Charles, an eccentric lottery winner living alone on a remote island, tries to make his dreams come true by hiring his favorite musician, Herb McGwyer, to play an exclusive, private gig. Unbeknownst to Herb, Charles has also hired Herb's former bandmate and ex-girlfriend, Nell, with her new husband to play the old favorite songs. As tempers flare and old tensions resurface, stormy weather keeps them all stranded on the island and Charles desperately searches for a way to salvage his dream gig.