The Beach Bum

The Beach Bum follows the misadventures of Moondog, a eccentric and rebellious stoner who lives a life of luxury in Florida, funded by his wealthy wife Minnie. After a night of partying, Moondog is forced to confront his past when he witnesses an intimate moment between Minnie and his friend Lingerie. Minnie later dies in a car accident, leaving Moondog with a frozen inheritance until he completes his novel. Moondog seeks revenge by vandalizing Minnie's mansion before escaping with a pyromaniac named Flicker for a night of debauchery. He later encounters an old friend, Captain Wack, who offers him a job on dolphin tours. However, a run-in with the law leads Moondog to adopt crossdressing as a disguise. With the help of Lingerie and Jimmy Buffett, Moondog must evade detection while finding inspiration to complete his novel and secure his inheritance.

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Some movies that have similar genres and were produced around the same time as The Beach Bum include The Holdovers, Parasite, The Wild Robot, A Real Pain, The Fall Guy, The Banshees of Inisherin.