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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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#14.

Pennies from Heaven (1981)

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"Pennies from Heaven" (1981), a visually stunning musical set during the Great Depression, stands out as a bold and ambitious entry in the Herbert Ross filmography. True to the provided description, the film draws heavily from the iconic style of Busby Berkeley, crafting elaborate and often surreal musical sequences that burst with color and movement. The story follows Arthur Parker, a sheet music salesman struggling to make ends meet in Chicago, as he navigates the complexities of a difficult marriage and a burgeoning love for the beautiful schoolteacher, Eileen, encountered during his work. The film's success lies in Ross's ability to juxtapose the grim realities of the era with the escapist fantasies of the musical numbers, creating a poignant and unforgettable experience. This film's inclusion on a "Best Herbert Ross Movies" list is entirely justified. Ross, known for his sensitivity to character and his skill in bringing stage productions to the screen, masterfully directs the complex narrative. He takes risks with the film's unique approach of integrating contemporary songs from the 1930s to underline the emotional intensity of the plot. With the film's daring choices that often border on the surreal to explore themes of love, loss, and the power of art, "Pennies from Heaven" exemplifies Ross's artistic ambition and his willingness to push the boundaries of the musical genre. Its intricate choreography, stunning visuals, and powerful performances solidify its place as a standout in his impressive body of work.

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