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).

!!This film provides examples of:

* ActingForTwo: YevgenyLeonov plays both Beliy -- ruthless murderer and Troshkin -- soft-spoken kindergarten teacher.
* BeingEvilSucks: {{Discussed}}. Troshkin does a very good of explaining why living as a criminal is hollow and pointless.
* 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 random guy to get civilian clothes for himself after the prison break.
* DisguisedInDrag: gang, to keep low-profile in Moscow, disguise themselves as bunch of old women. Then, [[WhatAnIdiot Cross-eyed tries to flirt with a girl he met on the street. And then enters men's room in the theater]].
* DirectorDisplacement: Many people think ''Gentlemen of Fortune'' was directed by Creator/GeorgiDanelia (who was 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 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 who Beliy met in Moscow to sell golden helmet but at least they can show places on site, so police orchestrates fake prison break just for them. Of course, it does not go as planned (instead of getting to 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.
* MacGuffin: Alexander the Great's helm.
* MeanCharacterNiceActor: Part of the ActingForTwo challenge for Leonov, as his real-life personality was much closer to Troshkin than to Belyi.
* PlayingAgainstType: by the time movie was made, Vitsin (Sad Sack) has made a successful career playing one of the soviet cinema's ComicTrio (as Coward), and has been typecasted to play weakling comedic characters with high-pitched voices. In this movie he plays truly tragical character who speaks with 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 surprise checkmate himself when Cross-eyed bungles his moves.
* TattooedCrook: Beliy. Troshkin has to make the same fake tattoos to pose as him. Apparently, film crew had a little too much fun with those tattoos, because there is no way kittens and lamp bulbs are parts of [[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 soft heart, loves children and [[EvenBadMenLoveTheirMamas his mother]], hates himself for stealing money, cooks the food, washes clothes, and works as a conscience for the whole gang
* WhichRestroomDilemma