"You're a disgrace to yourself and all those you've killed.."

- Henry Cooldown before the battle with Travis

Henry Cooldown (ヘンリー・クールダウン, Henrii Kuurudaun) is a recurring antagonist and a former secondary protagonist in the No More Heroes series. He is introduced as a 27-year-old American assassin, who was raised in Ireland. He is Travis Touchdown's older twin brother; it was unknown if his last name was also Touchdown until his full name, though never mentioned in-game until No More Heroes III, was revealed to be Henry Cooldown. To most (including Suda 51), he is known simply as Henry.

Henry is playable in No More Heroes 2: Desperate Struggle during the dream fight with Mimmy.

In in the first game, Henry has naturally smooth, auburn hair and blue eyes, and wears a full gray outfit, consisting of a grey waistcoat, trousers, a trouser chain, a white shirt and tie, and a long grey formal trench coat. His weapon is the Cross Sword, a beam katana similar in design to a broadsword, which (like Travis's Tsubaki Mk-III) doesn't have a receiver.

In the second entry in the series, Henry's skin appears more pale, and his hair is black instead of auburn, similar to Travis's. He wears a dark-grey waistcoat and trousers, along with a skull-shaped tie pin, an additional trouser chain, and a belt with a spade-shaped buckle. He no longer wears his trench coat.

During his appearance in the Bubblegum Fatale DLC, Henry's hairstyle is a lot messier and less clean cut, and he now wears shades (paralleling his twin), as well pinstripe waistcoat under a trenchcoat and a checkered tie.

Henry's appearance here differs greatly from the previous three titles. His hair is styled in a windswept spiky manner, and he adorns a black trenchcoat over a white dress shirt and a black waistcoat, with a tie of matching color. He also wears black boots, gloves, and trousers, and a spade-buckle belt like the one he wore before. His eyes are hidden behind sunglasses with dark, circular lenses, giving him the appearance of a stereotypical young, devout religious man. He now wields a second Cross Sword, dubbing them "Cursed Crucifix Blade[s]."

A black, spear-shaped tattoo runs up the bridge of his nose to his forehead, where an emerald-like gem is embedded. Upon close inspection, said gem appears resemble an eye, with a pupil in the center and a bump that looks like an eyelid at the top. During combat, it projects a glowing eye that flashes with different colors.

Upon entering "Barrage Mode," Henry becomes enveloped in green, glowing energy, with his Beam Katanas changing color to match.

Henry is nearly the exact opposite of his twin in terms of his personality, which he sums up as him being the “cool, handsome foil” to Travis during the true ending of No More Heroes. Whereas Travis is usually loud and boisterous, relying on bombastic one liners, jokes, and occasional bouts of rage to intimidate each of his opponents, Henry is calm, well-spoken and professional. Compared to his twin, he is far more suave and laid back, casually taunting Travis during his boss fight in the first game.

His personality in No More Heroes 2: Desperate Struggle remains fairly similar to his portrayal in the first game, however he seems to be more comfortable joking around Travis, best exemplified by the phone call that Henry makes informing Travis that he’d killed 3 more assassins, putting him in 5th rank. His further interactions with Mimmy also show that Henry’s personality has changed slightly between games, while still retaining his role as Travis's rival.

Travis Strikes Again: No More Heroes marks the beginning of a drastic change in his personality. When he ambushes Travis at his trailer, he acts in a delirious and antagonistic manor, mocking his brother and believing it's his duty to kill him after watching a particular "movie about God." As is seen when he leaves him with his men, Henry appears to express joy at the thought of Travis's death — behavior which the latter describes as "fucking savagery."

At some point in time before his reappearance in No More Heroes III, Henry's suppressed memories of his childhood began to resurface, resulting in him going completely insane. He becomes obsessed with his past and is hellbent on eliminating the sole remaining connection to it: Travis. Henry displays violent and erratic behavior during his encounter with his brother, going so far as to start cutting up a trash can into pieces for his own amusement. His madness is further displayed by his manic yelling and laughter during and after their battle. He also appears to have lost his Irish accent, now speaking with an American one.

Use at the start of a section to link to the main article on that subject.

</noinclude> Henry ignites a rivalry with Travis when he kills Letz Shake during their ranking match, earning him his brother's ire. Henry has a degree of shame for his younger twin, calling him "a disgrace to [him]self," but doesn't seem to outright despise him and even talks to him in a casual manner. He is also not above repaying him for saving him from captivity by — much to Travis's dismay — killing the three ranked assassins, and even coming to help him in his fight against Jasper Batt Jr (although this was likely just so the two could settle their score later on).

After watching a "movie about God" and uncovering his lost childhood memories, however, Henry begins to hate his twin. He regards him as a crybaby and considers it his responsibility as his older brother to kill him and sever the final link to his own past, much to Travis's disgust.

Use at the start of a section to link to the main article on that subject.

</noinclude>

Henry and Sylvia met each in college and got married ten years before the events of No More Heroes. According to him, she was a "big spender" and would randomly disappear (in order to go and con other assassins), believing his low income to be the reason. At some point after the ending of the first game and before the events of No More Heroes 2: Desperate Struggle, however, the two decided to divorce, most likely due to Travis and Sylvia's on-and-off-again affair.

Henry's proficiency in swordplay is one of his most noteworthy skills, and he is capable of wielding his Cross Sword to great effect. This is best shown when he kills Letz Shake and his son with one sword slash for each of them. Another example being how he can fight on even grounds against Travis, a highly skilled swordsman in his own right. Compared to his brother, who's fighting style is rougher and lacking in finesse, Henry's technique is far more graceful and refined, but no less deadly. In No More Heroes III, he further displays his skills through his dual-wielding of a pair of Cross Swords.

Henry displays inhuman levels of raw physical speed and strength. He is a quick fighter and is capable of dashing long distances, as well as being strong enough to throw Travis into the air, leaping to considerable heights and being able to take a surprising amount of punishment. In No More Heroes III, his strength and durability have been elevated to even greater heights. This much is shown when he manages to stay conscious after being cut in half at the waist, by which he is almost completely unfazed.

Henry is able to enhance his abilities and Cross Swords through the crystal embedded in his head. When he enters "Barrage Mode," he gains the power of teleportation, and can create large, long-ranged projectiles with heavy sword slashes. By plunging his Beam Katanas into the ground, he is able create multiple spinning rings of blades. He is also capable of extending his swords to a ridiculous length to attack with incredible range.

Through means unknown, Henry is able to come back to life.

Henry was born as the oldest of two twin boys. In an attempt to get away from his serial killer father, he ran away with his brother Travis and his half sister Jeane. They waded through snow, spending days in the woods and making an igloo in an effort to try to escape the cold. When they reached a major road, they were then surrounded by cars as henry was kidnapped by a car on the road. He was taken to Ireland and indoctrinated and raised into the Cooldown family. His memories were mostly erased and replaced by those of a Cooldown child, giving him his Irish accent.

When he was in college, he met and married Sylvia Christel.

In the de-canonised ending, they had a daughter named Jeane, shortly afterwards. It is unknown whether this is an allusion to his half-sister.

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, thus igniting a rivalry between the two.

He later challenges Travis to one final duel outside the Motel "NO MORE HEROES" after Travis becomes ranked first in the United Assassins Association. As their battle ensues, Henry reveals that he is both Travis' twin brother and Sylvia Christel's husband of ten years. He also is seen to have a daughter named Jeane, a mysterious child who shares the same name as Travis' half-sister and cat, seen following the credits looking at a painting of Henry and Travis attacking each other in front of the Santa Destroy flag with her mother, Sylvia.

Though it was heavily implied in the real ending of No More Heroes that Henry and Travis had honorably killed each other, this was not the case as the game's sequel, No More Heroes 2: Desperate Struggle, reveals that Sylvia interrupted the fight. Sylvia also reveals that she and Henry got divorced at some point between the two games.

Between the games, he somehow becomes encased in carbonite by Dr. Letz Shake, whom he had previously killed, but was later resurrected after Letz Shake's brain was placed inside an upgraded form of his Earthquake Maker, giving him total control over it. However, he is saved by Travis after he kills Dr. Letz Shake and is taken back to the Motel "NO MORE HEROES" to recover in Travis' motel room. Henry, suffering from hibernation sickness due to having been encased in carbonite for so long, fights Mimmy (a mixture of the anime girls and robots Travis watches) in a nightmare before awakening.

As repayment for rescuing him, as well as not wanting to look like the lesser of the two, Henry kills three ranked assassins and gets Travis to rank 5. After doing so, he left a long voicemail to his brother, letting him know of what he did for him and telling him not to die until they could settle their rivalry. Henry later assists Travis in the final boss fight against Jasper Batt Jr. He helps Travis by freeing him from the clutches of the mechanical arms of Jasper's floating car, as well as helping him see through Batt's trick, revealing that Jasper hadn't killed him, Sylvia, or Shinobu, and that their decapitated heads were fake. However, he leaves after Batt transforms into his third and final form, saying "It's not happening, brother. I can't be associated with that travesty. I mean, I got standards for fuck's sake!"

At some point in time, Henry forms a cultist organization called the Order of the Emerald Night. After the main events of the game, he and his men follow Shinobu to Travis's trailer in Texas. Upon their reunion, Henry belittles his twin for running away from civilization to do nothing but play video games. He speaks of a movie about a "super yoked guy with a hammer" and his troublemaking little brother who end up battling each other, which reminded him of his brother and made him decide to put an end to him. Henry departs from the area, leaving Travis and Shinobu to his subordinates, Kes and Rumors.

After Travis has killed most of the Galactic Superhero Corps, Damon Ricotello meets with an individual resembling Henry near a busy road at night. Damon pays the individual 30% of his entire company's shares to kill Travis, but he simply walks into traffic and gets repeatedly run over.

Following Travis's victory over Sonic Juice of the Galactic Superhero Corps, Henry anonymously emails Travis, threatening that his blade hungers for his blood and challenging him to meet in front of the motel like old times.

Once Henry shows up, his personality, appearance and voice are completely different from the previous games. He proceeds to tell Travis about a tale from their past, where both they and their sister Jeane escaped from their "serial killer father" into the snow, before Henry was picked up by mysterious individuals and indoctrinated into the Cooldown family. He notes that Travis cried the whole time, which infuriated him. He then battles Travis wielding dual Cross Swords, only for the fight to end once Travis bisects Henry at the waist. Somehow, Henry manages to survive having his legs cut off, and begins scurrying towards Travis, whilst angrily yelling at him to not cry. In response to this, Travis screamed as he mauls his upper body to death with his katana.

However, this was not the end for Henry. After Sylvia comes out to take out the trash and goes back inside, he appears in the motel room that she went into, looming in the window frame and looking down at Travis. Shortly afterward, he ambushes his brother in the bathroom with his Emerald Knights, while he's on the toilet. Henry begins wildly slashing Travis before cutting off head, killing him. Unbeknownst to him, Travis is able to return to life thanks to the Death Drive Mk II.

Henry's whereabouts after this encounter are unknown. In the post-credits scene, it is mentioned that he teams up with aliens to kill Travis and conquer the Earth in the future.

There are several Henry trading cards in the Design Materials set. These include Henry"_Design">"Henry" Design, "Henry" Expressions and Henry.