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Most of us will never have the opportunity to play against a World Champion, not individually and probably not even in a simul. If you're famous or rich, your chances improve remarkably. I guess that's one of the perks of success.
Garry Kasparov is generally considered if not the strongest, then one of the strongest, players in the game's history. He has certainly done as much or more for the promotion of chess than any World Champion.
Kasparov has played some games against amateur celebrities it would seem mostly to highlight chess, but perhaps also because Garry likes associating with these people. Whatever the reason or reasons, we are left with the results of these one-sided battles.
 David Letterman on the phone with Garry Kasparov
Between October 20 and December 1, 1989 Kasparov played the American talk show host, David Lettermen a game by phone. A pieced-together transcript of their conversations can be read on this member's blog.
Kasparov vs. Woody Harrelson
"As The Crowd Cheers, Actor Shows Killer Streak"
October 17, 1999 By Larry Evans
. . .Kasparov arranged a Eurotel Trophy match in Prague pitting Shirov against Judith Polgar, the highest rated woman in history. . . .
One of the spectators was actor Woody Harrelson, who was on his way back from a film festival in Karlsbad. He stole the show by playing a skittles game with Kasparov to prove he is also a "natural born killer" at chess.
The second game was played with a lot of banter as Woody tried the scholar's mate. Woody, who got tips from two grandmasters all along, jokingly asked the crowd to please refrain from giving his opponent any advice. In the end, Kasparov conceded a draw as Woody's entourage dragged him to his plane back to America.
In "Dutch Treat" June 17, 2000, Hans Ree added in passing:
Draw agreed. It has to be admitted that Harrison was helped by the grandmasters who were in Prague at the occasion of the match between Shirov and Judit Polgar, but that does not alter the fact that the so-called beginner's move 2. Qh5 makes quite a decent impression here.
On March 15, 2000 as a publicity stunt to inaugurate his new web site, Kasparov played the tennis icon, Boris Becker to a game of internet chess.
A aricle quoting CNN read:
NEW YORK -- On Tuesday, one of the chess's best players ever launched a Web site dedicated to the game. Garry Kasparov's site contains general fare such as interviews, advice and match-making services, but it will also serve as a worldwide stadium for some top matches. If fans could get past the predictable crush and access the site, they got a treat on Wednesday afternoon. The site showcased a live chess game between Kasparov and Boris Becker, the German tennis star. Becker played from CNN's studios in Berlin.
Kasparov was playing from the CNN studio in NYC.
Gordon Sumner (Sting) vs. Garry Kasparov
MTV
June 30, 2000
"Sting Battles Chess King Kasparov In Times Square"
by Kara Manning
Thank goodness Sting's ego isn't too fragile when it comes to his chess game.
The singer and four of his bandmates took time out from their North American tour to play World Chess Champion Garry Kasparov for a game at the ABC-TV studios in New York's Times Square on Thursday afternoon.
A very cool Kasparov, likely not quaking in his boots, played Sting, guitarist Dominic Miller, keyboardist Jason Rebello, trumpet player Chris Botti, and vocalist Russ Irwin simultaneously and defeated them all within 50 minutes. Sting, a proclaimed chess aficionado and an old friend of Kasparov, lasted the longest, finally losing to the master in 45 moves. The fastest to fall was Miller, whom Kasparov squashed in a mere nine moves.
The event, which marked the end of the World School Chess Championships, raised funds for Sting's Rainforest Foundation via a corporate sponsor. The match was also televised on the Times Square Jumbotron video screen, leading to some very baffled skyward stares from the glassy-eyed tourists and screaming "Total Request Live" fans milling about 44th Street.
At the conclusion of the match, Sting helped hand out trophies to the finalists of Kasparov's own pet project, the World School Chess Championships, an international Internet tournament on kasparovchess.com that began March 1 and included more than 600 schools worldwide. The finals, which encompassed six different schools from England, Israel, Norway, Australia, New York, and Indiana, culminated on Thursday. Israel's Elkana Elementary School won its division, New York's Hunter College School won the junior high division, and Norway's Norges Toppidrettsgymnas won the high school division.
Prior to the match, Sting spoke of how he transferred his passion for the game to his own motley crew of kids.
"I have six children, and I've always encouraged all of them to play chess," Sting said. "I think it helps to sort the brain out. You do this first and then you'll do that and you'll do that. It's a very good discipline to learn for a young mind -- hasn't helped me much," he joked, "but my children... I think it's good."
Kasparov chuckled at Sting's self-deprecating comment, and when he was asked what he thought of the performer's game, he (quite diplomatically) called Sting "a dedicated player," sending them both into laughter.
Sting and his band continue their three-month U.S. tour on Saturday in Wantagh, New York and in Saratoga Springs, New York on Sunday.
Proceeds from the event went to the "Rainforest" environmental-preservation group.
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