Henry grew up as a popular jock and football player and was a bully. In middle school, he severely tormented another kid and was noted to have "a real mean streak."
In late 2015, a vampire named Richard Beesome came to Sioux Falls, South Dakota looking for revenge on Annie "Alex" Jones. As he found her too pathetic to kill at the moment, he turned Henry, the most popular kid in school into a vampire as well to help build Alex's life up before they destroyed it and then killed her. To this end, Henry became Alex's boyfriend, pretending to be kind to her while really plotting behind her back.
After school one day, Alex and Henry leave together and are approached by one of her friends who has heard that she and Henry are in the lead for Prom Queen and King. Alex and Henry joke about it before Mr. Phelps walks by and reminds Alex about a test she has the next day. Alex is then picked up by Jody who is proud of her for fitting into a normal life. As they leave, Jody notices birth control pills in Alex's bag, indicating that she's planning on having sex with Henry.
At dinner, an annoyed Claire reveals that Alex and Henry plan to sneak off to Jody's cabin to have sex, prompting Jody to give Alex a highly awkward sex talk. During that time, Alex reveals that she and Henry haven't slept together, but she's preparing herself for when they do.
That night, Henry, beginning his and Richard's plan, attacks Mr. Phelps as he leaves the school and breaks his neck before hanging him from the school flagpole where everyone, including Alex, can see.
The next day, Alex and Henry arrive at school to find Mr. Phelps' body hanging upside down from the flagpole. School gets cancelled as a result and Alex leaves with Henry and they walk along a stream. Alex is distraught by Mr. Phelps' death as he'd believed in her and because of the way he died and tells Henry there's awful things out there. Alex admits she wasn't always the good person she is now and has done awful things in the past, remembering the terrible things she did while with Celia and her family of vampires. Henry reassures her that he doesn't care about her past and they kiss.
That night, Dean calls Alex asking where she is and tells her he's coming to pick her up as the custodian is a vampire. Alex tries to leave, telling Henry he needs to go but he attacks her, revealing himself to be a vampire to her.
After dumping Alex's cell phone, Henry takes her to Richard's nest in a former pool building on the high school campus where the two reveal their plan to Alex, including that Henry never really cared about her. Henry shows delight in his actions, leading to Alex spitting in his face. As the two vampires plan to kill Jody and Claire to get their revenge, Alex offers to help them find food and feed them with herself when the hunting goes dry. Richard starts to feed on Claire, but the vampires sense Sam Winchester enter the building and go to confront him instead. After Richard attacks Sam, Henry takes over the fight, beating on Sam with a two-by-four. Sam is eventually able to subdue Henry and take him captive.
After defeating Henry, Sam takes him to Alex who was freed by Dean after he killed Richard. Sam leaves Henry to Alex to deal with and Henry leers at her that he should've "tapped that." Alex just tells Henry to "dream of me" and then punches him in the face. After Alex punches Henry, Claire decapitates him from behind, killing Henry.
Powers and Abilities
Henry has all the powers and abilities of a normal vampire though not as strong as most as he was only a vampire for a few months.
- Super Strength - Henry was strong enough to break a man's neck and lift him up a flagpole. However, he wasn't stronger than a physically strong human such as Sam Winchester who was able to subdue him.
- Super agility - Henry possessed the agility to climb up a flagpole with a body and tie the body to it.
- Immortality - As a vampire, Henry was immortal unless killed.
- Invulnerability - As a vampire, Henry was invulnerable to most forms of harm.
Henry possessed all the weaknesses of a vampire.
Outwardly, Henry appeared to be a kind, caring young man who was worried about his girlfriend Alex. Henry also appeared to have remorse for his previous behavior when he was younger, such as "torturing" a kid in middle school.
In reality, Henry was sadistic and sociopathic. Its indicated that this side of him was not something that he gained when he became a vampire, but something that had preexisted given his comments about "torturing" a kid with his bullying in middle school. Even Richard Beesome noted that Henry had "a real mean-streak" that went beyond what even Richard desired. When he became a vampire and a part of Richard's revenge plot, Henry stopped suppressing his sadism and fully embraced it. Henry greatly enjoyed aiding Richard in building up and destroying Alex's life and took great pleasure in his own role in the plot. When ordered to murder Stephen Phelps, Henry went so far as to hang his body from a flagpole so he could enhance and enjoy the shock factor when people saw the murdered teacher. When the plot was revealed, Henry took great glee in explaining his own role to Alex and taunting her about it.
At the end of his life, Henry showed no remorse or even care for the lives that he had helped destroy. After being subdued by Sam Winchester and left to Alex and Claire to deal with, Henry did not attempt to apologize or beg for his life. Instead he expressed disappointment that he hadn't had sex with Alex when he had the chance.
- Aside from Boris's newly turned vampires in Live Free or Twihard, Henry is the youngest vampire in the show, having only been turned a few months before his appearance when Richard recruited him for his revenge plot.
- Jedidiah Goodacre went on to play to an vampire named Roman on The Originals who essentially that show's version of his Supernatural character although unlike Henry himself. Roman wasn't a sociopath and expressed remorse for his actions and was allowed to live by who he had wronged.