"Gal of Constant Sorrow '' The Simpsons episode Episode no. 588 Directed by Matthew Nastuk Written by Carolyn Omine Showrunner (s) Al Jean Production code VABF06 Original air date February 21, 2016 (2016 - 02 - 21) Couch gag The Simpsons family dressed as American football players reunites at the center and get in position, Homer tries to sneak Maggie in as a football but goes over the couch and smashes the wall where he finds the TV remote. Guest appearance (s) Bob Boilen as himself Kelsey Grammer as Sideshow Bob Natalie Maines as Hettie (singing voice) Kate McKinnon as Hettie Season 27 episodes (show) September 27, 2015 -- May 22, 2016 "Every Man 's Dream '' "Cue Detective '' "Puffless '' "Halloween of Horror '' "Treehouse of Horror XXVI '' "Friend with Benefit '' "Lisa with an ' S ' '' "Paths of Glory '' "Barthood '' "The Girl Code '' "Teenage Mutant Milk - Caused Hurdles '' "Much Apu About Something '' "Love Is in the N2 - O2 - Ar - CO2 - Ne - He - CH4 '' "Gal of Constant Sorrow '' "Lisa the Veterinarian '' "The Marge - ian Chronicles '' "The Burns Cage '' "How Lisa Got Her Marge Back '' "Fland Canyon '' "To Courier with Love '' "Simprovised '' "Orange Is the New Yellow '' Seasons 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29
who plays the homeless singer on the simpsons
Natalie Maines