Now, one of the most iconic “characters” in country music, Willie Nelson was already singing gospel songs at church, and performing at local dances in Texas before he was 10 years old. He wrote his first song at age seven! Nelson is known for his many hits as a songwriter and performer. They include the standard, “Crazy” made famous by Patsy Cline, his hit single “Bloody Mary Morning,” “Mamas, Don’t Let Your Babies Grow Up to Be Cowboys,” written by Ed Bruce, and performed with Waylon Jennings, and “On the Road Again.” “Always on My Mind,” co-written by Nelson’s session guitarist Johnny Christopher with Wayne Carson and Mark James, was a modest hit for several artists. Originally, it was recorded in 1972 by Brenda Lee, and shortly after, by Elvis Presley, for whom it was a bigger hit. Ten years later, among other awards, Willie Nelson would make it a multi-Grammy winner.

In the mid-80s, Nelson and Jennings teamed up with Kris Kristofferson and Johnny Cash to form The Highwaymen, a powerhouse group of country music “outlaws” that toured the world.

By then, Nelson and, to some extent, all his Highwaymen cohorts also caught the Hollywood bug! One superstar actor encouraged Nelson to give it a shot.

“’You’re a natural, Willie,’” Robert Redford told him when they met while flying cross- country, in 1979,” writes Henry C. Parke for INSP in Willie Nelson: Crooner & Cowboy.

Nelson called director Sydney Pollack, pitched himself as an actor, and was soon on set with Redford and Jane Fonda, in a supporting role in The Electric Horseman. More than 50 appearances in films and TV shows followed, including Once Upon a Texas Train with Richard Widmark, Ken Curtis, and Angie Dickinson, the 1986 version of Stagecoach with fellow Highwaymen, Kristofferson (Also in A Star Is Born 1976, and Two for Texas 1998), Cash, and Jennings, and Honeysuckle Rose, which featured Nelson’s “On the Road Again.” The song was nominated for an Academy Award. For a more in-depth look at Willie Nelson, as a Western actor, check out Willie Nelson: Crooner & Cowboy.