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When I was a child we lived near the NBC studio in Brooklyn. We saw and (in those days) spoke to them all. The list of celebrities is too long to even mention. Just being in Manhattan you see a ton of movers and shakers but as you get older you realize that they are just people like the rest of us.
Recently I purchased a quilt in a quilt shop in Pennsylvania Dutch country. The lady in the store complimented my taste and informed me that an almost exact quilt had been purchased days before by Johnny Mathis. She told me that I could tell that fact to everyone when I showed off the quilt. I informed her that she could tell all her customers that I bought the quilt and Mathis bought one just like it. This is how I really feel now. I sometimes feel sorry for the people in the spotlight. How awful it must be to not be anonymous and to have the entire world watching every move you make.
Only 2 weeks ago I saw Norman Reedus (Daryl from the Walking Dead) sitting outside Balthazar. I consider him the most famous celebrity I've come across because I'm a huge fan of the show. Prior to that I saw Cameron Diaz by SoHo last year.
Richard Burton walked past me at JFK airport a few years before he died. I've seen two presidents in motorcades, George H.W. Bush and Bill Clinton. I saw Mario Cuomo in the 1990s walking to work at his law firm. I saw Ed Koch in the parking lot at Shea Stadium after game 7 in 1986.
Not on the street, per se. But in restaurants, in theaters, etc.
The single most famous person - not counting the time I shook hands with Bill Clinton, because that wasn't quite so random; it was in conjunction with volunteering - was probably Katharine Hepburn. I actually had something I would have said to her, because we have a mutual acquaintance. But it was in a doctor's office, and I felt that would be unbearably intrusive.
I haven't lived in Manhattan since the early 90's, so my response is dated. I was terrible at recognizing people, but a lot of my friends were into celebrities and would point people out.
Only a few stand out:
Tom Selleck in an uptown bar. I had never really thought of him as good-looking but when I saw him in person I was really impressed..he had this almost glow about him.
Stephen Baldwin (who was amused I didn't recognize him) at Starbucks
the late Princess Diana (outside Christie's Auction House when she was auctioning her dresses)
the late Gerald Ford (he was in the crowd at a B'way show)
Bill O'Reilly (near Rockefeller Ctr, he had this intense crazy look, he scared me!)
Donald Trump (outside Trump Tower, prancing around as if he owned Manhattan)
Michelle Pfeiffer (Soho, I didn't recognize her but my friend did and even said hello)
John Williams and Steven Speilberg (Tanglewood)
Lyle Lovett (outside the Sheraton at 53rd & 7th Avenue)
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