Jeez, how the hell do you begin wiht this one.
In Ring Ability.
Hogan. The big knock on Hogan, he can't wrestle. Well in the WWE 80's, he edidn't have to. The program was changed and redirected towards children almost exclusively. No Blood, no sex, no violence, taht was the WWF of the 80's. This is what people today don't understand when they compare Cena to Hogan, totally different era and mindset of people. What Hogan lacks in skill in the ring, he more then made up for with crowd control. Hogan knew exactly how to read the crowd and perform towards that reaction.
Flair: The NWA/WCW of the 80's was the real wrestling program at the time. Flair without a doubt, is one of the best in ring technicians of all time. Stamina was insane. Flair could make people in one match. Hogan couldn't do that. Flair never seemed to have a real problem with putting over the younger guy. Hogan it seems only did that once, with the Warrior. Flairs technical skills were just amazing. I give the edge in this category to Flair.
Booking Value:
Hogan: For the better part of 15 years, Hogan owned the business. He was the main event of 7 of the first 9 Wrestlemanias, plus two huge marquee matches later against the Rock and McMahon. Hulk Hogan for better or worse, is the face of professional wrestling.
Ric Flair: While probably a huge draw to wrestling marks, Flair never had that mainstream achievment like the Hulkster. Flair couldn't even headline WM 8 in a championship match with Hogan on the card. Hogan takes this.
Legacy.
Hogan: Hogan simply doesn't get the business in this aspect. Hogan has lived off of his legacy for the better part of a decade now. Hogan seems like a very different man since Bash at the Beach 2000 with Russo. I think Russo's words got to him, and he will never admit it. Hogan deserved his spot on the top while in WWE inthe 80's and WCW in the 90's, like it or not. Hogan was the reason most people watched, as much as wrestlers want to bitch about it. The WCW guys have no arguement with Hogan. I'm talking the Benoits and Jerichos, which I love. They didn't deserve to get Hogan's spot, because people wanted to see Hogan, plain and simple.
This attitude Hogan has now with wanting to make the most at WM 23, is just bullshit. Ya, Hogan outdraws anyone in the current WWE, and that's a safe and fair assesment, but that's not the point. Hogan has never given back to the company that has made him who he was. He won't job without a power struggle, ask HBK. His ego won't let him deal with his age.
Flair: Flair gets it. People bitch about a 58 year old Flair wrestling every week. I say, why not. Flair is a big name, and if he helps to get someone over, then use his name. The problem is, and i'll get shit on for it, the younger guys in the WWE can't scratch Ric Flairs nutsack in the ring. I've said it once, I'll say it again, 58 year old Flair is more entertaining to watch in the ring then 75% of the WWE roster. Flair is willing to do the JOB, so he can stay as long as he likes. Flair takes this category.
So, imo, Flair means more to the business from a wrestling standpoint, but in entertainment, Hogan takes the cake. The main legacy will be of guys that come that have molded themselves in their images. Flair gives you two big guns right away with Triple H and HBK, who absolutley model themselves after the Nature Boy, whereas Hulk Hogan has left us with John Cena...