In 1933, Willson traveled to Hollywood by steamship via the Panama Canal. On board he cultivated a friendship with Bing Crosby's wife, Dixie Lee, who introduced him to the Hollywood elite and secured him a job with Photoplay, where his first article was about the newborn Gary Crosby. He began writing for The Hollywood Reporter and the New Movie Magazine, became a junior agent at the Joyce & Polimer Agency, moved into a Beverly Hills home purchased by his father, and became a regular at Sunset Strip gay bars, where he wooed young men for both professional and personal reasons. One of his first clients was Junior Durkin, whose career was cut short when he died in an automobile accident on May 4, 1935. Willson joined the Zeppo Marx Agency, where he represented newcomers Marjorie Belcher, Jon Hall, and William T. Orr. He was introduced to Judy Turner, a Hollywood High School student, in 1937, whom he renamed "Lana Turner" and got cast in small roles, finally introducing her to Mervyn LeRoy at Warner Bros. In 1943, David O. Selznick hired Willson to head the talent division of his newly formed Vanguard Pictures. The first film he cast was the World War II drama Since You Went Away with Claudette Colbert, Jennifer Jones, and Shirley Temple. He placed Guy Madison, Craig Stevens, and John Derek in small supporting roles. Willson eventually opened his own talent agency, where he nurtured the careers of his young finds, frequently coercing them into sexual relationships in exchange for publicity and film roles. In his book, Screened Out: Playing Gay in Hollywood from Edison to Stonewall, Richard Barrios writes, "talent agent Henry Willson... had a singular knack for discovering and renaming young actors whose visual appeal transcended any lack of ability. Under his tutelage, Robert Mosely became Guy Madison, Orison Whipple Hungerford Jr. was renamed Ty Hardin, Arthur Gelien was changed to Tab Hunter, and Roy Scherer turned into Rock Hudson. So successful was the beefcake aspect of this enterprise, and so widely recognized was Willson's sexuality, that it was often, and often inaccurately, assumed that all of his clients were gay." In her book "Natasha: The Biography of Natalie Wood", Suzanne Finstad confirms that "some of the would-be actors Willson represented were heterosexual, but a disproportionate number were homosexual, bisexual, or 'co-operated' with Willson 'to get gigs,' in the observation of Natalie 's costar Bobby Hyatt. ..." "if a young, handsome actor had Henry Willson for an agent, 'it was almost assumed he was gay, like it was written across his forehead,' recalls Ann Doran, one of Willson's few female clients." His most prominent client was Rock Hudson, whom he transformed from a clumsy, naive, Chicago-born truck driver named Roy Scherer into one of Hollywood's most popular leading men. The two were teamed professionally until 1966. In 1955, Confidential magazine threatened to publish an exposé about Hudson's secret homosexual life, and Willson disclosed information about Rory Calhoun's years in prison and Tab Hunter's arrest at a gay party in 1950 in exchange for the tabloid not printing the Hudson story. At his agent's urging, Hudson married Willson's secretary Phyllis Gates in order to put the rumors to rest and maintain a macho image, but the union dissolved after three years.