The Simpsons Season 36: Sideshow Bob's Return & a HUGE Plot Hole!

The legendary animated series The Simpsons has given audiences many laughs and unforgettable moments! It has been on-air for a long time!

Sideshow Bob's Return

One of the most anticipated returns in The Simpsons season 36, episode 2 ("The Yellow Lotus"), is none other than the mischievous Sideshow Bob! The episode aired in 2024! Played by the always-amazing Kelsey Grammer, Bob makes an appearance but there are several questionable points about this.

Also Read: The Simpsons Season 36: What's Next for Springfield's Most Famous Family?

A Massive Plot Hole

The Simpsons Sideshow Bob New Rake Season 36 1 Image

A big thing that really got viewers thinking, was Bob's new love interest, Tasha! She shows up as Bob's new wife to be and gets audiences asking lots of questions. The issue? There was never an explanation about his last marriage.

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Introducing Francesca

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Fans have long awaited Sideshow Bob's second wife. That is Francesca. What is she doing? In the season 17 episode called "The Italian Bob" she showed up! Played by Maria Grazia Cucinotta, Francesca lived in Italy. It's an odd twist to this Simpsons plot point as Bob moves to Italy looking for something different in his life! The episode has tons of humor in it and ends with a crazy plan! Both Bob and Francesca would even try and get the Simpsons. That didn't really stop at trying! That includes the antics of their kid named Gino.

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The Unfulfilled Potential

The Simpson family in Sideshow Bob's office in The Simpsons Image

What makes this so surprising for Simpsons fans, is that this whole plot was only introduced in a single episode. So the impact was small, especially when the next appearances focus just on Bob as he continues to make a name for himself as a sneaky villain. Francesca may have seemed minor. In many ways she wasn't!

She shows us a softer side of Bob, showing off a genuinely caring and affectionate relationship that most viewers never see.
The whole pairing of Bob and Francesca had matching crazy goals to hurt and even kill the Simpsons, adding an even crazier element to Bob's world! This unique and interesting mix would end in an interesting vow.
Their dynamic created a new way to enjoy Bob and Francesca may have been used as a more satisfying antagonist for the family but could have even worked well as a contrasting foil to the relationship between Marge and Homer.

Also Read: Lisa The Skeptic: The Simpsons Episode That Made Lisa Relatable

Sideshow Bob's Supporting Cast

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Fans never got to really see more about Sideshow Bob's unique world. Even Bob and his family. Some may know that he has a few close people he shares an affinity for, some who were briefly featured, in seasons 19.

Cecil, Bob's brother. Played by David Hyde Pierce. He came back, but never in a truly remarkable way!.
Robert Terwilliger Sr, played by John Mahoney.
Dame Judith Underdunk. Played by Tress MacNeille
Even the appearances with Selma never made Bob seem compelling.

If there was any real way to help bring out Bob's most iconic moments that's a path never followed. Bob's crazy shenanigans never reached its full potential! They would even go as far as adding his unique child Gino into the world, all the characters that went unnoticed really created a unique element of Sideshow Bob's history! Bringing some more love into Bob's world may give fans of The Simpsons more moments!

The Future of Sideshow Bob

The Simpsons (1989) TV Show Poster Image

While some may find Sideshow Bob episodes to be highlights, they can't all be winners, even with Kelsey Grammer as the well-loved star! The season 25 ("The Man Who Grew Too Much") episode gave fans of this show plenty to think about and season 29's "Gone Boy" looked to really add some closure to this storyline! That really helped set things up and helped make sense out of what seemed to have happened but there are so many other moments from Bob that fans really have hoped could appear once again!

It's a big surprise for fans! Those behind The Simpsons may have run out of story for this beloved antagonist! A possible solution may lie with bringing Francesca and Gino into the mix! What made them memorable may just give Sideshow Bob new twists to his already existing and interesting narrative. Who knows what The Simpsons may do and what really exciting things are possible when you dive back in this truly memorable family!