Kelsey Grammer returns as Sideshow Bob in The Simpsons short The Most Wonderful Time of the Year

Just when you thought Christmas, er, Halloween, couldn't get any more cheerful, it does. The tenth Disney+ The Simpsons short, "The Most Wonderful Time Of The Year," premiered on October 11th on the streamer and showboats the delightful Kelsey Grammer as the notorious and fan favorite Sideshow Bob. He teams up with other Disney villains to perform a reinvented and spoofed version of the holiday classic, "The Most Wonderful Time Of The Year."

In the three-minute musical piece, Bob once again captures the Simpsons and subjects them to his operatic singing on Halloween. But Bob isn't performing solo, for he recruited nearly all the infamous Disney antagonists to join him. It's a clever and hilarious narrative that only the animated sitcom could do since The Simpsons and its creative team aren't strangers to parodying Disney franchises.

Villains in the short include Cruella, Shere Khan, and Kaa from The Jungle Book, The Red Queen from Alice In Wonderland, Amos Slade from The Fox and the Hound, Maleficent from Sleeping Beauty, the Evil Queen from Snow White, and countless others. The segment also returned a one-time The Simpsons villain, Miss Lucille Botzcowski, aka the Babysitter Bandit, in a blink-and-you-'ll-miss-it scene.

I'm not going to give away the encore, as that'll be spoiling, but it involves Bart, the God of Mischief Loki, and a rake. So, draw your own conclusion if you haven't watched "The Most Wonderful Time Of The Year" yet.

Watch a clip from Disney+'s Twitter:

How Sideshow Bob became a Disney Villain and why "The Most Wonderful Time Of The Year" is a must-watch

When Disney Corp. acquired Fox Entertainment in 2019, it brought out all its properties, including The Simpsons, Family Guy, Bob's Burgers, and other Fox programming. Naturally, Sideshow Bob falls under the Disney Villain radar, and rightfully so. The bushel-haired Shakespearean actor turned Krusty's sidekick has a poignant revengeful arc that's mainly directed at Bart, as he was the one who unfoiled Bob's framing of the clown and sent him to prison. Since then, Bob had attempted to murder the 10-year-old on several occasions, but to no avail. It's the running of the gag that makes it comical and notable.

According to Inverse's interview with The Simpsons co-showrunner Al Jean, the long-time writer opens up regarding Sideshow Bob's legacy, the Halloween short, and working with Kelsey Grammer.

"Well, with these shorts, we always want to do something really different every time and special, and Kelsey's the best, and we have had the greatest relationship having him on the show. He's always there for us. He's always really nice and he loves to sing, which is one of the reasons he was cast as Bob by [the late] Sam Simon because he's got a great voice. So we thought him doing a Halloween version of “The Most Wonderful Time of the Year” would be great."

Jean additionally emphasized that it was an "honor" having Sideshow Bob coronated as a Disney Villain, a title only meant for the most "evil" of Disney characters.

"“Oh, I didn't even think of that. That's a great honor for Bob.”"

If you're a fan of both Disney and The Simpsons, such as myself, then I recommend watching "The Most Wonderful Time of the Year." It's the perfect Halloween inceration, and Grammer's performance is Emmy-worthy. Plus, Bart gets his revenge on his mortal enemy.

The Simpsons "The Most Wonderful Time of the Year" is now streaming on Disney+.