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Sullivan's Travels (1941)

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Storyline:
Sullivan is a successful, spoiled, and naive director of fluff films, with a heart-o-gold, who decides he wants to make a film about the troubles of the downtrodden poor. Much to the chagrin of his producers, he sets off in tramp's clothing with a single dime in his pocket to experience poverty first-hand, and gets some reality shock.
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Joel McCrea as John L. Lloyd 'Sully' Sullivan
Veronica Lake as The Girl
Robert Warwick as Mr. Lebrand
William Demarest as Mr. Jones
Franklin Pangborn as Mr. Casalsis
Porter Hall as Mr. Hadrian
Byron Foulger as Mr. Johnny Valdelle
Margaret Hayes as Secretary
Robert Greig as Burroughs (Sullivan's butler)
Eric Blore as Sullivan's valet
Torben Meyer as The doctor
Victor Potel as Cameraman
Richard Webb as Radio man
Charles R. Moore as Colored chef (as Charles Moore)
Almira Sessions as Ursula Kornheiser
Full cast
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