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  • Silas having to be a gruff, long-suffering Straight Man to the naivete of his audience is inherently funny:
    Silas: "So I was heading back to the hideout when suddenly, I had this funny feeling—"
    Steve: *hopefully* "Funny ha ha?"
    Silas: *patiently, but annoyed* "No, Steve, the other kind of funny".
  • Bob Ollinger's Mean Ass Shotgun gets a graphic novel introduction in the same manner as the high-profile boss-level criminals throughout the game, and gets repeated reverential mentions throughout the next level.
    • To add insult to injury, not only does Silas steal Bob's shotgun, when they have their duel at the end of the level, Bob doesn't get the courtesy of a cool graphic novel intro like other duel bosses. Or, again, his shotgun.
  • The fact the game runs on Unreliable Narrator leads to several near fourth-wall breaking moments of exploiting the narrative for a joke or two. One of the most notable examples is at the end of the first level, where the Hero-Worshipper of the Player Character claimed that (based on a Dime Novel he read) the level ended with a one-on-one duel with Pat Garrett - and then then Player Character claimed that didn't happen at all, and rewound the action to just a few moments before the "showdown" to tell how it really happened: he gets cold-cocked and arrested by Garrett, and has to break out of jail in the next level.
  • The mine. After you chased the enemies of the level through the maze of its bowels, you're eventually killed by the fall of an undodgeable mine cart. Cue Silas telling something like: "Of course, that's what would have happened if I had taken this way". Then, the story is rewound, while Silas takes another way.
  • Steve falls asleep during Silas' tale of chasing the Daltons in a swamp (his snores can be heard over Silas' voice). A bit later, Silas messes with the audience by adding Apaches in the area who try to kill you for no reason whatsoever, just to check if Steve was still attentive.
  • On the train level, Silas goes off to pee and the level continues with you walking through the same damn train devoid of mooks over and over and over with the audience mumbling about how true he's being until Silas comes back.
  • One of the levels of the game features the same story being told in three different ways, once by Ben, once by Dwight and once by Silas. The one by Dwight is according to a Dime Novel he's a fan of and it says that Silas "went in there alone to confront those criminals", and as he did so, one of the Marshals shouted, "Where are you going?! Are you crazy?!" In the game, we can hear that exact same line after Dwight recites it, but it comes out a little different...
    Marshal: Hey! Where do you think you're going, dumbass?! That rifle's mine!

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