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1* AlternativeCharacterInterpretation:
2** Some viewers have suggested that Chester'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.
3** 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 [[HiddenDepths the Critic]] [[JerkWithAHeartOfGold is taking really good care of him.]] [[SugarWiki/HeartwarmingMoments Aww...]]
4** Played for laughs in his ''Film/GuardiansOfTheGalaxy2014'' review, when his idea of young Peter getting abducted is him making up an alternate reality to deal with losing his mother.
5** On multiple occasions, Chester has implied that he's willing to have sex with other men in exchange for money or a warm place to stay, something eventually confirmed in the "conquering Canada" video. Is this PragmaticPansexuality, or is it an indication of Chester being genuinely bisexual?
6* SugarWiki/AwesomeMusic: [[http://thatguywiththeglasses.com/videolinks/thatguywiththeglasses/bum-reviews/34620-the-bum-reviews-song The Bum Reviews Song.]]
7* CharacterRerailment: The 2013-starting “Chester being used as a mouthpiece for SlutShaming 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.
8* CrossesTheLineTwice: A good deal of his humor, like mentioning that he once owned slaves, and question why the Nazis are always the bad guys.
9* HarsherInHindsight:
10** Before ''[[Film/{{Twilight}} Breaking Dawn]]'' came out, Doug was gleeing over how much he was going to enjoy it for the SoBadItsGood quality. Uh, yeah... didn't quite turn out that way.
11** Giggling about how the ''Film/ParanormalActivity'' 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.
12** Given everything that has come out about the company's mistreating their producers, Chester's PlayedForLaughs woobie about Channel Awesome treating him terribly isn't so entertaining.
13** 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 [[Film/{{Casper}} "Can I keep you?"]] Oh.
14* HePannedItNowHeSucks:
15** 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 ''Film/TheDarkKnightRises'' got.
16** Happened again when Doug dressed up as General Zod and thrashed ''Film/ManOfSteel''. Several fans (Angry Joe and Bennett The Sage included) really liked the movie, and this time, Doug didn't apologize for not liking it.
17* HilariousInHindsight:
18** The line in Chester's review of ''WesternAnimation/{{Up}}'' about that they should send all the people in the sky adds more hilarity when Pixar actually does run closely with it.
19** He starts his review of James Cameron's ''Film/{{Avatar}}'' with: "[[CharacterCatchphrase Oh, my God, this is the GREATEST movie I've ever seen in my life!]] There's [[WesternAnimation/AvatarTheLastAirbender this bald boy, who can control the wind]]... oops, [[SimilarlyNamedWorks wrong Avatar]]. Oh, my God, this is ''also'' the greatest movie I've ever seen in my life!" Four years later, WebVideo/TheNostalgiaCritic 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 ''Film/TheLastAirbender''.
20** 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 [[Film/CaptainAmericaCivilWar join the MCU]].
21* IronWoobie: 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.
22* LikeYouWouldReallyDoIt: Lampshaded in the review of ''[[spoiler:Film/TheMuppets2011]].''
23* {{Moe}}: Chester, and unlike most, he really does need to be taken home.
24* NauseaFuel: The JitterCam in ''Film/TheHungerGames'' review can all-too-easily induce motion sickness.
25* NightmareFuel: The ending of his ''Film/ParanormalActivity3'' review.
26* OneTruePairing: Even the Bum, despite his hatred for [[Film/{{Twilight}} Bella]], feels Jacob would've been a better boyfriend/husband for her than Edward.
27* RescuedFromTheScrappyHeap: 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, ObfuscatingStupidity and a {{keet}} personality with some manipulative and snarky qualities changed all that.
28* {{Squick}}: In ''WesternAnimation/TheLegoMovie'' review, both Chester and the audience are grossed out by what Critic apparently does with his Rogue figurine.
29* TearJerker:
30** The end of ''Film/WhereTheWildThingsAre'':
31--->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! [[MoodWhiplash Oh, and also, eat your vegetables]].
32** The Chicago snowstorm video, especially when he's crying on the ground at night. Not even [[SpecialEffectFailure Rob's obvious shadow]] detracts from it, considering Chester even says the CA company is forcing him to do this.
33** ''WesternAnimation/WreckItRalph'' is a bit like if you smooshed the Critic's reviews of ''Film/BabyGeniuses'' and ''Film/ScoobyDoo'' together for the maximum amount of pain you can inflict.
34** You knew it was coming, but seeing him lose his cozy Christmas room ''a week before Christmas'' is really cruel.
35%%* UglyCute: Even a bum can look adorable.
36* TheWoobie:
37** "I just want to belong!"
38** Also the ''2011 Chicago Snowstorm'' video.
39** And the search for the Necronomicon. "I'm not a religious man, but I now believe in the Devil."
40** 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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