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Hank Hickey is the estranged son of Professor Hickey the Criminology professor at Greendale Community College. He is the father of Sebastian Hickey and an avid player of the role playing game "Dungeons & Dragons". His first appearance is in the Season Five episode "Advanced Advanced Dungeons & Dragons". He is portrayed by actor/comedian David Cross.
During the study group's fifth year at Greendale, Hank Hickey was invited by his father Buzz to join the Save Greendale Committee for a game of Dungeons & Dragons. Although wary of the invitation he accepted anyway and showed up at Annie and Abed's apartment. After being given the character sheet of "Joseph Gordon Diehard" he learned Buzz would be playing his father "Sir Riggs Diehard". He accused the group of trying to force him and his father to reconcile. When everyone denied this, Hank collected the other players character sheets and redistributed them. He ended up getting the character of "Tristram Steelheart", a Cleric.
In game Hank asked that his character break away from the assembled quest party and head north instead of south. Annie tried to use her character "Hector the Well Endowed" to physically set him on the right path but he retaliated by having "Tristram" cast the spell "Torvin's Flesh of Fire". Tristram's spell destroyed the bridge the party was standing on sending everyone into "Skull River" below. Buzz confronted Hank about his attitude and demanded to know why he wasn't invited to his grandson's birthday party. Hank coldly told him the reason was because he actually wanted to enjoy the festivities.
Jeff tried to play peacemaker and brought up his own troubled relationship with his father. He told Hank and Buzz not to make the same mistake he did and salvage their relationship before it's too late. Abed interrupted and told Hank that if he wanted to keep playing he'd have to be sequestered. Due to Hank's actions in game the party was now split into two groups. Hank was uninterested in continuing until and his father made him a wager. Buzz put up his right to go to his grandson's birthday party based on the outcome of the game. Hank upped the ante by putting up his father's rights to attend Aunt Rachel's Thanksgiving and Christmas dinner. Buzz agreed and Hank went to Abed's room to resume playing with his new teammates.
When Abed returned from instructing the other group, Hank had "Tristram" heal Britta's character who was injured. He explained to the others that his animosity towards his father stemmed from constant neglect from Buzz when he was a child. Abed then informed Hank and his the party that they were being aproached by a pack of "Sky Spiders". Hank impressed everyone when he peacefully resolved the confrontation by taming the creatures. While Abed was with Buzz's group, Hank continued to bond with his party by singing an inspirational battle hymn. Abed returned and mentioned that the Sky Spiders flew Hank's party a fair distance and gave them instructions for the rest of the way to their objective, the Black Tower.
One of Hank's party members, Joseph Gordan Diehard (Dean Pelton), used a magical beacon to contact his "father" Sir Riggs Diehard (Jeff). The light made Hank aware that both groups were not far from the Tower and would soon be crossing each other's paths. By this point Hank had won the loyalty of his group with the exception of Pelton.