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I'll gladly debate the career of Pillman.
Saying he had a lackluster career is pretty simple minded, and I'm actually surprised if you legitimately followed it all the way through. A great talker, a great wrestler and a brilliant mind, he had so many highlights that while there he was saddled with some goofy crap like the dress and the Yellow Dog, they're total footnotes given how he was constantly evolving and finding new ways to be a highlight of the show, first his style and the matches with Liger, then as the raspy voiced chicken shit heel, to forming a team with Austin that is still talked about as an awesome unit despite only being around for eight months. Even when there was zero intent to try and use him, or put him in bad positions in this period he'd have matches that would steal the show, carrying guys like Alex Wright and Johnny B Badd to the best matches of their lives. His run as a Horseman took a group that hadn't meant anything for years and rejuvanted it with his new persona, and the Loose Cannon was not only the first of its kind and a groundbreaker when it came to what would ultimately result in the business getting hot again - real life edgy personalities instead of cartoon characters, but it also resulted in the most captivating promos and creative skits of the time. Clearly his worth was pretty significant, being the first wrestler of the period to become subject to a bidding war between Bischoff and McMahon, and taking himself out of midcard status to get a big money contract.
And while the car crash took away his in-ring ability, he was still banging out awesome promos, and the Gun and XXX Files angles, as much as you want to discredit them, when you try to make a point about people remembering the Yellow Dog, these aren't thought of in the same vain, and the fact you remember them goes lengths to showing how impactful they were at the time.
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