Moe falls for a flower vendor named Renee, and commits insurance fraud (with help from Homer) so he can keep the money and the romance coming.
* BaitAndSwitch: While Homer is in jail, Hans Moleman shows up with some books Homer can choose from. He picks up a book called "How To Tunnel Out Of Prison", says it could come in useful, and bashes Moleman over the head with it, knocking him out and allowing Homer to make his escape.
* EasilyForgiven: Even though Moe broke the law by committing insurance fraud and landed Homer in jail as a result, Renee is forgiving because he is at least trying to set things right.
* EpicFail: Homer takes Moe out to a nightclub to meet women. Moe strikes out badly each time he approaches someone.
* EverythingsBetterWithMonkeys: The movie Homer sees is ''Hail to the Chimp''.
* FlatCharacter: Renee. The writers admitted on the audio commentary that she has no real personality.
* GettingCrapPastTheRadar: At the end, Bart comments that there's a "balloon machine" in the bathroom. It's implied to actually be a condom dispenser.
* HeelRealization: Moe has one when he is seized with guilt about the insurance fraud scheme that got Homer sent to jail, because instead of bailing Homer out as he was supposed to, he instead planned to go to Hawaii with Renee. This inspires him to confess the whole thing to her.
-->'''Wiggum''': We're sendin' you to the chair!\\
'''Wiggum''': The interrogation chair.\\
'''Wiggum:''' Plug it in, boys!
* IgnoredEpiphany: Moe realizes he has to tell the police the truth to get Homer out of jail and that that's the right thing to do. Then he gets the idea to try a ZanyScheme that involves digging up two corpses and setting fire to the bar, which causes Renee to ditch him for good.
* MistakenForGay: When Moe was trying to get enough courage to tell Renee the truth, she asked if he was gay. When he said he wasn't she asked if he was married and he asked why she said "gay" first.
* MoodWhiplash: When Homer escapes from jail, he steals the book cart and rides it to the bar.
-->"Must kill Moe. Whee! Must kill Moe. Whee!"
* NiceJobBreakingItHero: Homer would have saved both he and Moe a lot of trouble if he just let Snake steal the latter's car. He realizes this as he's driving away. Homer makes this worse when he takes time out to go to the drive-in theater instead of parking the car on the train tracks.
* OhCrap: Homer when he tries to bail out of Moe's car, and ends up rolling back into it, when it's about to drop into the sea.
* PuffOfLogic: Homer's "ghost" appears to Moe to make him guilty. The trope is subverted during this exchange.
-->'''Ghost''': You killed me.\\
'''Moe''': You're not dead; you're just in jail.\\
'''Ghost''': Oh. ''[disappears, immediately comes back]'' Wait, I'm in jail because of you!
* ScrewThisImOuttaHere: In need of money, Moe announces that he's officially collecting all owed tabs. The barflies immediately run for the exit.
* ShoutOut: The title comes from ''Film/DoubleIndemnity''.
* StopSayingThat: Homer overhears Moe speaking about Hawai'i.
-->'''Moe''': Hawai'i here we come! Ananakooli, Makawani, Ana-ona, Nanawula Wa, Hawai'i... ha.\\
'''Homer''': (''overhearing'') Hawai'i? What about Hawai'i? Moe? Who's going to Hawai'i?! Am I going to Hawai'i?\\
''(Chief Wiggum knocks on Homer's cell bars with a nightstick.)''\\
'''Chief Wiggum''': Stop saying Hawai'i in there!
* UngratefulBastard: Moe's reaction to the barflies not wanting to pay their tabs.
-->"Ya ungrateful ingrates!"
* WhatHappenedToTheMouse: Whatever happened with that water heater explosion at the beginning of the episode?
** Moe wants Homer to wreck his car by parking it on train tracks. This fails due to reasons mentioned above.
** Moe tries to get out of trouble for this mess by wanting to fake his and Renee's deaths and torching the bar. She walks out on him upon hearing this.