Berlusconi: Condemned to Win
MovieSeptember 16, 2025•
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Documentary
Overview
Three-part series for ESPN capturing the rise of Silvio Berlusconi from his humble beginnings to the very top – from cruise ship crooner to AC Milan owner to Prime Minister of Italy.
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Cast
16 actors
Silvio Berlusconi
Self (archival footage)
Adriano Galliani
Self
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Fedele Confalonieri
Self
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Alexander Stille
Self
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Ruth Ben-Ghiat
Self
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John Foot
Self
Carlo Ancelotti
Self
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Paolo Tarozzi
Self
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Pippo Russo
Self
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Carlo Pellegatti
Self
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Vittorio Dotti
Self
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Paolo Taveggia
Self
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Andrea Scanzi
Self
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Edoardo Maturo
Self
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Dejan Savićević
Self
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Zvonimir Boban
Self