Since the 1989 premiere of FOX's long-running animated powerhouse The Simpsons, hundreds of guest stars have voiced characters on the show. But it took eight seasons for the show to book its first country music star, with Johnny Cash voicing the part of a "space coyote" that hapless Homer Simpson encounters during a pepper-induced hallucination.
Although previous episodes of the show had featured actress-singer Beverly D'Angelo (who portrayed Patsy Cline in the film Coal Miner's Daughter) as country starlet Lurleen Lumpkin, and real sometime-country singer Linda Ronstadt (in the classic "Mr. Plow" episode), a bona fide country legend got to sing in a season nine episode that aired February 22nd, 1998. The episode, titled "The Last Temptation of Krust," poked fun at Krusty the Clown's outdated comedy material (and penchant for seeking lucrative endorsements) and featured several stand-up comedians, including Jay Leno and Steven Wright. But it was Hank Williams Jr. who gave voice to a meaty, Western-themed jingle for "Canyonero," the sport utility vehicle that "smells like a steak and seats 35."
A brief segment of the tune, complete with the snapping of a whip — inspired in part by the classic Rawhide TV theme song sung by Frankie Laine in the Sixties — appears within the episode as Krusty takes young Bart Simpson for a spin in the "country-fried truck endorsed by a clown." In an unusual move, the show's producers liked the song so much they devoted an even longer segment to it which ran after the closing credits instead of during. Williams plays it straight even as he sings such laugh-inducing lyrics as "top of the line in utility sports, unexplained fires are a matter for the courts" and the 65-ton truck is seen bursting into flames and plowing throw a field, sending deer flying through the air.
Nearly 18 years to the day this episode aired, another country star was featured on The Simpsons. On Sunday (February 21st), in an episode titled "Gal of Constant Sorrow," Dixie Chicks singer Natalie Maines made her first appearance on the show since playing herself in a 2008 episode that also featured her fellow Chicks, Emily Strayer and Martie Maguire. This time, she provided the singing voice for Hettie Mae Boggs, a homeless woman whose beloved shopping cart is sent into the river by Bart. With dialogue voiced by Saturday Night Live cast member Kate McKinnon, Maines sings as Hettie several times during the episode, and the ode to her drowned cart is set to the mournful tune of the classic "Wayfaring Stranger." Simpsons show-runner Al Jean explained via Twitter that the Boggs character was based on someone similar that the episode's writer Carolyn Omine had read about.