139 Witty TV Shows on HBO Max: Laugh, Think, Enjoy

More about Beth Stelling: Girl Daddy

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More about Amy Schumer: Live at the Apollo (HBO)

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Fake Famous is an eye-opening documentary that delves into the mechanics of modern-day social media fame and its profound impact. Directed by Nick Bilton, this HBO feature offers a revealing look at how easily one can fabricate an influential online persona. The documentary follows a fascinating social experiment involving three ordinary individuals who are transformed into influencers through tactics like buying followers and staging fake luxury lifestyles. Through engaging interviews and behind-the-scenes footage, Bilton explores the disturbing reality behind social media fame, making viewers question the authenticity of what they see online. With exceptional editing by Tyler H. Walk and compelling cinematography by Guy Mossman, the film is both visually captivating and thought-provoking. Featuring authentic performances from Christopher Bailey, Dominique Druckman, and Wylie Heiner, Fake Famous is a must-watch for anyone curious about the illusions of social media and its cultural implications.

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Tom Jones (1963), directed by Tony Richardson and adapted from Henry Fieldings classic novel, is a cinematic delight set in 18th-century England. The film chronicles the rollicking adventures of Tom Jones, an illegitimate yet irresistibly charming young man who wins the hearts of many, including the beautiful Sophie Western. Starring the captivating Albert Finney as Tom and Susannah York as Sophie, the film brings history to life with wit, elegance, and a spirited rebelliousness. Noteworthy for its innovative techniques such as breaking the fourth wall and humorous sped-up motion sequences, Tom Jones was groundbreaking for its time. The lush Technicolor settings and John Addisons award-winning soundtrack only add to its appeal. Winner of four Academy Awards, including Best Picture and Best Director, this movie is a must-watch for its unique blend of humor, romance, and social commentary. Dive into an engaging period piece that continues to entertain and charm audiences.

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Larry David: Curb Your Enthusiasm on HBO offers a captivating blend of humor and wit, presenting a mockumentary-style comedy that chronicles the life of comedian Larry David. Created and produced by David, the shows improvisational nature ensures every episode is fresh and unpredictably hilarious. His honest yet awkward encounters, coupled with outstanding performances by Cheryl Hines as his patient wife and Jeff Garlin as his manager, create a balance of chaos and charm. The shows authenticity, inspired by Davids own experiences, has earned critical acclaim and several awards. With its unique comedic flair, iconic quotes, and memorable music like Luciano Michelinis Frolic, this series is a must-watch for anyone craving laughter and relatable life scenarios. Its an engaging dive into the comedic genius of Larry David, perfect for both long-time fans and newcomers.

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Wishful Drinking offers a compelling and deeply personal glimpse into the life of Carrie Fisher, best known for her iconic role as Princess Leia in the Star Wars franchise. Directed by Fenton Bailey and Randy Barbato, the HBO documentary captures Fishers sharp wit and candid humor as she shares intimate stories about her Hollywood upbringing, battles with addiction, and mental illness. Adapted from her popular 2008 stage performance, the film is a testament to Fishers resilience and unflinching honesty, making it an engaging watch. The unique production style by World of Wonder Productions adds an innovative touch, effectively blending sound effects with Fishers narrative to enhance both humorous and poignant moments. Perfect for fans of Fisher and those interested in personal tales of struggle and triumph, Wishful Drinking is a must-see for its heartfelt revelations and captivating storytelling.

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Frayed is a British-Australian comedy-drama series that stands out for its gripping plot and deeply relatable characters. Set in 1989, it follows a wealthy London housewife, Sammy Cooper, forced to return to her humble Australian hometown after her husbands death reveals their financial ruin. Created, written by, and starring Australian comedian Sarah Kendall, the series masterfully balances humor and raw human emotions, offering an authentic exploration of class disparity, pride, and buried pasts. The production quality is top-notch, with scenes shot in London and Sydney, and the music, featuring '80s hits, sets the perfect mood. The ensemble cast, including Matt Passmore as a former love interest and Robert Webb as Sammy's neurotic brother, adds depth and complexity. The clever screenplay ensures audiences are constantly engaged, making Frayed a must-watch for its blend of comedy, drama, and poignant life lessons.

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Avenue 5 is a must-watch for fans of witty, sharp, and imaginative storytelling. Created by the brilliant Armando Iannucci, this HBO series blends science fiction with comedy, set in a future where space tourism thrives. The show captures the chaos aboard the cruise ship Avenue 5, which, after technical failures, finds itself off-course, extending its journey to several years. Led by an outstanding cast, including Hugh Laurie as the charming yet incompetent Captain Ryan Clark, and Josh Gad as the obliviously vain billionaire Herman Judd, the characters bring humor and depth to an already enthralling premise. The production quality is top-tier, with impressive set designs and special effects. Fans of dark humor will appreciate Zach Woods' cynicism as Matt Spencer, while Rebecca Front’s role as the unofficial troubleshooter adds a relatable edge. Whether you're drawn to captivating sci-fi settings, enjoy high-quality comedic performances, or both, Avenue 5 offers an engaging and entertaining escape.

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More about David Cross: The Pride Is Back (HBO)

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More about Whoopi: Back to Broadway - The 20th Anniversary (HBO)

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Arli$$, an American sitcom aired on HBO from 1996 to 2002, offers a fascinating peek into the high-stakes world of sports management. Starring Robert Wuhl as the charismatic yet morally conflicted sports agent Arliss Michaels, the series combines humor, satire, and drama to explore the behind-the-scenes complexities of professional sports. With standout performances by Sandra Oh, Jim Turner, and Michael Boatman, the show delves into diverse issues such as race, sexuality, and media influence, making it both entertaining and thought-provoking. Notably, Arli$$ features cameos from real-life sports legends like Shaquille ONeal, adding authenticity and excitement. Its catchy theme song, Im in the Game, sets the tone for a captivating watch. For anyone interested in sports, sharp humor, or social commentary, Arli$$ is a must-see series that remains relevant and engaging.

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Bill Maher: The Decider is a must-watch stand-up comedy special for anyone who appreciates incisive humor and bold commentary. Released in 2007 by HBO, Mahers performance stands out for its fearless critique of politics, religion, and societal norms, delivered with his trademark satirical wit. Filmed live at the Berklee Performance Center in Boston, the special captures Mahers unique ability to blend humor with insightful commentary, engaging the audience while provoking thought. Fans of intelligent comedy and political satire will find Mahers unapologetic perspectives both entertaining and enlightening. From his witty takes on controversial topics to his memorable quotes, such as, We need more people speaking out, Maher proves why hes a staple in the realm of political comedy. Whether youre a long-time viewer or new to his work, The Decider is a powerful reminder of the importance of free thought and rebellion against conformity.

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Released in 2023, The Broadcast Boys Show is a must-watch for anyone intrigued by the high-paced world of broadcast journalism. This captivating series weaves an exhilarating narrative around a group of boys who unexpectedly join a national broadcast team. With its blend of thrilling scoops and ethical dilemmas, the show offers a rich tapestry of emotions and drama. The production, helmed by renowned figures Johnathan Hartmann and Paul McNealy, meticulously recreates the reality of live broadcasts, enhancing the viewing experience. Stellar performances by Jordan Elkins and Scott Harris breathe life into their characters, making the series engaging and relatable. Adding to the allure, the shows dynamic soundtrack, featuring The Hues Brothers and Stewart Bell, and its impressive Emmy nominations underline its quality. For a journey into the heart of broadcast journalism, The Broadcast Boys Show is an unmissable treat.

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The Chris Rock Show on HBO is a must-watch for anyone who appreciates sharp, unfiltered comedy. Hosted by Chris Rock, one of Americas top comedians, the show delivers a unique blend of raw humor, insightful commentary, and stellar celebrity interviews. The live audience setting adds a dynamic energy to Rocks weekly monologues and sketches, making each episode lively and unpredictable. With an impressive cast including the energetic Grandmaster Flash as DJ and witty Wanda Sykes, the show masterfully combines humor and social commentary, offering a reflective take on contemporary society and pop culture. Its award-winning writing and high-profile guest stars further elevate the shows appeal. Whether youre a comedy enthusiast or just looking for intelligent entertainment, The Chris Rock Show offers an engaging and thought-provoking experience that remains relevant today.

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Will Ferrell: Youre Welcome America. A Final Night With George W. Bush is a must-watch for comedy lovers and political enthusiasts alike. This 2009 HBO special showcases Ferrells brilliant ability to blend satire and impersonation, bringing to life the quirks and foibles of the 43rd President in a way that is both hilarious and thought-provoking. Produced by an accomplished team that includes Adam McKay and director Marty Callner, the show was initially a hit on Broadway before being adapted for television. Ferrell's performance, supported by actors Pia Glenn and Patrick Ferrell, offers a comedic yet critical lens through which to view George W. Bush's life, from his Texas roots to his post-presidency days. Taped before a live audience, the special resonates with an interactive vibe, enhancing the overall viewing experience. Nominated for an Emmy, it blends sharp political commentary with laugh-out-loud moments, promising a memorable watch.

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Chris Rock: Bigger & Blacker is an electrifying stand-up comedy special from 1999 that continues to resonate today. Filmed at Harlems iconic Apollo Theater and directed by Keith Truesdell, the HBO special showcases Chris Rocks incisive social, political, and celebrity commentary. Known for his sharp wit and no-holds-barred humor, Rock tackles subjects like gun control, tax cuts, and relationships, making the show both entertaining and thought-provoking. With its Grammy-winning success and critical acclaim, Bigger & Blacker is more than just comedy; its a powerful performance reflecting Rocks comedic genius and insightful social critique. Dont miss this landmark special that solidified Rock as one of the premier stand-up comedians of our time.

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Insecure, premiering on HBO in 2016, offers a refreshing and candid portrayal of the professional and personal lives of two African American women, spearheaded by the talented Issa Rae. Loosely based on Raes web series Awkward Black Girl, the show delves into themes of racial identity, relationships, and everyday struggles, making it exceptionally relatable and poignant. Set primarily in South Los Angeles, Insecure gives viewers a glimpse into authentic locations and vibrant community life. With standout performances by Issa Rae, Yvonne Orji, Jay Ellis, and Natasha Rothwell, each episode weaves humor, heartbreak, and hope into the narrative, reflecting the intricate layers of real-life experiences. Acclaimed for its honest storytelling and cultural representation, the series has garnered numerous accolades, including Golden Globe and Emmy nominations for Rae. The dynamic soundtrack, featuring artists like Jazmine Sullivan and Jorja Smith, complements the show’s vibrant essence. For anyone seeking an honest, entertaining, and thought-provoking series, Insecure is a must-watch.

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More about Shayla Rivera: It's Not Rocket Science (HBO)

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2 Dope Queens on HBO is a must-watch series that brings the hilarity and charm of the hit podcast to the screen in four one-hour specials. Hosted by the dynamic duo Jessica Williams and Phoebe Robinson, these specials are brimming with candid, side-splitting discussions on topics like hair, hot peen, and black nerdom. Filmed live at Brooklyns iconic Kings Theatre and directed by the esteemed Tig Notaro, the show captures the electric chemistry between Jessica and Phoebe and their ability to make every conversation feel engaging and relatable. Beyond the humor, “2 Dope Queens” is insightful and empowering, featuring guest appearances by popular comedians and celebrities, and incorporating exclusive content not found in the podcast. Their profound yet entertaining dialogue offers a fresh and genuine perspective, making each episode delightful and thought-provoking. With a soundtrack that perfectly complements each theme, this series is a joyous celebration of friendship and humor that everyone can enjoy.

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More about Frankie Quiñones: Superhomies (HBO)

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The Story of Late Night, released in 2021, is an enthralling docuseries that delves into the transformative history of late-night television, chronicling its profound impact on American pop culture and society over 60 years. Directed by Bill Carter and produced by CNN Original Series and Cream Productions, the series features rare archival footage and over 150 original interviews with late-night luminaries like Jay Leno and Jimmy Fallon. Spanning six hour-long episodes, the show explores key eras and showcases the dynamic evolution of late-night TV, making it a must-watch for anyone interested in television history, comedy, or cultural shifts. The compelling storytelling, combined with iconic musical highlights, makes The Story of Late Night an informative and nostalgic journey not to be missed.

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Jerrod Carmichael: 8 is a must-watch HBO stand-up special that showcases Jerrod Carmichaels distinctive comedic flair. Directed by fellow comedian Bo Burnham and filmed at the Masonic Hall in New York City, this performance is a masterclass in blending humor with thought-provoking commentary. Jerrods unique mix of observational humor, social consciousness, and personal introspection captivates the audience, making them laugh while also reflecting on deeper issues. Carmichael's engaging presence and intimate interaction with the crowd add a special touch to the show, creating a memorable viewing experience. Fans of smart, reflective comedy will appreciate how Carmichael uses his platform to tackle complex social and political topics. Not merely a comedian, but a commentator on modern life, Jerrod offers viewers a blend of wit and wisdom that's hard to find elsewhere. Whether you're a comedy aficionado or someone looking for an insightful laugh, Jerrod Carmichael: 8 is well worth your time.

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Angie Tribeca is a must-watch for comedy enthusiasts, offering a side-splitting spoof of classic police procedurals. Created by Steve Carell and Nancy Walls Carell, the series follows the dedicated yet hilariously deadpan detective Angie Tribeca, superbly played by Rashida Jones, and her dim-witted partner, Jay Geils. The show boasts a stellar cast, including Jere Burns and Deon Cole, whose comedic performances enhance the absurdity of their serious predicaments. Each episode is a clever parody filled with witty dialogues, unpredictable humor, and meticulously executed gags, making it impossible not to laugh. From its unique title sequences to its use of rescue dogs, Angie Tribeca is an entertaining gem that challenges convention and delights with its originality. Tune in for ingenious comedy and stay for the razor-sharp satire—a perfect binge for those seeking a comedic escape.

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Fast Foodies is a must-watch reality TV series that debuted in 2020, bringing together celebrated chefs Kristen Kish, Jeremy Ford, and Justin Sutherland. Each episode features these culinary stars as they compete to recreate and reinvent a celebrity guests favorite fast food dish. The show masterfully blends culinary skill, creativity, and humor, providing an entertaining and engaging experience for viewers. Produced by Ugly Brother Studios for truTV, the relaxed yet competitive atmosphere highlights not only the chefs exceptional talents but also their unique personalities. The series offers fascinating behind-the-scenes insights into how beloved fast food items from global chains like McDonald’s and KFC are ingeniously reimagined. Filmed during the height of the COVID-19 pandemic with strict safety protocols in place, Fast Foodies showcases the resilience and innovation of the culinary world. With memorable quotes and an eclectic soundtrack that enhances the narrative, this show is perfect for food enthusiasts and reality TV fans alike.

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Shoulder Arms is a timeless classic that showcases Charlie Chaplins unparalleled talent in blending humor with poignant commentary. This silent comedy, set during World War I, tells the tale of an ordinary boot camp private with dreams of heroism, providing audiences an escape with a series of hilarious and heartwarming moments. Chaplins innovative approach to portraying war through satirical and slapstick humor not only entertains but also offers a light-hearted perspective on a sensitive topic. Featuring striking performances, including the versatile roles by Chaplin's brother, Syd, and the enchanting presence of Edna Purviance, Shoulder Arms captivates with its comic timing and memorable characters. The film's historical and cultural significance has earned it a revered spot in the National Film Registry. Watching Shoulder Arms is an opportunity to appreciate early cinematic genius and enjoy a masterpiece that continues to inspire laughter and reflection over a century later.

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More about George Lopez: It's Not Me, It's You (HBO)

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More about T.J. Miller: Meticulously Ridiculous (HBO)

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The Private Life of Henry VIII is a captivating British film that offers a dramatic and engaging portrayal of the notorious King Henry VIII and his tumultuous marriages. Directed by the acclaimed Alexander Korda, this 1933 film not only highlights historical events but also brings them to life with dynamic performances, particularly by Charles Laughton, whose Oscar-winning portrayal of the king is both charismatic and compelling. Featuring Merle Oberons graceful Anne Boleyn and Elsa Lanchesters witty Anne of Cleves, the movie seamlessly blends drama with subtle humor. Its remarkable achievement as the first non-Hollywood film to win an Academy Award makes it a must-watch for film enthusiasts and history buffs alike. The films richly composed music by Kurt Schröder further adds to its allure, making The Private Life of Henry VIII an immortal classic that brilliantly captures the complex life of one of historys most fascinating monarchs.

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More about Entre Nos: LA Meets NY (HBO)

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More about Lewis Black: Red, White & Screwed (HBO)

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Divorce, an American television series on HBO, offers an engaging and heartfelt exploration of the complexities of ending a long-term relationship. Created by Sharon Horgan, the show features powerful performances from Sarah Jessica Parker and Thomas Haden Church, who compellingly portray Frances and Robert, a middle-aged couple navigating a protracted divorce. With its nuanced and often humorous look at broken relationships and the difficult paths toward healing, Divorce resonates with many viewers experiencing similar mid-life crises. The series stands out for its realistic portrayal of divorce, insightful writing, and talented cast, including Molly Shannon and Tracy Letts, who add depth and humor to the storyline. The eclectic soundtrack and touching theme song by Alabama Shakes enhance the emotional journey. Praised for its authenticity and captivating performances, Divorce is worth watching for anyone interested in a sophisticated, relatable, and occasionally humorous take on modern relationships.

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More about D.L. Hughley: Unapologetic (HBO)

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More about Tig Notaro: Boyish Girl Interrupted (HBO)

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Robert Klein: Unfair & Unbalanced is an engaging stand-up comedy special from HBO, spotlighting the legendary humorist Robert Klein. Released in 2010, this show captures Kleins exceptional ability to blend sharp social commentary with witty musical interludes, ensuring a memorable viewing experience. Known for his insightful and biting humor, Kleins performance is both thought-provoking and hilariously relatable, making it an absolute must-watch for fans of intelligent comedy. The live audience setting adds an electrifying energy to the production, showcasing Kleins expert timing and stage presence. Notably, this special is his ninth for HBO, underscoring his enduring appeal and the high quality of his work. With clever quips about aging and political satire, Kleins unique voice shines through, making Unfair & Unbalanced a perfect pick for mature audiences seeking both laughter and reflection.

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I Married a Witch (1942) is a charming, timeless classic that beautifully blends fantasy, romance, and comedy, directed by the acclaimed René Clair. The film tells the whimsical story of a 17th-century witch, Jennifer, who, after being burned by Puritans, curses the Wooley family, only to fall in love with the latest Wooley centuries later. The stellar cast, including Veronica Lake as the enchanting witch and Fredric March as her ill-fated love interest, delivers captivating performances. Notably, this film inspired the beloved TV series Bewitched, showcasing its enduring influence. Despite production tensions and its lack of awards, it remains highly regarded, listed among the 1001 Movies You Must See Before You Die. With a delightful score by Roy Webb and memorable quotes, I Married a Witch is a must-watch for those who appreciate enchanting storytelling and classic Hollywood humor.

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Funny or Die Presents is a must-watch for any comedy enthusiast. Launched on HBO in 2010, the series is the brainchild of comedic geniuses Will Ferrell, Adam McKay, and Chris Henchy, co-founders of the popular comedy site Funny or Die. This show brilliantly compiles an assortment of hilarious sketches, animations, music videos, and mockumentaries, offering a diverse array of comedic styles. The production leverages HBO's format to deliver content that transcends typical web videos, providing a polished and ambitious comedy experience. Featuring a star-studded lineup including Will Ferrell, Zach Galifianakis, and Judd Apatow, the show boasts exceptional comedic talent, spotlighting some of their best works. With interesting facts like the premiere episode featuring the Drunk History: Douglass & Lincoln sketch, the series promises not just laughs but memorable, culturally relevant content. Whether you're a fan of Ferrell’s wit or Galifianakis's experimental humor, Funny or Die Presents offers a unique comedy adventure worth diving into.

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A King in New York (1957), directed and produced by Charlie Chaplin, is an essential watch for anyone interested in classic cinema, satire, and comedic drama. This film marks Chaplins final leading role, showcasing his unparalleled talent in a poignant narrative about a dethroned monarch navigating the complexities of modern media and societal values. Shot in color and produced in Europe due to Chaplins exile from the U.S., the film captures his fearless critique of contemporary politics and media sensationalism. Featuring memorable performances by Chaplin, Maxine Audley, and Jerry Desmonde, A King in New York remains a timeless masterpiece enriched with humor, profound quotes, and a moving soundtrack. Its historical significance and insightful commentary make it not just a film, but a crucial cultural artifact.

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Whitney Cummings: Im Your Girlfriend is a must-watch for anyone seeking a hilarious yet insightful examination of modern relationships and gender dynamics. Premiering on HBO in 2016, this stand-up comedy special showcases Whitney Cummings at her best, delivering sharp and witty observations with candor and authenticity. Filmed live at The Broad Stage in Santa Monica, California, and directed by renowned director Marty Callner, the one-hour show offers a unique blend of personal storytelling and observational humor. Cummings candid take on monogamy, societal constructs, and gender roles will resonate with many, making it both relatable and thought-provoking. Whether youre a fan of her sitcoms 2 Broke Girls and Whitney, or new to her comedy, this special promises an engaging and entertaining experience filled with laughter and genuine moments of reflection.

More about Whitney Cummings: I'm Your Girlfriend (HBO)

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