Henry Jackson was born on November 15, 1974 to Barry and Linda Jackson in Georgetown, Kentucky. Barry Jackson was a banker and Linda worked part-time keeping the books for a small hardware store. From an early age, Henry displayed signs of enjoying the spotlight.

While most young boys dread family reunions and all the sloppy kisses demanded by aunts and grandmothers, Henry looked forward each year to the Jackson family gathering. As an only child, all the attention was showered on him and he enjoyed every minute of it. He would often stand up on the picnic tables and tell stories or otherwise draw attention to himself. One of Henry's favorite pastimes was staying up late at night and watching comedians on "The Tonight Show." He would memorize their jokes and mannerisms and the next morning, he would recite whatever Dan Ackroyd had said the night before. Most of his friends played air guitar to heavy metal albums, but Henry lip synched to Eddie Murphy stand up comedy routines.

At Scott County High School, Henry excelled both academically and socially. He was a good-looking young man and a starter on the soccer team. He had many dates and was never single for long. During high school, the drama club was his biggest love and frustration. Every year, Henry won the lead in the school play. And each year he attacked his script with fervor and dedication. He enjoyed the echo of his voice in the theatre and the way the boards of the stage creaked. Yet he was frustrated at the type of plays they produced. The drama teacher always seemed to choose silly plays, farces, and just down right stupid zany comedies. One year, the lead role was a stressed out husband who was trying to get his wife to the hospital for the birth of their child. The husband was supposed to be nervous and upset and generally run around the stage like a cartoon character. During each performance, Henry would slip into the school gym and play basketball in his costume. When his cue came, he would rush on stage drenched in sweat with his pulse racing. It made for a good effect, but Henry was still embarrassed by the production. His senior year, he had the role in a play entitled "Krazy Kamp" which was about high school counselors at a summer camp. Henry always hated movies like that, but at least they could throw in some raunchy jokes and have a few scenes where the boys peek in the girls' shower. Since "Krazy Kamp" would be shown to the high school and junior high school, it was sanitized to the point of being just plain dumb.

After graduation, Henry followed in his father's footsteps and attended Ole Miss. He majored in drama and excelled in all his classes. Finally, Henry was able to act in serious works of art. He developed a love for David Mamet and Sam Sheppard and many playwrights who were much more experimental. Since so many movies were filmed in the Oxford area, Henry also got to see how movie making worked and he hung around the sets, sometimes getting bit parts as an extra.

When Henry completed his degree at Ole Miss, he began looking 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. Their plays were the standard things 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 garnered a lot of sensation whenever they produced a play and Henry was intrigued. He thought that Oxtales might get enough attention for him to be noticed.

Henry auditioned for the director of Oxtales in the middle of a restaurant and was hired 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 is biding his time until he can move away from Oxford and join a much more influential company in a big city.