1990s Movies on HBO Max: Must-Watch Classics for Nostalgia

A Night at the Roxbury is a 1998 American comedy that brings the infectious humor of the famous The Roxbury Guys sketches from Saturday Night Live to the big screen. Directed by John Fortenberry and starring Will Ferrell and Chris Kattan, the film centers on two hilariously inept brothers, Steve and Doug Butabi, who dream of getting into LAs hottest nightclub, the Roxbury, and opening their own club. The film charms viewers with its quirky humor, memorable dance moves, and 90s nostalgia. Produced by Lorne Michaels and Amy Heckerling, and featuring standout performances by Ferrell, Kattan, and Molly Shannon, the movie is filled with laugh-out-loud moments. Its cult status is bolstered by iconic lines and memorable scenes, especially the characters' signature head-bobbing to What is Love by Haddaway. For fans of SNL and '90s comedy, A Night at the Roxbury is a must-watch that combines humor, heart, and a fantastic soundtrack.

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The Late Shift (1996) is a gripping and dramatic HBO film that delves into the tumultuous transition period in U.S. late-night television following Johnny Carsons departure from The Tonight Show at NBC. Directed by Betty Thomas, and based on Bill Carters novel, the film offers a fascinating behind-the-scenes look at the intense rivalry between David Letterman and Jay Leno for the coveted late-night spot. Featuring stellar performances from Kathy Bates, who earned an Academy Award nomination for her role as Helen Kushnick, John Michael Higgins as David Letterman, and Daniel Roebuck as Jay Leno, The Late Shift delivers a nuanced and compelling portrayal of the television industry. With a finely executed screenplay by George Armitage, intriguing quotes, and a matching soundtrack by Ira Newborn, this film is a must-watch for anyone interested in media history, television drama, or simply seeking an exceptionally well-crafted story.

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Oasis: Supersonic is a must-watch for any music lover or fan of the iconic British rock band Oasis. This 2016 documentary, helmed by director Mat Whitecross and produced by Asif Kapadia, delves into the bands tumultuous rise to fame, from two unruly brothers in Manchester to global rock icons. Featuring intimate interviews and unseen footage, it provides a raw and engaging look at the chaos, controversy, and creativity that defined Oasis. The film also benefits from insightful commentary by members like Liam and Noel Gallagher, as well as the bands 20th anniversary Knebworth concerts. Whether youre a long-time fan or new to their music, Oasis: Supersonic offers a compelling narrative filled with nostalgia, exceptional music, and rare personal insights that make it an essential watch.

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The Little Things (2021), directed by John Lee Hancock, is a gripping psychological thriller that keeps audiences on the edge of their seats. Centered around a weary deputy sheriff, Deke (Denzel Washington), and an ambitious detective, Jim Baxter (Rami Malek), the film delves deep into their hunt for a serial killer. The narratives focus on the little things that could make or break a case adds layers of suspense and intrigue. Denzel Washington's nuanced performance, portraying a seasoned lawman haunted by his past, is both compelling and deeply human. Rami Malek's portrayal of Detective Baxter brings a palpable intensity and vulnerability. Jared Leto's chilling performance as the prime suspect, Albert Sparma, earned him an Oscar nomination for Best Supporting Actor. With a script that dates back to 1993 and interesting trivia like the reunion of Washington and Leto from Virtuosity (1995), The Little Things promises a cinematic experience enriched with nostalgia and powerful storytelling. The film's captivating performances and intricate plot make it a must-watch for thriller enthusiasts.

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Music from Another Room is a deeply emotional and romantic film that explores the intriguing concept of destiny. Starring Jude Law, Jennifer Tilly, and Jon Tenney, the film weaves a touching narrative about a young man named Danny who believes he is destined to marry a girl he helped deliver as a child. Directed by Charlie Peters and produced by Brad Krevoy and Steve Stabler, the film was initially intended for theaters but premiered on HBO in 1998. It features a compelling and relatable cast, a beautiful soundtrack with tracks from Leo Kottke and The Be Good Tanyas, and cinematically engaging scenes courtesy of John Thomas. The storyline of love, fate, and personal transformation makes it a must-watch for anyone drawn to heartfelt narratives. Its rich character development and poignant dialogues like Fates behind everything add depth, making it resonate long after the credits roll.

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King Richard (2021) is a compelling biographical drama that tells the inspiring story of Richard Williams and his relentless dedication to molding his daughters, Venus and Serena Williams, into tennis legends. Directed by Reinaldo Marcus Green and produced by Star Thrower Entertainment, the film highlights themes of perseverance, family support, and unwavering commitment to ones dreams. Will Smith delivers a captivating performance as Richard Williams, showcasing the characters determination and charm. Supported by Aunjanue Ellis as the strong, nurturing mother, and stunning portrayals by Saniyya Sidney and Demi Singleton as Venus and Serena, the cast brings a remarkable authenticity to the story. Unique for its focus on the parent behind the sports icons, the movie offers a fresh perspective on a well-known narrative. With executive producers Venus and Serena Williams and a powerful soundtrack featuring Beyoncé, King Richard is a must-watch for its heartwarming and motivational storytelling.

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Trial by Fire directed by Edward Zwick, is an intensely gripping biographical drama that brings to light the troubling case of Cameron Todd Willingham, executed for allegedly killing his three children. Despite scientific evidence and expert testimonies supporting his innocence, these were ignored, highlighting severe flaws in the criminal justice system. The films exceptional production by Allyn Stewart, Kipp Nelson, Alex Soros, and Edward Zwick offers viewers a thought-provoking exploration of human prejudice and the devastating impact of wrongful convictions. With riveting performances from Jack OConnell as Willingham and Laura Dern as Elizabeth Gilbert, the film powerfully portrays the human side of this tragedy. The movie is not only a compelling drama but also a critical commentary on justice, making it a must-watch for those interested in thought-provoking cinema that challenges societal issues.

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If These Walls Could Talk is a powerful and thought-provoking anthology film that explores the controversial topic of abortion through the lives of three women in different eras—1952, 1974, and 1996. Anchored by stellar performances from Demi Moore, Sissy Spacek, and Cher, the film delves into the emotional and moral dilemmas faced by each woman. Directed by Cher and Nancy Savoca, the narrative unfolds within a single house, cleverly illustrating the shifting societal attitudes towards abortion over five decades. With its evocative soundtrack by Cliff Eidelman and rich, layered storytelling, If These Walls Could Talk offers a gripping and empathetic portrayal of womens rights and personal choice. This compelling piece of cinema not only challenges viewers to reflect on the issue of abortion but also serves as a significant cultural commentary that remains relevant today. Dont miss this HBO classic that continues to spark meaningful conversation.

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Sleepless in Seattle, released in 1993 under the direction of Nora Ephron, delivers a timeless romantic comedy-drama that remains beloved today. This heartwarming tale follows Sam Baldwin (Tom Hanks), a grieving widower whose life takes an unexpected turn when his young son calls into a radio show, sparking interest from women across the nation, including journalist Annie Reed (Meg Ryan). The script, crafted by Ephron along with David S. Ward and Jeff Arch, deftly weaves themes of love, loss, and serendipity. Notably, the film is enriched by a soulful score from Marc Shaiman and standout performances from its cast. Trivia buffs will appreciate insights like the inspiration behind the film's title and the surprising scarcity of shared screen time between Hanks and Ryan. With its endearing storyline and memorable quotes, Sleepless in Seattle is a beautifully crafted cinematic experience that evokes both laughter and tears, making it a must-watch for any romantic at heart.

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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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Definitely, Maybe is a charming 2008 film that offers a fresh take on the classic romantic comedy. Directed by Adam Brooks, the movie stars Ryan Reynolds as Will Hayes, who recounts his past relationships to his inquisitive daughter, Maya, played by Abigail Breslin, transforming his love life into an intriguing mystery. Set against the vibrant backdrop of New York City, with scenes filmed in iconic locations like Central Park and Brooklyn, the film captures the essence of romantic nostalgia. The stellar cast, including Elizabeth Banks and Isla Fisher, delivers engaging performances, with Reynolds showcasing his charisma and range. Breslin's heartfelt portrayal of young Maya adds an emotional depth that resonates. With a soundtrack featuring timeless hits like Bob Dylan's Times They Are A-Changin', the film weaves music beautifully into its narrative. The definitely, Maybe boasts clever storytelling and delightful performances making it a must-watch for romantic comedy enthusiasts.

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Mannequin Two: On the Move, a 1991 romantic-comedy-fantasy from HBO, charms with its unique storyline and delightful performances. Directed by Stewart Raffill and set in a Philadelphia department store, this sequel breathes life into an enchanted prince-turned-mannequin, who can only be freed by a kiss from a special girl. William Ragsdale plays Jason, the endearing employee aiding the prince, while Kristy Swanson enchants as Jessie, the key to breaking the curse. Adding to the films humor is Terry Kisers portrayal of Count Spretzle, the comical villain. Though it didnt find box office success, its quirky plot and heartwarming moments have earned it a cult following. With memorable quotes and a charming soundtrack, Mannequin Two: On the Move is a delightful escape that promises laughter, romance, and a touch of magic—a perfect blend for a nostalgic movie night.

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