good, dark, clever

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Lost in Translation (2003)

Plot Summary:

Two lost souls visiting Tokyo -- the young, neglected wife of a photographer and a washed-up movie star shooting a TV commercial -- find an odd solace and pensive freedom to be real in each other's company, away from their lives in America.


IMDB Rating: 7.7

IMDB Votes: 480000

Genere: Comedy, Drama

Country: USA, Japan

Duration: 102 min

Plot tags: melancholic, atmospheric, offbeat, psychological, artsy, emotional, art house, visual, contemplative, heartbreaking

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Fear and Loathing in Las Vegas (1998)

Plot Summary:

Raoul Duke and his attorney Dr. Gonzo drive a red convertible across the Mojave desert to Las Vegas with a suitcase full of drugs to cover a motorcycle race. As their consumption of drugs increases at an alarming rate, the stoned duo trash their hotel room and fear legal repercussions. Duke begins to drive back to L.A., but after an odd run-in with a cop, he returns to Sin City and continues his wild drug binge.


IMDB Rating: 7.5

IMDB Votes: 298000

Genere: Adventure, Comedy, Drama

Country: USA

Duration: 118 min

Plot tags: surreal, psychedelic, atmospheric, road movie, mind bending, cult classic, dark comedy, disturbing, mindfuck, cerebral

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Thank You for Smoking (2005)

Plot Summary:

Nick Naylor is a charismatic spin-doctor for Big Tobacco who'll fight to protect America's right to smoke -- even if it kills him -- while still remaining a role model for his 12-year old son. When he incurs the wrath of a senator bent on snuffing out cigarettes, Nick's powers of "filtering the truth" will be put to the test.


IMDB Rating: 7.5

IMDB Votes: 227000

Genere: Comedy, Drama

Country: USA

Duration: 92 min

Plot tags: black comedy, entertaining, dark comedy, political, humorous, funny, satirical, hilarious, feel good, indie film

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Birdman or (The Unexpected Virtue of Ignorance) (2014)

Plot Summary:

A fading actor best known for his portrayal of a popular superhero attempts to mount a comeback by appearing in a Broadway play. As opening night approaches, his attempts to become more altruistic, rebuild his career, and reconnect with friends and family prove more difficult than expected.


IMDB Rating: 7.7

IMDB Votes: 657000

Genere: Comedy, Drama

Country: USA

Duration: 119 min

Plot tags: surreal, psychological, dark comedy, black comedy, psychedelic, independent film, clever, intellectual, atmospheric, enigmatic

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