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