Charles, an eccentric lottery winner, lives alone on a remote island and tries to make his dreams come true by hiring his favorite musician, Herb McGwyer, to perform an exclusive, private concert. Unbeknownst to Herb, Charles has also hired his ex-girlfriend and ex-partner, Nell, with her new husband in tow, to perform his old hits. As tempers flare and old tensions resurface, a stormy weather traps everyone on the island and Charles desperately searches for a way to save his dream job.