Black Widower

"The wedding was very tough on you. And the honeymoon is going to be...murder!"

- Sideshow Bob

"Black Widower" is the twenty-first episode of season 3. It was written by Jon Vitti, Sam Simon and Thomas Chastain and directed by David Silverman. Kelsey Grammer guest stars as Sideshow Bob.

Synopsis

 * "Selma decides to marry her prison pen-pal, Sideshow Bob. When he gets out of prison, he convinces the Simpson family he has changed for the better, but Bart remains skeptical and is determined to find out what Bob is really up to."

Plot
The Simpsons are having dinner with Selma and her new boyfriend, but it turns out it is Bart's enemy Sideshow Bob. During dinner, he tells the story of his terrible time at the prison. He wins an Emmy that gets taken away. He tells he wanted to kill Bart, but also he changed. Then he tells the story of how he and Selma met, which was during a prison pen-pal program. He supposedly turns a new leaf after he met Selma. He was released from the prison, and the story ends. Everyone enjoyed it except Bart. Then Sideshow Bob asks Selma to marry him, and she eagerly accepts.

Sideshow Bob makes an appearance in the Krusty telethon, and he tells Krusty there are no hard feelings. Bart is terrified of his soon-to-be new uncle, since Bob swore he'd get revenge on Bart for having him sent to prison for framing Krusty for robbery, and he would never trust him. The wedding is almost cancelled when Sideshow Bob admits he hates Selma's favorite show, MacGyver, but is saved by Homer when he says when Marge watches her shows he goes for a walk or drinks some beers and comes back still in love. Bob decides he will go for a walk when MacGyver is on TV, and all is resolved.

During the wedding, everyone is happy, that is except Bart. However, everyone encourages him to let go of the past. Selma and Bob send Patty and the Simpsons a honeymoon video during which Bob goes crazy toward one of the staff demanding a room with a fireplace. During the honeymoon, while MacGyver is on, Bart realizes Bob is about to try and murder Selma.

At the hotel, Bob is walking around when his room explodes. After making a 'tearful' call to the front desk, he returns to the burnt out room expecting to see Selma's remains waiting for him, only to find Bart waiting with the police. Selma slaps Bob for trying to kill her, and tells him she wants a 'separation'. Bob asks how Bart worked out his plan. Bart explains, in Selma's video, Bob was eager to have a fireplace in their room and Bart noticed the gas tap. Bob turned the gas on before going for a walk knowing Selma wouldn't be able to smell it as she had lost her senses of smell and taste due to a bottle rocket accident as a child. Knowing she would smoke following MacGyver and the match would be enough to cause an explosion, he ran and told Homer... and after several failed attempts to explain it to him, he told Marge instead and they raced to the hotel just in time.

Bob is confused as to why the room exploded if Selma was stopped. Chief Wiggum admits they were having celebratory cigars outside the room when he threw a match into the gas-filled room accidentally. Bob is taken away, swearing to get out the next time the Democrats are in power. Everyone admits Bob had fooled nearly everyone, and thanked Bart for never losing his distrust.

Production
"Black Widower" was written by Jon Vitti and directed by David Silverman. For a long time, the show's writers had wanted to craft an episode revolving around a "mystery", and so executive producer Sam Simon consulted Thomas Chastain, from the New-York based Mystery Writers of America group, to help. With the assistance of Chastain, the writers were able to include a number of small clues and details into the episode so that the viewers would be able to solve the mystery before it's conclusion.

The character of Sideshow Bob returns in this episode, after last being seen in season 1's "Krusty Gets Busted", in which he was arrested and imprisoned. Bob's animation model was revamped and updated for this episode in order to reflect the style of Brad Bird. Kelsey Grammer guest starred and returned to voice Bob. Grammer initially expected Bob to be a one-time role, but it eventually became one the most popular roles he ever played, as well as one of the show's most iconic characters, and thus became a recurring role.