Will Rogers, Fanny Brice, and Fred Stone numbered among the family's friends, after they moved to Forest Hills, an upscale neighborhood in the New York City borough of Queens.

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.

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,[8] and Roy Scherer turned into Rock Hudson.

"[9] 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.

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.