Production
"Listen to the Rain on the Roof" was written by series creator Marc Cherry and series writer Jeff Greenstein and directed by Larry Shaw. Cherry's decision to advance the storylines by six months for the third season premiere came as a response to the series' problematic second season. Cherry stated that he regretted most of the second season, as scheduling problems made it difficult to plan the season's storylines. "One of the problems I had with Season 2 was that I had to keep going with the previous year's stuff," he explained. "I learned you have to go back to square one to build up the tension again." The cast also expressed disappointment in the second season; James Denton considered leaving the show and Marcia Cross confessed: "I've been at Marc's door plenty of times going, 'You've got to be kidding.'" Cherry stated that the six-month time jump would help the storylines develop quicker, as the second season's storylines lagged. He added: "And I'm going to work much harder to criss-cross all the women's stories so that their lives bump up against each other."
To help refresh the show, several new writers were hired, including Greenstein, Joe Keenan, who also served as an executive producer, and Bob Daily, who was also a producer. Daily commented, "When we came on in season three, the mandate was to bring the show back to its roots. That meant having plotlines spring from relatable experiences, no matter how operatic or convoluted." For the season's main mystery, Cherry and the writers wanted to incorporate more of the series' regular characters rather than bringing in various new ones, like they had done in the second season with Betty Applewhite (Alfre Woodard) and her family. They developed the Orson plot line around the "idea that one of our women marries a guy who has dark secrets and possibly a violent streak." Cherry opined: "I thought there was something exciting about that, but real and relatable." Greenstein commented that the writers worked backwards from the second season's cliffhangers to develop the Orson storyline, forsaking the original material that had been developed earlier. The cast responded positively to the new material for the season.
The episode is the first to feature Kyle MacLachlan as a series regular. He originally appeared as Orson Hodge in a string of episodes at the end of the second season. The Orson character was originally planned as a romantic interest for Susan, according to executive producer Tom Spezialy, until Cherry decided to pair Orson with Bree. Additionally, when Orson was introduced toward the end of the second season, he was originally to be a con artist. A character portrayed by Julie White appeared in the second season finale and would have been Orson's accomplice, but the entire storyline was discarded in favor of the mysterious disappearance of Orson's wife and White's character was not seen or mentioned again. MacLachlan commented that his character is "desperate to make this relationship with Bree work. Anything that tries to knock that apart becomes a threat." Cherry called Orson Bree's perfect match, but added that their similarities "will ultimately prove to be the downfall of the relationship."
Kiersten Warren also returned to the series as Nora Huntington after being introduced at the end of the second season. On her storyline, Warren commented, "There’s a lot of families who are going through this. Not quite the surprise ooh, boo, child, but children from other marriages and trying to meld these families. I think a lot of people have to deal with it. I think it’s fantastic that they’re doing this on the show." Dougray Scott made his debut in this episode as Ian Hainsworth, Susan's romantic interest. Cherry opined that the character "can legitimately rival Mike for affections." Daily commented on the storyline, saying: "Talk about dark comedy — we're trying to find the humor in these two people bonding over the fact that they each have a partner in a coma." Scott called his character "bumbling at times," adding, "He kind of blossoms after he rediscovers his romantic juices with Susan."
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