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Best Herbert Ross Movies

13th Nov 2025
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Herbert Ross, a master of the musical and romantic comedy, left an indelible mark on Hollywood. From the glitz and glamour of "Funny Girl" to the poignant drama of "The Goodbye Girl," his films captured the essence of human relationships with wit, charm, and unforgettable performances. His direction and ability to coax stellar work from actors cemented his status as a cinematic icon. His legacy continues to resonate with audiences today, making him a beloved figure in film history. Now it's your turn to celebrate the best of Herbert Ross! We've compiled a list of his most memorable films, and we want to hear your opinion. Which of his movies do you consider to be his finest work? Cast your vote and help us determine the ultimate Herbert Ross masterpiece. Let your voice be heard!

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Best Herbert Ross Movies

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#13.

Boys on the Side (1995)

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"Boys on the Side" (1995), directed by Herbert Ross, follows the unlikely journey of three women navigating life, love, and loss. After a painful breakup, singer Jane answers a personal ad from real estate agent Robin, who is living with AIDS, seeking a travel companion. Their cross-country road trip from New York City to Los Angeles expands when they pick up Holly, a friend of Robin's, who's fleeing an abusive relationship in Pittsburgh. Each woman brings a unique personality and set of struggles, and the film focuses on their burgeoning friendship and individual growth. This film is a testament to Herbert Ross's talent for crafting character-driven narratives that explore complex emotions. Ross, known for his sensitivity and understanding of female relationships, expertly portrays the bond between the three women, showcasing their vulnerabilities and triumphs as they support each other. While exploring heavy themes like illness, domestic violence, and sexual identity, Ross imbues "Boys on the Side" with warmth, humor, and a compelling sense of hope, solidifying its place among his best works, alongside films like "Steel Magnolias" and "The Goodbye Girl," known for their poignant exploration of human connection.

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