During the '60's, Saylor played in various rock bands, one being "E. O. Doggett." They lived and toured in an old school bus, true-to-life Merry Pranksters, opening for artists such as Johnny Winter, The Music Machine, and Shiva's Head Band. At the age of 24, he signed his first recording contract.

Moving to Houston, Saylor formed another band, "The Front Porch Swing." In 1983, when Hurricane Alicia hit Houston, they co-wrote and released the comic "Alicia," a hit with local radio stations. Saylor also wrote the theme song for United Cerebral Palsy, and was the winner of the Texas State Poetry Contest. In the 1990's, he went to California, playing San Francisco, Oakland, Berkeley, appearing at venues like the Freight and Salvage. Inevitably, Saylor returned to his Texas roots, performing in Austin at venues such as Chicago House, the Outhouse, and Headliner's East.

New Rose Records released Calvin Russell's 1991 cover of Saylor's Crossroads on the album "Sounds of the Fourth World." It has subsequently been released on four of Calvin's albums, as a single, and by The Urn, a Dutch band.

In 1993, New Rose released Saylor's CD, That's Just the Way it Goes, recorded in Nashville. Music critics compared it to "a Shake Russell feel, only from a little more matured view. Smooth back home vocals entwined with a variety of accompaniments ...that veer toward country, blues, rockin' blues, and light jazz make for a pretty good listen."

In 1997, Nanci Griffith, accompanied by Lyle Lovett, recorded and released Saylor's Dress of Laces, on "Other Voices Too." In 1998, Saylor was chosen the Houston Music Council's Acoustic Artist of the Year, and had various songs recorded on a number of compilation albums. Saylor has just returned from a tour of France, where he not only performed, but was also interviewed by several magazines, including Crossroads. His most recent CD, Graven Image, a collective of lifetime experience, is now available from Last Call Records.