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Soviet comedy (with elements of tragedy) about kindergarten teacher (Troshkin) who looks exactly like hardened criminal Beliy and gets recruited by police to infiltrate his old gang in prison (while Beliy himself is doing time in another prison) to find previously stolen helmet of AlexanderTheGreat. Written by Creator/GeorgiDanelia, Viktoriya Tokareva and Aleksandr Seryj (who also directed the film).

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!!This film provides examples of:

* ActingForTwo: YevgenyLeonov plays both Beliy -- ruthless murderer and Troshkin -- soft-spoken kindergarten teacher.
* AssassinOutclassin: After Beliy escapes from prison, he meets up with an associate of his at a construction site. However, the associate has previously met Troshkin and assumes that Beliy is an impostor, so him and a friend of his jump Beliy. Beliy manages to push the friend off a building and then kills his associate with the guy's own gun (the last part isn't shown but can be inferred).
* BeingEvilSucks: {{Discussed}}. Troshkin does a very good of explaining why living as a criminal is hollow and pointless.
* BewareTheNiceOnes: While, for most of the film, Troshkin is only pretending to be a cold-blooded murderer, he does it effectively enough to convince two of the Docent's own partners. Additionally, when he finally faces off against his CriminalDoppelganger, he manages to temporarily disarm the criminal before the latter pulls a gun. It's stated early in the film that Troshkin is a WorldWarTwo vet.
* BungledSuicide: [[spoiler: Sad Sack's]] offscreen suicide attempt.
* CoolHelmet: The MacGuffin.
* CriminalDoppelganger: Beliy to Troshkin
* ChessMotifs: There is a chessboard in prison cell (!) and Sad Sack wins a few games with a random guy to get civilian clothes for himself after the prison break.
* DisguisedInDrag: The gang, to keep a low profile in Moscow, disguise themselves as a bunch of old women. Then, [[WhatAnIdiot Cross-eyed tries to flirt with a girl he meets on the street. And then enters the men's room in the theater]].
* DirectorDisplacement: Many people think ''Gentlemen of Fortune'' was directed by Creator/GeorgiDanelia (who was a co-writer and art director).
* EvenEvilHasStandards: By the end of the movie his gang decide to turn themselves in and bring Troshkin to the cops, because they think he killed an elderly woman doctor.
* HeelFaceTurn: After spending time with Troshkin, the crooks see the error of their ways.
* GreatEscape: Beliy's buddies don't know the exact addresses of whom Beliy met in Moscow to sell the golden helmet, but at least they can show the places on-site, so the police orchestrates a fake prison break just for them. Of course, it does not go as planned (instead of getting to the already-prepared spot with money and civilian clothes, they end up 30 kilometers away with no money, no clothes and [[RuleOfFunny all covered in concrete]]), but all in all it still goes surprisingly successful.
** Later in the film, Beliy ends up escaping as well.
* MacGuffin: AlexanderTheGreat's helm.
* MeanCharacterNiceActor: Part of the ActingForTwo challenge for Leonov, as his real-life personality was much closer to Troshkin than to Beliy.
* MirrorMatch: At the end, Troshkin and Beliy square off, and the timid kindergarten director actually manages to temporarily disarm the knife-wielding criminal (it's stated early in the film that he's a WorldWarTwo vet). The fight ends when Beliy pulls a gun.
* PlayingAgainstType: By the time movie was made, Vitsin (Sad Sack) has made a successful career playing one of the Soviet cinema's ComicTrio (as the Coward), and has been typecasted to play weakling comedic characters with high-pitched voices. In this movie he plays a truly tragic character who speaks with a hoarse voice and [[spoiler:tries to commit suicide]].
* ReversePsychology: Troshkin gives the Cross-eyed a speech seemingly mocking an honest citizen's life and glorifying a thief's life, but does it in a way that makes it into exactly opposite.
--> '''Troshkin''': Steal, get drink - get in prison. Steal, get drink - get in prison. Glorious!
* ShownTheirWork: The director made the movie right after he did his time in prison and portrayed his own personal experiences about the criminal life. Also all the [[http://en.wikipedia.org/wiki/Fenya criminal slang]] that characters speak is genuine.
* SpiderSense: Beliy has this. He can always sense police traps ahead.
* SurpriseCheckMate: [[JustifiedTrope Justified]]. Sad Sack wins this way in the hotel, because his opponent is a [[TheGamblingAddict gambling addict]] and will play anything. He then receives a surprise checkmate himself when Cross-eyed bungles his moves.
* TattooedCrook: Beliy. Troshkin has to make the same fake tattoos to pose as him. Apparently, the film crew had a little too much fun with those tattoos, because there is no way kittens and lamp bulbs are parts of the [[http://en.wikipedia.org/wiki/Criminal_tattoo#Criminal_tattoos Russian criminal tattoo ideography]].
* TheChick: Vasily Alibabaevich. He was incarcerated for petty fraud (mixing gasoline with donkey urine and then selling it), has a soft heart, loves children and [[EvenBadMenLoveTheirMamas his mother]], hates himself for stealing money, cooks the food, washes clothes, and acts as a conscience for the whole gang
* WhichRestroomDilemma: Happens during the DisguisedInDrag scene, when Cross-eyed enters the wrong bathroom at the theater.