Mob Boss Suit Fitting
Related to Badass in a Nice Suit, Man of Wealth and Taste, and Sharp-Dressed Man - those suits have to come from somewhere. This is a scene where the boss is conducting his regular business while a tailor is taking his measurements for a new suit. Most frequent in mafia stories, though also common in corporate and political thrillers. This can be done as an Establishing Character Moment to depict a character as clearly being the boss, as it implies he's very comfortable with the idea of the other characters as his subordinates. Bonus points if he talks freely around his tailor about things that should be kept secret, as this shows the tailor himself may also be a subordinate — or too intimidated to ever dream of betraying his client. In the case of a villainous character (usually the Big Bad, though not always), this can also be used to show how evil he is (or at least a Corrupt Corporate Executive), ordering out atrocities with mundane nonchalance to show that these are his routine operations. The likelihood of the tailor surviving this encounter is inversely proportional to how nervous he seems while accomplishing his task. In the case of a character who is on the hero's side, the amount of interaction between the boss and the tailor will reveal much about the nature of the boss.
- The boss pays more attention to the tailor's work (usually in a negative fashion) than the business at hand: almost always a case of Obstructive Bureaucrat.
- The boss pays absolutely no attention to the tailor, merely complying with the necessity of standing still and moving as needed: usually a sign of Badass in a Nice Suit, and the sign of a Reasonable Authority Figure.
- In an E-Trade advertisement, the E-Trade baby does this, talking to the audience while Enzo takes his measurements.
- There's a scene in Snatch. where Frankie Four Fingers talks with his boss Avi while being fitted for a suit in London. Played more for comedy than anything else, because Frankie is an underling rather than a boss, and some of the suits he is trying on are both a bit outdated and will change very quickly between takes. (For example, he'll be fully in a suit for one take, then a couple of seconds later he'll be half dressed in another, totally different suit from a different era).
- In Payback, Carter, one of the Co-Dragons for the Big Bad who is presented as running the city where the story takes place, is seen putting on a suit as he gives orders about how he wants Villain Protagonist Porter taken care of.
- In The Tourist, Reginald Shaw has a Mob Boss Suit Fitting, even insisting that the tailor remain when his mooks arrive. He takes a report from his cronies, and uses the tailor's measuring tape to strangle one of them when he makes a mistake. Only at the end of the scene does he comment to the tailor, mentioning that the suit fits him very nicely.
- A variation in The Untouchables, with Al Capone talking business while getting a straight-razor shave from a barber.
- How to Succeed in Evil (the novel for sure, probably the podcast too) features, actually, many of these. Edwin Windsor's tailor is not just such a consummate discrete professional that a consulting supervillain can talk freely in front of him, he's actually one of his closest and most dependable cronies. Edwin's favored mode of re-centering himself and rebuilding his morale after any big setback is by having a new suit fitted.
- Played with on Star Trek: Deep Space Nine, in the season 4 premier "Way Of The Warrior". Captain Sisko calls Garaknote in for a fitting while he's having a staff meeting concerning the Klingons' plans to invade Cardassia. Garak is even mindful enough to ask Sisko if he's sure he doesn't want him to come back after the meeting instead of taking Sisko's measurements now.
- Lex Luthor has been shown in this kind of scene.
- The Cape had a scene with Peter Fleming and Scales meeting at a tailor to discuss buisness. Although Scales is just there to talk, Fleming insists on buying him a suit as well.
- In the Netflix Daredevil series, there's a variant involving Wilson Fisk introducing one of his subordinates to his tailor. Fisk himself doesn't need a fitting, of course, because the tailor already makes all of his suits and knows his measurements. The scene is used more to introduce the tailor, as he's the source of all of Fisk's knife and bullet resistant clothing.
- This Robot Chicken spoof of Star Wars has Emperor Palpatine flipping out at Darth Vader over the phone for losing the Millennium Falcon, only for Alphonso the barber to cheerfully suggest hiring a bounty hunter.
Palpatine: (Hangs up) I just want to sit in a hot bath and cry!Alphonso: You're looking for some guys? What about a bounty hunter? You know, a guy who looks for a guy for money! My sister's dating one!Palpatine: Alphonso, you're a lifesaver!!!