Moondog, a
substance-abusing poet, leads a
hedonistic and pseudo-
nomadic lifestyle in and around the
Florida Keys while working on his new book. Despite perceptions that he is past his prime, he enjoys local notoriety as a legendary figure. His indulgent lifestyle is funded by his wealthy wife Minnie, which draws disapproval from their daughter Heather and agent Lewis. Throughout his journeys, Moondog engages in promiscuous relationships, while Minnie has a secret affair with his friend,
R&B singer Lingerie. After arriving late to Heather's wedding in Miami, Moondog's infidelity leads to a drunken altercation with the groom, Frank, in front of the guests. Later, Minnie reveals her affair during a conversation with Heather about Moondog's behavior. Meanwhile, Lingerie introduces Moondog to a potent strain of cannabis found in
Jamaica, which he credits for his success. At the reception, Moondog reconciles with Heather and Frank before witnessing an intimate moment between Minnie and Lingerie. Following a night of intoxicated karaoke and dancing with Minnie, Moondog survives a car accident but Minnie succumbs to her injuries. Half of Minnie's estate goes to Heather, while Moondog's share is frozen until he completes his novel. In response, Moondog seeks revenge by vandalizing Minnie's mansion with a group of homeless individuals. To avoid imprisonment, he agrees to a year of
rehabilitation but later escapes with a
pyromaniac named Flicker. The two engage in a night of debauchery before parting ways as Moondog makes his way back to Miami. Back in Miami, Moondog encounters "Captain Wack", an old friend and alleged Vietnam veteran who offers him a co-captain position on dolphin tours. However, a tour with
great white sharks results in Captain Wack sustaining a severe injury. As the law pursues him, Moondog reunites with Lingerie, who confesses to the affair but claims Minnie truly loved him. Inspired by a dream and experience shared with Lingerie and Jimmy Buffett, Moondog adopts
cross-dressing to evade detection. The police close in on Lingerie's property, prompting Moondog to flee to Key West with Lingerie's assistance and a supply of the Jamaican weed. Motivated, Moondog completes his poetic memoir titled
The Beach Bum, which earns him a
Pulitzer Prize. The lawyer informs him that his inheritance is unfrozen, and Moondog demands it in physical cash on a large sailboat. During a celebration, he sets the money on fire, causing an explosion. Moondog survives, but the crowd is preoccupied with the raining money as he drifts away on the boat, laughing. ==Cast==