He studied journalism at the University of Texas at Austin and worked for a publishing house in Austin and was business and production manager for the Southern Methodist University Press in Dallas. Wittliff finished a draft in 1979 and Universal Studios green-lighted the film with a budget of $14 million.
In 1964, he started his own publishing house, Encino Press. The last book from the Encino Press was Blue & Some Other Dogs by John Graves, issued in 1981. Wittliff wrote Country (1984), and the film would have been his directorial début, but he quit after his cinematographer was fired.
Wittliff met Willie Nelson in the late 1970s and he was a writer on Honeysuckle Rose (1980) and Barbarosa (1982), both of which starred Nelson.
Wittliff agreed to write a script based on Nelson"s album Red Headed Stranger (1975). The studio wanted Robert Redford to play the "Red Headed Stranger," a role Nelson had envisioned for himself.
Redford turned the part down and Nelson and Wittliff returned their advances to buy the script back. Wittliff went on to direct and co-produce (along with Nelson) the film Red Headed Stranger (1986).
In 1986, Wittliff founded the Southwest Writers Collection at Texas State University, which featured work by authors and songwriters from Texas and the American Southwest.
In 1996, he founded the Wittliff Collection of Southwestern and Mexican Photography at the university. The university"s holdings, now renamed the Wittliff collections, have grown to become one of the most extensive archives of Southwestern materials in the United States, a centerpiece being the papers of writer Cormac McCarthy. The archive also features an exhibition containing items from Lonesome Dove.
Wittliff is also a distinguished photographer.
His photographs are included in the books Vaquero: Genesis of the Texas Cowboy (2004), Louisiana Vida Brinca (2006), and A Book of Photographs from Lonesome Dove (2007).
In 1959, he was initiated as a member of the Tau chapter of Kappa Sigma at the University of Texas and in 2012 became the fraternity"s 79th recipient of the Manitoba of the Year distinction.