Production
"Half-Decent Proposal" was written by consulting producer Tim Long and directed by Lauren MacMullan. Serving as assistant director for MacMullan was Raymond Persi, who later became, according to current showrunner Al Jean, one of the series' "best regular directors." The episode was first broadcast on the Fox network in the United States on February 10, 2002. The idea for the episode was pitched by James L. Brooks, who is one of the series' co-creators and executive producers. He suggested an episode in which Artie Ziff returns and offers Homer a million dollars in exchange for spending a weekend with Marge, trying to convince her to divorce Homer. He also wanted the episode to parody the film Indecent Proposal. Ziff's wealth had been established in the season 4 episode "The Front", in which it was revealed that he had become an "internet-billionare." The setpiece of "Half-Decent Proposal", in which Homer's snoring is keeping Marge awake during the night, was pitched by Long's ex-girlfriend. Originally, at one point in the episode, there would be a sequence in which Homer travels to Silicon Valley in the wheel well of a jet. The sequence was based on a news story that the Simpsons writers were "really obsessed with." The episode was one of the first to suggest that Lenny and Carl has an intimate relationship. This revelation garnered scrutiny from the series' fans, who, according to Jean, were "very angry" over it.
"Half-Decent Proposal" was animated in a very complicated manner. In the DVD audio commentary for the episode, director MacMullan stated that a couple of sequences in the episode were "reaching too far" for the animation process to be "reassembled correctly." One example, she mentioned, is the scene in which Marge remembers Ziff's assault from "The Way We Was". Ziff's assault is shown as hands reaching for Marge, and was put together by MacMullan in postproduction. Right after Marge's sisters Patty and Selma send an e-mail to Ziff, the e-mail's path is elaborately shown through a "trip through the computer wires." MacMullan stated that, even though she found the scene "illogical," she maintained that it was "done with great effort." Because the characters at Ziff's prom had to wear 70's styled wardrobe, the animators had to come up with new designs for the character's clothes. Several of the designs were pitched and drawn by Ron Hauge, a former Simpsons writer who was responsible for coordinating character designs on the series for many years. The dance that Ziff performs at the prom was pitched by MacMullan, and the prom locale was drawn using a photo reference. A scene in the episode shows Homer and Lenny signing on to become oil workers. The manager who hands them a paper clip can be seen smoking, and originally, MacMullan suggested that the manager "puts his lit cigarette out in the can, and blows his other arm off." She pitched the idea to Jean, who responded by writing "I wouldn't." The episode's complicated and lengthy animation process was so strenuous that it led the Simpsons animators to start calling MacMullan "Lauren MacMultiplane".
"Half-Decent Proposal" features the return of Artie Ziff, and the first time since the season 2 episode "The Way We Was" that he was portrayed by American comedian Jon Lovitz. Even though Ziff appeared in the season 4 episode "The Front" as well, Lovitz was not available during the episode's recording session, and the character was instead voiced by Dan Castellaneta, who is one of the series' main cast members. Jean stated that Lovitz, who has voiced a variety of characters on The Simpsons before, is one of the staff's "favourite guest-stars." The episode also features the first and only appearance of Baron von Kissalot. In the episode, Marge is charged $912 for a taxi drive back to Springfield. She sarcastically tells the taxi driver to send the bill to "Baron von Kissalot", who turns out to be a real person. The character, which was pitched by former show runner David Mirkin and portrayed by Castellaneta, has become one of the writers' favourites, and was series animation director Jim Reardon's favourite joke of the entire season. Castellaneta also voiced a couple of the ants who are put on fire at the oil tower. The Simpsons staff debated whether the ants would speak or make any sound at all, with series co-creator Matt Groening being notably hesitant to them being voiced.
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