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Movies like Come Again Smith (1919)

Joe Smith Jr., the son of a millionaire, is challenged by his father to earn his own living instead of depending on his father's money. One year later Joe is broke, dirty, homeless and hanging out with other derelicts on a New York City park bench. A chance meeting with businessman Ned Stervens results in Joe being invited to stay in Stevens' house for a week, to make Stevens' point to his acquaintance Frank Overton---a shady stockbroker--that given a chance, even a tramp like Joe can better himself. Joe finds himself in love with Stevens' sister Lucy and unwittingly becomes party to a scheme by Overton to swindle Lucy out of her money.