Dobson was part of the outlaw country movement and spent time in the 1970s with Townes Van Zandt, Blaze Foley, Mickey White, Rex "Wrecks" Bell, Guy Clark, Steve Earle, Rodney Crowell, and "Skinny" Dennis Sanchez.

[2] He took off from school for several years and spent some time in Colombia; eventually, he returned to Houston and enrolled at the University of St. Thomas, graduating with a degree in Spanish in 1966.

He shared a house with Rodney Crowell and "Skinny" Dennis Sanchez and began to meet other songwriters, including Guy Clark, Townes Van Zandt, and Mickey White.

[5] Dobson also appeared in Heartworn Highways, a documentary that featured members of the Texas music scene - some living in Nashville - including Van Zandt, Clark, Steve Earle, and Rodney Crowell.

He worked on shrimp boats in Galveston and oil rigs in the Gulf with Rex Bell when he needed money and a break from the industry, but he kept writing and playing even when he was on the ocean.

He wrote the oft-recorded song "Baby Ride Easy" on a drilling rig off the shore of Louisiana before he first headed to Nashville.

In the late 1980s, Dobson formed the group State of the Heart with Mike Dunbar as producer and Susie Monick as banjo and mandolin player.

[11] Dobson co-wrote many songs with friends and fellow songwriters including: "Blue Collar Blues" with Ron Davies; "Hole in my Heart" with Steve Earle; "Long Gone Love Song" with Mickey White; "Love Train", "She's Gone to Memphis", and "Welcome to the Wild Side of Me" with Susanna Clark; "Old Friends" and "So Have I" with Guy and Susanna Clark; "One Bar Town" and "Que se yo?"

with Pinto Bennett; "Pony Ride" with Hal Ketchum; "Uncertain Texas" with Rodney Crowell; many songs with Susie Monick; and the album Plenty Good People with W.C.