Henry was a farmer who worked hard morning till night and did not know what joy was. He was gray from his long beard to his rough boots. When his house in Kansas was carried off to the Land of Oz by a cyclone (The Wonderful Wizard of Oz), Henry mortgaged his farm in order to rebuild. This crisis, combined with the stress of Dorothy's prolonged disappearance and sudden reappearance, took a toll on his health, and his doctor ordered him to take a vacation. He took Dorothy with him on an ocean voyage to Australia, where he had cousins, but during this trip Dorothy was lost again during a storm, and for several weeks Henry believed she had drowned. She suddenly returned again, courtesy of the Nome King's Magic Belt (Ozma of Oz).
On their return to America, Henry visited Bill Hugson, a relative of his wife, while Dorothy stayed with friends in San Francisco. While traveling to meet him, Dorothy was lost in an earthquake and thought to be dead. Henry traveled back to Kansas alone, where Dorothy later reappeared after having enjoyed another adventure to the Land of Oz. (Dorothy and the Wizard in Oz)
Eventually, the cost of the cyclone damage and the travel expenses added up. Henry and Em confessed to Dorothy the extent of their financial problems, and revealed to her that their farm was on the verge of foreclosure. Dorothy solved this problem for them by bringing them to live with her in the Emerald City, as permanent guests of Princess Ozma. They were given a suite of rooms in the Royal Palace of Oz and Henry was given the job of "Keeper of the Jewels" in Ozma's treasure hoard for the purpose of keeping him occupied. (The Emerald City of Oz)
- The Wonderful Wizard of Oz (first appearance)
- Ozma of Oz
- The Emerald City of Oz
- The Scarecrow of Oz
- The Magic of Oz
- Glinda of Oz
Frank Alexander portrayed him as a villain in Larry Semon's 1925 Wizard of Oz film.
In the VeggieTales episode "The Wonderful Wizard of Ha's", both Uncle Henry and his wife Aunt Em were substituted by a father (Dad Asparagus) to retell "The Prodigal Son", a biblical parable from the Gospel.
In the American television program Lost, there is a character named Benjamin Linus who told survivors his name was Henry Gale and claimed to have arrived on the island via hot air balloon.