I would pick Bret Hart's career. Reason being is simple, he was born and raised in a wrestling family, but despite being the son of a renowned performer, he made it on his own merits. I'm sure that being the son of Stu Hart didn't hurt at certain twists and turns in his career. However, he still had to produce and he couldn't and didn't rely on that as his ticket to stardom. He didn't rest on his laurels either with that distinction, and when the play called for it he played his part well in Stampede Wrestling, as a young up and comer, he said it best on his DVD retrospective that no one could take a shit kicking like him, and he was right. His feud with Dynamite Kid alone proved that. It's true that his first few months with the then-WWF were underwhelming but once his tag team got started with "The Anvil" Jim Neidhart, that's what things really started to pick up.
With that said, what intrigues me about Bret Hart was his ability to tell a story in the ring, yes it's true he was a champion during a commercially weak time in the WWF, and he left the promotion before things really took off. Some even say that his leaving was a big shot in the arm for the Attitude Era and that quite possibly that era would not have been the same without it. It's very likely, after all, the Mr. McMahon character really came to be through the "Montreal Screwjob."
The biggest reasons I would have loved to have a career like Bret Hart's are the following:
The stories in his book, like anything else in the world of entertainment and sports. I do feel some things are a subject of embellishment and sometimes fabrication. But even if that is the case, I do indeed feel strongly that a lot of what Bret Hart wrote about had truth to it. I've no doubt of that, if he took creative license to enhance some of these stories, so be it. I mean, he's in the wrestling business to begin with, hyperbole and embellishment are prerequisites of his job. There was just something great about the way he put this book together, and it's my favorite book of any wrestler. I've read a few others but none compare to what Bret wrote. I think the fact that it wasn't published by WWE is the biggest reason why I liked it so much. A lot of his stories about seeing the world and meeting people from other countries and sharing their perspectives on life made this a very interesting read. Basically, if I met someone who had no prior interest in wrestling but wanted to read about someone who was in the business, I'd say pick up Bret's book.
His presence in the ring, man I know that he wasn't the biggest or the baddest on the surface. After all his character wore pink for most of his career. But it worked and he sold it. His ring psychology was great, put him against Kevin Nash, he'd cut him down to size just look at how he wrapped Nash's legs around the ring post to wear the big guy down at Survivor Series 1995, then an inside cradle from out of nowhere starts Bret's third WWF Title reign. Put him in against Yokozuna, and Bret's prowess comes into play when dealing with someone he can't lift. Like he said during the Summer of 1993, "I may not be able to slam Yokozuna, but I know I can beat him". Then put him in there with a guy closer to his style and physical size, i.e. his brother Owen Hart or Shawn Michaels and it was an in-ring version of human chess within the storyline. Bret did it so well, I loved it. The detractors who say he had no "charisma", I beg to differ. Sure, he didn't have the most intense promos when it came to his talking but I thought he was well spoken, but for that lack of intensity his body language more than made up for it. Just go back and watch WrestleMania X, Bret Hart's reaction to Owen catching him in a victory roll was classic. Bret's expression said "What did I do wrong?" he was brimming with self doubt and it was sold flawlessly. Those were things Bret Hart had that I have to say a lot of wrestlers these days just don't have. Bret excelled at that. Body language should be just as big a factor in gauging someone's charisma as anything verbal, in my opinion at least.
In all, I put Bret Hart in a personal Top 10 of my favorite wrestlers. There are so many moments to list here, that it'd take an eternity to name them all. But moments like SummerSlam 94, WrestleManias 12 and 13, Survivor Series 92, Stampede Wrestling, his first WWF World Title reign and so on. Again, we all know he doesn't have the name recognition's some of wrestling's other powerhouses but he still contributing great memories to the wrestling world. And if you're a hardcore fan, there's no way you could ever deny such a thing. For me, I'd pick Bret Hart just because of how well he could make what happened in the ring look like an actual battle. The Excellence Of Execution was a nom de guerre that just rolled right off the tongue as the late, great Gorilla Monsoon used to dub him.