I haven't seen the 30 for 30 yet, but it's my most vivid memory of a sports event as a kid for sure and I haven't watched a single sporting event more than that fight.
Douglas' issue was in his heart, he was just never REALLY a prize fighter. He was twice as toosly as his father, super long arms, devastating knockout power and was really, really athletic. But he lacked the work ethic and just never quite found any consistency. People forget his was his second time fighting for a heavyweight title (he fought Tony Tucker and lost in 87 for the IBF belt) and he was ranked in the top-4 in spite of all that.
Tyson was just a total mess by that point - from the turnover in his camp, to this basically being a total tuneup fight to there just being no controlling influence in his life. He wasn't just out of shape, he looked uncoordinated and just wasn't sharp in anything he did. Douglas fought his best fight to date. That's what happens.
As for Tyson's place in history - I still think and stick to the fact that I think Tyson is the best boxer i've ever seen - or at least the 84-89 iteration. Physically more explosive, more powerful, illusive - and he could also take a shot (Tony Tucker hit him with a BOMB in the 1st or 2nd round of their unification fight and Tyson walked right through it)... Just as a physical specimen, he was different. The guy post-Douglas was never the same guy, even when he regained the title.
I think the 'he didn't face the greats' thing is a bad criticism of his early years. Holyfield was a Cruiserweight until late 89, and the Holyfield fight was pretty much signed for October of 1990 anyway. It's not like they were avoiding him. Holyfield put on a lot of size from 89-92 though but in 90, I don't think there was enough of him to beat Tyson if Tyson had a quality camp. And I like Holyfield a lot more than most.
The problem for Tyson and the 'greats' thing was he came along in a period where Holmes and Spinks had transitioned out and that next wave of Holyfield, Lewis, Ruddock, etc- weren't quite there yet. That or he absolutely exterminated anyone who would have had a shot of being great.
I've already mentioned him twice, but if Tyson doesn't exist, Tony Tucker would have legitimately had a shot at being an all time great heavyweight and up until Douglas (who Tucker absolutely smashed) - was by far Tyson's toughest opponent. Had he not shattered his hand in round 2, he might have won the fight (he won the first two rounds, including the uppercut I discussed earlier). But Tucker is on a list of a lot of guys who Tyson ran through that just never quite found their footing after getting beat by him. Tucker also found coke after the fight, so there's that. That being said - he still beat Frank Bruno twice, flat-lined Berbick and Spinks. Also put away Ruddock in 91. So I dunno. I just think that's kind of a weird thing to put on Tyson.
You fight who you fight and they never dodged anyone in that time period.