Dubbed "Barnum of the Buttes" by The Denver Post, Oakley is best known for G. William Oakley's Heritage Square Opera House "Nostalgic Theater" adaptations of such classic melodrama as The Drunkard, The Streets of New York, and Sweeney Todd, literary works such as Dr. Jekyll and Mr. Hyde, Frankenstein, and Sherlock Holmes, and original works including Call of the Yukon.

His productions also featured "vaudeville olio" variety numbers showcasing the musical and comedic talents of his repertory company interspersing jokes with modern-day spoofs ranging from Shakespeare's Romeo and Juliet as houseflies to Michael Jackson's "Thriller".

Oakley's Heritage Square Opera House in Golden, Colorado (1971–1988) and the historic Goldenrod Showboat at Laclede's Landing on the St. Louis Mississippi waterfront (1975–1985) became popular icons for his brand of theater.

In 1962–63 he worked as a house parent at Sunny Hills Residential Treatment Center for Children in San Anselmo where he met Rayda Pomroy whom he married in 1963.

At CSU he met his mentor Dr. Dean Wenstrom who convinced him to try stage acting, which led to his first role as William of Normandy in Alfred, Lord Tennyson's Harold.

Oakley's Heritage Square Opera House in Golden, Colorado (1971–1988) and the historic Goldenrod Showboat in St. Louis (1975–1984) became the most popular icons for his brand of theater.

Oakley said his favorite part of the show as the Olio where he incorporated modern-day themes and movies such as a production of Michael Jackson's "Thriller" spoof on film noir.

He designed the new 350-seat, two-story venue top to bottom as a dinner-theater that operated under the imprimatur Gaslight Enterprises DBA G. William Oakley's Heritage Square Opera House.

Gaslight-Goldenrod Associates was a combination of investors from Gaslight Enterprises aka the Heritage Square Opera House, and theater producer Frank Pierson and his business partner Don Franz of the St. Louis Ragtimers trio.

Under Oakley's direction the Goldenrod mirrored its sister theater in Colorado as dinner-theater that included a buffet dinner with piano entertainment, silent films with live piano accompaniment, the comedy melodrama and vaudeville olio repertory cast, and shared a traveling creative team and production crew with the Opera House in Colorado.

Oakley produced the Annual National Ragtime and Traditional Jazz Festival from 1975 to 1984 with the Goldenrod as host of the week-long event that featured famed singer Pat Yankee and the Turk Murphy Jazz Band of San Francisco, Carol Leigh, Lew Green and the Original Salty Dogs of Chicago, a dozen other bands and score of solo musicians who entertained in the Goldenrod's theater and festival's adjoining barges.

In 1979 Oakley worked as a comedic consultant with producers Ashton Springer and Frank Pierson for the musical Whoopee which played six months on Broadway.

The revival of the 1928 Eddie Cantor vehicle Broadway musical started at the Goodspeed Theater Opera House in East Haddam, CT. Oakley later directed the show's national tour, which received rave notices throughout its nine-month run.

Also of note was the Rick and Ruby Rock and Roll Revival musical comedy directed by Bob Lacey and starring Monica Ganas, Rick Right and J. Raoul Brody, which enjoyed an extended run, and the musical revue Dawgs, a spoof of the Broadway shows Cats, by Milt Larson of Hollywood's Magic Castle fame.