Songfacts®:

• This twangy tune is performed in the Coen Brothers movie The Ballad of Buster Scruggs by the actors Willie Watson and Tim Blake Nelson. The latter plays Buster Scruggs, a cheerful singing cowboy, who is challenged to a duel by Willie Watson's cuter, faster and younger rival. They sing this bittersweet duet as (spoiler alert!) Buster's drifts off to Heaven after being shot.
• The song was written by bluegrass singer-songwriter Gillian Welch and her musical partner David Rawlings. Welch recalled to Billboard that Joel Coen reached out to the pair with specific instructions for the tune.
  
  "He said they needed a duet between two singing cowboys, one the more established one and one the younger, faster, better-looking sweeter singer, and that the duet needed to be sung between them once one of them is dead," Welch recalled.
  
  Welch added that she came up with the basic idea while driving across New Mexico on a cross-country trip. She ran it by Rawlings, it seemed to fit and they started working on it adding "a bunch of yodelling."
• Once they'd completed their demo, Welch and Rawlings played it for Joel Coen, accompanied only by an acoustic guitar. "He really liked it. I don't know if he was expecting the yodeling," the songstress recalled. "All he said after we played it for him was 'It's perfect.' We laughed and talked for a minute and he said, 'Will you play it again?'"
• "When a Cowboy" earned a nomination for Best Original Song at the 2019 Academy Awards, where Gillian Welch and David Rawlings performed it. "Shallow," from A Star Is Born, won the award.