More than 100 of Sykes' songs have been recorded by John Prine, Rosanne Cash, The Judds, Jerry Jeff Walker, and George Thorogood, although he may be best known for co-writing "Volcano", the title track of Jimmy Buffett's 1979 album.

[1] Sykes has released at least fifteen albums including I'm Not Strange, I'm Just Like You, and It Don't Hurt to Flirt, His television debut was performing "B.I.G.T.I.M.E" as a musical guest on Saturday Night Live in 1980.

[2] After hitchhiking to the Newport Folk Festival in 1967, Sykes saw Arlo Guthrie perform "Alice's Restaurant Massacree" and was inspired to pursue music as a full-time career.

[3] Sykes' first job in music was performing at a Holiday Inn in downtown Charleston, South Carolina after auditioning with "Alice's Restaurant Massacre".

In New York Sykes met and befriended songwriters Jerry Jeff Walker, Emmylou Harris, John Prine, Kris Kristofferson, Gary White, and Loudon Wainwright III.

[5] In January 1979, Kris Kristofferson and Rita Coolidge asked Sykes to attend an event for UNICEF in New York City.

In the fall of 1993, Sykes made a deal with the renowned publisher Carlin International and built The Woodshed Recording Studio.

[10] Teaming up with Dallas businessman and investor Kelcy Warren in 1997, Sykes began to expand the work of his Woodshed recording studio and opened new publishing companies.

The two formed a new label, Syren Records, which released Sykes' next two albums, rocker Advanced Medication for the Blues in 1998 and Americana-friendly Don't Count Us Out in 2001 which features duets with friends like Iris DeMent, John Prine, Rodney Crowell, and Susan Marshall.

KSME released a "best-of" album in 2012 called 20 Most Requested featuring songs like a Prine co-write "You Got Gold," a heartfelt autobiographical ballad "Broken Home," and Jimmy Buffett hit "Volcano."

The album was recorded in Nashville by engineer and producer Brent Maher (The Judds, Kenny Rogers, and Willie Nelson) and released in 2016.

The album contained "No Ordinary Blue", a song by Prine and Sykes written in the mold of "You Got Gold" and "Long Monday".

Sykes made his acting debut as the lead character in the 1972 cult film Summer Soldiers,[15] directed by Japanese avant-garde filmmaker Hiroshi Teshigahara (Woman in the Dunes).