Moe hires Homer to be his wingman so he can score a date, but Homer ends up being the babe magnet. Meanwhile, Marge is shocked to find that her hairdresser has been dyeing her hair blue all these years and decides to go gray for a new, mature look.
Tropes:
- Blonde, Brunette, Redhead: Patty & Selma are revealed to be respectively blonde and redheaded, but their hair turned gray because of the smoke and ash that comes from their constantly smoking cigarettes. Marge is, obviously, the brunette.
- Bowdlerise: The scene in which the female Moe look-a-like proceeds to hang herself (After Moe muses that there's a woman out there for every man) is censored on the UK's Channel 4 and Sky Showcase airings, but to different degrees - the former ends the scene as quickly as it starts, with her looking sadly out her window, whilst the latter keeps the scene largely intact up until the last couple of seconds where she slips the noose around her neck.
- Call-Back: In "The Last Temptation of Homer", Mr. Burns tried to deploy a team of winged monkeys but they couldn't fly and he told Smithers to continue the research. It now seems to have paid off.
- Charlie Brown Baldness: Lampshaded when the Simpson kids freak out over how there's no border between their hair and their heads.
- Coincidental Accidental Disguise: As Marge goes to find Homer, a series of mishaps gradually make her look like the Wicked Witch of the West.
- Crazy Cat Lady: The Trope Namer discovers her Spear Counterpart in a Crazy Dog Man.
- Dating Catwoman: In the final gag of the episode, Maggie gives her longtime nemesis Gerald a Big Damn Kiss, much to his delight.
- Everyone Has Standards: Moe was a Satanist, until they asked him to leave.
- Exact Words: Homer tries to distract himself from Marge’s gray hair by imagining her as a Bond Girl. He gets Judi Dench.
- Jerkass Has a Point: Though Patty and Selma don't have a high opinion of Homer, they know him well enough to point out to Marge how he really feels about her hair; something Marge doesn't realize until they tell her.
- Literal-Minded: Mr. Burns’s wingman is actually a World War 1 era tail-gunner, who served under him.
- Non-Standard Character Design: The episode lampshades how Bart, Lisa and Maggie don't have any distinction between their head and their hair. All three go into a panic mode
thinking about it too much, with Bart shouting "What ARE we?!" and Lisa trying to forcibly draw herself a hairline with a sharpie. - The Reveal:
- Sherri and Terri are actually conjoined triplets, with the third one seeking revenge.
- Patty and Selma never went grey. It’s just smoke and ash from their constant smoking covering up their natural colours, ginger and blonde, respectively.
- Same Surname Means Related: Lisa picks up a supermarket tabloid to read about "Cousin Jessica."
- Series Continuity Error: Marge is shocked that she's had gray hair for all these years, when the season five finale "Secrets to a Successful Marriage" revealed that Marge has been "...gray as a mule" since she was 17 and regularly dyes her hair herself. Though another question remains: Marge was seen with blue hair when Homer first met her in "The Way We Was" when both of them were high school seniors (or, at least, Marge was. It's implied that Homer is older than her, though he could have been left back due to bad grades). Did she dye her hair then or was this before she started going gray?
- However, the episode does justify this by stating that the dye she uses is erasing her memory of needing it whenever she uses it.
- Shout-Out: When a series of accidents make Marge look like the Wicked Witch from The Wizard of Oz, a flying monkey is briefly seen in the background. The Witch's Leitmotif also plays.
