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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 Alexander the Great. Written by Georgi Danelia, Viktoriya Tokareva and Aleksandr Seryj (who also directed the film).

Tropes used in Gentlemen of Fortune include:

  • Acting for Two: Yevgeny Leonov plays both Beliy -- ruthless murderer and Troshkin -- soft-spoken kindergarten teacher.
  • Being Evil Sucks: Discussed. Troshkin does a very good of explaining why living as a criminal is hollow and pointless.
  • Bungled Suicide: Sad Sack's offscreen suicide attempt.
  • Cool Helmet: The MacGuffin.
  • Criminal Doppelganger: Beliy to Troshkin
  • Chess Motifs: 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.
  • Disguised in Drag: gang, to keep low-profile in Moscow, disguise themselves as bunch of old women. Then, Cross-eyed tries to flirt with a girl he met on the street. And then enters men's room in the theater.
  • Even Evil Has Standards: 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.
  • Heel Face Turn: After spending time with Troshkin, the crooks see the error of their ways.
  • Great Escape: 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 all covered in concrete), but all in all it still goes surprisingly successful.
  • MacGuffin: Alexander the Great's helm.
  • Mean Character, Nice Actor: Part of the Acting for Two challenge for Leonov, as his real-life personality was much closer to Troshkin than to Belyi.
  • Memetic Mutation: as it always happens to popular soviet films every single phrase from the movie became a meme. Every. Single. One.
  • Playing Against Type: by the time movie was made, Vitsin (Sad Sack) has made a successful career playing one of the soviet cinema's Comic Trio (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 tries to commit suicide.
  • Shown Their Work: 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 criminal slang that characters speak is genuine.
  • Spider Sense: Beliy has this. He can always sense police traps ahead.
  • Surprise Checkmate: Justified. Sad Sack wins this way in the hotel, because his opponent is a gambling addict and will play anything. He then receives surprise checkmate himself when Cross-eyed bungles his moves.
  • Tattooed Crook: 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 russian criminal tattoo ideography.
  • The Chick: Vasily Alibabaevich. He was incarcerated for petty fraud (mixing gasoline with donkey urine and then selling it), has soft heart, loves children and his mother, hates himself for stealing money, cooks the food, washes clothes, and works as a conscience for the whole gang
  • The Producer Thinks of Everything: aforementioned game of chess in the hotel is real. You can deduce all the moves by what you see in the movie. In the first game Sad Sack successfully pulls off chess gambit and actually plays surprisingly well for a criminal.
  • Which Restroom Dilemma
  • The Woobie: Sad Sack. Before his life turned to crime he had a wife and a son and was hinted to be a normal citizen, member of intelligentsia. Now he is petty thief with long rap sheet, no home, no prospects in life and son thinking he's dead.
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