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  • In the first mission, after you shake the cops and get back to Sammy's Bar, the song "I Fought The Law" plays on the radio. Cue Lincoln and his friends joke about how in this case, the law lost.
  • Combined with a Moment of Awesome and Heartwarming Moment, Donovan just casually admitting to have been helping Lincoln Clay murder the Marcano family.
  • If you screw up in a story mission, Agent Maguire looks confused as he examines his files, wondering how the hell that worked.
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  • When Lincoln is helping out at a community kitchen serving gumbo to people the first few customers just thank him or comment on his helping the community, then after you serve her a woman says, "Don't get old Lincoln, it's a fucking shitshow".
  • Baron Saturday's Amusement Park Crosses the Line Twice by being an immensely racist cartoon depiction of a real life religious icon spouting nonsensical erroneous facts about Voodoo. The humor value being that after you go through the park shooting up white supremacists and lynching their leader, the locals comment on how happy they were it happened while the radio can just mention the park was "controversial" for its portrayal of voodoo among the Black population.
  • A Brick Joke where Donovan says he managed to get all of the files on the Marcano gang by stealing them from the FBI as well as their surveillance equipment. Then, later in the game, Agent Maguire growls about how they could have dealt with Lincoln and his gang if someone hadn't stolen all of their files as well as their surveillance equipment.
  • Lincoln waking up Donovan by pretending to be a Vietnamese soldier is horribly inappropriate and cruel, but also hilarious.
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    • It's even funnier when Donovan pulls his gun on Lincoln in a panic, and then complains that he nearly shot Lincoln's head off. Lincoln then snarks "Now we're even", implying Donovan pulled this exact same "prank" on him back when they were in Vietnam!
    Donovan: Kiss my ass!
    (Lincoln makes a mock smooching noise at Donovan)
  • Remy Duvall's Villainous Breakdown culminates in him going on an unhinged, drunken rant live on the air, and getting dragged kicking and screaming away from the microphone.
  • Occasionally, you can hear Burke sing the patriotic Irish drinking song "A Nation Once Again" during sitdowns.
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