I've been watching King of the Hill for years and I always wondered how Hank is not with it despite how cool he was based on flashbacks of his late teen years. And then it hit me; Hank Hill peaked in high school! I know this is probably obvious to almost everyone, but I feel like such an idiot for not realizing it immediately ?
All of them peaked in high school. Especially Bill. I think when Hank broke his ankle in that football game after showing off, he decided to be much more low-key for fear that something bad will happen to him if he brags about something (as pointed out in the episode about the Olympic torch).
Looking at Hank and how awkward he can be it would've been difficult to believe he'd ever been a popular jock in high school, but the reasons he acts that way are stated above (i.e. the ankle snapping incident) and because of Cotton's harse parenting towards him, the same goes with Bill in his present state as a fat, balding, pathetic sad sack.
The only one of them that is still believable that he was a jock in his present state is Boomhauer.
There was one episode where Dale tells a story about when they were on the team bus traveling home from a football game and that everyone except for Hank mooned the opposing team's bus. Hank held up a sign congratulating the other team on a good game. Hank was never as popular in high school as he likes to claim.
I agree wholeheartedly. Hank was never a cool guy. He might have excelled at football but he was always a square. This was obviously a result of the harsh way he was raised by Cotton.
If he were popular, he certainly probably could have gotten somebody better than Peggy. Even with her, a flashback shows how completely awkward he was around her, still calling her "Miss Platter" after dating like three months.
On the other hand that girl that gave him mono was more attractive, but, like she said, "It could've been anybody."
There were two past flashbacks that made him seem more popular, however. One is when they all went out carousing to send Bill off to the Army. Then there was the one where Hank was making fun of "fat" people, and another where he, Dale, and Bill ended up totaling Boomhauser's Mustang.
Hank may have been a jock, but he was never a cool kid. He wasn't an outcast by any means, but I can't picture him being part of the popular crowd, either. He had his little circle of friends (Dale, Bill and Boomhauer) and was content with that.