When I think old school, I think Frank, Dean, and Sammy, cats like that.
If I was really on my game (back in the day), I probably could have photographed all of those guys, but now they're gone. It wouldn't have been anything like their Phil Stern heydays, but still something that could have happened. Maybe Frank at the White House or something. Just to say you did it, that you shook Frank's hand, as they say.
I guess there's still a chance to do Don Rickles, which would be cool.
Blind item alert:
I was at a fundraiser at Bob Hope's house (with then VP Bush), and another photographer (A+ list with B list name recognition) walked up to Rickles and started talking to him about a book project he was working on, Rickles cut him off and said, "Are you a cop? You look like a f#cking cop. I don't talk to cops."
Anyway, when you think about cultural icons that you need to photograph, you usually don't think about the people that it's still possible to do. I guess if you did, you'd have to start working towards achieving that goal.
Prince is one of those people that I should photograph. I saw him (only once) in concert, and spent the whole time thinking about all the photographs I could be making.
Marlon Brando, shouldda maybe couldda, but too late.
I wonder who else?