37 Bittersweet Movies on HBO Max: Laugh, Cry, Repeat!

Bittersweet movies on HBO Max are renowned for their unique blend of emotions, offering viewers a narrative that sways between the joyous and the melancholic. This genre often explores complex human experiences, juxtaposing moments of happiness against underlying tones of sadness or longing. Through intricate storytelling and carefully crafted plots, these films highlight the beauty of life's imperfections. Audiences are drawn to the genuine, relatable scenarios that bittersweet movies on HBO Max present, where the highs and lows of life are portrayed with equal reverence. In these films, character development is often rich and multi-dimensional, portraying individuals who are neither wholly good nor irredeemably bad. The protagonists in bittersweet movies on HBO Max frequently grapple with personal conflicts, transformative journeys, or poignant relationships that leave lasting impacts. Supporting characters play significant roles in driving the story forward, adding depth and complexity to the narrative.

Let Them All Talk

Let Them All Talk
Reunion cruise filled with unresolved relationships and secrets

Released: 2020

Platform: Max

Rating: R

Run time:

Cast
Meryl Streep, Candice Bergen, Dianne Wiest, Lucas Hedges, Gemma Chan

Let Them All Talk is a 2020 drama helmed by acclaimed director Steven Soderbergh and scripted by Deborah Eisenberg. The film centers on renowned author Alice (Meryl Streep) who embarks on a transatlantic journey with her longtime friends Susan (Dianne Wiest) and Roberta (Candice Bergen) to rekindle old bonds and mend emotional scars. Joined by Alices well-meaning nephew Tyler (Lucas Hedges) and her ambitious new literary agent Karen (Gemma Chan), the film unfolds aboard the majestic Queen Mary 2 with an authentic ambiance heightened by on-the-spot dialogue improvisation. Why watch it? The unique setting aboard a real transatlantic crossing and the stellar performances from a distinguished cast breathe life into a story of friendship, forgiveness, and personal growth. The spontaneous dialogue lends an air of authenticity, making the characters' interactions feel genuine and relatable. Steven Soderbergh's deft direction, combined with the ensemble's chemistry, ensures an engaging and emotionally rich cinematic experience that should not be missed.

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Nights in Rodanthe (HBO)

Nights in Rodanthe (HBO)
Midlife love blooms in a coastal inn

Released: 2008

Platform: Max

Rating: PG-13

Run time:

Cast
Diane Lane, Richard Gere, Christopher Meloni, Carolyn McCormick, Pablo Schreiber, Mae Whitman, Charlie Tahan

Nights in Rodanthe is a heartfelt 2008 romantic drama directed by George C. Wolfe, set against the picturesque North Carolina coastline. This emotionally powerful film follows Adrienne Willis and Dr. Paul Flanner as they navigate their personal struggles and find solace in each other over one transformative weekend. Richard Gere and Diane Lane deliver deeply compelling performances, bringing depth to their characters vulnerabilities and resilience. The films authentic setting, enhanced by a specially built inn-turned-vacation-rental, invites viewers into its serene yet emotionally charged atmosphere. Coupled with a poignant soundtrack featuring Emmylou Harris In Rodanthe, the movie beautifully encapsulates themes of love, healing, and the complex nature of human relationships. With its moving storyline and strong performances, Nights in Rodanthe offers a touching escape into a tale of second chances and emotional restoration.

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The Pentagon Wars (HBO)

The Pentagon Wars (HBO)
Military comedy about bureaucratic inefficiency and corruption

Released: 1998

Platform: Max

Rating: R

Run time:

Cast
Kelsey Grammer, Cary Elwes

The Pentagon Wars is a darkly comedic HBO film from 1998 that delivers a biting satire on military bureaucracy. Based on Colonel James G. Burtons book, it follows his quest to expose the flaws in the Bradley Fighting Vehicles development, shedding light on government mismanagement and corruption. Directed by Richard Benjamin and bolstered by a stellar cast, including Kelsey Grammer, Cary Elwes, and Viola Davis, the movie infuses humor into a serious narrative, making its poignant message both engaging and accessible. With a script that cleverly adapts real-life events, the film underscores the importance of integrity and the challenges whistleblowers face. The Pentagon Wars is a must-watch for its sharp wit, captivating performances, and thought-provoking themes about accountability within powerful institutions.

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Rocket Science (HBO)

Rocket Science (HBO)
Stuttering teenager navigates world of high-school debate

Released: 2007

Platform: Max

Rating: R

Run time:

Cast
Reece Daniel Thompson, Anna Kendrick, Nicholas D'Agosto, Vincent Piazza, Margo Martindale, Utkarsh Ambudkar, Denis O'Hare, Aaron Yoo

Rocket Science is a must-watch for its unique blend of humor and heartache, framing the story of a stuttering teenagers journey to find his voice amid the high-stakes world of high school debate. Directed by Jeffrey Blitz, who himself overcame a stutter, this 2007 HBO film provides an authentic and nuanced portrayal of teenage struggles. The films realistic settings in Baltimore and Trenton and standout performances—especially by Reece Daniel Thompson and Anna Kendrick—bring depth to its characters, making their triumphs and tribulations deeply relatable. Furthermore, the movie is enriched by its evocative soundtrack featuring The Velvet Underground and others, enhancing the emotional landscape of the story. Compelling lines like Sometimes finding the answer means changing the question resonate with audiences, offering wisdom and introspection. Rocket Science is not just a film about debating; it's an inspiring narrative about overcoming personal battles and finding one’s voice, making it a poignant and uplifting experience for viewers.

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Spirited Away (Japanese Audio)

Spirited Away (Japanese Audio)
Japanese girl navigates spirit world to survive

Released: 2001

Platform: Max

Rating: PG

Run time:

Cast
Rumi Hiiragi, Miyu Irino, Mari Natsuki, Takashi Nait?

Spirited Away, directed by the legendary Hayao Miyazaki and released by Studio Ghibli in 2001, is a must-watch for animation enthusiasts and movie lovers alike. This critically acclaimed, Oscar-winning film tells the enchanting story of Chihiro, a 10-year-old girl who finds herself navigating a mystical spirit world to save her parents from a curse. With hand-drawn animation that combines Japanese mythology and Shinto elements, the film offers a visually stunning and deeply imaginative experience. Rumi Hiiragi's portrayal of Chihiro effectively captures her growth and determination, while Miyu Irino and Mari Natsuki deliver compelling performances as Haku and Yubaba, respectively. The film's soundtrack, featuring beautiful themes like One Summer's Day and Always With Me, further enhances its emotional depth. Not only is Spirited Away the highest-grossing film in Japanese history, but it also broke barriers as the first non-English language film to win the Academy Award for Best Animated Feature. Dive into this mesmerizing world and discover why it continues to captivate audiences around the globe.

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Sweetie

Sweetie
Complex tale of family dysfunction and mental illness

Released: 1989

Platform: Max

Rating: R

Run time:

Cast
Genevieve Lemon, Karen Colston, Tom Lycos, Sally Bongers

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Philomena (HBO)

Philomena (HBO)
Irish woman seeks son, sold by nuns

Released: 2013

Platform: Max

Rating: PG-13

Run time:

Cast
Judi Dench, Steve Coogan

Philomena is a gripping 2013 drama based on the heart-wrenching true story of Philomena Lee, whose son was taken from her decades ago while she was forced to live in a convent. Directed by Stephen Frears and featuring an evocative screenplay by Steve Coogan and Jeff Pope, the film is an emotional journey that delves deep into themes of loss, faith, and forgiveness. Judi Dench delivers a masterful performance as Philomena, bringing warmth and depth to her character, while Steve Coogan shines as journalist Martin Sixsmith, adding a compelling layer to the narrative. The film successfully balances its poignant subject matter with surprising elements of humor, enhancing its universal appeal. It received critical acclaim, earning four Academy Award nominations, including Best Picture and Best Actress for Dench. With its powerful storyline, remarkable performances, and an evocative score by Alexandre Desplat, Philomena is a must-watch for those who appreciate true stories of resilience and hope.

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In the Gloaming (HBO)

In the Gloaming (HBO)
A poignant drama exploring AIDS, family dynamics

Released: 1997

Platform: Max

Rating: PG

Run time:

Cast
Glenn Close, Bridget Fonda, Whoopi Goldberg, Robert Sean Leonard, David Strathairn

In the Gloaming, released by HBO in 1997, is a poignant drama directed by Christopher Reeve, navigating the emotional journey of Danny, a young man with AIDS spending his final days with his family. The compelling performances, particularly by Robert Sean Leonard as Danny, and Glenne Headly, David Strathairn, and Whoopi Goldberg in supporting roles, deeply resonate with viewers. Reeves directorial debut masterfully combines sensitivity and depth, underscored by Michael Kamens evocative score and the melancholic title track. The narrative not only explores themes of love, family, and mortality but also raises awareness about AIDS with dignity and care. Recognized with multiple Primetime Emmy nominations and awards, In the Gloaming stands out for its heartfelt storytelling and impactful direction. This film is a must-watch for its emotional depth, stellar performances, and unforgettable directorial vision, offering a moving reflection on life and relationships.

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Up in the Air (HBO)

Up in the Air (HBO)
Corporate downsizer navigates work, love, and travel.

Released: 2009

Platform: Max

Rating: R

Run time:

Cast
George Clooney, Vera Farmiga, Anna Kendrick, Danny McBride

Up in the Air, directed by Jason Reitman and featuring George Clooney, is a must-watch for its poignant storytelling and outstanding performances. Released in 2009, this comedy-drama follows Ryan Bingham, a corporate downsizer on the brink of earning ten million frequent flyer miles, whose life is upended by a budding romance with a fellow traveler and an ambitious young colleague. Adapted from Walter Kirns novel, the film masterfully explores themes of isolation, connection, and the impact of modern corporate culture. Clooneys compelling portrayal, complemented by Vera Farmiga and Anna Kendricks dynamic performances, earned the film six Academy Award nominations. With an engaging screenplay, heartfelt quotes like Lifes better with company, and a memorable soundtrack, Up in the Air offers both emotional depth and thought-provoking insights. Dont miss this critically acclaimed cinematic experience that resonates with the complexities of contemporary life.

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Trainwreck (HBO)

Trainwreck (HBO)
Modern woman navigates love and personal growth

Released: 2015

Platform: Max

Rating: R

Run time:

Cast
Amy Schumer, Bill Hader, Brie Larson, Colin Quinn, John Cena, Tilda Swinton, Vanessa Bayer, Mike Birbiglia, Ezra Miller, Dave Attell, Jon Glaser, Randall Park, Norman Lloyd, LeBron James

Trainwreck (HBO) is an engaging 2015 romantic comedy directed by Judd Apatow and written by Amy Schumer, who draws from her own life experiences to craft a story both hilarious and heartfelt. The film follows Amy, a commitment-phobic magazine writer whose carefree lifestyle is turned upside down when she meets Aaron, a sports doctor who challenges her views on love and monogamy. Featuring standout performances from Schumer and co-star Bill Hader, Trainwreck is a fresh take on modern romance. The movie's humor and relatable characters have earned it acclaim, including Golden Globe nominations for Schumer's performance and the film itself. With a dynamic supporting cast, including Brie Larson and cameos from sports stars like LeBron James, Trainwreck offers not just laughs but a poignant exploration of personal growth and relationships. The memorable soundtrack enhances the film's lively atmosphere, making it a must-watch for comedy and romance fans alike.

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Watership Down

Watership Down
Animated rabbits undertake a perilous journey

Released: 1978

Platform: Max

Rating: PG

Run time:

Cast
John Hurt, Richard Briers, Michael Cox

Why You Should Watch Watership Down Watership Down, a 1978 British animated adventure-drama directed by Martin Rosen, is a compelling adaptation of Richard Adams's novel. The story follows a group of rabbits seeking a safe haven after their warren's destruction. Their journey tests their bravery, highlights friendships, and portrays a gripping battle against tyranny. Despite its adorable protagonists, the film's mature and dark themes captivate adults, proving animation's power beyond a child's medium. Martin Rosen faced the formidable task of directing and producing his first feature film using innovative techniques, such as hand-drawn rotoscoping, to enhance its realism. The film features stellar voice acting from talents like John Hurt and Richard Briers, bringing depth to unforgettable characters. Watership Down's unforgettable soundtrack, including Art Garfunkel's hit Bright Eyes, enriches the viewing experience. The film’s accolades, including the Saturn Award for Best Animated Film, underscore its pioneering role in animation. Watch Watership Down for a poignant, visually stunning journey that transcends age and genre.

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Uptown Girls (HBO)

Uptown Girls (HBO)
Privileged woman becomes nanny to precocious girl.

Released: 2003

Platform: Max

Rating: PG-13

Run time:

Cast
Brittany Murphy, Dakota Fanning, Marley Shelton, Donald Faison, Jesse Spencer, Austin Pendleton, Heather Locklear, Mark McGrath, Dave Navarro

Uptown Girls, a 2003 American comedy-drama available on HBO, offers a heartwarming and humorous story about unexpected friendships and personal growth. Starring Brittany Murphy as Molly Gunn, a carefree daughter of a rock legend facing financial ruin, and Dakota Fanning as Ray Schleine, a wise but demanding 8-year-old, the film captivates with their unlikely bond. Directed by Boaz Yakin, the film beautifully showcases New York City and boasts strong performances—Murphys charm and Fannings astonishing maturity shine through, making their character arcs truly compelling. Jesse Spencer and Heather Locklear add depth with their roles, ensuring a well-rounded cast. With intriguing trivia, authentic piano pieces played by Fanning, and memorable lines like Every story has an end, but in life, every ending is just a new beginning, Uptown Girls promises a delightful viewing experience filled with laughter, tears, and life lessons.

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Chungking Express

Chungking Express
A whimsical exploration of love in Hong Kong

Released: 1994

Platform: Max

Rating: PG-13

Run time:

Cast
Tony Leung, Brigitte Lin, Takeshi Kaneshiro, Faye Wang

Chungking Express (1994), directed by the visionary Wong Kar-wai, is a cinematic gem that weaves together two compelling love stories set against the vibrant backdrop of Hong Kong. The films unique narrative style and visually striking depiction of unrequited love and fleeting connections make it a must-watch. With standout performances from Brigitte Lin, Tony Leung Chiu-wai, Faye Wong, and Takeshi Kaneshiro, the movie captivates with its blend of melancholy and hope. The film's rich soundtrack, featuring songs like California Dreamin' and Faye Wong's cover of Dreams, adds emotional depth, while interesting tidbits, such as its improvised script and authentic Hong Kong settings, lend an authentic charm. Chungking Express is more than a movie; it's a poignant exploration of love, loss, and the serendipity of encounters, making it an essential experience for any film enthusiast.

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The Lovers (HBO)

The Lovers (HBO)
Unfaithful couple rekindles romance through surprising affair

Released: 2017

Platform: Max

Rating: R

Run time:

Cast
Debra Winger, Tracy Letts, Aidan Gillen, Melora Hardin, Tyler Ross, Jessica Sula

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American Splendor (HBO)

American Splendor (HBO)
Ordinary life through comic book lens

Released: 2003

Platform: Max

Rating: R

Run time:

Cast
Paul Giamatti, Hope Davis, James Urbaniak, Judah Friedlander

American Splendor, released by HBO in 2003, is a unique biographical comedy-drama that delves into the life of Cleveland file clerk Harvey Pekar, the genius behind the American Splendor comic book series. Directed by Shari Springer Berman and Robert Pulcini, the film stands out by blending performances from actors, real-life footage, and animations from Pekars comics, creating a rich, multifaceted narrative. Paul Giamattis profound portrayal of Pekar, alongside Hope Davis and Judah Friedlander, brings humor and empathy to the screen. Winning the Grand Jury Prize at Sundance and earning an Academy Award nomination for Best Adapted Screenplay, the film highlights the extraordinary in the ordinary. Quotes like Ordinary life is pretty complex stuff reveal its deep philosophical undertones. Including iconic tracks from Marvin Gaye and OK Go, American Splendor is a film that transcends traditional storytelling, making it a must-watch for those who appreciate nuanced, innovative cinema.

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Casablanca

Casablanca
Timeless love story set in wartime Morocco.

Released: 1942

Platform: Max

Rating: PG

Run time:

Cast
Ingrid Bergman, Humphrey Bogart, Paul Henreid, Claude Rains, Conrad Veidt, Peter Lorre, Dooley Wilson, Sydney Greenstreet, Leonid Kinskey, S. Sakall, Madeleine Lebeau

Casablanca (1942) is a timeless American romantic drama set against the dramatic backdrop of World War II in Vichy-controlled Morocco. Directed by Michael Curtiz and featuring iconic performances by Humphrey Bogart, Ingrid Bergman, and Paul Henreid, the film delves into themes of love, sacrifice, and resistance. Despite a troubled production, Casablanca emerged as a masterpiece, winning three Academy Awards, including Best Picture. Its memorable lines like Heres looking at you, kid and Well always have Paris have entered the cultural lexicon. The captivating chemistry between the leads and the compelling narrative make Casablanca a must-watch for anyone interested in classic cinema. The films powerful soundtrack, including As Time Goes By, enriches its emotional depth. If you appreciate classic film artistry, impactful storytelling, and unforgettable performances, Casablanca is a cinematic experience not to be missed.

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Modern Times

Modern Times
Silent film, Chaplin's satirical view on industrialization.

Released: 1936

Platform: Max

Rating: G

Run time:

Cast
Charlie Chaplin, Paulette Goddard, Ira Morgan

Why You Should Watch Modern Times (1936) Modern Times is a timeless masterpiece that remains relevant and engaging even decades after its release. Directed by and starring Charlie Chaplin, this silent comedy poignantly critiques the dehumanizing effects of industrialization. The film portrays Chaplin’s iconic Tramp character struggling to survive the monotonous grind of factory work, offering a compelling mix of humor and heartache. With Chaplin’s ingenious direction and memorable performances from Paulette Goddard and Henry Bergman, the movie delivers both satire and social commentary, capturing the struggles of the Great Depression era. Its innovative use of sound effects and music—despite being a silent film—adds to its charm, with Chaplin's composition Smile becoming an enduring classic. Selected for preservation in the United States National Film Registry, Modern Times is not just historically significant but also universally relatable in its depiction of human resilience and the quest for dignity. A must-watch for film enthusiasts and social historians alike.

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Forgetting Sarah Marshall (HBO)

Forgetting Sarah Marshall (HBO)
Heartbroken composer vacations, meets love at resort.

Released: 2008

Platform: Max

Rating: R

Run time:

Cast
Jason Segel, Kristen Bell, Mila Kunis, Russell Brand

Forgetting Sarah Marshall is a captivating 2008 rom-com that marries heartbreak with hilarity. Directed by Nicholas Stoller and produced by Judd Apatow, the film follows Peter Bretter (Jason Segel) as he tries to mend his broken heart in Hawaii, only to find his ex, Sarah Marshall (Kristen Bell), vacationing at the same resort with her new rockstar boyfriend (Russell Brand). The chemistry between Segel, Bell, Brand, and Mila Kunis, who plays a warm-hearted receptionist, is magnetic. With a script penned by Segel, the movie boasts a blend of laugh-out-loud moments and genuine emotion drawn from real-life experiences. Filmed in the breathtaking Turtle Bay Resort in Oahu, its stunning visuals add to the appeal. The memorable soundtrack and witty quotes enrich the viewing experience, while its relatable themes and engaging performances make it a must-watch for anyone seeking a perfect mix of comedy and romance.

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Ordinary Love (HBO)

Ordinary Love (HBO)
Couple navigates love and cancer's challenging journey

Released: 2020

Platform: Max

Rating: R

Run time:

Cast
Lesley Manville, Liam Neeson

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The Tale of the Princess Kaguya

The Tale of the Princess Kaguya
A magical adventure of a bamboo cutter's daughter

Released: 2013

Platform: Max

Rating: PG

Run time:

Cast

The Tale of the Princess Kaguya, a 2013 Japanese anime by Studio Ghibli, is a visually and emotionally compelling masterpiece directed by Isao Takahata. Based on the folktale The Tale of the Bamboo Cutter, the film tells the poignant story of Kaguya, a tiny nymph found and raised by a bamboo cutter and his wife, who blossoms into a resilient young woman. Renowned for its unique watercolor art style, a departure from traditional Ghibli animation, the movie captivates with its breathtaking visuals and touching narrative. Featuring exceptional voice acting by Aki Asakura, Takeo Chii, and Nobuko Miyamoto, the film resonates deeply through themes of love, loss, and self-discovery. The enchanting score by Joe Hisaishi and its award-winning recognition, including an Oscar nomination, further solidify its acclaim. This film is a must-watch for its innovative artistry and profound storytelling, making it a timeless piece of cinematic beauty.

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Celeste and Jesse Forever

Celeste and Jesse Forever
Unraveling love story of best friends turned spouses

Released: 2012

Platform: Max

Rating: R

Run time:

Cast
Rashida Jones, Andy Samberg, Elijah Wood, Emma Roberts, Will McCormack, Ari Graynor, Eric Christian Olsen, Chris Messina

Celeste and Jesse Forever (2012) is a compelling romantic comedy-drama that delves into the complexities of maintaining a friendship after a divorce. The film stars Rashida Jones and Andy Samberg as a once-married couple who navigate their intertwined lives with humor and poignancy. Directed by Lee Toland Krieger, the movie stands out for its realistic portrayal of relationships, enriched by impressive performances from a stellar cast including Emma Roberts and Elijah Wood. Written by Jones and Will McCormack, the screenplay offers a refreshing take on love and friendship, masterfully balancing light-hearted moments with emotional depth. The beautiful Los Angeles backdrop and a well-curated soundtrack further elevate the storytelling. Garnering critical acclaim, the movie was nominated for an Independent Spirit Award for Best First Screenplay. Viewers should watch Celeste and Jesse Forever for its genuine, relatable narrative and its insightful examination of the joys and pains of moving on.

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Night on Earth

Night on Earth
Five taxis, five cities, one night

Released: 1991

Platform: Max

Rating: R

Run time:

Cast
Gena Rowlands, Winona Ryder, Armin Mueller-Stahl, Fred Elmes

Night on Earth, directed by Jim Jarmusch, is a 1991 film that takes viewers on a global journey through five compelling vignettes, each set in a different city on the same night. The movie masterfully explores human connections and cultural diversity through the interactions between taxi drivers and their passengers. With an international cast including Winona Ryder, Gena Rowlands, and Roberto Benigni, each story blends humor and melancholy, providing a rich tapestry of urban life. Critically acclaimed for its unique narrative style and the iconic cinematography of Frederick Elmes, the film offers a visual feast despite being predominantly shot in New York and Los Angeles. The soundtrack, composed by Tom Waits, adds an atmospheric touch that complements the film’s mood. Whether you're drawn to heartfelt storytelling, character-driven plots, or simply a fan of Jarmusch's unique directorial flair, Night on Earth is a cinematic experience not to be missed.

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Her (HBO)

Her (HBO)
Lonely writer falls in love with AI

Released: 2013

Platform: Max

Rating: R

Run time:

Cast
Joaquin Phoenix, Amy Adams, Rooney Mara, Olivia Wilde, Scarlett Johansson

Her (2013), directed by Spike Jonze, is a captivating and thought-provoking sci-fi romantic drama that ventures into the depths of human connection and the evolving relationships in a technology-driven world. Starring Joaquim Phoenix as Theodore Twombly and Scarlett Johansson as the voice of Samantha, an AI, the film delicately portrays love and loneliness. The meticulous production design creates a visually stunning near-future Los Angeles, enhancing the emotional narrative. Critically acclaimed, Her won the Academy Award for Best Original Screenplay and features a memorable soundtrack by Arcade Fire. The films exploration of human emotions, aided by stellar performances and insightful direction, makes it a must-watch for anyone intrigued by the intersection of technology and intimacy.

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42 (HBO)

42 (HBO)
Biographical film about baseball legend Jackie Robinson

Released: 2013

Platform: Max

Rating: PG-13

Run time:

Cast
Chadwick Boseman, Harrison Ford, Nicole Beharie, Christopher Meloni

42, the 2013 biographical sports film directed by Brian Helgeland, is an inspiring tribute to Jackie Robinson, the first African American to break Major League Baseballs color barrier with the Brooklyn Dodgers. This powerful drama authentically captures the struggles and triumphs of Robinsons career against a backdrop of rampant racial discrimination. The film stars Chadwick Boseman, whose portrayal of Robinsons resilience and dignity is both convincing and moving, alongside Harrison Ford as the courageous Dodgers executive Branch Rickey, and Nicole Beharie as Robinsons steadfast wife, Rachel. With its dramatic baseball scenes, historical accuracy, and profound emotional depth, 42 is more than a sports movie—its a compelling story of courage and change that resonates with audiences. The films soundtrack and meaningful quotes add an extra layer of authenticity and emotion. 42 is a must-watch not only for sports enthusiasts but for anyone moved by tales of perseverance and social justice.

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Pom Poko

Pom Poko
Shape-shifting raccoons battle urban development in Japan.

Released: 1994

Platform: Max

Rating: PG

Run time:

Cast

Pom Poko is a visually stunning 1994 animated film that combines the ingenuity of Studio Ghibli with the directorial brilliance of Isao Takahata. This movie is an essential watch for its rich animation, compelling narrative, and poignant environmental commentary. The plot follows a group of magical shape-shifting raccoon dogs, or tanuki, who valiantly fight to save their forest from urban development in Tokyo. The film not only entertains with its whimsical elements and humor but also deeply resonates through its exploration of cultural and environmental themes. With an outstanding voice cast—including Shinchou Kokontei, Makoto Nonomura, and Yuriko Ishida—who deliver emotionally charged performances, Pom Poko captures both the spirit and the struggles of its characters. The captivating soundtrack by Shinichiro Ikebe enhances the movie's immersive experience, blending traditional Japanese songs with enchanting new compositions. Awarded Best Animated Feature at the 22nd Japan Academy Prize in 1995, Pom Poko offers a touching, thought-provoking, and thoroughly enjoyable cinematic journey. Don’t miss this masterpiece that eloquently merges folklore, humor, and a compelling call for environmental preservation.

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Happy Together

Happy Together
A tumultuous love story in Buenos Aires

Released: 1997

Platform: Max

Rating: NR

Run time:

Cast
Tony Leung, Leslie Cheung, Chang Chen, Christopher Doyle

Happy Together (1997) is a poignant Hong Kong romantic drama by acclaimed director Wong Kar-wai that delves deeply into the turbulent relationship between two men, Ho Po-wing (Leslie Cheung) and Lai Yiu-fai (Tony Leung Chiu-wai). Set against the vibrant backdrop of Argentina, the film masterfully captures the raw emotions and complexities of love, frustration, and passion. With stunning cinematography by Christopher Doyle, the films unique visuals and storytelling make it a compelling watch. Leslie Cheung and Tony Leung deliver powerful performances that explore vulnerability and longing, making their characters deeply relatable. The film also boasts a memorable soundtrack featuring classics like Happy Together by The Turtles. Packed with awards and international acclaim, including the Best Director award at the 1997 Cannes Film Festival, Happy Together is a significant LGBTQ+ film that offers a profound, artistic look at human relationships.

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The Farewell (2019) (HBO)

The Farewell (2019) (HBO)
Family fakes wedding to bid grandma farewell.

Released: 2019

Platform: Max

Rating: PG

Run time:

Cast
Awkwafina, Tzi Ma, Diana Lin, Ines Laimins, Shuzhen Zhao, Hong Lu

People should watch The Farewell (2019) not just for its compelling and heartfelt storyline, but for its masterful direction by Lulu Wang. Inspired by her real-life experiences, the film eloquently navigates cultural differences and family dynamics as it follows a Chinese-American woman, played by Awkwafina in a career-defining role, grappling with her familys decision to keep her grandmothers terminal diagnosis a secret. The movies nuanced portrayal of Eastern and Western values is complemented by poignant performances, especially from Shuzhen Zhou as the lively Nai Nai. Shot in Changchun, China, the cinematography captures the essence of Wangs roots, making it a beautiful visual homage. The evocative score by Alex Weston, paired with classical and Chinese pop music, enhances the cinematic experience. Recognized with awards and nominations, including a Golden Globe for Awkwafina, The Farewell is a touching exploration of love, lies, and cultural identity that resonates universally.

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The Tale of the Princess Kaguya (Japanese Audio)

The Tale of the Princess Kaguya (Japanese Audio)
Japanese princess's life unfolds in stunning animation

Released: 2013

Platform: Max

Rating: PG

Run time:

Cast
Aki Asakura, Kengo Kora, Takeo Chii, Nobuko Miyamoto, Atsuko Takahata

The Tale of the Princess Kaguya, directed by Isao Takahata and produced by Studio Ghibli, is a 2013 animated masterpiece that blends mysticism, tragedy, and romance. Adapted from a 10th-century Japanese folktale, this story of a tiny nymphs transformation into a beautiful woman brims with emotional depth and cultural richness. Uniquely animated with watercolor and pencil, the film took eight years to complete, reflecting its grand vision and meticulous craftsmanship. Notably, it was Takahatas final film, enhancing its poignant legacy. With compelling performances by Chloë Grace Moretz, James Caan, and Mary Steenburgen, the film resonates with its timeless quotes and evocative soundtrack. Recognized globally, it earned a nomination for Best Animated Feature at the 87th Academy Awards and won the Audience Award at Fantastic Fest. This film is a must-watch for its extraordinary artistry, emotional gravitas, and profound storytelling.

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While We're Young (HBO)

While We're Young (HBO)
Middle-aged couple befriends youthful, hip pair

Released: 2015

Platform: Max

Rating: R

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Cast
Ben Stiller, Naomi Watts, Adam Driver, Amanda Seyfried, Charles Grodin, Adam Horovitz

Released in 2015, While Were Young is a brilliantly crafted film blending drama and comedy to explore lifes pivotal issues. Directed by Noah Baumbach, known for his unique storytelling, the film follows a middle-aged couple who find their lives invigorated by a friendship with a free-spirited younger couple. This dynamic juxtaposition offers a keen exploration of tradition versus innovation. With stellar performances by Ben Stiller, Naomi Watts, Adam Driver, and Amanda Seyfried, the film captures the nuances of mid-life crises and youthful exuberance with authenticity. Its rich cinematography, directed by Sam Levy, and eclectic soundtrack, featuring artists like David Bowie and LCD Soundsystem, further elevate the narrative. While We're Young is a reflective yet entertaining film, praised for its insightful scripting and visual beauty. It's a must-watch for anyone fascinated by the complexities of life transitions and the evolving nature of relationships.

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The Skeleton Twins (HBO)

The Skeleton Twins (HBO)
Estranged twins reunite, confront personal challenges together

Released: 2014

Platform: Max

Rating: R

Run time:

Cast
Bill Hader, Kristen Wiig, Luke Wilson, Ty Burrell, Boyd Holbrook

The Skeleton Twins is a poignant 2014 comedy-drama that delves into the complexities of sibling relationships, mental health, and personal redemption. Directed by Craig Johnson, the film stars Bill Hader and Kristen Wiig in their first dramatic roles, showcasing their exceptional range beyond comedy. Following estranged twins who reunite after near-death experiences, the film balances humor and deep emotion, portraying raw, relatable struggles. Shot within a mere 22 days, the movies authenticity is amplified by stellar performances and compelling cinematography by Reed Morano. Award-winning at Sundance for its screenplay, The Skeleton Twins is a must-watch for its heartfelt storytelling, memorable quotes, and evocative soundtrack, making it both entertaining and profoundly moving.

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Pom Poko (Japanese Audio)

Pom Poko (Japanese Audio)
Japanese folklore raccoons fight urban development

Released: 1994

Platform: Max

Rating: PG

Run time:

Cast

Pom Poko, a 1994 gem by renowned filmmaker Isao Takahata and Studio Ghibli, blends fantasy and heartfelt themes in an unforgettable narrative. This animated masterpiece centers on a group of magical tanuki (Japanese raccoon dogs) who resist urban development threatening their home. Utilizing their shape-shifting abilities, the tanuki transform into humans, objects, and even spirits to fight for their survival, creating a compelling and imaginative storyline. Directed by Takahata, known for his detailed and fantastical storytelling, Pom Poko offers humor intertwined with deep messages on environmental conservation. Featuring standout vocal performances by Shinchô Kokontei, Makoto Nonomura, and Yuriko Ishida, the film captures perseverance, hope, and cunning spirit. With nominations for prestigious awards and a stirring soundtrack by Tokiko Kato, Pom Poko is a unique blend of epic drama and fantasy, making it a must-watch for anyone passionate about animation and meaningful storytelling.

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They All Laughed (HBO)

They All Laughed (HBO)
Romantic comedy about private detectives and infidelity

Released: 1981

Platform: Max

Rating: PG

Run time:

Cast
Ben Gazzara, Audrey Hepburn, John Ritter

They All Laughed is a hidden gem from 1981 that masterfully combines humor, drama, and romance under the direction of Peter Bogdanovich. This romantic comedy explores the lives of private detectives who become personally entangled with the women theyre meant to surveil, offering a heartfelt and funny look at love and friendship amidst lifes challenges. Featuring memorable performances by John Ritter and Dorothy Stratten, whose final role is poignantly honored, the film is an ode to complex human emotions. The production faced obstacles, including the tragic loss of Stratten, but Bogdanovich’s unique storytelling and his incorporation of timeless music by Frank Sinatra and Ella Fitzgerald make the film a delightful cinematic experience. Though it did not win awards, the rich performances and emotional depth have garnered esteemed praise. Watch They All Laughed for its charming narrative, its celebration of old Hollywood, and its beautifully poignant portrayal of human connections.

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You Were My First Boyfriend | Now Streaming | HBO Original

You Were My First Boyfriend | Now Streaming | HBO Original
Exploring first love and heartbreak on HBO

Released: 2

Platform: Max

Rating: T

Run time:

Cast

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How To Eat Fried Worms (HBO)

How To Eat Fried Worms (HBO)
Boy engages in worm-eating dare contest

Released: 2006

Platform: Max

Rating: PG

Run time:

Cast
James Rebhorn, Kimberly Williams-Paisley, Tom Cavanagh, Luke Benward, Hallie Eisenberg

HOW TO EAT FRIED WORMS, a 2006 family comedy on HBO, is a delightful watch based on the beloved 1973 book by Thomas Rockwell. The story centers around 11-year-old Billy, who bravely faces school bullies by accepting a dare to eat ten creatively cooked worms in one day. Filled with humor and childhood mischief, this movie perfectly captures the essence of childhood imagination, fear, and triumph under the direction of Bob Dolman. With standout performances by Luke Benward as Billy, Hallie Kate Eisenberg as supportive friend Erika, and Adam Hicks as the menacing bully Joe, the characters are both relatable and endearing. Notably, the worms are made using pasta and gummy candies, ensuring no real insects were harmed and making the revolting scenes hilariously memorable. Featuring a playful score by Robert Folk and an engaging soundtrack, this film is a heartwarming and entertaining choice for families.

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Stranger Than Paradise

Stranger Than Paradise
Immigrant experiences American oddity with relatives.

Released: 1984

Platform: Max

Rating: R

Run time:

Cast
John Lurie, Eszter Balint, Richard Edson, Tom Dicillo

Stranger Than Paradise, a 1984 black-and-white absurdist comedy directed by Jim Jarmusch, is a must-watch for fans of unique storytelling and minimalist cinema. The film, starring John Lurie, Eszter Balint, and Richard Edson, depicts an unconventional yet poignant narrative of a New Yorkers interactions with his Hungarian cousin and his best friend. Set against the stark backdrops of Lake Erie and the drab streets of Cleveland and Detroit, the movies simplicity and charm shine through its long, uninterrupted takes and offbeat dialogue. Despite its low budget, the films impact was profound, earning it the Caméra dOr at the Cannes Film Festival and a Special Jury Prize at Sundance. The minimalist soundtrack, featuring Hungarian music and Screamin Jay Hawkins, enhances its quirky appeal. This cult classic captures the essence of the immigrant experience and showcases Jarmuschs distinctive directorial style, making it essential viewing for cinephiles.

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Amarcord

Amarcord
Italian village life through a nostalgic lens

Released: 1974

Platform: Max

Rating: R

Run time:

Cast
Magali Noel, Bruno Zanin, Pupella Maggio, Armando Brancia, Giuseppe Rotunno

Amarcord, a 1974 film by the iconic Italian director Federico Fellini, is a nostalgic, semi-autobiographical comedy-drama that offers a vibrant, dreamlike portrayal of 1930s Italy. The film is set in Fellinis hometown of Rimini and brims with eccentric characters drawn from his childhood memories. An amalgamation of reality and fantasy, Amarcord is a celebration of lifes absurdities and a poignant longing for the past. The films richly detailed settings, meticulously recreated in Rome, transport viewers into Fellinis world, while Nino Rotas evocative score enhances its whimsical atmosphere. Pupella Maggio, Armando Brancia, and Magali Noël deliver memorable performances, bringing warmth and humor to the narrative. Awarded the Academy Award for Best Foreign Language Film, Amarcord is not just a film but an enchanting experience that reminds us of the joy and beauty found in remembering. This timeless masterpiece is a must-watch for its captivating blend of humor, pathos, and artistic brilliance.

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Dinner With Friends (HBO)

Dinner With Friends (HBO)
Two couples reconcile their turbulent friendships.

Released: 2001

Platform: Max

Rating: R

Run time:

Cast
Dennis Quaid, Andie MacDowell, Greg Kinnear, Toni Collette

Dinner With Friends, an HBO film released in 2001 and based on Donald Margulies Pulitzer Prize-winning play, delves deeply into the intricate dynamics of relationships. Directed by Norman Jewison, this compelling narrative revolves around two couples whose long-standing friendship is shaken by a sudden divorce, prompting them to introspect on their own marriages. Featuring stellar performances by Dennis Quaid, Andie MacDowell, Greg Kinnear, and Toni Collette, the film portrays relatable characters navigating through emotional turmoil and societal expectations with nuance and sensitivity. Offering not just a powerful storyline but also thoughtful dialogue, such as Gabe’s poignant reflection, Do you know what scares me? The possibility of living a long life, the film engages viewers on philosophical and emotional levels. The soul-stirring soundtrack complements its evocative atmosphere, making Dinner With Friends a must-watch for anyone interested in the complexities of human relationships, friendship, and the transformative journey of marriage.

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About This Collection

Heartfelt films mixing joy and sorrow.

Bittersweet movies on HBO Max offer a blend of heartwarming moments and emotional depth, often leaving viewers with a sense of both sorrow and joy. These films masterfully balance poignant storytelling and genuine emotion. For those seeking a reflective and moving experience, bittersweet movies on HBO Max provide the perfect mix of melancholy and hope.

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