Needing to drum up some extra money in order to get to New York, the Legends end up getting involved with a Chicago mobster, while Spooner, Astra, and Gideon manage to catch up to the others.
Tropes:
- Armor-Piercing Response: Nate tries to get Gary to get over his submissive fetish and find someone who appreciates him for being himself. Gary retorts that Nate tends to go into relationships that have no chance of ever happening as a way to avoid And Then What?.
- Big Eater: Gideon stuffs her face whenever presented with food.
- Blonde, Brunette, Redhead: The wig seller has three bob-cut wigs in these colors. Sara and Ava outright refuse the blonde ones.
- Bribe Backfire: Of a sort. The Legends spend all their money on wigs and for the clerk to let them escape out the back door. However, they never said anything about him keeping quiet, and as soon as the police enter he rats them out.
- The Bus Came Back: Zari switches out with her 1.0 counterpart, because her hacker skills are needed to interrogate the robot Hoover.
- Butterfly of Doom: Once again, averted. Sara, Zari, and Astra are constantly meddling with the timeline when they're not supposed to be.
- Cannot Keep a Secret: Eddie's associate Ricky. This gets exploited, as they use his chattyness to get the word out on the Bullet Blonde performance.
- Casual Danger Dialog: Gary gives Nate some couple counseling while they are fighting off Robot-Hoover's thugs.
- Chekhov's Gun: Astra offhandly mentions that Bottoni has a fear of spiders when she met him in hell. Later, Spooner uses that fear to get him to back off Maude.
- Continuity Nod:
- After their adventure with Hoover a few episodes ago, Nate states that he is done with trains for the rest of the trip.
- Sara has a plan to use Constantine's never-ending whiskey fridge to sell it to the speakeasy and make some money.
- Nate references Gary's relationships with Kayla, Ava, and John as examples of his attraction to powerful people who boss him around. While Gary doesn't name them directly, his response is all about Nate's relationships with Amaya and Flannel!Zari.
- Contrived Coincidence:
- When the gang is trapped at the end of an alley while escaping the police, they just so happen to stand in front of the back door of a speakeasy, one in which the password to enter is "password", and allows anyone, regardless of race, to be a customer. Slightly subverted since the original idea was to simply hide out in the mansion until things died down, which would have likely worked.
- Spooner, Astra, and Gideon just happen to sit down on the train right next to a mobster's girlfriend, who takes a liking to the three and saves them from being thrown off the train due to not having tickets. Said mobster is also the one who owns Eddie's bar, allowing them to reconnect with the Legends very easily.
- Cut Lex Luthor a Check:
- Zari actually has the idea to sell the infinite amount of booze with the help of Eddie. Unfortunately, this only causes Bottoni to show up and throw him out of the bar due to no longer buying from him.
- Astra uses her magic to conjure up First Class tickets.
- Dance Battler: Sara and Ava tie up Robot Hoover during their dance while making it look like All Part of the Show.
- Didn't Think This Through:
- Sara's plan to use Constantine's whiskey fridge right in the middle of the Prohibition Era ends up causing a bit of an issue.
- Astra's meddling with Maude's contract leaves the latter dealing with a very angry, abusive boyfriend, who also happens to be one of the top mobsters in Chicago.
- Domestic Abuse: Poor Maude is suffering this from Bottoni. Thankfully, Astra and Spooner eventually manage to convince her to leave.
- Girl on Girl Is Hot: The audience is shocked when Sara and Ava have a Big Damn Kiss at the end of their act, until they explain that they aren't sisters, whereupon everyone applauds.
- I'm Not Doing That Again: Ava's plan initially had three of them ride the train to New York, while the other three hung out in Constantine's (now Zari's) pocket dimension mansion. Nate tells Ava that he's done with trains.
- Informed Attribute: The wig seller pointedly ignores Zari, supposedly because she's not white, but acknowledges Sara and Ava, whose skin is maybe half a shade lighter than hers.
- Just Train Wrong: Ross Bottoni's club has an Art-Deco style painting of the New York Central's 20th Century Limited hanging on his wall. The problem is that it's 1925, while that particular iteration of the train is from 1937, streamlined Hudson and all (the wheel arrangement wouldn't even exist until 1927, two years after this episode takes place).
- Literal-Minded: When Astra sarcastically calls Spooner "Captain Sharpe", Gideon doesn't get it and corrects Astra that her name is actually Spooner.
- Lured into a Trap: Zari's plan to attract Robot-Hoover with the Bullet Blonde performance works perfectly.
- The Mafia: The Legends run into another one, this time Chicago mob boss Ross Bottoni, a character made for the series, instead of using Al Capone.
- Missed Him by That Much: Astra, Spooner and Gideon learn that the Legends are hosting a party nearby and rush straight to the scene, but arrive just after everyone leaves — though they do find Zari's lost phone, confirming that they had been there.
- Nice Guy: Zari notes that Eddie is the only person so far who has been non-judgemental and absolutely friendly to them from the start. This is the reason she cannot just stand by and watch him lose his bar.
- Nice Job Breaking It, Hero: The Legends supplying Eddie with booze causes Bottoni to throw him out due to him no longer buying his booze.
- Nice to the Waiter: The episode's main plot happens because Gary was a very generous tipper to their waitress.Gary: "$20 for a six-top seems fair to me!"
- No Equal-Opportunity Time Travel:
- The clerk at the hat shop refuses to acknowledge Zari due to her not being white.
- Averted with the speakeasy the group run into, which caters to anyone, regardless of race.
- Also averted with Spooner, Astra, and Gideon, as the former two don't have anyone remark upon their skin color on the train.
- Oh, Crap!: Spooner and Astra, when they realize Gideon has taken Maude's place at the Masqueradies performance. She manages without problems though.
- Paper-Thin Disguise: Gideon has a very different face from Maude; even in a masquerade ball mask they're clearly different people. But somehow Bottoni never noticed until the mask came off.
- The Password Is Always "Swordfish": Not this time, as Nate tries it when asked if they are there to see the Sapphire String. Turns out the actual password is..."password." Zari's shindig gets the slightly better "rutabaga."
- Politically Correct History:
- The speakeasy the crew run into is one of the very few that allows people from all races and nationalities into, which Nate notes is very uncommon for 1925 Chicago.
- Eddie immediately pegging Zari as Muslim when she says she doesn't drink for reasons of faith is historically odd, to say the least. Islam was largely unknown in the USA in the 1920s; the Temperance movement, which led to Prohibition, was driven by mainstream Christianity.
- The crowd at the party all seem fully supportive of Sara and Ava's relationship — at least, once it's established that they're not sisters (although, oddly enough, this isn't entirely inaccurate; Marlene Dietrich's lesbian kiss in the 1930 film Morocco was considered scandalous but was a huge draw).
- Relatively Flimsy Excuse: Since being a lesbian wasn't exactly welcomed in this era, the papers all call the Bullet Blondes sisters instead, which grosses out Sara and Ava.
- Saying Too Much: Gideon has a habit. In particular, when she finds out the name of someone notable.
- Screw the Rules, I'm Doing What's Right!: When Astra hears that Maude will eventually be murdered by Bottoni, and the latter will not be charged for it, she refuses to just let the timeline play out that way.
- Shout-Out: Nate guessing that the password to the speakeasy is swordfish is one to the Marx Brothers movie 'Horse Feathers.
- Speak in Unison: Sara and Ava when the wig seller shows off his wigs.Sara and Ava: "No blondes!"
- Spiders Are Scary: Ross Bottoni's greatest fear is arachnophobia, which Astra subjected him to back when she was ruling Hell.
- Traveling at the Speed of Plot: Astra, Spooner, and Gideon manage to catch up with the Legends ridiculously fast.
- Wig, Dress, Accent: Well, only the first one, but Sarah and Ava need to find wigs to cover their hair, since their identities as the Bullet Blondes has now become well known all across the country.
