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Chaos fills the office of investment broker and trust fund manager Hugh Mansfield. His nephew, John Francis Mansfield III, arrives to announce that he is getting married the next day to Gloria Mitchell, the same day as his twenty-fifth birthday. Hugh's secretary, Miss Burke, then informs her employer that if John does marry, Hugh must turn over the young man's $10,000,000 trust in its entirety. Through his talent for bad investments, however, Hugh has managed to lose $5,000,000 of the fund. Fearing that he might be sent to prison for embezzlement, Hugh contemplates various forms of suicide, but decides to fake insanity instead. When Gloria sees the newly "insane" Hugh, she calls off the wedding. John takes his uncle to the Stephanowsky Sanitarium, hoping that he will be judged sane by the psychiatrists. Hugh is placed in a room with patient Revello, who designs ladies hats from kitchen utensils. At his sanity hearing the next day, Hugh masquerades as noted psychiatrist Dr. Rumbold, and after John is mistaken for his uncle, he is declared insane and committed in Hugh's place. While trying to escape, John bumps into nurse Madge Reilly and asks her to marry him so that he can inherit his grandfather's estate. When she refuses, John jumps the wall and steals a truck. Madge chases after him with the help of taxi driver Stinky Fink, but after catching him, John bribes Stinky into taking him into town. Rather than taking John home, however, Stinky delivers the would-be heir to the gambling den of gangster Slugs Bennett, with the idea of ransoming the young man. Slugs is against the idea until John punches him. When Slugs asks for $10,000 to free John, Hugh offers instead to pay the gangster $20,000 to keep him. After Hugh's check bounces, however, John convinces the gangster to allow him to get married. Madge is forced into the marriage, while Hugh has his feet dipped in cement. Realizing that they need Hugh's signature to collect the inheritance, Slugs races back to his men before they can drop the "crazy uncle" in the river. Hugh, however, gets out of the cement, then sneaks down the fire escape. The gangsters follow Hugh's footprints to a costume shop, but Hugh manages to elude them. John, Madge and the gangsters wait for Hugh at his office, and when Hugh arrives and begins to confess all, government agent Juniper informs him that, instead of being penniless, he is one of the richest men in the country, as the government wishes to buy his numerous abandoned mines. Hugh then offers to turn over the business to John, as he plans to go to Hollywood to design hats with Revello.