I'm watching December to Dismember because I hate myself and Big Show just walked out and FUCK does he look awful. IIRC he got sent home/fired or whatever not long after this (maybe even the next night) and it's made me think; what is the worst condition physically that guys have ever worked in? Yoko right at the end looked awful, but he always did. Pillman at the end was sad too. Any others?
Oh man, Yokozuna looked AWFUL at the end of his life, and no surprise. Jake Roberts after his comeback attempt in 96 was a total mess as well and looked like he should be on the deathwatch list. Scott Hall in WCW 99/00 aged 20 years in that span. There was a while with Austin during his bad period in 02 where he looked like he was in constant pain every week (and he probably was). Randy Savage in TNA was a disaster.