After the death of his beloved mother, middle-aged accountant Lenny Freeman quits his job to follow his dream of becoming a standup comedian. Freeman bids a fond farewell to his coworkers, who barely acknowledge him, and takes his mother's 1953 Oldsmobile on a road trip to Las Vegas, where he intends to audition for a standup competition run by Vegas showman Monte Guy. Freeman, an obsessive fan of vaudeville and other early 20th century comedy, becomes confused by the more obnoxious and transgressive humor preferred by the people he meets. Along the way, he picks up a hitchhiker nicknamed Hitch whose previous rides are shown to have either disappeared or died mysteriously. When Hitch learns that Freeman intends to become a standup comedian, he shares career advice and agrees to become Freeman's manager.
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