Question: who plays the homeless singer on the simpsons
Answer: 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