Beginning his career as a professional child actor and model at the age of ten, Olden is best known for his television roles; as "Drag" in the ABC Weekend Special: The Joke's On Mr. Little and as "Robbie Stuart" on the 1980s TBS sitcom Rocky Road.

After a series of auditions to evaluate his acting, singing and dancing abilities, Olden landed the title role and immediately began rehearsals for a full-scale production of the musical at the famed Aquarius Theatre in Hollywood, which co-starred comic Dick Shawn.

[1] Over the next several years, Olden continued to work as a child actor and model, appearing in numerous national commercials and print advertorials until making the transition to television in 1981 with a guest-starring role on the situation comedy Flo.

[1] In the satirical special, Olden appeared opposite Dick Van Dyke (as the token "grown-up"), as well as other future child stars Corey Feldman and Billy Jacoby.

[3][4] In his review of the special, Baltimore Sun television critic, Bill Carter singled Olden out, writing "The main kid, called George in the show, has a kind of chip-on-the-shoulder mien; but he sings as sweetly as a choirboy.

[6] Later that same year, Olden followed up with guest-starring television roles, appearing on the daytime soap opera General Hospital and an episode of Little House on the Prairie titled He Was Only Twelve.

[7] In the film, Olden played a young skateboarder who debates the merits of the Silver Surfer with Jesse Lujack (Richard Gere) at a news-stand on the streets of Los Angeles.

[1][10] On the series, Olden played Robbie Stuart, a typical "girl crazy" teenager who, along with his two sisters, inherits an ice cream parlor on the Pismo Beach boardwalk from his recently deceased parents.

[14] After leaving show business, Olden left Hollywood and moved to the Dallas–Fort Worth area working as a real-estate agent at Coldwell Banker Residential Brokerage where his specialties included home marketing, buyer representation, and investor strategies.