Jeopardy! contestants are some pretty smart individuals. However, I notice that they struggle with pop culture categories more often than not. That was the case in the recent Final Jeopardy!, as two of the three contestants thought Diana Ross was 95 years old.
As Ken Jennings said, Tony Bennett and Diana Ross are way beyond the contestants' time, and Diana might not be a spring chicken anymore, but come on now! I just feel bad for the guy who went all in with the answer and lost his streak as returning champ!