Gentlemen of Fortune is a 1971 film from the Soviet Union directed by Aleksandr Seryj, and written by Georgi Danelia, Viktoriya Tokareva and Seryj.
Archaeologists on a dig discover a priceless treasure: an ancient helmet, five kilograms of solid gold, which once belonged to Alexander the Great. The helmet is promptly stolen by a hardened criminal named Beliy aka "Dotsent" (played by Yevgeny Leonov) and his sidekicks Gavrila ("Sad Sack") and Fedya ("Cross Eyes"). The three crooks are soon arrested, but not before they manage to hide the gold helmet.
Enter Yevgeny Troshkin (also played by Leonov), a mild-mannered principal of a kindergarten, who happens to be a dead ringer for the hardened criminal. The cops persuade Yevgeny to help them in a scheme to retrieve the helmet. Yevgeny will be placed in prison alongside minions Gavrila and Fedya, where he will impersonate Beliy while the real Beliy is sent to jail elsewhere. The authorities will then allow the three to seemingly escape from jail, whereupon Gavrila and Fedya will presumably lead Yevgeny to the helmet. The escape is bungled but the guys do make it out, accidentally picking up a fourth convict named Vasily on the way. However, it turns out that Gavrila and Fedya don't know where their boss hid the helmet. Madcap adventures ensue as the schoolteacher and the two dumb crooks try and find it.
This film provides examples of:
- Assassin Outclassin': 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 he 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).
- Being Evil Sucks: Discussed. Troshkin does a very good of explaining why living as a criminal is hollow and pointless.
- Beware the Nice Ones: 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 Criminal Doppelgänger, he manages to temporarily disarm the criminal before the latter pulls a gun. It's stated early in the film that Troshkin is a World War II vet.
- Bungled Suicide: Sad Sack's offscreen suicide attempt.
- The Chick: Vasily Alibabaevich. He was incarcerated for petty fraud (mixing gasoline with donkey urine and then selling it), has a soft heart, loves children and his mother, hates himself for stealing money, cooks the food, washes clothes, and acts as a conscience for the whole gang.
- Cool Helmet: The MacGuffin, a solid gold helmet that belonged to Alexander the Great.
- Criminal Doppelgänger: Beliy to Troshkin. A mild-mannered kindergarten teacher is Identical Strangers with a hardened criminal.
- Chess Motifs: There is a chessboard in the prison cell (!) and Sad Sack wins a few games with a random guy to get civilian clothes for himself after the prison break.
- Disguised in Drag: The gang, to keep a low profile in Moscow, disguise themselves as a bunch of old women. Then, Cross-eyed tries to flirt with a girl he meets on the street. And then enters the men's room in the theater.
- Dub Name Change: Sad Sack is named Raspy in some dubs and subtitled versions.
- Even Evil Has Standards: By the end of the movie his gang members decide to turn themselves in and bring Troshkin to the cops, because they think he killed an elderly woman doctor.
- HeelFace 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 the people 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 all covered in concrete), but all in all it still goes surprisingly well.
- Later in the film, Beliy ends up escaping as well.
- Incredibly Conspicuous Drag: The crooks end up escaping in drag. It's not only incredibly conspicuous, one of the crooks still tries to hit on girls and tries to use the men's bathroom.
- MacGuffin: Alexander the Great's helmet, five kilograms of solid gold.
- Mirror Match: 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 World War II vet). The fight ends when Beliy pulls a gun.
- Mood Whiplash: During a funny scene where Troshkin is making Alibabaevich and Crosseyes play a kindergarten game, Troshkin makes Crosseyes leave the room. He walks back in and tells the gang that Raspy hung himself.
- Off-into-the-Distance Ending: The other three guys in Beliy's criminal gang are attempting to turn themselves in. Yevgeny, whom they think is Beliy, gets back out of the cop car—and he's now bald, because he's finally taken off the toupee. The other three, thinking that the cops have already shaved Beliy's head, run off in terror. The movie ends with Yevgeny chasing them as they run off down the snowy road.
- Reformed Criminal: When Troshkin tries to contact one of Beliy's former associates, he informs him that last time they met he promised to throw him down the stairs because he was out. After reminding him of the promise he does exactly that.
- Reverse Psychology: Troshkin gives 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 the exact opposite.Troshkin: Steal, drink — go to prison. Steal, drink — go to prison. Glorious!
- 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 a part of the criminal slang that the characters speak is genuine. The rest contains some random words because the authors did not want to spread jail slang. For example, people in Russia right now are sure, that редиска (radish) means bad man.
- Smash Cut: Vasily, who has become The Chick, is cooking dinner for the rest of the gang. He has something in a pan, and he tries to set a match to it. He is surprised by an enormous tower of flame rising far above his head. Cut to the entire building on fire and burning to the ground, as Vasily and the others watch from the outside.
- 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 a 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, 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 Russian criminal tattoo ideography.
- Thieves' Cant: Before going into prison, Yevgeny is schooled by a policeman in thieves' cant. Later, Yevgeny makes a point of reversing this, teaching Fedya the normal Russian words for criminal slang.
- Title Drop: Fedya meets an old childhood friend, and they are catching up when Yevgeny interrupts the conversation and bluntly tells the other man that Fedya is a thief. When Fedya later complains about this Yevgeny explains that the other guy was jealous. While his old friend lives a boring life with a Monday to Friday office job, Fedya is a "gentleman of fortune" who lives a life full of excitement and thrills.
- Wet Cement Gag: The fake breakout involves the characters getting into an empty tanker. They get the wrong car by mistake, so not only are they away from the planned hiding spot, they also need new clothes thanks to this trope.
- "Which Restroom" Dilemma: Happens during the Disguised in Drag scene, when Cross-eyed enters the wrong bathroom at the theater.