37 Best Witty Movies on HBO Max to Watch Now

Witty movies on HBO Max offer an engaging and delightful experience for audiences looking for sharp humor and clever dialogue. These films are characterized by their intelligent scripts, often filled with rapid-fire exchanges, playful banter, and satirical observations about life and society. The genre spans across various settings and periods, from contemporary comedies to period pieces, all unified by a sophisticated sense of humor that challenges and entertains viewers. The hallmark of these movies is their ability to balance humor with thoughtful commentary, making them a favorite among those who appreciate a more cerebral form of entertainment. The characters in witty movies on HBO Max are typically well-developed and multidimensional, each person possessing a quick wit and a strong sense of individuality. These protagonists, often charming and flawed, navigate through convoluted plots and amusing situations that showcase their cleverness and adaptability.

Last Week Tonight with John Oliver

Last Week Tonight with John Oliver
Satirical news commentary with John Oliver

Released: 2

Platform: Max

Rating: T

Run time:

Cast

Last Week Tonight with John Oliver is a refreshing late-night talk and news satire show that delves into weekly news, politics, and current events with unmatched wit and humor. Hosted by the incisive and sarcastic John Oliver, this HBO series promises a unique and thought-provoking take on contemporary issues. Created by Oliver and a team of talented producers, the show boasts a strong writing team of comedians and is filmed in New York Citys CBS Broadcast Center. Highly acclaimed and decorated with numerous awards, including Emmys and a Peabody Award, the show offers insightful and often provocative commentary. Its engaging satire has drawn favorable comparisons to The Daily Show, cementing its status as a must-watch for those seeking both entertainment and enlightenment. Dont miss out on Olivers sharp observations and memorable quotes that tackle complex topics with clever humor.

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Naked Gun 33 1/3 (HBO)

Naked Gun 33 1/3 (HBO)
Hilarious undercover cop disrupts bomb plot.

Released: 1994

Platform: Max

Rating: PG-13

Run time:

Cast
Leslie Neilsen, Priscilla Presley, George Kennedy, O.J. Simpson, Fred Ward, Anna Nicole Smith

Naked Gun 33 1/3: The Final Insult is a 1994 American comedy gem and the last in the hilarious Naked Gun series. Starring the iconic Leslie Nielsen as the bumbling Lt. Frank Drebin, the film showcases his efforts to prevent a bombing at the Academy Awards. Written by Pat Proft and David Zucker and directed by Peter Segal, it promises a blend of slapstick humor and clever puns. The ensemble cast, including Priscilla Presley and O.J. Simpson, add charm and comedic flair to the story. Despite being titled The Final Insult, a planned fourth film was shelved after Nielsens death in 2010, making this movie a bittersweet end to a beloved series. With memorable quotes, a quirky soundtrack, and scenes shot during actual events like a baseball rain delay, this film captures the essence of comedic genius. Watching it is a perfect tribute to Nielsens comedic legacy and a guaranteed laughter-filled experience.

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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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Be Cool (HBO)

Be Cool (HBO)
Mafia boss dives into music industry chaos.

Released: 2005

Platform: Max

Rating: PG-13

Run time:

Cast
John Travolta, Uma Thurman, Vince Vaughn, Cedric the Entertainer, André Benjamin, Steven Tyler, Robert Pastorelli, Christina Milian, Harvey Keitel, Dwayne 'The Rock' Johnson, Danny DeVito

Be Cool (2005), a sequel to Get Shorty, is a captivating comedy-crime film directed by F. Gary Gray. The story follows Chili Palmer, a former mobster turned movie producer, now venturing into the music industry. This film promises a blend of humor and intrigue as Palmer navigates through a series of comic misadventures while managing a promising young singer. Featuring stellar performances by John Travolta, Uma Thurman, Dwayne The Rock Johnson, and Vince Vaughn, Be Cool combines top-notch acting with a compelling storyline. The movies delightful meta-humor, memorable quotes, and engaging soundtrack, including performances by The Rock, make it a must-watch. Whether for the comedic brilliance, the intriguing plot, or the fantastic music, Be Cool offers something for everyone, ensuring an entertaining experience from start to finish.

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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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Heartbreakers (HBO)

Heartbreakers (HBO)
Mother-daughter con artists swindle wealthy men

Released: 2001

Platform: Max

Rating: PG-13

Run time:

Cast
Sigourney Weaver, Jennifer Love Hewitt, Ray Liotta, Jason Lee, Jeffrey Jones, Gene Hackman

Heartbreakers, an engaging comedic drama from 2001, offers an entertaining blend of humor, romance, and clever schemes. Directed by David Mirkin and boasting a stellar cast including Sigourney Weaver and Jennifer Love Hewitt, the plot revolves around a mother-daughter con artist team targeting wealthy men for lucrative divorce settlements. Complications arise when genuine love enters the picture. Filmed across picturesque locations in California and Florida, the movie showcases the charm and acting prowess of Weaver and Hewitt, alongside strong performances from Ray Liotta and Jason Lee. Noteworthy trivia, like Elvis Presley's Rolls-Royce and Gene Hackman's character inspired by Howard Hughes, adds interesting layers. Though not heavy on awards, the film's memorable quotes and catchy soundtrack by John Debney and Marvin Gaye provide added delight. Heartbreakers is a must-watch for its intriguing plot, charismatic performances, and delightful blend of comedy and drama.

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Get Shorty (HBO)

Get Shorty (HBO)
Mobster turns film producer in Hollywood chaos

Released: 1995

Platform: Max

Rating: R

Run time:

Cast
John Travolta, Gene Hackman, Rene Russo, Danny DeVito

Get Shorty is an unmissable gem in the crime-comedy genre, seamlessly blending humor, satire, and thrilling elements. Directed by Barry Sonnenfeld and based on Elmore Leonards novel, this 1995 release tells the captivating story of a Miami mobster, brilliantly portrayed by John Travolta, who unexpectedly delves into the chaotic world of Hollywood. With a stellar cast featuring Gene Hackman, Rene Russo, and Danny DeVito, Get Shorty showcases sharp dialogue and intriguing characters. Travolta's standout performance as Chili Palmer earned him a Golden Globe, adding another reason to watch. The film's wit, humor, and insider look at Hollywood's underbelly, combined with a memorable soundtrack, make Get Shorty a must-see. It's a compelling tale of crime meeting cinema, delivering both laughs and thrills in equal measure. Don't miss out on this classic that masterfully captures the absurdity and allure of Tinseltown.

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The Women (2008) (HBO)

The Women (2008) (HBO)
Upscale women navigate friendship and betrayal.

Released: 2008

Platform: Max

Rating: PG-13

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Cast
Meg Ryan, Annette Bening, Eva Mendes, Debra Messing, Jada Pinkett Smith, Carrie Fisher, Cloris Leachman, Debi Mazar, Bette Midler, Candice Bergen

The Women (2008) is a modern, riveting update of the 1939 George Cukor classic, masterfully directed by Diane English and produced by talents like Victoria Pearman and Mick Jagger. This compelling film delves into the lives of New York high-society women who stand by their friend Mary, portrayed poignantly by Meg Ryan, as she navigates the turmoil of her husbands affair with the captivating Crystal, played by Eva Mendes. Featuring an all-female cast, including Annette Benings fierce portrayal of Sylvie Fowler, the movie is a celebration of female solidarity, friendship, and self-discovery. Unique in its feminist roots and laced with memorable quotes, The Women offers both emotional depth and witty commentary. Its eclectic soundtrack by artists like Liz Phair and Miranda Lee Richards adds to the films modern charm. A must-watch for its stellar performances and empowerment narrative, it beautifully underscores the enduring bonds between women.

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Dear White People (HBO)

Dear White People (HBO)
Satirical drama exploring racial tensions in college

Released: 2014

Platform: Max

Rating: R

Run time:

Cast
Tyler James Williams, Tessa Thompson, Kyle Gallner, Teyonah Parris, Brandon Bell, Brittany Curran, Justin Dobies, Marque Richardson, Malcolm Barrett, Dennis Haysbert

Dear White People, directed by Justin Simien, is an engaging satirical drama-comedy that delves deeply into the complexities of racial identity in a supposedly post-racial America. Focusing on escalating racial tensions at a predominantly white university, the film brilliantly blends humor with thought-provoking social commentary. Featuring standout performances by Tessa Thompson, Tyler James Williams, and Kyle Gallner, it portrays a range of diverse characters grappling with identity and prejudice. The film highlights key societal issues through its clever script and incisive dialogue, providing a powerful reflection on contemporary racial dynamics. Recognized for its insightful storytelling, Dear White People won the U.S. Dramatic Special Jury Award for Breakthrough Talent at the 2014 Sundance Film Festival. By tackling these themes head-on, the movie serves as both an entertaining and intellectually stimulating experience, making it essential viewing for anyone interested in understanding and discussing race relations in modern society.

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Trail of the Pink Panther (HBO)

Trail of the Pink Panther (HBO)
Clouseau's trail unfolds posthumously through news interviews.

Released: 1982

Platform: Max

Rating: PG

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Cast
Peter Sellers, David Niven, Herbert Lom, Joanna Lumley, Richard Mulligan, Capucine, Robert Loggia, Harvey Korman, Burt Kwouk

Trail of the Pink Panther, a 1982 comedy gem, ingeniously stitches together unseen archival footage to revive Peter Sellers legendary portrayal of Chief Inspector Jacques Clouseau. Directed by Blake Edwards, the film follows journalist Marie Jouvet, brilliantly played by Joanna Lumley, as she delves into the baffling disappearance of Clouseau. Despite Sellers passing, his comedic genius shines through, ensuring fans can still relish the bumbling inspectors antics. The movies captivating plot, nostalgia-infused humor, and Henry Mancinis iconic soundtrack make it a fitting tribute and a must-watch for Pink Panther enthusiasts. Dive into the charm and wit that defines this beloved series!

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Sex and the City (HBO)

Sex and the City (HBO)
Four New York women navigate love, fashion

Released: 2008

Platform: Max

Rating: R

Run time:

Cast
Sarah Jessica Parker, Cynthia Nixon, Kristin Davis, Kim Cattrall

Sex and the City (2008) is more than just a romantic comedy-drama; its a cultural touchstone that encapsulates the vibrant, tumultuous lives of four iconic women in New York City. Directed by Michael Patrick King, who ensured the film stayed true to its roots, this movie offers a seamless continuation of the beloved HBO series. Starring Sarah Jessica Parker, Kim Cattrall, Cynthia Nixon, and Kristin Davis, the film delves into deep themes like love, heartbreak, career struggles, and social issues, all while delivering sharp wit and unforgettable performances. Engaging quotes, a stellar soundtrack, and the chance to see beloved characters in new yet familiar scenarios make this a must-watch. The awards it garnered, from the Golden Trailer Award to the NewNowNext Award, attest to its quality. For fans of the original series and newcomers alike, Sex and the City is an empowering, entertaining exploration of friendship and love in the modern world.

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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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The Family (HBO)

The Family (HBO)
Mafia family in witness protection causes chaos

Released: 2013

Platform: Max

Rating: R

Run time:

Cast
Robert De Niro, Michelle Pfeiffer, Tommy Lee Jones, Dianna Agron, John D'Leo

The Family (HBO) is a must-watch for fans of dark comedy and action thrillers. Directed by Luc Besson, this 2013 film stars Robert De Niro as Fred Blake, a former Mafia boss who enters the Witness Protection Program with his family, only to find that old habits die hard. Set in France, the movie masterfully blends humor and tension, offering an entertaining narrative driven by stellar performances from Michele Pfeiffer, Dianna Agron, and John DLeo. The screenplay, adapted from Tonino Benacquistas novel Malavita, delves into family dynamics against a backdrop of crime and vengeance. With its unique mix of action, comedy, and drama, coupled with Alexandre Desplats evocative soundtrack, The Family delivers a captivating cinematic experience. Whether youre drawn to gripping plots or nuanced character portrayals, this film provides a well-rounded entertainment package. Dont miss this intriguing exploration of life and loyalty within a Mafia family.

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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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Legally Blonde (HBO)

Legally Blonde (HBO)
Sorority girl conquers Harvard Law stereotypes

Released: 2001

Platform: Max

Rating: PG-13

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Cast
Reese Witherspoon, Luke Wilson, Selma Blair, Ali Larter, Matthew Davis, Jennifer Coolidge, Raquel Welch, Victor Garber, Holland Taylor, Oz Perkins, Linda Cardellini, Jessica Cauffiel, Alanna Ubach

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Metropolitan

Metropolitan
Upper-class Manhattan youths navigating romance

Released: 1990

Platform: Max

Rating: PG-13

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Cast
Carolyn Farina, Edward Clements, Chris Eigeman, John Thomas

Metropolitan, a 1990 American romantic comedy directed and written by Whit Stillman, is an insightful exploration of the lives of affluent college graduates in Manhattan. The film is celebrated for its sharp wit, engaging dialogues, and complex characters. Despite its minimal budget and cast of newcomers, Metropolitan masterfully delves into themes of morality, love, and social class, providing a unique perspective on the privileged upper class often underrepresented in cinema. Notable performances include Edward Clements as the intellectual outsider, Tom Townsend, and Chris Eigeman as the cynical, humor-filled Nick Smith. The films endearing romance and perceptive social commentary, encapsulated by Carolyn Farinas Audrey Rouget, make it a compelling watch. Garnering an Academy Award nomination for Best Original Screenplay and winning an Independent Spirit Award for Best First Feature, Metropolitan stands out as a nostalgic yet timeless piece that resonates with viewers seeking thoughtful entertainment.

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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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Deadpool (HBO)

Deadpool (HBO)
Sarcastic superhero navigates violence with humorous quips.

Released: 2016

Platform: Max

Rating: R

Run time:

Cast
Ryan Reynolds, Morena Baccarin, T.J. Miller, Gina Carano, Ed Skrein, Stefan Kapicic, Rachel Sheen, Stan Lee, Brianna Hildebrand, Taylor Hickson, Jed Rees, Leslie Uggams, Karan Soni, Kyle Cassie

Deadpool is a groundbreaking addition to superhero cinema, blending humor, action, and romance in a way that sets it apart from its peers. Released in 2016 and directed by Tim Miller, the film stars Ryan Reynolds as Wade Wilson, a mercenary who becomes Deadpool after a rogue experiment grants him accelerated healing powers. With witty dialogue, dark humor, and a relentless quest for revenge, Deadpools unique personality brings a refreshing twist to the genre. Morena Baccarin, T.J. Miller, and Ed Skrein deliver strong performances that complement Reynolds iconic portrayal. The film's production journey, from comic to screen, is an inspiring tale of persistence, spearheaded by Reynolds himself. This movie's R-rated humor and action-packed sequences redefine the superhero narrative, making it a must-watch. Its record-breaking box office success, critical acclaim, and engaging soundtrack, including hits like X Gon' Give It to Ya by DMX, further solidify Deadpool as a cultural phenomenon.

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Teen Titans Go! to the Movies

Teen Titans Go! to the Movies
Teen Titans seek recognition in superhero Hollywood

Released: 2018

Platform: Max

Rating: PG

Run time:

Cast
Greg Cipes, Scott Menville, Khary Payton, Tara Strong, Hynden Walch, Will Arnett, Kristen Bell

Teen Titans Go! To the Movies, released in 2018, is a delightful animated superhero comedy film that brings both laughter and action. Based on the popular television series Teen Titans Go!, this film follows the entertaining journey of the Teen Titans as they seek fame on the big screen. Directed by Peter Rida Michail and Aaron Horvath, the movie charms with its witty plot and unique characters, each voiced by talented actors like Greg Cipes, Scott Menville, and Khary Payton. The film not only delivers humor and excitement but also includes intriguing trivia, such as Nicolas Cage fulfilling his dream of voicing Superman. With a dynamic soundtrack featuring artists like T.I. and Michael Bolton, and recognition like a nomination for Best Animated Feature at the 2019 Critics Choice Awards, this film is a must-watch for its amusing storyline, vibrant animation, and nostalgic appeal.

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Everybody Wants To Be Italian (HBO)

Everybody Wants To Be Italian (HBO)
Romantic comedy about mistaken Italian heritage

Released: 2007

Platform: Max

Rating: R

Run time:

Cast
Jay Jablonski, Cerina Vincent, John Kapelos, John Enos, Richard Libertini, Marisa Petroro

Everybody Wants to Be Italian is a delightful romantic comedy that charms audiences with its humorous take on love and identity. Directed by Jason Todd Ipson, the film follows Jake, a man humorously entangled in a love triangle while pretending to be Italian to win over Marisa, a spirited veterinarian. The stellar performances by Jay Jablonski and Cerina Vincent bring warmth and authenticity to their characters, making their journey relatable and enjoyable. Produced by David M. Garonzik and Jaime Burke, this film masterfully blends romance and comedy with cultural nuances, offering a light-hearted and heartwarming narrative. The engaging storyline is complemented by Peter Rafelson’s lively soundtrack, featuring spirited Italian folk tunes and classic American hits. Garnering accolades like the Audience Award for Best Film at the Dahlonega International Film Festival, Everybody Wants to Be Italian is a must-watch for anyone seeking a feel-good film that celebrates the quirks of love and the joy of togetherness.

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White Men Can't Jump (HBO)

White Men Can't Jump (HBO)
Streetball hustles unite unlikely basketball duo

Released: 1992

Platform: Max

Rating: R

Run time:

Cast
Woody Harrelson, Wesley Snipes, Rosie Perez, Tyra Ferrell

White Men Cant Jump is a must-watch film for anyone who enjoys a mixture of comedy, drama, and sports. Directed by Ron Shelton and starring Woody Harrelson and Wesley Snipes, this 1992 gem brings to life the vibrant streetball culture of Los Angeles, blending humor with compelling interracial dynamics. Harrelson and Snipes play rival basketball hustlers who ultimately join forces, delivering high-energy performances that keep viewers entertained from start to finish. The films authenticity is elevated by on-site shooting at real street basketball courts and actors wearing their own clothes. Rosie Perez adds another layer of charm as Gloria, an aspiring Jeopardy! contestant. With a captivating soundtrack featuring artists like Queen Latifah and Riff, White Men Cant Jump transcends typical sports films, offering meaningful quotes and thought-provoking moments. For its unique blend of heart, humor, and hustle, this movie stands the test of time and is a delightful watch for diverse audiences.

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Hannah and Her Sisters (HBO)

Hannah and Her Sisters (HBO)
Exploration of family dynamics and personal crises

Released: 1986

Platform: Max

Rating: PG-13

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Cast
Woody Allen, Mia Farrow, Michael Caine, Barbara Hershey, Dianne Wiest, Lloyd Nolan, Max von Sydow, Carrie Fisher

Hannah and Her Sisters, directed by Woody Allen, is a poignant and humorous 1986 American comedy-drama that intricately explores the lives of three sisters—Hannah, Lee, and Holly. Through the lens of Thanksgiving dinners hosted by Hannah, the film delves into the sisters emotional intricacies, familial bonds, and relational complexities. Shot primarily in New York City, it showcases Allens affection for the city and features standout performances from Mia Farrow, Barbara Hershey, Dianne Wiest, Michael Caine, and Woody Allen himself. The film’s authenticity is heightened by Allen’s choice to allow actor improvisation, making the interactions feel genuine and relatable. The story's charm is further amplified by its award-winning screenplay and captivating cinematography. Hannah and Her Sisters garnered multiple accolades, including three Academy Awards. With a compelling narrative, remarkable performances, and a heartfelt soundtrack, this film is a must-watch for aficionados of nuanced, character-driven storytelling.

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The Weekend (HBO)

The Weekend (HBO)
Comedic getaway sparks unexpected romantic complications

Released: 2019

Platform: Max

Rating: R

Run time:

Cast
Sasheer Zamata, Tone Bell, DeWanda Wise, Y'lan Noel, Kym Whitley

The Weekend (HBO) is a refreshing 2019 romantic comedy that diverges from typical rom-com clichés, offering viewers a genuinely engaging and heartfelt experience. Directed by Stella Meghie, the film showcases Sasheer Zamata as Zadie, whose weekend getaway at her mothers bed and breakfast turns into a rollercoaster of emotions with her ex-boyfriend, Bradford (Tone Bell), and his new girlfriend, Margo (DeWanda Wise). Set against beautiful and captivating locations, the movie delivers comedic awkwardness, poignant revelations, and meaningful self-discovery. Stellar performances from the cast and a unique indie soundtrack by Robi Botos enhance its charm, creating a compelling narrative of love, growth, and forgiveness. The clever, relatable dialogues, combined with the talented casts chemistry, make The Weekend an enjoyable and thought-provoking watch for those seeking a fresh take on romance and comedy.

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Mistress America (HBO)

Mistress America (HBO)
Ambitious student navigates life with adventurous stepsister

Released: 2015

Platform: Max

Rating: R

Run time:

Cast
Greta Gerwig, Lola Kirke

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Fever Pitch (HBO)

Fever Pitch (HBO)
Obsessive baseball fan struggles with romantic relationship

Released: 2005

Platform: Max

Rating: PG-13

Run time:

Cast
Drew Barrymore, Jimmy Fallon

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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

Run time:

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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I, Tonya (HBO)

I, Tonya (HBO)
Tonya Harding's gritty rise and tragic downfall

Released: 2017

Platform: Max

Rating: R

Run time:

Cast
Caitlin Carver, Margot Robbie, Sebastian Stan, Julianne Nicholson, Bobby Cannavale, Allison Janney

I, Tonya, a 2017 biographical sports black comedy-drama, offers a riveting portrayal of figure skater Tonya Hardings tumultuous life, from her challenging childhood to her infamous role in the 1994 Winter Olympics controversy. Directed by Craig Gillespie and penned by Steven Rogers, the film stands out with its mockumentary format, featuring gripping interviews and sensational performances by Margot Robbie as Tonya, Sebastian Stan as Jeff Gillooly, and Allison Janney, who earned an Academy Award for her role as Tonyas abrasive mother. The movie sheds light on the complexities of truth, ambition, and societal pressures, highlighted by compelling quotes like, America. They want someone to love, but they want someone to hate. The powerful soundtrack adds a nostalgic touch, further enhancing the film’s emotional depth. Whether you're a sports enthusiast or a fan of masterful storytelling, I, Tonya is a must-watch for its intense drama, dark humor, and thought-provoking narrative.

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Gary Gulman: Born on 3rd Base | Now Streaming

Gary Gulman: Born on 3rd Base | Now Streaming
Gary Gulman's humor-filled streaming special

Released: 2

Platform: Max

Rating: T

Run time:

Cast

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Rory Scovel: Religion, Sex, and a Few Things In Between

Rory Scovel: Religion, Sex, and a Few Things In Between
Rory Scovel tackles provocative themes in comedy

Released: 2

Platform: Max

Rating: T

Run time:

Cast

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The Devil Wears Prada (HBO)

The Devil Wears Prada (HBO)
Ambitious journalist navigates high-fashion magazine world.

Released: 2006

Platform: Max

Rating: PG-13

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Cast
Meryl Streep, Anne Hathaway, Stanley Tucci, Simon Baker, Emily Blunt, Adrian Grenier

The Devil Wears Prada, directed by David Frankel and based on Lauren Weisbergers best-selling novel, is an engaging drama-comedy that premiered in 2006. It follows Andrea Sachs, played by Anne Hathaway, a naive young journalist who becomes the assistant to Miranda Priestly, the formidable editor of Runway magazine. Meryl Streep delivers a chilling and memorable performance as Miranda, with an icy demeanor that has become iconic. Stanley Tucci and Emily Blunt add depth and humor, portraying the intricacies of the high-pressure fashion world with nuanced performances. Notably, the film features spectacular fashion, thanks to costume designer Patricia Field. With award-winning performances, unforgettable quotes, and a soundtrack that complements its vibrant scenes, this film offers both a critical look at the fashion industry and a compelling story of personal growth. Whether for its stellar cast, insightful narrative, or striking visuals, The Devil Wears Prada is a must-watch.

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Ted 2 (HBO)

Ted 2 (HBO)
Mischievous teddy bear fights for legal rights

Released: 2015

Platform: Max

Rating: R

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Cast
Mark Wahlberg, Seth MacFarlane, Amanda Seyfried, Giovanni Ribisi, John Slattery, Jessica Barth, Morgan Freeman

Ted 2, directed by Seth MacFarlane, is a hilarious sequel to the 2012 hit film Ted. With a blend of heart and humor, it follows the beloved teddy bear, Ted, and his best friend, John Bennett (Mark Wahlberg), as they navigate a legal battle to prove Teds personhood and save his marriage. The witty screenplay by MacFarlane, Alec Sulkin, and Wellesley Wild, combined with a stellar cast including Amanda Seyfried as Teds spirited lawyer, makes for an engaging cinematic experience. Seth MacFarlanes unique comedic voice shines through Teds character, delivering a mix of charm and vulgarity that is both endearing and laugh-out-loud funny. Noteworthy cameos, including Morgan Freeman as a civil rights attorney, add depth and intrigue. Inspired by real legal struggles for non-human rights, Ted 2 offers not just comedy but a thought-provoking narrative. With its memorable quotes, delightful soundtrack, and commercial success, its a must-watch for comedy lovers seeking more than just laughs.

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Baby Mama (HBO)

Baby Mama (HBO)
Career woman hires surrogate, chaotic hilarity ensues.

Released: 2008

Platform: Max

Rating: PG-13

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Cast
Tina Fey, Amy Poehler, Sigourney Weaver, Greg Kinnear, Dax Shepard, Romany Malco, Steve Martin

Baby Mama (HBO) (2008) About Baby Mama Baby Mama is a heartwarming comedy-drama that takes you on a rollercoaster of emotions and laughter. The plot centers on a successful, single businesswoman, portrayed by the ever-charming Tina Fey, who yearns for motherhood but faces infertility. Enter Amy Poehler, playing the quirky and unpredictable surrogate, adding chaos and hilarity to the mix. This unlikely duo must navigate the intricacies of pregnancy and the unexpected hurdles of impending motherhood. Actors Tina Fey’s stellar performance as Kate Holbrook, combined with Amy Poehler’s humorous portrayal of Angie Ostrowiski, creates a delightful dynamic. The supporting role by Greg Kinnear as the kind-hearted juice bar owner adds depth and warmth to the narrative. Making / Production Directed and written by Michael McCullers, Baby Mama infuses humor into the theme of motherhood, making it both relatable and entertaining. The film’s well-crafted screenplay and engaging storyline promise a good laugh and heartfelt moments. Why Watch? Watch Baby Mama for its brilliant comedic timing, the dynamic chemistry between Fey and Poehler, and its touching storyline. It’s a perfect blend of humor and heart, making it a must-watch for anyone needing a dose of laughter and warmth.

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Aqua Teen Forever: Plantasm

Aqua Teen Forever: Plantasm
Animated adventure of supernatural fast-food items

Released: 2022

Platform: Max

Rating: R

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Cast
Dana Snyder, Carey Means, Dave Willis, Dave Willis

Aqua Teen Forever: Plantasm, released in 2022, invites viewers into the bizarre and hilarious world of the Aqua Teens—Frylock, Master Shake, and Meatwad. This film embarks on a rollicking adventure against the backdrop of zany humor and unconventional storytelling. The trio, joined by their lewd neighbor Carl, faces off against the tyrannical corporate overlord Amazin. Engaging dialogues, unpredictable plots, and frantic humor guarantee nonstop entertainment. With intricate animation, a creatively rich script, and stellar voice acting from Dana Snyder, Carey Means, and Dave Willis, Aqua Teen Forever: Plantasm extends the beloved series into an exciting new territory. The movie's uniqueness lies in its delightfully eccentric characters and signature comical style. For anyone seeking a wild, comedic journey filled with memorable lines, quirky music, and unmatched animation, this film is a must-watch. Dive into the absurdity and laughter that only the Aqua Teens can deliver!

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Real Time with Bill Maher | Season 22 Now Streaming | Max

Real Time with Bill Maher | Season 22 Now Streaming | Max
Bill Maher's Season 22 streaming on Max

Released: 2

Platform: Max

Rating: T

Run time:

Cast

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Our Flag Means Death | Now Streaming | Max Original

Our Flag Means Death | Now Streaming | Max Original
Piracy-themed comedy streaming on Max Original

Released: 2

Platform: Max

Rating: T

Run time:

Cast

Our Flag Means Death is a must-watch comedy sitcom streaming on HBO Max, inspired by the audacious true story of Stede Bonnet, a wealthy aristocrat who abandons his privileged life to become a pirate. Created by David Jenkins, known for his work on People of Earth and The Flight of The Conchords, the series is a delightful blend of history and humor. Starring Rhys Darby as the quirky and inexperienced pirate captain, and Taika Waititi as a surprisingly sensitive Blackbeard, the show features witty dialogue, charming characters, and comical adventures. With its clever writing, exceptional performances, and a uniquely fun take on historical events, Our Flag Means Death promises an engaging and entertaining viewing experience. Catch it now to enjoy the captivating transformation of a gentleman into a pirate amidst laughter and historical intrigue.

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Curb Your Enthusiasm | The Final Season Now Streaming

Curb Your Enthusiasm | The Final Season Now Streaming
Final season of witty, socially awkward antics

Released: 2

Platform: Max

Rating: T

Run time:

Cast

Curb Your Enthusiasm: The Final Season is a must-watch for anyone who appreciates sharp wit and limitless humor. This season delivers the same relentless, situational comedy that has cemented Larry Davids series as iconic. Larry Davids portrayal of a fictionalized version of himself, perpetually tangled in lifes absurd predicaments, ensures a consistent stream of laughs and relatable cringe-worthy moments. The improvisational nature of the shows dialogue gives each episode a spontaneous feel, making the interactions genuinely hilarious. Guest appearances from various celebrities add an extra layer of charm and surprise. The humor, often stemming from the everyday and mundane, is elevated by superb performances from the cast, including Jeff Garlin and Susie Essman. Combined with its award-winning storytelling and nostalgic, catchy soundtrack, this final season offers both closure and endless entertainment, making it essential viewing for fans and newcomers alike.

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About This Collection

Sharp, clever films streaming on HBO Max.

HBO Max offers a delightful selection of witty movies that blend clever humor with smart storytelling. From sharp comedies to satirical dramas, these films provide laugh-out-loud moments and thought-provoking dialogue. Explore the diverse world of witty movies on HBO Max and enjoy narratives that entertain and stimulate the mind. Don't miss out on these clever cinematic gems.

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