My family likes Water Boy and we watch it often.
At one point, Coach Klein drops his pants to show Bobby his tattoo of Roy Orbison.

My wife is a decade younger than I am and told me the last time we watched it (a few weeks ago) the she wouldn't know Roy Orbison if she heard him.
I think I probably mentioned Pretty Woman before suddenly saying, "Well, I'm sure you've heard the Travelling Willburys, he was a part of that when he was older."

Nope.

That didn't help either.