Sean Waltman reminds me of Lex Luger to some degree. Not in terms of apperance or anything but in the way that he's associated with other wrestlers.
Sean Waltman has been associated with and surrounded by some of the biggest and/or best wrestling names of the past 15 years or so. Hulk Hogan, Shawn Michaels, Triple H, Kevin Nash, Scott Hall and Eric Bischoff are examples of what I mean. These are guys that, at times, have been among the very very best at what they do. Some of them have been great in the ring, some great on the mic and some great in both areas. Sean Waltman is someone that isn't great on the mic, isn't great in the ring but has attained a certain level of "greatness" if you will by being associated with these guys. At the time, they were so good at what they were doing that they made Sean Waltman look good by default.
While it might be ideal that, in most cases, a wrestlers personal life doesn't have an effect on how they're viewed by the fans in the ring, it's not an ideal world. Sean Waltman's antics in his personal life, his problems with drugs and reputation as a burn out and backstage problem have become well known. When a wrestler's personal problems are thrust so much into the forefront, it can be hard to not judge the guy overall by this problems and not just by what you see in the ring when he's doing his job.
In Waltman's case, you have an average guy that's not nearly as good as some says that he is and he's a basket case in his personal life and that's only served to lower his opinion in the eyes of some.