All 53 Maggie Gyllenhaal Movies (in Order)

Amber Powell
21 min readMar 18, 2024

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Dive into the world of Maggie Gyllenhaal as we uncover her diverse portfolio of movies. From leading roles to supporting characters, Gyllenhaal has shown versatility and talent in each film. Stay tuned as we discuss her most notable performances and delve into the cinematic journey of this remarkable actress.

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1. Waterland (1992)

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Waterland, “ a 1992 British drama directed by Stephen Gyllenhaal, takes viewers back in time to 1974 Pittsburgh as a high-school history teacher reflects on his past life during WWII. The film, based on the novel of the same name by Graham Swift, weaves together a complex tale of family, relationships, and the human experience, all set against the backdrop of war.

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2. A Dangerous Woman (1993)

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In the gripping drama “A Dangerous Woman, “ Martha Horgan, a bright yet sheltered woman with an intellectual impairment, lives with her aunt Frances in a small town. Known for telling the truth, even in the most difficult situations, she embarks on a journey of self-discovery and forms unexpected bonds.

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3. The Patron Saint of Liars (1998)

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The Patron Saint of Liars” is a compelling drama film from 1998, directed by Stephen Gyllenhaal. Based on a novel by Ann Patchett, the movie tells the tale of a woman named Eliza (played by Dana Delany) who escapes her abusive husband by running away and becoming pregnant. Seeking solace and a sense of belonging, she enrolls in a Catholic school for girls.

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4. Homegrown (1998)

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Homegrown” (1998) is a dark comedy set in the secluded paradise of NW California, where three unsuspecting marijuana farmhands experience a shocking twist when their boss is brutally murdered, leaving a new world of chaos and crime in their wake. Now, with a bloody thirst for freedom, they turn to harvesting, processing, and selling the precious crop themselves. As they embark on a treacherous journey into the dangerous world of drug trafficking, they must face corrupt cops, crime bosses, a ruthless killer pilot, and their own insatiable greed.

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5. Resurrection (1999)

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Resurrection” is a gripping 1999 drama film that tells the story of Elizabeth, a woman crippled in a tragic auto accident that took the life of her husband. In an unexpected turn of events, Elizabeth starts developing extraordinary healing powers. Initially, she uses these abilities to heal herself, but soon realizes that her powers are capable of reaching even deeper wounds — those between her and her estranged mother.

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6. Shake, Rattle and Roll: An American Love Story (1999)

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Shake, Rattle and Roll: An American Love Story” is a captivating drama that takes us on a journey through the 1950s music scene. A close-knit group of high school friends form a rock band, quickly gaining popularity as they capture the essence of the burgeoning rock ’n’ roll movement. As they gain fame, external forces such as record labels meddling in their creative decisions threaten to tear them apart.

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7. The Photographer (2000)

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The Photographer” is a 2000 American comedy-drama film about a Photographer who faces the dire consequences of losing everything dear to him. He must find ten magical photographs within a single evening or risk losing it all. As the night unfolds, the Photographer embarks on an intense and humorous journey through the intricate world of New York City.

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8. Cecil B. Demented (2000)

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In “Cecil B. Demented, “ the eccentric and insane film director, Cecil B.

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9. Riding in Cars with Boys (2001)

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Riding in Cars with Boys” is a 2001 heartfelt comedy-drama directed by Penny Marshall, starring Drew Barrymore, Steve Zahn, and Adam Garcia. Set in 1965, the film revolves around a young single mother who, despite her ambitious dreams of becoming a writer, faces the challenges of raising a son at the age of 15 and dealing with a drug-addicted husband.

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10. Donnie Darko (2001)

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In the dark and surreal world of Donnie Darko, a troubled teenager is pushed to the edge by enigmatic visions of a man in a large rabbit suit. The film, with its hypnotic visuals and haunting atmosphere, will leave viewers questioning the nature of reality and the consequences of manipulation.

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11. Confessions of a Dangerous Mind (2002)

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Confessions of a Dangerous Mind” is a thrilling, dark comedy film that retells the fascinating life of Chuck Barris, a well-known game show impresario whose memoir claimed he had been a CIA hitman. Directed by George Clooney, this cinematic experience stars Sam Rockwell as Chuck Barris, Drew Barrymore as Patricia Watson, and George Clooney himself in a small but significant role.

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12. 40 Days and 40 Nights (2002)

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40 Days and 40 Nights” is a heartwarming yet wild comedy about a young man named Matt who swears off masturbation for the forty days of Lent. As fate would have it, Matt encounters the love of his life, a captivating woman named Erin, and he struggles to resist his newfound desire for her. This hilarious romp explores the complexities of sexuality and sexual attraction, while showing that sometimes love can be found in the most unexpected places.

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13. Secretary (2002)

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Secretary” (2002) is a captivating drama-comedy that delves into the hidden world of sexual role playing and submission. Directed by Steven Shainberg and starring James Spader, Maggie Gyllenhaal, and Jeremy Davies, the film follows a young woman recently released from a mental hospital who takes on the position of secretary for a demanding lawyer. Their relationship soon spirals into a twisted, sadomasochistic affair that blurs the lines between professional and personal.

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14. Adaptation. (2002)

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Adaptation. (2002) weaves a tale of loneliness, driven by a struggling screenwriter’s desperate attempts to adapt the unconventional ‘The Orchid Thief’ by Susan Orlean. This quirky comedy-drama, directed by Spike Jonze and starring Nicolas Cage, Meryl Streep, and Chris Cooper, brings to life a unique world filled with unconventional characters and themes.

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15. Casa de los babys (2003)

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Casa de los babys” (2003) brings a poignant and dramatic look into South American family life while exploring the challenges of adoption in the region. Directed by John Sayles and starring Daryl Hannah, Maggie Gyllenhaal, and Mary Steenburgen, the film follows six women as they are forced to remain in the country while awaiting approval to adopt a baby.

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16. Mona Lisa Smile (2003)

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Mona Lisa Smile” takes viewers back to 1953, where a free-thinking art professor challenges traditional social roles at the prestigious Wellesley College for women. Julia Roberts stars as the influential and charismatic professor who encourages her students, played by Kirsten Dunst and Julia Stiles, to question their assumed futures and break free from societal norms.

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17. Criminal (2004)

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Criminal” is a captivating comedy-crime-drama film released in 2004. Directed by Gregory Jacobs and featuring an ensemble cast of John C. Reilly, Diego Luna, and Maggie Gyllenhaal, the movie tells the story of two con artists attempting to outsmart a currency collector by selling him an authentic-looking counterfeit version of an extremely rare currency bill.

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18. In the Company of Women (2004)

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In the Company of Women” is a captivating documentary that delves into the impact of women on independent filmmaking over the last two decades. This thought-provoking film offers unique insights into the experiences of influential female filmmakers and their journey to break barriers in the male-dominated world of cinema.

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19. The Misbehavers (2004)

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The Misbehavers” is a gripping documentary that unveils the story of a small, yet determined group of guerrilla filmmakers as they undertake an audacious project at the 2004 Sundance Film Festival. Dubbed as Operation: Altitude, these filmmakers aim to create their own film festival from the ground up in less than no time. Join these visionaries as they navigate through the challenges of booking a venue, marketing their unique film, drawing in acquisition reps and filling their screenings beyond capacity.

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20. Strip Search (2004)

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Strip Search” is a gripping and thought-provoking drama film, expertly directed by Sidney Lumet, released in 2004. Following two parallel stories set in the aftermath of 9/11, the film delves into the complex issue of personal freedoms weighed against national security.

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21. The Dying Gaul (2005)

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The Dying Gaul” is a gripping drama, romance, and thriller movie released in 2005. Directed by Craig Lucas and featuring a screenplay by the same author, it boasts an impressive cast including Peter Sarsgaard, Campbell Scott, and Patricia Clarkson. The film tells the story of a grief-stricken screenwriter who unwittingly enters into a complex relationship with a woman and her film executive husband. This three-way connection unfolds with chilling results, creating a high-stakes, emotionally charged narrative.

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22. Happy Endings (2005)

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Happy Endings” is a whimsical and witty comedy-drama from 2005, delving into the unexpected and unpredictable nature of life, love and familial ties. Written and directed by Don Roos, the film weaves together a tapestry of multiple intertwined stories, offering viewers a fresh and intriguing cinematic experience.

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23. The Great New Wonderful (2005)

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In the heart of a post-9/11 New York City, The Great New Wonderful (2005) navigates through a series of interconnected tales that each echo the city’s anxiety and uncertainty. The stories revolve around a determined security guard who saves the day with a cake, a woman trying to find her lost love, and several other characters who find themselves in unexpected situations.

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24. The 20th IFP Independent Spirit Awards (2005)

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The 20th IFP Independent Spirit Awards” is an iconic event that celebrates the achievements of independent filmmakers from across the USA. In 2005, the 20th edition of the awards was held, featuring a star-studded ceremony that brought together Hollywood’s elites and indie legends.

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25. Trust the Man (2005)

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Trust the Man” is a compelling, thought-provoking drama-comedy film that explores the complexities of relationships and the lengths one will go to save a failing marriage. Directed by Bart Freundlich and written by him alongside Julianne Moore, the film stars big names like David Duchovny, Julianne Moore, and Billy Crudup, giving it an immediate draw for viewers.

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26. Paris, I Love You (2006)

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Experience an intricate tapestry of love, comedy, and drama with 2006’s “Paris, I Love You, “ directed by several renowned directors including Olivier Assayas, Frédéric Auburtin, and Gurinder Chadha. This anthology film takes viewers on a passionate journey through the city of love, Paris, exploring the diverse forms and impacts of love that can be found within the streets.

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27. 2006 Independent Spirit Awards (2006)

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Experience the essence of independent filmmaking at the 2006 Independent Spirit Awards, an annual celebration honoring the creativity and achievements of low-budget and indie films. Hosted by popular comedian Sarah Silverman, this 2-hour event showcases the best of independent cinema through its talented cast, including director Hany Abu-Assad and actress Amy Adams.

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28. Sherrybaby (2006)

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Sherrybaby” is an intense drama film released in 2006, directed by Laurie Collyer and written by her as well. It stars Maggie Gyllenhaal as the central character, Sherry. The movie’s runtime is just over an hour and a half long.

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29. World Trade Center (2006)

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World Trade Center” is a harrowing drama that recounts the events of September 11, 2001, through the eyes of two Port Authority police officers. Set against the backdrop of the catastrophic collapse of the Twin Towers, the story follows the officers as they desperately try to escape from the rubble. With its PG-13 content rating and a runtime of 2 hours and 9 minutes, this thrilling film delves deep into the emotional turmoil of the tragedy and underscores the heroism of those who risked their lives to save others.

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30. Stranger Than Fiction (2006)

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Stranger Than Fiction” is a charming and whimsical comedy-drama that blends elements of fantasy and narration. The film takes us into the life of Harold Crick, played by Will Ferrell, a dull and uninspired I. R. S. auditor living in Chicago. What makes his life even more peculiar is that, out of nowhere, Harold discovers he is the subject of an unexpected narrator who mysteriously guides his every move. His mundane existence starts shifting with strange and remarkable events, transforming even his love life and career.

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31. Monster House (2006)

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Prepare to embark on a heartwarming and hilarious journey with ‘Monster House’, the 2006 adventure-comedy film directed by Gil Kenan. Join our three young protagonists as they stumble upon a shocking secret: their neighbor’s house is alive, breathing, and incredibly terrifying. This is no ordinary home; it’s a monster in its own right, with the power to swallow up everything in its path.

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32. The Dark Knight (2008)

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The Dark Knight” masterfully brings the iconic DC Comics superhero, Batman, to life through a riveting journey filled with action, crime, and drama. Directed by Christopher Nolan and written by Jonathan Nolan, David S. Goyer, and Christopher Nolan, the movie stars a stellar cast including Christian Bale, Heath Ledger, and Aaron Eckhart.

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33. Crazy Heart (2009)

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Crazy Heart” is a poignant drama set in the world of country music. Jeff Bridges plays a fading country music singer, who is forced to confront the dysfunction in his life amidst a doomed romance with a journalist.

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34. Away We Go (2009)

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Away We Go” (2009) follows an expectant couple, Burt and Verona Farlander (John Krasinski and Maya Rudolph), on a cross-country quest to find the ideal “family home. “ Navigating through bizarre misadventures and reconnecting with loved ones, Burt and Verona learn to define “home” on their own terms. Supported by a star-studded ensemble, including Allison Janney, this touching comedy-drama by director Sam Mendes will captivate and inspire audiences alike.

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35. Nanny McPhee Returns (2010)

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In the heartwarming comedy “Nanny McPhee Returns, “ young mother Isabel Green (Maggie Gyllenhaal) struggles to run her family farm as her husband is away at war. Nanny McPhee (Emma Thompson), with her uncanny magic and unconventional approach, steps in to teach a powerful lesson to Isabel’s children and two spoiled cousins. The farm may be in turmoil, but Nanny McPhee brings light and fun to their lives, turning their frowns upside-down.

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36. The 82nd Annual Academy Awards (2010)

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The 82nd Annual Academy Awards, hosted by Steve Martin and Alec Baldwin, bring together Hollywood’s finest for a night of glamour, celebration, and recognition. With Carey Mulligan, Macaulay Culkin, and Bradley Cooper in attendance, the awards ceremony promises an unforgettable evening filled with heartfelt speeches, stunning performances, and unexpected surprises.

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37. Hysteria (2011)

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Hysteria, directed by Tanya Wexler, is an enchanting comedy-romance that explores the true story of Mortimer Granville’s groundbreaking invention — the first vibrator, conceived in the name of medical science. Set in the 19th century, the film transports viewers to a time when social norms were vastly different, and unconventional treatments for women’s health sparked controversy.

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38. Won’t Back Down (2012)

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Won’t Back Down” is a gripping drama that follows the inspiring journey of two mothers in the face of adversity. Maggie Gyllenhaal and Viola Davis bring exceptional depth to their roles as determined educators who take a stand against the rigid bureaucracy of their children’s failing inner-city school. Through sheer persistence and unyielding passion for their children’s future, they risk everything to bring about meaningful change.

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39. Bam150 (2012)

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Join the exclusive exploration of the renowned Brooklyn Academy of Music (BAM) in the intriguing documentary, Bam150. Directed by Michael Sladek, this film provides an unprecedented behind-the-scenes look at the nation’s oldest performing arts center, showcasing its rich history and impact on the world stage. Featuring illuminating interviews with groundbreaking artists such as Laurie Anderson, Robert Wilson, and the legendary Pina Bausch, Peter Brook, and Merce Cunningham, Bam150 celebrates the center’s extraordinary past and presents the vibrant performances that continue to captivate audiences today.

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40. White House Down (2013)

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White House Down” is a thrilling, action-packed movie that unveils a daring attack on the White House. When a Capitol police officer, played by Channing Tatum, happens to be on a tour of the presidential residence with his young daughter, he finds himself in the middle of an attempted coup d’état. A heavily armed group of paramilitary invaders storms into the White House, determined to seize the president.

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41. The Fire Rises: The Creation and Impact of the Dark Knight Trilogy (2013)

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Dive into the captivating world of the Dark Knight Trilogy with the intriguing documentary, ‘The Fire Rises: The Creation and Impact of the Dark Knight Trilogy’. Travel behind the scenes, delve into the meticulous crafting of a modern cinematic masterpiece, and explore the profound effect this trilogy has had on filmmaking. Featuring interviews with the film’s stars like Christian Bale, Michael Caine and Eion Bailey, get an insider’s perspective on the creation process.

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42. River of Fundament (2014)

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River of Fundament, “ a fascinating and enigmatic film, is an avant-garde project inspired by Norman Mailer’s novel Ancient Evenings. Released in 2014, this intriguing collaboration between Matthew Barney and Jonathan Bepler delves into a vast landscape of creativity and unconventional ideas.

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43. Frank (2014)

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Frank is a darkly humorous and unconventional comedy-drama set against the vibrant backdrop of the alternative music scene. When young, ambitious musician Jon (Domhnall Gleeson) stumbles upon an unusual pop band led by the elusive and unsettling Frank (Michael Fassbender), he jumps at the opportunity to join the group. However, Jon soon realizes that he has bitten off more than he can chew as he navigates the band’s eccentricities and intricacies.

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44. The 68th Annual Tony Awards (2014)

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The 68th Annual Tony Awards, a stunning celebration of the world of Broadway, captivated audiences in 2014. Hosted by the incomparable Hugh Jackman, this star-studded event brought together fans and industry professionals alike to recognize outstanding achievements in the theatre. The awards showcased the best of musical theatre, with memorable performances by stars like Kevin Adams and Terence Archie.

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45. The 67th Primetime Emmy Awards (2015)

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Prepare to witness the grandeur of the television industry as the finest moments in U. S. prime time television are celebrated at the 67th Primetime Emmy Awards. Hosted by the esteemed Academy of Television Arts and Sciences, this highly-anticipated event recognizes the most outstanding achievements in television programming from June 1, 2014 to May 31, 2015.

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46. 73rd Golden Globe Awards (2016)

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The 73rd Golden Globe Awards are an annual celebration honoring excellence in film and television, hosted by the renowned actor and comedian Ricky Gervais. This star-studded event, which took place in 2016, is presented by the Hollywood Foreign Press Association and features top talents from film and television industries. The Golden Globes have a long-standing tradition of acknowledging exceptional performances and films, serving as a precursor to the upcoming Academy Awards.

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47. Hostiles (2017)

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Hostiles, released in 2018, is a powerfully dramatic western film set in 1892. The story focuses on a legendary Army Captain, played by Rosamund Pike, who is reluctantly tasked with escorting a Cheyenne chief and his family through treacherous terrain. As the group navigates their way through Montana’s rugged landscape, they find themselves in the midst of a horrifying murder that unravels the harsh realities of the American West.

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48. Stand for Rights (2017)

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In 2017, the critically acclaimed telethon “Stand for Rights” hit the small screen, urging viewers to take a stand for their rights. With a star-studded lineup including Fred Armisen, Will Arnett, and Alec Baldwin, this three-hour event was a powerful and engaging way to raise awareness and support for the American Civil Liberties Union (ACLU).

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49. The Kindergarten Teacher (2018)

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The Kindergarten Teacher, “ directed by Sara Colangelo and starring Maggie Gyllenhaal and Gael García Bernal, tells the story of a passionate and dedicated kindergarten teacher in New York City. The film dives into the depths of her obsession with one of her students, whom she believes to be a child prodigy.

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50. The Sound of Silence (2019)

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Experience the compelling drama of “The Sound of Silence” (2019). In this thought-provoking film, we meet Peter Sarsgaard’s character, a successful “house tuner” in New York City, who specializes in fine-tuning the acoustics of people’s homes to manipulate their emotional states. With a combination of advanced science and an unmatched understanding of the human mind, he is able to create the perfect atmosphere for his clients.

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51. Running with Beto (2019)

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Running with Beto” is a riveting documentary that provides an exclusive glimpse into Beto O’Rourke’s groundbreaking campaign to dethrone Ted Cruz in the 2018 U. S. Senate race.

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52. Best Summer Ever (2020)

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Best Summer Ever” is a heartwarming musical that tells the story of Sage and Anthony, who met and fell in love at a dance camp in Vermont. When Sage unexpectedly enrolls in the same high school as Anthony, they must navigate the challenges of high school life, including the drama of cliques, the antagonism of an evil cheerleader, and the family secret that threatens to keep Sage’s world from unraveling. With a star-studded cast, including Shannon DeVido, Rickey Alexander Wilson, and Madeline Rhodes, this engaging and uplifting film promises to make your heart sing.

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53. The Lost Daughter (2021)

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The Lost Daughter” is a captivating drama film that delves into the complexities of motherhood and the intricacies of family dynamics. Released in 2021, it stars Olivia Colman, Jessie Buckley, and Dakota Johnson, and is directed by renowned actress Maggie Gyllenhaal. The movie is set on a beach vacation and takes a gripping turn as the central character starts to grapple with past troubles.

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