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 (1993-1997), 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, the incredibly tastless Take Thats at WCW in the form of the "Billionaire Ted" skits, 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. 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. These days, this era only gets brought up if somebody wants to mock or embarrass Vince and/or the WWE.
Despite WCW acquiring many of the WWF's major 80s talent, the state of the programming was no different to the Fed's back in the mid '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. Even when Hogan himself arrived to the company, he was playing a tired-looking version of his old character, having lost significant muscle mass and trying in vain to exude the charisma he held in his WWF heyday. While WCW did achieve short-term success with the extremely popular nWo angle, many of its non-nWo elements could be considered "dork age" in an of themselves, particularly if you were a holdover from the NWA & Georgia Championship Wrestling days.
Fans of the WWE have been complaining about the new "PG Era", since it's been erected in 2008, 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.
If there's any reason besides the PG rating that people have complained about present day WWE, it's people feeling the company is far too formulaic and predictable, pointing partially to WWE's suffocatingly tiny main event scene (especially when it comes to faces), especially their insistence on placing John Cena on a tier far above the rest of the roster for most of his 13+ year career, even when whatever he's doing is comparatively unimportant, and even years after large portions of the audience had gotten sick of him. The controversial departure/firing of CM Punk, the career-ending injuries of Daniel Bryan (almost immediately after they had finally pulled the trigger on him as a main event talent) and seeming going out of their way to demote and bury anyone the audience actually wants to see did nothing to help this. Some have even drawn comparisons to the aforementioned 1993-1997 era (even drawing humorous parallels between that era's Diesel and present day's Roman Reigns, whose main event push has been notoriously controversial), as staring in 2014, WWE's ratings have been in steady decline. WWE's main roster has even been consistently overshadowed by their own developmental brand, NXT, since about 2014, carried by great indie talents.
WWE's Women's/Divas Division had something of a golden age in the early 2000's, with Lita and Trish Stratus carrying the division well along with several other talented women. Once they both retired at around the same time, the division fell off a cliff. While the women were largely chosen based on their looks before this, it was around this time where WWE seemed to stop taking the women's in-ring ability into account at all, instead compiling a roster of almost entirely former models and cheerleaders who could barely wrestle (there were a few of exceptions to the rule such as Mickie James, Beth Phoenix, Natalya and Paige, but they ended up being Demoted to Extra and/or released from the company). They eventually inflated the roster with so many mediocre women that they created a second Women's Championship, the Divas Championship, which fans have complained looks like a toy and has been nicknamed the "Tramp Stamp Title" for its gaudy pink and silver butterfly design...and then retired the actual Women's Championship shortly afterward when they mass-released many of the most talented women. WWE have even essentially given up on maintaining the heel/face alignment for its women's division, instead opting to have the women be whatever suits the situation best, with wrestlers just suddenly being heel or face for completely unexplained reasons. The perpetual push of the largely untalented Bella Twins as the centerpieces of the division, regardless of if they are heel or face this week, has also turned many people off on it. An attempt by WWE to engineer a "Divas Revolution" in mid-2015 failed so spectacularly badly that it became co-winner of WrestleCrap's "Gooker Award", with "highlights" including one half of the aforementioned Bella Twins, Nikki, saying "Wins? Loses? Who cares?" (What's worse, Nikki was actually being praised at the time by critics for improving her in-ring work.) As of 2016, this particular Dork Age seems to be coming to an end, with Brie Bella taking an extended leave and Nikki Bella suffering a career-threatening neck injury and can never work full time again, WWE bringing up actual female wrestlers who are getting longer matches, retiring the Divas Championship and bringing up a new Women's Championship and are slowly being allowed to have gimmicks and characters again. After the second Brand Split, though, things have been so much better for both Raws and SmackDowns women's division, with the women occasionally having part in the main events of both Raw and SmackDown. With divisions built on the likes of Charlotte, Sasha Banks, Alexa Bliss and Becky Lynch (and all having distinct characters), and with old stars returning (as Mickie James and Nikki Bella came back after the Brand Split), women's wrestling in WWE might be better than ever.
New Japan Pro-Wrestling was the toast of the 90's in japanese pro wrestling...and then Antonio Inoki started to feel the pressure of MMA's popularity, alongside a number of legends of the sport either leaving and creating their own feds or just straight up retiring right around 1999. What resulted was that for most of the 2000's, NJPW had the dual problem of "Inoki-isms" polluting the product, not pushing many young stars, and giving pushes and title shots to people who didn't deserve it (namely: MMA guys thanks to Inoki's insistance). It took a buy-out of Inoki and nothing less than a herculean effort by Hiroshi Tanahashi to pull NJPW out of this Dork Age and back into the popular consciousness of both western fans and japanese fans.
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.
The Undertaker's overall supernatural gimmick is an 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 (2000-2003), the only time he left the supernatural aspect of his gimmick, is seen as a Dork Age itself.
For most, its entire existence is a Dork Age, but Hulk Hogan's tenure as the on-screen authority figure from 2010-2013 is generally considered its all time low point (and that includes TNA's pre-2004 years, which were so terribly booked and vulgar that even the company barely acknowledges anything from that period). In fact, TNA from that point onward is often looked at in this light. Despite making large improvements since Hogan's departure, this period was so damaging to the company and its reputation that it has essentially been in perpetual danger of going under ever since, with issues including wrestlers getting either late or no payment and serious production flaws, causing most of their signature top talent (including TNA Original AJ Styles, Sting and Samoa Joe), to depart. Most fans have given up on TNA and absolutely refuse to watch it, and TNA has been bouncing around from network to network trying to maintain it's TV deal, and just barely succeeding.
Much like the WWE Divas' example above, the TNA Knockouts suffered this after the first departure of their top star, Gail Kim. Memorable incidents include Jenna Morasca vs Sharmell, The Beautiful People becoming a Spotlight-Stealing Squad, the "lock box" title change, the introduction of Karen Jarrett as an authority figure, and even a Fingerpoke Of Doom — and this is barely scratching the surface of what happened over the course of this period. Even after Gail's return in 2011, the division was still in the rut (for example, Eric Young, a man, remained one half of the Knockouts Tag Team Champions with ODB for over a year until the titles were finally vacated and retired by Brooke Hogan), and it wasn't until 2013-2014, with the debuts of Taryn Terrell and Havok and the return of Awesome Kong did the division really begin to recover. Just like the Hogan example, this period was so damaging to the division's reputation that their contributions to the mainstream rise of women's wrestling have been either glossed over or forgotten entirely.