The Four Horsemen (Flair, Anderson, Blanchard) were the best heels in wrestling prior to 1996. Yokozuna, Vader, and Andre the Giant for a time were not far behind. Even Sergeant Slaughter and Jake Roberts were extremely hated. Anybody who says Ted Dibiase was one of the best heels is out to lunch. Dibiase was essentially a gimmick but all this revisionist history paints him in a better light as a great wrestler.
Please. I was there, he did nothing for anyone until he got into managing.
As a 29 year old, I agree with harrythem with who he picked as the two best heels of all time. For the three year period it lasted, Hollywood Hogan was the best heel of all time. I know there is a lot of hate on this site for the man because fans believe he singlehandedly killed WCW (which he did not) and threatens both the future of WWE and TNA, but you got to give the man credit where credit is due. Go back and Youtube some of his work between 1996 and 1999. Watch every Nitro and Thunder from that period. His heel turned ROCKED the wrestling world. It drew millions of households to watch WCW for three years. The moment he turned heel, the ratings went through the roof. The moment he lost the World Title after two years, ratings dropped. The moment he took a three month break, WCW's ratings plummeted. People hated him, old grandparents in the stands were even throwing garbage at the guy. But they sat their ass in the seats or tuned in just to see him get his ass kicked. And it took a good 15 months for that to happen and it never really did until Goldberg two years later. Watch his NWO commercials, watch his interviews, the guy stirred up fans to the point where people wanted to hurt him and get in the ring at him (I recall one fan even going after him in a steel cage). WWE fans hated him even more than WCW fans, because his presence in WCW threatened WWE's existence. Of course, Eric Bischoff was a great heel himself (and one of the best) and he made Hogan even more hated. I've shown old WCW to some friends and my dad and I've never seen such a hated reaction to a wrestler. Hogan and the NWO (much more heel than the Horsemen ever could be) made wrestling appear real and fans ate it up like it was real. And in reality, Hogan came up with a lot of what he said and did on the fly. It was genius. He reinvented himself as a better character than Vince could ever make him and it was the most successful period of money making in the wrestling business. All thanks to Hulk Hogan/Eric Bischoff. Without them, WWE would have put the world title on either Duke the Dumpster Drose or Issac Yankem, pushed guys like that instead of guys like Triple H, Stone Cold and The Rock, the Inyourhouse ppv would happen 8 times a year for 15 years and we'd be on Inyourhouse 120, Vince would have millions instead of billions, and the wrestling world would be missing the second best heel in wrestling history.
The second best heel (maybe the best when all is said and done) is Vince McMahon. McMahon's character, as amazing as it was and still is, is not all that original because he essentially copied the character Eric Bischoff created for himself a year earlier in WCW. McMahon was the WWE version of Eric Bischoff. And instead of killing the character like Bischoff did in 1999 (BIG MISTAKE), Vince ran with it to this day because he realized he was after Hogan the greatest heel in the business and that he could draw HUGE money by hanging on to the character. He knew he could never create another Hulk Hogan but he knew he could create a heel character almost as big that could combat Hogan's. Vince has always been competitive with Hogan, trying to paint himself as the master of wrestling and destroy Hogan's legacy along with anyone who challenged him (Randy Savage, Bret Hart etc). And I'll give Vince credit, he's done an amazing job with the WWE over the years, with his Mr. McMahon character, and stomping out legacies. But Hogan made WWE for him and WCW for Bischoff and will make TNA for Dixie even as a 60 year old gimp. Vince will never be able to stamp out Hogan's legacy as the man who made wrestling. Vince has always been second to Hulk Hogan and with a heel Hogan in the wrestling world it's only going to be a matter of time before Vince and his boy Triple H are second best and possibly out of business.
And Triple H hasn't been all that good a heel since 2000/2001. He just looks like such a great heel because there aren't many good heels anymore. Michaels in his prime was twice the heel Triple H EVER was.