In 1999, Billy made his cinematic debut in the Warner Bros comedy The Big Tease. Though initially cast in a minor cameo, Billy unexpectedly became a standout presence in the film, garnering attention beyond his anticipated role. This Hollywood comedy, starring Craig Ferguson, follows a Scottish hairdresser’s humorous journey to Hollywood as he vies for glory in an international hairdressing competition. Billy’s appearance, though brief, left a lasting impression.

Following this success, John McKitterick and Juan Andres were approached later that same year by acclaimed director Todd Downing with a concept that would once again place Billy in the spotlight. The animated film, titled Jeffrey’s Hollywood Screen Trick, was set to star Billy alongside characters Carlos and Tyson. Production on this innovative project commenced in the spring of 2000, with the film’s release following in 2001.

Drawing inspiration from the light-hearted charm of gay romantic comedies, Jeffrey’s Hollywood Screen Trick cleverly parodied the genre, presenting a satirical take through a dynamic eleven-minute short film. Utilizing stop-motion animation, the film brought to life hundreds of Billy Dolls in a whimsical and captivating manner. This creative endeavor was met with critical acclaim, earning the title of Best Short Film at the Philadelphia International Gay & Lesbian Film Festival in 2001.

Building on the momentum of these successes, Billy and Carlos were soon at the center of yet another cinematic project. The film Billy 2000: Billy Goes To Hollywood featured a series of segments inspired by the beloved figures of the Billy Doll collection, including Master Billy, Cowboy Billy, Sailor Billy, Wall Street Billy, and San Francisco Billy. Each vignette celebrated the unique persona of these figures, further cementing Billy’s place as a cultural icon in both film and animation.