Henry Jackson was born on November 15, 1994, to Barry and Linda Jackson in Georgetown, Kentucky. Barry was a banker, and Linda worked part-time keeping the books for a small hardware store.

From an early age, Henry enjoyed the spotlight. While most young boys dread family reunions and all the sloppy kisses demanded by aunts and grandmothers, Henry looked forward to the Jackson family gathering each year. As an only child, all the attention was showered on him, and he enjoyed every minute of it. He often stood up on the picnic tables and told stories or otherwise drew attention to himself.

One of Henry's favorite pastimes was staying up late at night and watching comedians on the late-night talk shows. He memorized their jokes and mannerisms, and the next morning, he recited whatever the best comedians had said the night before. Most of his friends played air guitar to heavy metal albums, but Henry lip-synced to stand-up comedy routines.

At Scott County High School, Henry excelled both academically and socially. He was a starter on the soccer team, and as a good-looking young man, he dated often and was never single for long.

The high school drama club was his biggest love and frustration. Every year, Henry won the lead in the school play and attacked his script with fervor and dedication. He enjoyed the echo of his voice in the theatre and the way the stage boards creaked. Yet he was frustrated with the frivolous plays they staged. The drama teacher always chose silly farces and downright dumb zany comedies.

One year, Henry played a stressed-out husband trying to get his wife to the hospital for their child's birth. The nervous husband was supposed to generally run around the stage like a cartoon character. During each performance, Henry played basketball in his costume until his cue came when he would rush onstage drenched in sweat with his pulse racing. It was a good effect, but Henry was still embarrassed by the production.

His senior year, the play was "Krazy Kamp," which was about high school counselors at a summer camp. Henry always hated movies like that, but he thought at least they could throw in some raunchy jokes and a few scenes where the boys peek in the girls' shower. But since "Krazy Kamp" would be performed for the high school and junior high school, it was sanitized until it was simply stupid.

After graduation, Henry attended his father's alma mater: Ole Miss. He majored in drama and excelled in all his classes. Finally, he was able to act in serious works of art. He developed a love for David Mamet, Sam Sheppard, and many more experimental playwrights. Whenever a movie was filming nearby, Henry hung around the sets to see how movie-making worked. Sometimes he even got day work as an extra.

When Henry completed his degree at Ole Miss, he looked for theatre companies to join. He had a chance with a small theatre in Memphis and another one in Jackson, but they were conservative companies who staged the standards like "Our Town" and "Death of a Salesman." Henry wanted to be on the vanguard, and he wanted attention.

A local company called Oxtales had always created a sensation whenever they produced a play, and Henry was intrigued. He thought Oxtales might get enough attention for him to be noticed.

Henry auditioned for the director of Oxtales in the middle of a restaurant, and she hired him on the spot. He immediately started working for the group and was fortunate enough to avoid prosecution for a play called "Snopes," which sent the director to prison.

As each Oxtales production comes and goes, Henry continues to earn acclaim for his skill. He's gaining experience and biding his time until he can join a much more influential company in a big city.