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  • Alternative Character Interpretation: The pirates in "Pirate Chantey". Do they sing progressive sea shanties out of fear of their captain overhearing them and executing them? Or do they genuinely respect her and women? They are shown singing the shanties with great gusto and their shanties, should they be true, had them accommodating and praising women despite their captain's presumed absence.
    • How much of a Bad Boss the captain is is debatable. While executing the man was clearly Disproportionate Retribution, she did decide to lead the pirates into continuing their singing. Whether she was Not So Above It All and genuinely enjoyed singing, wanted to rally up her men's sprits or just callously wanted to wash over the murder is debatable.
      • Seeing the Irish pirate accidentally stabbing his crewmate with a knife and the pirates continuing to sing, perhaps murders are either commonplace under the captain or commonplace in the era.
  • Hilarious in Hindsight:
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    • This spoof of Mighty Morphin' Power Rangers uses Zords that resemble not the dino ones, but the ones in Choujin Sentai Jetman, which would have been adapted instead.
    • Keegan-Michael Key used to host The Planet's Funniest Animals. He's like the black Bob Saget! And then there's clips like this...
    • Barack Obama shouting out to Key and Peele about three months after this. It was taken to the next logical conclusion here.
    • One of the players in the "East/West Bowl 2" sketch is a Hawaiian with a very long name. About a day after the video was posted on YouTube, a Hawaiian woman was denied a driver's license because her name was too long to fit on it.
    • The Anger Translator skit following the first debate included a line about Mitt Romney getting more reboots than Spider-Man. Since then, Spider-Man has been rebooted again.
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    • Another one of the "Obama's Anger Translator" skits had Luther brag about playing Halo 4 all day if Obama didn't get re-elected. Key would later voice the lead character for HUNT the TRUTH, a Viral Marketing campaign for Halo 5: Guardians.
    • One sketch is about '70s funk music and the tendency towards Word Salad Lyrics. "Uptown Funk" would prove that this was far from dead.
    • In the "Obama Raps" sketch, a rapper in the street says, "I'm the boss and the king!", after which Obama, played by Peele, pulls up in his limo, takes the mic and says, "I'm the leader of the free world" and drops the mic. At the 2016 White House Correspondents Dinner, Obama's last dinner as President, he ended his speech with a mic drop, saying, "Obama out!".
    • One of the funniest Key & Peele skits is one where terrorists bemoan that the TSA's dumb (to us) policies are actually stopping them from carrying out attacks. In Jordan Peele's Get Out, Rodney, a TSA agent, comes to Chris's (the protagonist's) rescue at the end. TSA saves the day once again.
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    • Just the whole premise of Luther, as senator Cory Booker has not only gained popularity for embodying some Angry Black Man mannerisms himself, but also bears a surprising resemblance (looks and voice) to Key.
    • In one of the stand-ups between sketches in s1ep4 "The Branding", Key mentions how neither he or Peele could be rappers. Then one year later, they starred in Epic Rap Battles of History's Gandhi vs. MLK Jr and Michael Jordan vs. Muhammad Ali.
    • Just the large number of Nightmare Fuel moments for a comedy series in general, now that Peele has successfully broken into the horror genre after Get Out.
    • One sketch is about what Forest Whitaker as a toddler would be like, with Peele's face photoshopped onto an actual toddler in one of the landmark unsettling moments in the series. In 2019, Peele would follow Whitaker's footsteps by becoming the host of The Twilight Zone.
    • The sketch where the valets gush about their favorite movies, starting from Iron Man before escalating to Kiss Kiss Bang Bang, is a double whammy. Kiss Kiss Bang Bang's writer and director Shane Black would helm Iron Man 3 and eventually Key would be cast in Black's The Predator.
    • At one point during the "Continental Breakfast" skit, Peele's character becomes fascinated over a spork.
    • One sketch jokingly claimed that every black person on the planet has "The Shining". In the sequel Doctor Sleep, the deuteragonist is a black girlnote  who possesses the shining.
    • Latrell, the Camp Gay office worker bears a strong (and ironic) resemblance to rugby player Israel Folau, who in 2019 made a series of homophobic comments that cost him his positionnote , which led to Christian fundamentalists declaring that he was persecuted.
  • Fridge Brilliance: The school's name in "If Hogwarts Were an Inner-City School" is called "Vincent Clortho Public School for Wizards". Clortho is very similar to Clotho, one of the sisters of fate from Greek Mythology who's responsible for spinning the thread of human life and deciding who should be born and who should die.
  • Memetic Mutation:
    • The picture of Peele's character sweating heavily in the "Clear History" sketch is used by many as a response emote that can be summed up as an Oh, Crap!.
    • The "Obama Meet & Greet" short, where Obama greets black guests like bros but is coldly professional to white guests, sometimes gets used in fan videos representing fandoms embracing or rejecting various installments of their series.
  • One-Scene Wonder: In the "Les Mis" sketch, Nicole Parker breaks out some serious singing pipes.
  • Paranoia Fuel: Luther: "I got Tweets fo' yo' ass! Y'all best follow me... or I'll follow YOU!"
  • Squick:
    • Obama trolling Republicans leads to one of the older ones cutting off his own tongue.
    • In the "Dubstep" sketch, when the music makes Key freak out and mutilate himself by pulling out a tooth and ripping off one of his fingernails.
    • "Soul Food", wherein two friends constantly try to one-up each other by ordering more extreme varieties of down-home cooking; while their demands start off delicious enough, if decidedly unhealthy, they quickly escalate into repulsively inedible fare (and, by the end, cannibalism).
  • They Changed It, Now It Sucks!: The switch from a live studio to an overarching plot where the two drive through the desert in Seasons 4 and 5 took some getting used to. To say nothing of the sketches getting noticeably darker in their humour.
  • Uncanny Valley: The effect of pasting Peele's head onto the body of a 5-year-old is hilariously unsettling.
  • Unfortunate Implications:
    • Invoked and weaponized - both Key and Peele are from interracial families (white mom/black dad, though Jordan Peele grew up with a white mom and never knew his biological father), making disciplining the child in public a little difficult...
    • Discussed in another standup bit, about the classic song "Baby It's Cold Outside", before introducing their own version.
  • The Woobie:
    • Wendell is a sad and lonely man with multiple issues, and needs a hug badly. In "The Power of Wings", just as he is finally living out his fantasy of being a romantic hero in a music video, before he can rescue the princess, the money runs out and his dreams fall to pieces.
    • In "High on Potenuse", Peele's character looks like a kicked puppy when the credit for his original joke is stolen and everyone scorns him.
    • Mr. Williams is driven insane by a rowdy student and loses his teaching license while said student coasts through life. Even the sketch itself seems to take pleasure in his undeserved misfortune.
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