History YMMV / ToBoldlyFlee

* UnintentionalPeriodPiece: The subplot of the government trying to censor the internet was an obvious TakeThat towards the then-recent SOPA controversy.

*** Its possible to watch this movie and not know who [[spoiler: Creator/JamesRolfe]] is (or know, but simply not recognize him). They both seem to realize this, since at no point is this person named, so it could still be intentionally funny as TheUnreveal.

** Lewis Lovhaug was adamant that Mechakara remain a serious threat while the film was shooting, and it shows. Lewis maintains his usual intensity during his performance as Mechakara, [[TheComicallySerious despite the goofy shenanigans that's going on around him]]. As a result, he ends up being the only villain who comes away with any dignity by the end of the film.

** Lewis Lovhaug was adamant that Mechakara remain a serious threat while the film was shooting, and it shows. Lewis maintains his usual intensity into his performance as Mechakara, [[TheComicallySerious despite the goofy shenanigans that's going on around him]]. As a result, he ends up being the only villain who comes away with any dignity by the end of the film.

* EvilIsSexy:
** Despite him being a blatant TakeThat, Prick's smooth voice, prettiness and sharp fashion sense still earned him quite a bit of love.
** And there are still plenty of people who'd be more than happy to KneelBeforeZod.
** As with every other appearance by him in WebVideo/AtopTheFourthWall, Mechakara has fawning fangirls. It's the voice.
** Turrell too, no matter how hammy.
** Rob as sleazy, handsy, manipulative, abusive, forever-smirking Christopher Clodd in ''Part 5''.

* MoralEventHorizon: The Executor having a disgusting amount of fun electro-torturing Luke. He deserved his gory death at that point.

** Snob threatening Luke that they'll capture Critic and turn him into the next Creator/TommyWiseau. A promise that's scarier than it sounds, but at the time Critic was suicidally depressed but also a hero, and it spurred Luke on to fight. Fast forward to reboot, and there's a big portion of the BrokenBase who find the "new" Critic just as fascinatingly bad as any Wiseau character, and Doug's commentary of ''Film/TheRoom2003'' has him relate to the guy a lot.
*** Revelations from his collaborators as part of the #[=ChangeTheChannel=] campaign have shown that during the film's production Creator/DougWalker displayed a lack of both basic filmmaking knowledge and general awareness about how miserable his team was that comes across as distinctly Wiseau-ian.

** The controversial scene where Mecha-kara assimilates the Nostalgia Chick getting played as a rape joke, was already bad with the knowledge neither Creator/LindsayEllis or Creator/LewisLovhaug were comfertable doing the scene, but if got even worse in 2021, when Lindsey admitted she had been raped during her college years. This means Doug unknowingly wrote a scene where Lindsey would have to relive one of the most traumatic experiences of her life.

** Snob threatening Luke that they'll capture Critic and turn him into the next Creator/TommyWiseau. A promise that's scarier than it sounds, but at the time Critic was suicidally depressed but also a hero, and it spurred Luke on to fight. Fast forward to reboot, and there's a big portion of the BrokenBase who find the "new" Critic just as fascinatingly bad as any Wiseau character, and Doug's commentary of ''Film/TheRoom'' has him relate to the guy a lot.

* CondemnedByHistory: Released at the height of Website/ChannelAwesome's fame in 2012, ''To Boldly Flee'' was initially seen as funny, emotional, and overall genuinely impressive for a scrappy team of Internet personalities. Even among those who disliked Creator/DougWalker's decision to kill off WebVideo/TheNostalgiaCritic to focus on his passion project ''WebVideo/DemoReel'', it was generally considered a good swan song for him. However, changing tastes in internet media, increasing disdain from [[OldShame the special's own contributors]], and the Critic's hasty revival after ''Demo Reel'' failed would prompt reappraisals for the worse. The humor was seen as clumsy and immature at best and flat-out offensive at worst (with [[ShallowParody surface-level, if not inaccurate parodies]] and frequent {{shout out}}s as crutches), the drama felt [[DeathIsCheap cheapened by the Critic's revival]], the plot was considered unfocused and meandering, the commentary on the then-recent SOPA/PIPA bills was deemed [[{{Anvilicious}} preachy]] and [[UnintentionalPeriodPiece badly dated]], and the Critic's death was seen as a mistake. After the Not So Awesome document revealed the ugly circumstances of its ''deeply'' TroubledProduction in 2018 (and caused the site and its community to collapse in disgrace as a result), ''To Boldly Flee'' became universally seen as a troubled, overly long, self-indulgent point of no return for the site, which ''nobody'' looks back on fondly.

** The SUCKA plot while something of a time capsule is sadly really relevent to this day. Content creators still battle with the demonotizations & having works taken down. The FOSTA-SESTA bill gave us a microcosm of what would happen if section 230 were compromised more universally. Not only did it make everyone it was set up to protect less safe, it demonstrated how when told they might be held liable for what people do on their site, in this case sex trafficking. They will shut down anything remotely to do with it (which is why several sites have blanket nsfw bans).
*** This has in no way stopped legislators from trying to enact more general versions of FOSTA. Their like bills to repeal daylight savings, one pops up every few years.

* AuthorsSavingThrow: The Plot Hole spawning in space is used as a catch-all fix for every fan-enraging inconsistency on the site, most prominently Spoony and Dr. Insano being the same character in ''Kickassia'' when they're separate characters otherwise. Well, that and the Aesop that there will always be inconsistencies in any art, just go with it. According to a few producers, they got irritated enough with Doug and Rob explaining anything that didn't make sense with "PlotHole!" that they made fun of it in their videos for a while.

*** The special sees Rob Walker portraying a CorruptCorporateExecutive who treats his employees like dirt and wants to destroy the critics, and Cinema Snob betrays them and joins with him after becoming disillusioned with their cause. In real life, it's now known that Rob Walker and Mike Michaud treated the Channel Awesome personalities like dirt, and when everyone else abandoned the site, Brad Jones sided with the Walkers and Michaud and denounced the others.

* CondemnedByHistory: Released in 2012 when the standing and popularity of Website/ChannelAwesome was arguably at its zenith, it was initially well-received, being seen as funny, emotional, and overall a genuinely impressive feat for a scrappy team of Internet personalities. The only real point of contention was the decision to kill off WebVideo/TheNostalgiaCritic so Creator/DougWalker could focus on his dream project ''WebVideo/DemoReel'', and even those who disagreed with the choice to do so generally liked the special overall, saying that at least it acted as a good swan song for the character. However, after ''Demo Reel'' flopped and the Critic was hastily revived, opinions on the special shifted. Not only was killing off the Critic now universally seen as a mistake, changing tastes led to a reappraisal of the special for the worse. Its massive runtime was criticized as bloated, its humor was seen as clumsy and immature, its attempts at drama now rang hollow for many, its frequent use of pop culture references became seen as a crutch, and its [[{{Anvilicious}} heavy-handed]] commentary on the controversial intellectual property legislation being discussed in Congress at the time was seen as [[UnintentionalPeriodPiece badly dated]]. Even many of those who had participated in the special's making began to express open disdain for it. The final nail in the coffin came in 2018 when the Not So Awesome document revealed (among other things) serious behind the scenes troubles that permanently tainted the reputation of the special as a whole. Even with Channel Awesome's best days well behind it and the site reduced to a shadow of its former self, there are still those who look back at the earlier specials with at least some degree of fondness. ''To Boldly Flee'', however, is universally seen as a troubled, overly long, self-indulgent mistake that played a major role in setting the stage for the website's fall from grace.

* CondemnedByHistory: Released in 2012 when the standing and popularity of Website/ChannelAwesome was arguably at its zenith, it was initially well-received, being seen as funny, emotional, and overall a genuinely impressive feat for a scrappy team of Internet personalities. The only real point of contention was the decision to kill off WebVideo/TheNostalgiaCritic so Creator/DougWalker could focus on his dream project ''WebVideo/DemoReel'', and even those who disagreed with the choice to do so generally liked the special overall, saying that at least it acted as a good swan song for the character. However, after ''Demo Reel'' flopped and the Critic was hastily revived, opinions on the special shifted. Not only was killing off the Critic now universally seen as a mistake, changing tastes led to a reappraisal of the special for the worse. Its massive runtime was criticized as bloated, its humor was seen as clumsy and immature, its attempts at drama now rang hollow for many, its frequent use of pop culture references became seen as a crutch, and its [[{{Anvilicious}} heavy-handed]] commentary on the controversial intellectual property legislation being discussed in Congress at the time was seen as badly dated. Even many of those who had participated in the special's making began to express open disdain for it. The final nail in the coffin came in 2018 when the Not So Awesome document revealed (among other things) serious behind the scenes troubles that permanently tainted the reputation of the special as a whole. Even with Channel Awesome's best days well behind it and the site reduced to a shadow of its former self, there are still those who look back at the earlier specials with at least some degree of fondness. ''To Boldly Flee'', however, is universally seen as a troubled, overly long, self-indulgent mistake that played a major role in setting the stage for the website's fall from grace.

* CondemnedByHistory: Released in 2012 when the standing and popularity of Website/ChannelAwesome was arguably at its zenith, it was initially well-received, being seen as funny, emotional, and overall a genuinely impressive feat for a scrappy team of Internet personalities. The only real point of contention was the decision to kill off WebVideo/TheNostalgiaCritic so Creator/DougWalker could focus on his dream project ''WebVideo/DemoReel'', and even those who disagreed with the choice to do so generally liked the special overall, saying that at least it acted as a good swan song for the character.\\
\\
However, after ''Demo Reel'' flopped and the Critic was hastily revived, opinions on the special shifted. Not only was killing off the Critic now universally seen as a mistake, changing tastes led to a reappraisal of the special for the worse. Its massive runtime was criticized as bloated, its humor was seen as clumsy and immature, its attempts at drama now rang hollow for many, its frequent use of pop culture references became seen as a crutch, and its [[{{Anvilicious}} heavy-handed]] commentary on the controversial intellectual property legislation being discussed in Congress at the time was seen as badly dated. Even many of those who had participated in the special's making began to express open disdain for it.\\
\\
The final nail in the coffin came in 2018 when the Not So Awesome document revealed (among other things) serious behind the scenes troubles that permanently tainted the reputation of the special as a whole. Even with Channel Awesome's best days well behind it and the site reduced to a shadow of its former self, there are still those who look back at the earlier specials with at least some degree of fondness. ''To Boldly Flee'', however, is universally seen as a troubled, overly long, self-indulgent mistake that played a major role in setting the stage for the website's fall from grace.

* UnderminedByReality: The climactic scene and resolution is the Nostalgia Critic choosing to make a HeroicSacrifice as a way to save everyone, with this being treated as the endpoint of his character arc and a sign that he's become a truly good and selfless person despite being created as nothing more than a shallow jerk. Though already a bit of a self-aggrandizing moment, it becomes very difficult to take seriously when one learns that, in real life, Doug had abruptly chosen to retire the site's main draw in favor of gambling everything on [[WebVideo/DemoReel a show that would ultimately bomb]], and everyone present immediately realized that this would have knock-on effects on their careers, as many people would stop coming to the site (not helped by the film repeatedly bringing up the idea of this being an EndOfAnEra). Essentially, what was treated in the film as giving up his life to save his friends was seen by those same friends in real life as him throwing them under the bus for the sake of what they viewed as a VanityProject.

However, after ''Demo Reel'' flopped and the Critic was hastily revived, opinions on the special shifted. Not only was killing off the Critic now universally seen as a mistake, changing tastes led to a reappraisal of the special for the worse. Its humor was seen as clumsy and immature, its attempts at drama now rang hollow for many, its frequent use of pop culture references became seen as a crutch, and its [[{{Anvilicious}} heavy-handed]] commentary on the controversial intellectual property legislation being discussed in Congress at the time was seen as badly dated. Even many of those who had participated in the special's making began to express open disdain for it.\\

** While the SUCKA Bill was meant to be a TakeThat to the SOPA Bill, it also had the unintentional prediction of companies constantly abusing DMCA take downs on several critics (some of them being part of Channel Awesome), with the closest being how [=ShoPro=] [[LoopholeAbuse exploited small courts to take down]] WebVideo/ThatDudeInTheSuede's videos and mortally wound the channel with copyright takedowns.