It's worth noting that Professional Wrestling and the guys at WWE in particular, are known for having photographic memories, acknowledging as canon almost everything that has happened in pro wrestling (in their own promotion and those promotions that intersected extensively with theirs, at least) since the early 1960s, and sometimes even events before then. So according to WWE's bible, as it were, every age (even if it's a dorky one) is considered legitimate, with more recent eras having precedence, and few Retcons. (This means that Doink is still a face, no matter how much that might rankle.)
In the early '90s, Hulk Hogan had retired to try acting — then came back to wrestling for the competition, The Ultimate Warrior had decided that he was bigger than wrestling and disappeared, and Vince McMahon was on trial for steroid trafficking. Given all of this, one could forgive the WWF for dropping the ball a bit — but with a failure of the scope of the "New Generation" era, which gave us Lex Luger as a main-event Face, Doink the Clown's misguided Heel-Face Turn, Wrestling Doesn't Pay in full effect, horribly bad Take Thats at WCW in the form of the "Billionaire Ted" sketches, and some of the worst pay-per-view events on record (even if you were guaranteed a great Bret Hart and/or Shawn Michaels match every show), there's an awful lot to forgive. These days, it only gets brought up if somebody wants to mock or embarrass Vince and/or the WWE.
1995 would be the nadir of the Dork Age, since that was supposedly the year the company was at its lowest in losing money. For most of the year, Kevin Nash was WWF Champion, who arguably one of the most limited champions in the ring that they ever had and was unquestionably one of the worst money draws (JBL was worse at the box office). It wasn't entirely his fault, though; he really didn't have much to work with as far as main event feuds went, since the only three wrestlers people wanted to see challenge Diesel were Shawn Michaels, Razor Ramon, and Bret Hart. Problem is, Diesel-Bret III didn't occur until November (after being subjected to the Diesel-Sid and Diesel-Mabel feuds), Razor was saddled with Jeff Jarrett (and then, the 1-2-3 Kid), and Diesel-Shawn II was held off until April 1996. Not to mention that, as a face, they ruined Nash's character by turning him from a badass into yet another overgrown boy scout goody two shoes babyface when audiences had already grown tired of them.
WCW was also in the same state as WWF back in the early '90s. At that point in time a much smaller company, they tried to emulate WWF's overtly cartoonish characters, coming up with characters such as Arachniman, The Juicer and the DynamicDudes. Then there were the infamously terrible skits that TBS helped produce, such as the one where Sting and Jake "The Snake" Robertsshot laser beams out of their eyes. Don't forget about Oznote Nash dressed up as the Wizard with a fake beard and gigantic puke-green robe, although that was probably more TBS wanting to cross-promote than anything else.
Fans of the WWE have been complaining about the new "PG" rating since it's been erected, claiming that it's neutering the product for the sake of being "family-friendly" again (as well as claims that it's all a deluded attempt to aid Linda McMahon's hopeless run for the US Senate). Then, the NXT riot on Raw happens and fans are buzzing about what is the most exciting and freshest angle in years. Then, WWE decides to release the most "over" of the rioters, indy darling Bryan Danielson, because he choked out Justin Roberts with the man's tie on camera. Despite the fact that ten years ago, dropping "Stone Cold" Steve Austinoff a bridge and lighting Kane on fire was standard fare, Danielson's actions were deemed too menacing and too violent for the project. Fandom now has even more ammo to proclaim that the PG Era will kill WWE.
This turned out to be premature, as Danielson was brought back a few months later and then given the United States Championship. As of January, he still has the belt and appears to be pushed as the "ladies man" of Monday Night Raw.
It Gets Better with Daniel Bryan winning the Smack Down Money in the Bank match at the eponymous 2011 PPV and announcing he'll cash it in at WrestleMania 28 (assuming nothing goes wrong, of course). And then Bryan won the World Heavyweight Championship at the Tables, Ladders, and Chairs PPV event. Fandom, commence your rejoicing.
While WWE hasn't gotten back to its old ballsyness (it's now a word), things have improved, at least partially due to CM Punk repeatedly insulting the company.
Ring of Honor had a big one from October 2008 to September 2009, right when Adam Pearce took over booking duties from Gabe Sapolsky. This change was most evident with the line between the big shows (PPVs, TV Tapings, Anniversary shows, Supercards of Honor, etc.) and everything else. Most of these "B-shows" (even said so by Austin Aries, which did not sit well with many people) had traded quality for a more streamlined approach. As good as it sounded on paper, being stuck with a B-market label turned fans off from the product. The Final Countdown Tour in September 09 helped ROH regain fan confidence (along with the Austin Aries, Kenny Omega, and Davey Richards de-facto round robin in October and November), ended the dork age and set the stage for their bounceback in 2010.
It should be noted that The Undertaker is a high aversion to The Dork Age. His character is firmly from the era of ridiculous gimmicks of the late 80s through the mid 90s, yet is essentially the same character in the modern era, trappings and all. Many fans just accept that when he appears, he's essentially a character out of time.
On the other hand, his "American Badass" time is seen as a Dork Age itself.