I wanted to be photographed by Yousuf Karsh.
I didn't manage to get that done.
I also wanted to be, and was, photographed by Herb Weil back in the mid '80s.
When I lived in Coronado, Herb was recommended to me by my neighbor, Doug Baldof.
Doug was a woman. She acted in several TV commercials. She had had her actress portfolio shots done by Herb based on someone else's recommendation.
Herb was in LA and Herb shot a lot of aspiring actors/actresses (John Travolta, Sissy Spacek, Mark Hamill, Linda Carter - to name a few).
I wasn't an aspiring actor, but Doug convinced me it wouldn't hurt to test the waters.
I drove up to LA, right to his house.
We hopped in his car after I transferred my climbing (rock and ice) gear, frisbee, golf clubs, and skateboard I had brought to use as props and hit locations he used in and around Hollywood for about 3 hours.
I learned a boatload about on-location portrait shooting by being the subject, and got a few print media modeling gigs through the same San Diego agency Doug was with.
FWIW - Herb cost me $150 (about $400 in today's $$$s) plus prints.