Lot of ppl in this thread don't realize the legends from the last generation of fighters are NOT that far removed in skill level from the current generation. It ain't like the difference between the 1st Gen fighters and the 2nd gen fighters. THAT was a huge gap.
Now we're on the 3rd gen and the skill gap is NOT that big! Plus the last gen fighters were generally a lot tougher ppl than today's "athletes." Matt Hughes got popped hard in the nuts by Frank Trigg, pounded on for like 2 solid mins after that, and THEN picked him up over his head and ran him all the way across the ring and slammed him into Hughes' corner. And won that fight. Guys today (with some exceptions) just aren't made that way. A lot of them would fold in positions like that.
Point is, the LHW legends from the last gen (guys like Chuck, Wand, Shogun, Rampage, Randy, Vitor, Lil Nog, and even Tito) would likely still give the current guys today a LOT of problems. And imo the last gen guys would win more than they'd lose against today's guys.
Prime Chuck today imo would be top 5 for sure. Very possibly top 3. The two guys I see giving him the biggest problems are Jones and DC (when DC was LHW). Those are hard fights for Chuck. But I've always liked prime Chuck's chances against Jones more than any other LHW legend. His style and attributes pose interesting problems for Jones. I would've leaned toward Jones to win....but I wouldn't be shocked at all if Chuck pounded him out, either.
Chuck vs DC would've been fun too. And completely different than Chuck vs Jones. I really don't know how that would have gone. I think DC probably has the style and attributes to beat prime Chuck. He probably would've been a harder fight for Chuck than even Jones would've been.