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For NYC, these are folks (in no particular order) who I think the typcial man on the street somewhere outside of the city would automatically think r"New York" when their names are mentioned
Derek Jeter (maybe some other dead or retired athletes too, like Babe Ruth, Joe Namath, or Mickey Mantle)
Rudy Guiliani (after 9/11 he WAS New York)
Jay Z (or other famous rapper.producer maybe Sean, Russel Simmons, Fitty Cent)
Spike Lee
Woody Allen
Martin Scorcese
Rev. Al Sharpton (controversial, but with a TV show on MSNBC eveybody knows him)
J-Lo (the Bronx represents)
Barbara Streisand (Brooklyn represents--and with staying power too)
Rupert Murdoch
(gotta have a media/biz face for NY, but frankly most folks outside here wouldn't recognize the name of any of the most powerful biz people here)
Derek Jeter? Over Joe DiMaggio, Babe Ruth, Roger Maris or Mickey Mantle?
Boss Tweed
Donald Trump
Ted Williams
James "Whitey" Bulger
John F. Kennedy
Ben Affleck
Matt Damon
Paul Revere
Samuel Adams
Edward Kennedy
Thomas Tip O'Neil
The Pixies/Aerosmith
There are a large number of people who were born in Boston, but not all are known to be from here. Damon and Affleck have all either starred in, or directed movies set in the city.
Derek Jeter? Over Joe DiMaggio, Babe Ruth, Roger Maris or Mickey Mantle?
Boss Tweed
Donald Trump
I was tryng to stick to living people.
But yeah, The Donald certainly represents the New York business wheeler/dealer type to a lot of folks and he's probably a better choice for that type.
But Boss Tweed, DiMaggio, Ruth, Mantle--all good choices, depending on what generation you're from, but all dead too. Maybe Jeter's Ford commercials aren't national, but they're all over the place here, plus the Captain of the NY Yankees is still pretty well known outside the city.
1) Stephen Colbert
2) Pat Conroy
3) Darius Rucker (Hootie and the Blowfish lead singer)
4) Joe Riley (has been Mayor since 1975)
5) Roddy White (Pro Bowl WR for Atlanta Falcons)
6) DuBose Heyward (man who helped write Porgy & Bess)
7) Bill Murray (very well-known actor who owns part of minor-league baseball team)
8) AJ Green (WR for the Bengals)
9) Thomas Gibson (star with Jenna Elfman on Dharma & Greg)
10) Art Shell (first African-American NFL coach in modern era)
Michael Dell
Willie Nelson
Sandra Bullock
Matthew McConaughey
Lance Armstrong
Lyndon B Johnson
Lady Bird Johnson
Stevie Ray Vaughn
Clifford Antone
Nolan Ryan (lives in Georgetown)
The Fabulous Thunderbirds
Tom Kite
for the Chi? i could say the obviuos like mj oprah etc. or kanye west or twista, but al capone is well known for sure. id say some other nuts like john wayne gacy, john dillinger n bugs moran, Karl Marx... howabout Ray Kroc? - (mcdonalds hq in oakbrook) and um Hillary Clinton and Harrison Ford went to Maine North? ernest hemingway? architect Frank Lloyd Wright? ,Smashing pumpkins, Bill Murrray n john/jim Belushi? jennifer hudson, jenny mccarthy, bernie mac...
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