|Portrayed by||Rich Sommer|
|First appearance||Smoke Gets in Your Eyes|
|Occupation||Sterling Cooper Draper Pryce|
Head of television department
Sterling Cooper Advertising Agency
Head of television department (former)
|Child(ren)||Beatrice, Nathan, Steven Crane|
Harold "Harry" Crane began working at Sterling Cooper as an account man but later became the head of the Sterling Cooper Advertising Agency's newly formed television department, eventually rising to be the head of Sterling Cooper Draper Pryce's television department. ("Shut the Door. Have a Seat") He attended the University of Wisconsin.
Harry was a not-very-aggressive employee of Sterling Cooper. One day he accidentally received Ken Cosgrove's paycheck and discovered that Ken was being paid a great deal more than he was. This led to Harry take some initiative. He pitched a controversial episode of "The Defenders" to a representative of Belle Jolie lipstick because due to the controversy the advertising would be a bargain. The client declined since abortion was too controversial but Roger congratulated Harry for his initiative. In response, Harry said he wanted to be the head of a new television department for Sterling Cooper Advertising Agency. He makes the case that all the other agencies have one. His request was granted and he then asked for a raise to 310 dollars a week. He eventually settled on 225 dollars. "You drive a hard bargain," quips Roger. Upon returning home, he told Jennifer, who responded to Harry by telling him that she and the baby are proud about his promotion. ("The Benefactor")
Harry tended to be different from the other junior executives with whom he hung around in that he appeared to be faithful to his wife, Jennifer. However, at an office party, he got drunk and made love with Pete Campbell's secretary, leading to his temporarily sleeping at the office, before eventually making up with his wife after being emotionally moved by Don Draper's Kodak Carousel pitch. In later years, he demonstrated no qualms about being unfaithful to his wife, being known for trying to pay prostitutes with traveler's cheques, having sex with his friend Paul Kinsey's girlfriend, and attempting to have sex with Megan Draper in exchange for help with her career.
Harry was known for doing many inappropriate things. For example, after Don's 40th birthday party, Harry expounded at length at the office on how sexually excited he was by Megan Draper's performance of Zou Bisou Bisou, oblivious to Megan's presence behind him. Later when Megan went to him for assistance with her career, Harry assumed the meeting would involve a sexual quid pro quo, to Megan's disgust, and he easily falls into Paul Kinsey's girlfriend's manipulative trap to sleep with her so that he would not be able to assist Paul in escaping the Hare Krishnas. Likewise he obliviously rejected Joan's firing of her secretary Scarlett, infuriating Joan, and was known to storm into executive meetings, completely misunderstanding the situation. Harry was also at fault for the firing of Sal Romano. When the company's largest client, Lee Garner, Jr. of Lucky Strike, was angered when Sal Romano rebuffed his sexual advances, he told Harry he wanted Sal "gone". Instead of informing Don about the request, Harry did nothing. Had Harry informed higher ups, they would have kept Sal away from Garner. Since no one was informed, when Garner saw Sal, he blew up and threatened to take his business elsewhere, leading to Don having to unceremoniously fire Sal.
The senior executives disliked Harry, particularly Don Draper, Frank Gleason, and Joan Holloway Harris. Shortly before the decision to sell SC&P to McCann Erickson, the partners decided to offer Harry a partnership based on his importance to the company and despite their dislike of him. However, he delayed answering them too long, so the sale happened before he became a partner, leading to him losing out on a large profit.
Harry continued in his role as head of the television department at Sterling Cooper & Partners. His network of connections within the television industry and Hollywood increased. Harry spent a considerable amount of time in California.
Harry Crane first appeared to take his style cues from Bert Cooper, with a bow tie and slicked back hair. Harry's style and personality both changed during the 1960s. His role as head of the television department brought him into contact with the culture of the west coast and he eagerly embraced the more extreme fashion trends of the 1960s, in contrast to Don Draper, who retained the conservative suits and ties fashionable in the 20th century despite the expanded fashion choices available to men in the late 1960s. Harry traded in the Bryllcreem for the dry look and mutton chop sideburns. His bow tie was replaced by an ascot or scarf. The drab grey colors were exchanged for bright colors, patterns and prints.