Gal of Constant Sorrow - wikipedia Gal of Constant Sorrow `` 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 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 `` Gal of Constant Sorrow '' is the fourteenth episode of the twenty - seventh season of the animated television series The Simpsons, and the 588th episode of the series overall. It aired in the United States on Fox on February 21, 2016. Contents 1 Plot 2 Reception 3 References 4 External links Plot During breakfast, Marge Simpson discovers a loose tile on the floor and says that she 'll have to call a handyman. Homer Simpson gets the hint that he 's not handy and decides to replace the tile himself. He succeeds with the help of an online tutorial, but soon realizes that he has trapped the family cat Snowball II inside the floor. Meanwhile, Bart Simpson is participating of sled race on a hill, but Milhouse Van Houten is slowing them down, because he 's scared. Bart knocks Milhouse off, but he loses control of the sled and hits the shopping cart of a homeless woman named Hettie Mae Boggs, throwing it and all of her things into a frozen river. Feeling guilty, he invites Hettie to the Simpsons ' house. Hettie is getting too comfortable in Bart 's closet, so she decides to give Bart one dollar per day as a rent. Lisa Simpson soon realizes Bart 's suspicious income, and discovers Bart 's scheme, but Bart convinces her not to tell Marge, because if she does so, Hettie will get kicked out of the house. They also discover Hettie 's incredible talent for music, so Lisa invites her to stay in her closet. During the recordings of one of her songs, Bart warns Lisa that she should n't be doing that, because if Hettie lets her down, Lisa wo n't be able to deal with her emotions. Lisa showcases the song to Mr. Dewey Largo, her music teacher. He is initially hostile, saying he 's come to hate music, but he is convinced to let her keep her idealism until she is taught by Mrs. Ortner the following year. She then seeks Mayor Quimby and Krusty the Clown where she manages to arrange a concert and a NPR interview for Hettie. However, during the interview, Hettie reveals that she 's a drug and heroin addict. Lisa is shocked when she also discovers that Hettie could be very violent to the point of shooting someone ( and possibly her parents ) in the face. Meanwhile, Homer manages to free the cat from the walls, but he also traps Santa 's Little Helper inside. Later, Bart and Lisa come clean about Hettie to Marge, but Homer interrupts the conversation by falling through the roof trying to rescue Santa 's Little Helper. Marge reveals that she has already rescued him. She also tells Homer about Hettie, but Hettie has gone missing with her concert in thirty minutes. Homer and Bart manage to find Hettie drinking on Cletus Spuckler 's farm while Lisa is distracting the concert 's audience by playing her saxophone. After a conversation and almost getting shot in the face, Homer manages to bring Hettie to her concert, but Lisa had failed to entertain the crowd, so the place is almost empty. Lisa is heartbroken about Hettie, so she decides to sing one last song dedicated to Lisa, who decides to forgive her. During the credits, Hettie is shown playing in a rehab clinic only for the interns to escape to Moe 's Tavern through a secret tunnel. One of the interns, Disco Stu, comments that the bar is dirtier than the tunnel. Reception `` Gal of Constant Sorrow '' scored a 1.4 rating and was watched by 3.10 million viewers, making it Fox 's highest rated show of the night. Dennis Perkins of The A.V. Club gave the episode a B+ stating, `` For all the griping about The Simpsons overstaying its welcome, it does n't take much for the show to win back viewers ' trust and affection. The characters and pieces are all in place, just waiting for the right tune to start moving in a semblance of their former hilarious harmony. For the second episode this season, credited writer Carolyn Omine pitches her script with a deftness and an understanding of the Simpsons that makes an episode fairly sing. '' References Jump up ^ Porter, Rick ( February 23, 2016 ). `` Sunday final ratings : ' Shark Tank ' adjusts down ''. TV by the Numbers. Retrieved February 23, 2016. Jump up ^ Perkins, Dennis. ( February 21, 2016 ). `` Bart and Lisa 's musical friend finds a note of sweet silliness on The Simpsons ''. The A.V. Club. Retrieved February 22, 2016. External links `` Gal of Constant Sorrow '' on IMDb `` Gal of Constant Sorrow '' at TV.com `` Gal of Constant Sorrow '' at theSimpsons.com The Simpsons episodes 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 Season 27 `` 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 '' Retrieved from `` https://en.wikipedia.org/w/index.php?title=Gal_of_Constant_Sorrow&oldid=789737754 '' Categories : 2016 American television episodes The Simpsons ( season 27 ) episodes Homelessness in popular culture Hidden categories : Tv.com template using numeric id Talk Contents About Wikipedia Español Français Gaeilge Українська Edit links This page was last edited on 9 July 2017, at 07 : 22. 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Question: who plays the homeless singer on the simpsons
Answer: Natalie Maines