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  • Alternative Character Interpretation:
    • He's not really homeless, he's just crazy and thinks he is. Think about it, we rarely see him outside, he looks suspiciously clean and well-fed and he hangs around Critic's house constantly, who we know offered him a place to stay and a job reviewing new movies.
    • And if he really is homeless, this gives an interpretation of his relationship with the Critic: the reason he's in surprisingly good condition is that the Critic is taking really good care of him. Aww...
    • Played for laughs in his Guardians of the Galaxy (2014) review, when his idea of young Peter getting abducted is him making up an alternate reality to deal with losing his mother.
  • Awesome Music: The Bum Reviews Song.
  • Character Rerailment: The 2013-starting “Chester being used as a mouthpiece for Slut-Shaming and Political Correctness-complaining” deal thankfully didn't last too long, and he went back to being adorable, fun and commenting on various issues in Hollywood.
  • Crosses the Line Twice: A good deal of his humor, like mentioning that he once owned slaves, and question why the Nazis are always the bad guys.
  • Harsher in Hindsight:
    • Before Breaking Dawn came out, Doug was gleeing over how much he was going to enjoy it for the So Bad, It's Good quality. Uh, yeah... didn't quite turn out that way.
    • Giggling about how the Paranormal Activity movies are anti-men and wondering if that makes him a "menimest" is adorable. Three episodes later, when the above film comes along, brokenly raging about it'll teach girls that this is how men will treat you when you're pregnant, makes you wonder if he's okay.
    • Given everything that has come out about the company's mistreating their producers, Chester's Played for Laughs woobie about Channel Awesome treating him terribly isn't so entertaining.
    • Aww, look at the Bum's Youmacon video where he's all freaked out. You just want to take him home and... wait, a con report says Doug really did get scared because people were constantly asking "Can I keep you?" Oh.
  • He Panned It, Now He Sucks!:
    • Despite all of Doug's apologies for maybe being too harsh and his detailed explanations of why he didn't like it, he was subject to the same shit that everyone who didn't like The Dark Knight Rises got.
    • Happened again when Doug dressed up as General Zod and thrashed Man of Steel. Several fans (Angry Joe and Bennett The Sage included) really liked the movie, and this time, Doug didn't apologize for not liking it.
  • Hilarious in Hindsight:
    • The line in Chester's review of Up about that they should send all the people in the sky adds more hilarity when Pixar actually does run closely with it.
    • He starts his review of James Cameron's Avatar with: "Oh, my God, this is the GREATEST movie I've ever seen in my life! There's this bald boy, who can control the wind... oops, wrong Avatar. Oh, my God, this is also the greatest movie I've ever seen in my life!" Four years later, The Nostalgia Critic sounds very like Chester when he declares that Avatar: The Last Airbender is, indeed, one of the greatest shows he's ever seen in his life in his review of The Last Airbender.
    • His comments about Spider-Man joining the Avengers in a few reviews, such as The Incredible Hulk and The Avengers, seemed unlikely at the time due to Sony exclusively holding the character's film rights. Come 2016, and Sony and Marvel have worked out a deal, allowing Spider-Man to join the MCU.
  • Iron Woobie: You've got to admit he's pretty good at carrying on with life without all that much complaint. True, that might be because he's high and drunk most of the time, but still.
  • Like You Would Really Do It: Lampshaded in the review of The Muppets (2011).
  • Moe: Chester, and unlike most, he really does need to be taken home.
  • Nausea Fuel: The Jitter Cam in The Hunger Games review can all-too-easily induce motion sickness.
  • Nightmare Fuel: The ending of his Paranormal Activity 3 review.
  • One True Pairing: Even the Bum, despite his hatred for Bella, feels Jacob would've been a better boyfriend/husband for her than Edward.
  • Rescued from the Scrappy Heap: Chester was never hated, but even Doug noted that he existed for a while just so that he could do a funny voice. A friendship with the Critic, mass woobie-dom, Obfuscating Stupidity and a keet personality with some manipulative and snarky qualities changed all that.
  • Squick: In The LEGO Movie review, both Chester and the audience are grossed out by what Critic apparently does with his Rogue figurine.
  • Tear Jerker:
    • The end of Where the Wild Things Are:
      So, you might be wondering what's the moral of the story, kids? The moral of the story is... deal with it! Just... deal with it! Your family's not perfect? Deal with it! You're trapped on an island with monsters? Deal with it! You live in a pine cone where people occasionally urinate on you and throw feces at you always saying that they left their change at home even though I see them pay for a hooker just on the side of the street?! A hooker that could pleasure them probably not nearly as well as I could?! Deal with it! *starts crying* Have a good cry and then deal with it! Bite your finger until it starts to bleed, cry, and deal with it! Forget this cruel, horrible world, die alone in the dark, then bite your finger until it starts to bleed, cry, and deal with it! Oh, and also, eat your vegetables.
    • The Chicago snowstorm video, especially when he's crying on the ground at night. Not even Rob's obvious shadow detracts from it, considering Chester even says the CA company is forcing him to do this.
    • Wreck-It Ralph is a bit like if you smooshed the Critic's reviews of Baby Geniuses and Scooby-Doo together for the maximum amount of pain you can inflict.
    • You knew it was coming, but seeing him lose his cozy Christmas room a week before Christmas is really cruel.
  • The Woobie:
    • "I just want to belong!"
    • Also the 2011 Chicago Snowstorm video.
    • And the search for the Necronomicon. "I'm not a religious man, but I now believe in the Devil."
    • Partly his own fault for taking LSD 'cause he thought it'd be boring, but the Youmacon video had him completely terrified by all the strange things he was seeing.

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