Production
The script for "Bart the Lover" was written by Jon Vitti, who wanted an episode centered around Mrs. Krabappel that examined what it was like to have Bart as a student. Executive producer Mike Reiss pitched the idea of having Bart answer Mrs. Krabappel's personal ad. It was the first episode of the show to feature Mrs. Krabappel in a prominent role. The subplot where Homer tries to clean up his language was written partially in response to the many complaints the show had been getting about the language on the show. Near the end of the episode, there is a montage where Homer has a series of bad experiences that cause him to curse, although the scene always cuts out before he can be heard swearing. While recording Homer's lines for that sequence, Dan Castellaneta was told to include the cursing. According to Mike Reiss, by coincidence, some eight year old children were allowed to visit the studio the day those lines were recorded. Reiss recalls that "their eyes were as big as saucers" after hearing Homer curse. The ending of the episode was largely pitched by James L. Brooks, who wanted a scene where the entire family got together to write Woodrow's final letter to Edna.
The episode was directed by Carlos Baeza. In the background of the classroom, there are several portraits of past United States presidents. These were added for the scene where Bart tries to think of a name for his fictional letter writer, and sees a portrait of Woodrow Wilson. Woodrow's voice was performed by Harry Shearer, who did an impression of Ricardo Montalbán. The picture Bart sends Edna is of NHL and WHA star Gordie Howe. The writers had originally wanted to use a picture of American football player Johnny Unitas, but were unable to get the rights to use his image for free. Howe, their second choice, was suggested by Al Jean, who had been a Detroit Red Wings fan growing up. At the end of the episode, Howe's NHL and WHA statistics are shown because the writers decided to try something different to fill time.
During the opening sequence in which Bart's class watch a film about zinc, a character in the film tries to shoot himself in the head. The Fox censors objected to this, so the producers had to claim that the character was not aiming at his head. For the name of the yo-yo trick that Bart performs for Milhouse, the writers had wanted to use a term that was slang for masturbation. They proposed several names to the censors, and "Plucking the Pickle" was the term they deemed acceptable.
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