- Creator Backlash:
- Rob told Uncle Yo pretty soon about the Executive Meddling of being ordered by Michaud to rush something out, and Doug's Fandom Nod-heavy Critic review of the special calls this his "fuck you I'm tired and I have nothing else to offer" follow-up.
- MikeJ revealed in 2018 that he'd only been offered the chance to make his video when several other reviewers had already declined, he wasn't reimbursed for his efforts, and he made precisely zero money from its inclusion on the DVD.
- Creator's Pest: Rob hated playing The Meditation Guy, and he only existed because Doug was compulsed to change things at the last minute. In Welshy's Shut Up And Talk episode, both he and Doug discuss how badly Rob's character was received, and Doug Suspiciously Specific Denials that he had anything to do with the writing of those segments.
- The Danza: The role of Carl Custer is played by Uncle Yo, whose real name is Karl Custer.
- Enforced Method Acting: As shown in the Dragonbored bloopers, Doug shook the little girl actor (named Brynn, and don't look at the comments of that) by the head to make her drunk wave look more believable.
- Executive Meddling: According to Rob in an Uncle Yo interview, they really weren't going to do any more yearlies, but Michaud told them in late January that the fans expected something, and they had to race from there.
- Franchise Killer: Of the TGWTG anniversary specials. After To Boldly Flee, no-one really wanted to do another big crossover (Due to either moving away, thinking it was a Tough Act to Follow or just being burned out). By making The Uncanny Valley an anthology, it was hoped that this would make production easier for future specials and allow the other reviewers to showcase their talent. However, aside from Darkside of the Internet and The Reviewers (which only lasted a few episodes), none of them really made any major impact on fans. This resulted in the sixth-year anniversary passing by rather uneventfully, aside from a passing mention in the Nostalgia Critic's review of Blues Brothers 2000. A 10th anniversary special, titled The Devil's Jesters, was in the works, however the mass exodus of contributors from the site following the #ChangeTheChannel movement put the kibosh on that.
- Milestone Celebration: Five years of TGWTG.com.
- Playing Against Type: Doug Walker, who normally plays subby, impulsive Jerkass Woobies, plays Jimbroth, a medieval Fish out of Water hero.
- Reality Subtext:
- The epilogue has Diamanda being told she also blew up Critic as well as Rob and Nash. She gets confused, asks why he was behind the camera as a director and then expresses disappointment that she didn't know he felt that way. This is in reference to the only director character Doug has played.
- In Darkside Of The Internet, after talking about how the internet can lead to death threats sent to a person's home, it cuts to Allison Pregler.
- There's also a good reason why it cuts right to Doug as New!Critic after talking about how some internet celebrities take to Alter-Ego Acting to hide low self-esteem.
- Troubled Production: Behind the scenes problems were toned down a lot compared to the earlier anniversary specials, on account that it was an anthology where Mike Michaud and the Walkers had more limited control. But some issues did pop up:
- Michaud pressured the Walkers to rush out something to commemorate Channel Awesome's five year anniversary. However, most of the site's contributors — by now understandably not keen making the specials — declined to make contributions to the anthology.
- Mike Jeavons revealed in 2018 that he'd only been offered the chance to make his short film for the special, Internet Dating and Me, because of these refusals. Mike wasn't reimbursed for his efforts, and he made precisely zero money from his short's inclusion on the DVD.
- Doug faced some backlash when the blooper reel for his short, Dragonbored, showed him shaking a child actress by her head to make her drunken waving look more convincing.
- What Could Have Been:
- Lewis Lovhaug was offered to make a short, but he declined so that he could work on an Atop the Fourth Wall DVD. Had he taken the offer, it would have revolved around the origins of Lord Vyce and how he started his fight against the Elder Gods.
- Phelous was asked to make a film, but he refused, most likely due to the fact that he wouldn't be reimburshed.
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