Winning a lawsuit against the Nostalgia Critic for ripping him off.
While searching for the Necronomicon, the Critic has taken all his drugs, letting him be a bit more eloquent as he tells the Critic off for making him do all the work. "MY hard work, Critic! MY! HARD! WORK!"
While Doug's real review for Breaking Dawn talks about the movie's problems far more passionately, Chester still gets points for being horrified that Edward and Bella didn't use protection and the movie manipulating the minds of teenage girls over a topic as grisly as abortion.
Generally, how he manages to be completely scathing towards Bella and Edward while still keeping in-character and not coming off as an Author Filibuster by Doug.
Media!Chester: We're going to turn you into the manliest person on earth by giving you the gayest costume possible.
Other!Chester: This is the forties, do we even know gays exist yet?
Media!Chester: Hey, we're the media, if we don't put a camera on it, it's not real.
An example based more on Doug's performance in the Wreck-It Ralph review. After voicing his disillusionment on being a sell-out due to his astounding popularity, Chester starts the review in an unusually somber manner. As it goes on, there's this subtle escalation of the cheery and hyper disposition we all know and love Chester for that really needs to be seen. At the end of the review, he contemplates for a moment and realizes what just happened... and marches right back to his adoring public!