In the spirit of all those “who would win in a fight between…” threads - how about, what would be the unfairest match-up you can imagine?
e.g. Stephen Hawking vs. a High School physics exam.
George W. Bush vs. Eminem in a free-style “battle”.
Holyfield vs. Kasparov - 10 rounds in a ring.
Manhattan the moderator vs. a newbie “l33t” poster asking the “-gry” question in GQ…
Redneck homophobe vs. Esprix in the Pit.
Me vs. the rest of the beer.
Actually, that one’s about done.
Arnold Schwartzenegger vs. Woody Allen
The thought came to me when I read someone discussing likely actor for the part of Quail in Philip K. Dick’s story “We can Remember it for you Wholesale” vs. the actor who played Quaid (they changed the name because of our VP ) in the movie Total Recall. A more unlikely substitution is hard to imagine. But it would make a great uneven match.
I can just see the verbal sparring between the monosyllabic giant and the neurotic intellectual. The taunting could get ugly.
How 'bout James Randi vs. Uri Geller? But then, that one’s been done already.
Dick Cheney vs. high-voltage conductors
Howie Mandel vs. Leo Buscaglia
And the most unfair matchup of all:
George W. Bush vs. the captain of your local 5th grade debating team
USA vs Iraq
Comming soon (unfortunately)
Bippy
From this page, South Africa v Canada at the Cricket World Cup. By way of reference, Canada lost to a middling South African province (i.e., one of 11 South African state teams) by over 200 runs two days ago. Records will undoubtedly fall.
Jack Chick versus anyone with two brain cells.
Any other country vs England (at any sport invented in England).
Kraag the Defiler. Son of Tragg the Six-Armed, heir to the House of Kragarr and weilder of the mighty Sword of Zagarr.
vs.
Earnest P. Schotts. Son of Milton S. Schotts. Certified Public Accountant and resident of 324 Meadowbrook Lane, Spooner Wisconsin.
Lets get it on!
Inky, I totally thought of Herbert Kornfeld from the Onion when I read your post. I think Herbert could take out Kraag. 
The Rock vs. Leonardo DiCaprio- in a cage match.
You and me against the world…
[sub]Oh, how I hate that song… yet, I had to post[/sub]
From way back in Junior High:
The 12 year old girl down the block vs. me.
I never want to take a beating like that again in my life.
** Inky ** I used to live in Spooner, WI and they have some pretty tough accountants up their. (A tough account isn’t much or course, but…
Tupac vs the World.
Looks like the world won.
Up their what? And why would anyone want a tough accountant up their anything?
C-3P0 against the ED-209.
Cecil v. William Poundstone.
The Hulk vs. Mr. Furious.
The Shoveler: C’mon, you’re really strong! You lifted a city bus once!
Mr. Furious: Well, actually, it was more of a shove than a lift, and the bus driver kind of helped by having his foot on the gas pedal…
Fear the Letta Openah of Death!
Cthulhu vs Britney Spears
Jesus Christ vs Phelps
George W vs a pretzel
(obligatory Monty Python ref): The government Minister For Housing vs. This small patch of brown liquid.