I started watching wrestling in '94 and I was pretty much stuck on the status quo as far as cheering for faces and booing the heels. So its fairly easy for me to remember the first heel I cheered for and that was the Rock circa late '98 to mid '99.
I mean come on, Corporate Rock was so entertaining that it was impossible not to cheer him. This was when he was "spinning nursery rhymes", as Austin would say. You know: Know your role and shut your mouth, lay the smackdown, drag your candy ass up Know Your Role BLVD, hang that right onto Jabroni DR, and proceed to checking your candy ass into the Smackdown Hotel. Not to mention this is when he started saying and the Rock means, the Rock says, shine it up real nice turn that sum bitch side ways, and this is not sing a long with the Rock. He cut some classic promos during this time. My favorite was: "The Rock has a nursery rhyme for you Stone Cold and it goes like this, Mary had a little lamb. Well I'll tell you what piss on the lamb, piss on Mary, and piss on you because the Rock's gonna out there tonight a do what he does best and that's lay the smackdown on your rudy poo candy(doesn't finish because the fans sing a long). Hey don't do it because the Rock guaran-damn-tees to prove to you, you, this goof holding the camera, this chick gawking at the Rock, he's gonna prove to the millions and millions of the Rock's fans exactly why the Rock is the great one, exactly why the Rock is the chosen one, and exactly why beyond a shadow of a doubt the Rock is the best damn WWF Champ there ever was. If you smell(interrupted by the fans again). Uh huh Philly this ain't sing a long with the champ. If you smell la la la la la what the Rock....... is......... cooking!" Best damn promo ever. Look it up on YouTube. Its called why the Rock is the great one.