Harry Shearer announced today that after more than 25 years of voicing beloved characters on The Simpsons—including Mr. Burns, Ned Flanders, Principal Skinner, Kent Brockman, and bus driver Otto—he would be leaving the show. The greatest animated show of all time—and what some may consider the greatest television show, period—has never been afraid to delve into musical numbers, so Music Times dug up six of the best songs performed by Shearer's characters across the program's run, including plays on Disney songs and Guns N' Roses classics.

"It's High to Be Loathed" by Mr. Burns

One of our favorite musical performances from a character voiced by Shearer comes from none other than Mr. Burns, the nuclear power magnate who has been associated with his voice actor more today than any other. Burns is rarely one to expend too much energy but that all changes when he discovers that Abe "Grandpa" Simpson formerly moonlighted as professional wrestler Gorgeous Godfrey—a vain villain styled after real-life Gorgeous George. He attempts to lure both Grandpa and other former wrestlers back into the ring, but Abe is hesitant, remembering how much he was loathed for his role. Burns explains that being hated is actually a blessing, citing himself as an example: "You've got to love to be hated / find the good in being bad / Oh, the crowd is full of gentlemen / but they've paid to see the cad." Burns reveals that Gorgeous Godfrey inspired his young self to take the role of a villain in becoming an entrepreneur.

"Tribute to Mr. Burns" by Mr. Smithers

There's some sort of psychological study to be done in noting that both Mr. Burns and his obsessively loyal assistant Mr. Smithers are voiced by the same man. Either way, it makes sense that if the latter were to ever break out in a musical number, it would be a tribute to the man who he is almost creepily close to. Smithers does his all to help Mr. Burns attempt to win over Marge when she gets a job (in the appropriately-titled "Marge Gets A Job") by singing a song-and-dance revue in honor of his boss: "He loves to smoke / enjoys a joke / Why, he's worth ten times what he earns/ He's Mr. Burns!" The performance is one of many references to Citizen Kane that have been made throughout the show's run. Real-life vocalist Tom Jones makes an appearance during the episode, chained up by Mr. Burns to force him to perform for Marge and Homer.

"Welcome To The Jungle Gym" by Ned Flanders

Flanders hasn't gotten nearly enough attention in the reports on Shearer's leaving the show, but we'd argue he's the most important role that the voice actor has taken in the program. Although The Simpsons' neighbor has sung plenty of traditional spirituals throughout the show's history—such as "Amazing Grace" and "Onward Christian Soldiers"—his best musical moment was when he adapted a sleazy rock 'n' roll classic to his conservative needs. After Marge attempts to introduce Rod and Todd Flanders to a more adventurous lifestyle, Flanders attempts to dissuade them with a song titled "Welcome to The Jungle Gym," which explains the dangers of traditional childhood pastimes, in a similar fashion to how Axl Rose explained the seedier side of Los Angeles with the Guns N' Roses' "Welcome to The Jungle." Oddly enough, Flanders has performed sleaze rock before, singing "Dirty Deeds Done Dirt Cheap" by AC/DC with Homer in a previous episode.

"See My Vest" by Mr. Burns

The Simpsons combined several Disney animated films as influences for the episode "Two Dozen and One Greyhounds." Santa's Little Helper fathers 25 puppies, which Mr. Burns volunteers to adopt. Although he adopts one as his own ("Little Monty"), it's soon discovered that he intends to make a coat out of the rest of them. Although the plot clearly draws inspiration from 101 Dalmations, the song "See My Vest" is a melodic play off of "Be Our Guest" from Beauty and The Beast, where Burns shows off his collection of clothing made from exotic animals. Director David Mirkin believes that the song is one of the best in the history of the show.

"Old Man River" by Dr. Hibbert

Dr. Julius Hibbert is another character on the show voiced by Shearer, demonstrating just how wide his range could be. He doesn't get much time to sing on The Simpsons but the good doctor's 30-second bit during the episode "Tall Tales" is well worth it. The episode revolves around a number of disconnected tales that all deal with American folklore. One, based on Mark Twain's Tom Sawyer and not a tall tale per se, revolves around the river adventures of Tom (Bart) and Huck (Nelson), and features the deep-voiced Hibbert singing the traditional folk song "Ol' Man River" while traveling the presumed Mississippi. We should note that Shearer doesn't actually get vocal credit for the song portion, as Thurl Ravenscroft (also the voice of Tony The Tiger) stepped in to sing.

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