Artist Disillusionment: What Bischoff said was probably true, that Hart was a broken man when he came to WCW. He considered WWF his home and Vince a father figure, and he felt betrayed. And truthfully, even if they did have an angle for him (which they didn't), and it was good, he would have still been unhappy. He was never the same after Montreal.
Of course, being in WCW having his time and the best years of his career wasted by a company who had no idea what to do with him didn't help. As he recounted on his "Broken Skull Sessions" interview with "Stone Cold" Steve Austin, at one point he sat down and had a talk with Dustin Rhodes (who was also in the same boat of being misused by WCW after leaving the WWF), and while Dustin was literally in tears as he talked about how he still couldn't help but love the business, a broken and worn-out Hart just asked "What's to love?"
Breakup Breakout: After he split from the Hart Foundation, Bret was catapulted to the main event. Ironically, Jim "The Anvil" Neidhart was initially considered to be the stronger performer. Bret's singles push came during the WWF's infamous steroid scandal, where McMahon wanted to push someone smaller. To Bret's credit, the breakup wasn't infamous like what happened to The Rockers, although Anvil, like Jannetty, never really found a proper home afterwards, drifting in and out of WWE every few years with stops in ECW, WCW and various independents.
Missing Episode: His match against Tom Magee, which is notable in that he was able to carry the otherwise talent-free Magee to a good match, was considered lost to the ages until 2019. The WWE promptly made a documentary around and eventually showed the entirety of the match for their Network platform.
Money, Dear Boy: His run in WCW. He was thinking about his and his family's future over his career.
Bret's "I Quit" match with Bob Backlund at WrestleMania XI was described by Bret as his worst pay-per-view match ever (though not so much the fault of Backlund, whom Bret respected). Not only did Bret feel the frequent submission holds "stunk the building out," Roddy Piper, as guest referee, kept sticking a live microphone in their faces and yelling "Whaddya say?" in an over-the-top voice that came off goofy, making the match impossible to take seriously. According to Bret, "nobody laughs during my matches unless I want them to!"
His cowboy gimmick from his early WWF days was something he felt very uncomfortable with, as he never really felt like a cowboy to begin with. And he hated country music.
Bret came to regret the heel promos he made derisively accusing Shawn Michaels of being gay, stating leaning on the homophobia made him uncomfortable. It probably doesn’t help that Bret and Shawn’s mutual friend Pat Patterson is an openly gay man.
Bret Hart was close to jumping to WCW in the early 90's, but declined at the 11th hour, because he didn't like WCW's then attendance numbers of their house shows. He also almost jumped in 1989, at the behest of Ric Flair, but was lowballed in an offer by Jim Herd.
It's unknown how fast, or even if, Hart would have risen without it. But apparently, Vince McMahon actually started to push Hart after SummerSlam 1992 because of his match with the British Bulldog. Allegedly, Hart had to drag his brother-in-law around the entire match because the latter was coming down off a cocaine binge the previous night.
Had Hulk Hogan's ego not gotten in the way, causing Vince McMahon to change plans completely, we might have seen Bret Hart vs Hulk Hogan at SummerSlam 1993.
Obviously, the Survivor Series 1997 match. As Bret tells it, the original finish was a disqualification finish where the Hart Foundation and DX would brawl again, and Bret would've surrendered the belt on Raw the next night.
If Vince hadn't backed out of the contract not only could the Montreal Screwjob have been avoided, but the plans for Wrestlemania 14 were to have Bret and "Stone Cold" Steve Austin wrestle for the title in a rematch of their Wrestlemania 13 classic. This time, Austin would have won.
Was originally considered to play Batman in Batman Unchained before production was canceled because Batman & Robin was a flop at the box-office and was panned by audiences and critics.
The tag match mentioned for Only Sane Man on the main page? The Undertaker was supposed to have been in Bret's spot, who would have fit in much better with Warrior, Kamala and Shango than Bret did.
According to Bret himself, Sean Waltman and Scott Hall approached him during a mid-90's European Tour to become the head of the The Kliq (which Shawn didn't know about due to being on a different tour).
In a similar manner to The Self Destruction of The Ultimate Warrior, WWE had planned to release an unflattering documentary about Bret titled Screwed: The Bret Hart Story, with its primary focus on the Montreal Screwjob. Bret mending fences with the WWE led to the much more favorable Bret "Hit Man" Hart: The Best There Is, The Best There Was, The Best There Ever Will Be documentary. The negative interviews recorded for Screwed were subsequently scrapped, and Bret's more positive relationship with many of the subjects interviewed means it is unlikely they will ever be released.