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