Preface - After reviewing my analysis, I realized that it.....kinda sucks.
Nonetheless, here is my viewpoint:
Shawn Michaels vs. Bret Hart: Who's the better man.
Wrestling Ability: Tie.
To me, it's a bit absurd to try and compare Shawn Michaels to Bret Hart in terms of who the overall better wrestler was. It's like trying to compare Joe Montana to Jerry Rice (or for us hockey fans, Patrick Roy to Wayne Gretzky). Bret and Shawn had different wrestling styles.....and were masters of their own respective styles. In my opinion, HBK and Bret are 2 of the 4 greatest wrestlers of all-time (Kurt Angle and Dynamite Kid being the other two). In the end, I don't think it matters that HBK had more speed, agility, and aerial ability. Similarily, I don't think it matters if Bret had greater mat skills and sold moves in a far more realistic way. In the end, both guys were wrestling geniuses in their own way.
Charisma: Tie:
I'm a little surprised at how many people are be-littling Bret's charisma. During the early mid-90's, Bret was the #1 face carrying the WWE in Hulk Hogan's absence. Bret had tons of international appeal, and did a great job in portraying the "no-nonsense / good guy" image. Even when Bret Hart was an American hating heel, the guy generated great heat in the Hart Foundation.
Anyone that watched the WWE in 1997 knows what I'm talking about. The guy got massive face pops in Canada and generated spectacular heel heat in the U.S. An argument can be made that a large part of Bret's success, came from the fact that he was portraying his real life beliefs (and hence - his promos/attitude came across as very real).
Bottom line? Bret was majorly over as a heel AND a face. HBK on the other hand, had more "flair" and probably had Bret beat in terms of the controversy he created (i.e. DX, MSG incident, etc.).
However - HBK's greatest success was always as a heel. Like many other wrestlers, HBK simply could not deliver in the same way as a face. Bret on the other hand, CARRIED THE COMPANY as a major face.
So in conclusion here, I'll have to say "draw" for charisma. Bret showed an ability to be over big time as both a heel and a face. HBK created more overall controversy .
Overall Wrestling Legacy: Bret Hart
In my opinion, Bret's wrestling legacy overshadows HBK's. Bret had(s) more international appeal than HBK in my opinion, and also showed an ability to CARRY the company as both a heel AND a face. Almost anyone can "make it" as a heel. However - it takes someone truly special to reciprocate that as a face.....and Bret delivered from that standpoint. All the great ones have done this: Steve Austin, The Rock, Hulk Hogan, Undertaker, and Bret Hart.
In terms of "who had more memorable matches" (which ties in to overall wrestling legacy IMO), I'd call it a draw.
However, I'd argue that "backstage conduct" falls under wrestling legacy and Bret Hart easily wins hands down here. Bret was a team player for the most part, and almost always did jobs when asked to. Bret had the respect of almost anyone worth a damn backstage (i.e. Undertaker). HBK on the other hand, was a complete brat....and often times went out of his way to belittle others, etc. HBK refused to do jobs, etc. to many people on numerous occassions. HBK was a complete dick to emerging talents such as The Rock. HBK faked an injury to get out of dropping the title to Bret at Mania. At Wrestlemania 14, HBK tried to get out of his match with Austin (until Taker threatened to beat the shit out of him).
So - in terms of overall wrestling LEGACY, I'll have to go with Bret. Both men have had NUMEROUS 5 star matches. Both men had the ability to carry almost ANYONE. However - Bret's international appeal and classy backstage demeanour gives him the nod IMO.
Better current mental State: HBK
It truly saddens me that a guy as great as Bret simply refuses to let go of an event that happened over 10 years ago. It's debatable as to whether Bret screwed Bret or Vince screwed Bret 10 years ago, but Bret sure as hell is screwing Bret at current. EVERY time HBK's name is brought up to Bret nowadays, Bret can't resist taking shots at him (instead of being the "bigger man" and saying, "You know what? It happened 10 years ago. Let's drop it."). HBK on the other hand, truly seems like a guy who is trying to walk the path of spirituality. HBK acknowledges that he was a dick back in the day, and genuinely seems like he's trying to be a better person.
As the years go by, HBK's legacy continues to grow....based on his current wrestling matches and current backstage conduct, etc. "Montreal" on the other hand, seems to grow in relevance as it relates to Bret's wrestling legacy.....and that's sad. The more relevance "Montreal" has, the more it takes away from Bret's overall wrestling legacy....and THAT is a shame. However - Bret is digging his own grave as far as I'm concerned.
Overall - HBK
Although I think Bret has HBK beat in terms of overall wrestling impact, I still choose HBK for reasons NON-wrestling related. After an extremely troubled and tumultous youth, HBK finally seems to be happy....and seems to be walking down the right path. Bret on the other hand, just seems to be misreable...a guy that can't let go of the past.....a guy that keeps dwelling on the past. The funny thing here, is that a lot of Bret's fans have adopted the same mentality (which perhaps explains why a lot of Bret's fans still seem so passionate/angry about Montreal?).
Although Bret probably did more and achieved more than HBK did in his wrestling career (IMO), I also believe that as time goes on, HBK's legacy will continue to get bigger.....while Montreal will grow in relevance as it relates to Bret (which in effect, will continue to diminsh Bret's overall legacy).
At this rate - I think HBK will live a happy life one day after wrestling. Bret on the other hand (and his fans), will continue to be misreable for the most part while dwelling on the past.