In DX, I never really saw him as a Heel or overall. He just didnt really play the bad guy well. The Did though. As Popular as he was, he always knew to play a real unlikable guy well and I actually give him a lot of credit for that.
Without strife, your victory has no meaning.
Without strife, you do not advance.
Without strife, there is only stagnation.

^ Yes. His reign on top during the Attitude Era was my favorite of his runs he had as a heel.

My Favourite part was when he had Steph at his side. He’d wear Denim Vests and Flat Hats.
I did also like the Hunter Hearst Hempsley era.
Without strife, your victory has no meaning.
Without strife, you do not advance.
Without strife, there is only stagnation.

He was probably at his most popular as a solo wrestler in 2002. He was very fresh coming off of his return, and he never wrestled as a babyface main eventer prior to then. He had a real hunger to get back in the ring evidently, and he made his presence known for sure. With this said, I wasn't thrilled about his heel turn in the Summer since he was already long established as a heel, and the company needed a big fan favorite after losing Stone Cold, The Rock, and Hulk Hogan all in a short amount of time. Shawn Michaels was a reliable fan favorite but I wouldn't have minded seeing him make his return as a heel against a babyface Triple H back then, as much as I could understand WWE wanting Shawn Michaels to have a positive crowd reaction for his comeback.