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