Smiling Jack, voiced by John DiMaggio in Vampire: The Masquerade - Bloodlines, is a fictional character in the Vampire: The Masquerade universe.
Smiling Jack is a rebellious vampire in the Brujah Clan. Formerly a second mate to a pirate captain, Jack settled down in Barbados. While drunk, he was offered immortality in exchange for fighting against the Ventrue. For years he undermined the Ventrues, eventually leading to the final death of Sebastian LaCroix. Afterward, he ventured back into pirating.