Henry Cooldown is a 30-year-old (27 in No More Heroes) American assassin, since raised in Ireland, and Travis' twin brother. He wears a full gray outfit and wields the Cross Saber, a beam katana similar to Travis' Tsubaki Mk-III. He is first encountered as a shadowy figure in the Senton Splash Tunnel of Santa Destroy, on Travis' way to the ranking match versus Letz Shake. Henry and Travis meet face-to-face, after Henry kills Letz Shake before Travis does and thus ignites a rivalry between the two. He later challenges Travis to one final duel outside of the "NO MORE HEROES" motel after Travis becomes ranked first in the UAA. As their battle ensues, Henry reveals that he is both Travis' twin brother and Sylvia's husband of 10 years. The outcome of their fight is left open. In No More Heroes 2, Henry is divorced from Sylvia, and was somehow defeated by Dr. Letz Shake, leading to an unintended rescue by Travis. He is then playable for one battle in a nightmare, fighting an anime-styled girl named Mimmy. After waking up, he kills the assassins ranked 5 and 6 for Travis and saves him during the final boss fight. He leaves during the boss's final form, refusing to help fight because even being associated with the outlandish boss would hurt his reputation.