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Charles, an eccentric lottery winner, lives alone on a remote island and tries to make his dreams come true by inviting his favorite musician, Herb McGwyer, to a private and exclusive concert. Unbeknownst to Charles Herb, Herb also enlists his former bandmate and ex-girlfriend Nell, with her new husband in tow, to perform old hits. As tempers flare and old tensions resurface, a storm traps them all on the island, leaving Charles desperately searching for a way to save his dream job.