"He defeats people by putting them up other people's asses! That better happen in the new Dark Knight movie! The Joker will be like 'I am going to kill everyone!' and Batman will be like 'You are going inside an ass!' Bloo-bloo-bloo-bloo-splut! THE END!"
Bitch in Sheep's Clothing: Not that he doesn't have lots of nice moments too, but he used his "innocent harmless bum" persona in a plan to destroy the world (and succeeded as well!), took money from a church and wibbled at Nash to convince him not to tell Holly, always defends the Critic but also acts like the voice for his entitled fans, and tries to steal things at cons.
Breakout Character: Bum Reviews has become one of the most popular features on That Guy's website. Quite a feat for a spin off character.
Butt Monkey: In his coverage of the 2011 Chicago Blizzard.
"And at the end they play the famous theme song! *sings said theme song with added lyrics*"
"This is Chester A. Bum saying... CHANGE!! YA GOT CHANGE!?!? OH COME ON, HELP A GUY OUT WILL YA!!! C'MON, CHANGE!!! I promise I'll use it to educate people on the difference between a subversion, an inversion, and an aversion!"
The 2012 Christmas episodes have "Don't go away Christmas, I want to stay in this room!"
Caustic Critic: Usually averted. Chester is convinced every film is the greatest he's seen in his life, while Doug's real views given at the end are almost always at least lukewarmly positive. The exceptions don't really change his style that much either.
Comically Missing the Point: All this time, Chester was wishing on stars to help him out, and it turns out he needs to work hard, even get a job. Then he says perhaps he should wish on a star for that.
Crazy Memory: He seems to go through a lot of crazy stuff like having been an Asian boy scout.
Credits Gag: For the first four years, the episode's end credits would contain a small comment that always begins, "Seriously," that outlines what Doug really thought of the movie.
That blurb was eventually dropped for a complete second video outlining what Doug really thought of the movie. That series morphed into Sibling Rivalry in late 2012, where Doug would bounce his opinions off his brother Rob, who'd give his own opinion.
"So Tiana saves up all her money, and she finally gets her own restaurant! But these two guys are like: (as the two guys) 'We have to close you down because we found a higher bidder!' (as Tiana) 'It's because I'm black, isn't it?' (as the two guys) 'Well, it's the 1920s, so sure.'"
Ironically, the film itself goes out of its way to avoid even mentioning racism, despite its prevalence at the time being historical fact. The scene Doug references is the only one that comes close.
Despair Event Horizon: After nearly freezing to death in a night snowstorm, his reviews started giving more focus to flaws in movies, instead of just scatterbrained gushing about everything.
Expy: The first Nostalgia Critic video was actually the Critic acting like the future Chester A. Bum doing Transformers (2007). This is given a nod with the Critic doing Revenge of the Fallen, and Bum popping up after he leaves, asking if the Critic stole his act.)
Not to mention this being brought to its logical conclusion with the Dark of the Moon review when right at the start of the Critic's review, he gets a letter informing him that Chester's suing him for stealing his act (in case you're curious, there IS a review... of Chester's when the judge asks how he'd review it).
Foreshadowing: The Paranormal Activity 4 review was surprisingly negative for a movie that Doug actually enjoyed. The next episode, Wreck-It Ralph, has him going through a hard-to-watch breakdown because he doesn't have fun in his job anymore.
In the review of "Pirates of the Caribbean: On Stranger Tides", he constantly says "I'm Johnny Depp!" while wiggling his fingers and staring at the camera after pointing out a couple of Fridge Logic parts.
Chester A. Bum: They just cut to the credits before anything else happened. What do you think they're doing!? She's taking off his sheep's clothing! He's riding her hood! She's blowing his house down! The better to eat her with! She's taking him to grandma's house! He's checking under her hood! Holy smokes, I could make a book of these.
Hype Backlash: In-universe example. The Bum actually gave a negative review to Citizen Kane, and this was one of the reasons. (It was a joke of course, Doug mentions at the end that he likes Citizen Kane.)
A lot of his criticisms towards District 9 was disagreeing with the movie being as ground breaking as people made it out to be.
Innocently Insensitive: When he showed up in the Critic's press conference for James and the Giant Peach, he stated genuinely that it was the best LP he ever saw in his life, but because he was also yelling about how the fans deserved better, Critic still looked like he'd been punched.
It's a Long Story: Pretty often. Just one variation is "I was a slave once! ...but it's a boring story."
Possibly the most extreme case was the end of his review for Paranormal Activity III. The light cuts out, he gets shot by Teddy Ruxpin, and we see red eyes and hear "come dream with me tonight...". Followed immediately by the usual classical music for the credits.
More Popular Spin Off: Doug's vlogs. Not that Chester still isn't loved, it's just Doug's talent for "real" reviewing took a lot of people by surprise.
Motor Mouth: Something the other bums never quite managed to pull off.
Mysterious Middle Initial: Though one episode reveals that at one point, he was a smooth-talking, shades-wearing car salesman who introduces himself as "Chester Alfred B."
"I used to be an Asian boy scout!" And adds. "Wasn't that a weird week."
"Not Making This Up" Disclaimer: Once an episode, usually Punctuated! For! Emphasis!. For example: "So Mulder and Scully are out to stop evil doctors by using a paedophile priest who is also a psychic! I swear to God, I am not making that up! More movies need paedophile priests who are psychics!"
Obfuscating Stupidity: Chester's surface persona is too in-your-face brain-fried to be taken seriously. However, much of his commentary is actually insightful and well-phrased.
Omnicidal Maniac: During Part 2 of Linkara's review of Countdown, Chester hijacks all of Earth's nuclear weapons and plots to take over the world (OF COURSE!). He finally gets fed up with arguing with the Critic about it and just destroys the entire planet.
OOC Is Serious Business: While reviewing The Avengers, Doug literally breaks character, takes off the fright wig, and says in a serious tone how wonderful the movie is. And he does it again at the end to make sure you know to go see it.
Subverted in his Citizen Kane review. Chester was unusually serious throughout, going on and on about how he thought the film was crap and everyone who calls it "the greatest movie ever made" is an idiot. Of course, that was the whole joke of the review, and Doug himself likes the film.
He spends a lot of time calling out on the flaws of them in a much snarkier way than he usually does.
Morality Pet: People being nasty to him is usually a way of showing their Jerkass-ness and Critic giving him money and offering a place to stay manages to get the interviewer in True Internet Story to begrudgingly admit that Critic's a Jerk with a Heart of Gold.
Not So Different: He thinks Ask That Guy's a douche and Ask That Guy thinks Chester is disgusting, but they've both been in porn, both have fantasies (we hope) about killing their parents and both have a talent for evading lawful punishment.
Precision F-Strike: Chester drops a couple of F-bombs in his Iron Man 2 review, mostly because he's impersonating Samuel L. Jackson.
Progressively Prettier: While it would be unfair to expect Doug to make himself look like a real close-to-death bum for a five minutes episode made on a next-to-zero budget, Chester used to at least have a load of make-up-as-dirt on his face and hair like he'd had an accident with something electrical. Now he just looks like he needs an updated wardrobe and a haircut.
Chester: I don't live with lights, cars or electricity and I get along just fine! Please shoot me.
The Stinger: Chester always adds an extra punchline about the movie into his calls for "CHAAAAANGE!" at the end of the videos. The end credits had a written stinger too (in which Doug Walker gave a one-sentence summary of how he actually about the movie, always starting with "Seriously, though..."), but that's been replaced by a separate and longer "Doug's Review" video that runs below the Bum Review.
You Bastard: He thinks the audience is sick for watching him nearly freeze to death in a snowstorm for entertainment.
"This is Chester A. Bum saying, CHANGE? YA GOT CHANGE?! AW, C'MON! HELP A GUY OUT, WOULD YA? C'MON, CHANGE! ...COME ON! I'LL EVEN RAMBLE ON ABOUT A DIFFERENT THING EVERY EPISODE WHILE THE CREDITS ROLL! My voice is pretty sexy."