There are two basic forms to this kind of discussion. One is the nominally serious kind, popular among comic-book fans, where you try to argue who would win based on an accurate assessment of each character's abilities and weaknesses. This is the kind of thing that leads to discussions of whether Kirk would beat Picard. (The answer, as I hope most of you know, is Kirk, 'cause Picard's a wuss who believes in that Prime Directive nonsense, while Kirk is a good old-fashioned macho imperialist who believes in imposing his values, and his libido, wherever he goes.) The other type of discussion is the silly kind, where you pick pop-culture characters you grew up with and dream up outlandish reasons why one would kick the posterior of the other.
The best example of the silly approach was WWWF Grudge Match, created in 1996 by two graduate students at Cornell University, Brian Wright and Steve Levine. They started with the burning question of who would win in a fight between Gary Coleman and Webster, and they went on from there. No serious attempts were made to argue the strengths and weaknesses, thankfully; it was just an excuse for riffing on the trivial things we remembered about these characters, like so, from Lucky the Leprechaun vs. the Trix Rabbit:
BRIAN: I can't believe I ever lose to this guy.
I don't think you've really looked at kid's cereal in quite some time, Steve. ALL kid's cereals are the same: cardboard-based delivery systems used to administer high quantities of sucrose to children. Sure, they may change the coloring or the flavoring a bit, but they're all essentially identical. So, yes, Trix are like Froot Loops (tm) and Fruity Pebbles (tm), but they are also like Cap'n Crunch (tm), Frosted Flakes (tm), Sugar Smacks (tm), and Kaboom (tm). And what does that mean? ABSOLUTELY NOTHING! If I wanted, I could go on my own tangent about how Tony the Tiger (tm), Diggum (tm), Toucan Sam (tm) ad nauseum could parallel Trix and/or Lucky in order to try to show why Lucky would succeed, but I don't want to waste our readers' valuable time with irrelevant and highly subjective side arguments. Besides, the last thing you want to do is bring the Flintstones universe into this discussion. That would then leave me no choice but to mention how Lucky could call upon his cousin, The Great Gazoo, to law down some covering fire on Trix' sorry butt.
And when's the last time you really looked at the Energizer Bunny (tm)? What does the EB do? Again, ABSOLUTELY NOTHING! If the scenario had Trix carrying the cereal with someone else trying to get it from him, then being related to EB could be an asset . One could imagine the Trix Rabbit carrying the cereal whilst cereal icons from all over the commercial world have their diabolical plans foiled as they look to see their failing Device of Destruction (tm) is powered by the ever unreliable SuperVolt (t m) battery. But that isn't the case here. Trix actually has to do something, namely get the cereal from Lucky. In that same situation, EB would just go around in circles and beat his little drum. Hardly an ally.
And just to clarify, yes I do think Lucky is in fact Lucky. You don't get named Lucky, The Nose, or Scarface without it being applicable. And I think you know what I'm getting at here. Two words, Steve: Mob ties.
The site has gone through several different incarnations, and now does only one match a month (the current one is "Pac-Man vs. the Tribbles"). Its best years were in the late '90s, the golden age of the net-geek discussion; it's another product of the time when the Internet had its own subculture, rather than just being a part of the broader culture. But the old matches are great fun to read; my favorites include "Captain Kangaroo vs. Mr. Rogers," "English Soccer Hooligans vs. the French Army," "John McClane vs. the Death Star," and "Scooby-Doo vs. the X-Files." The fun of the Grudge Match was that unlike a lot of pop-culture spoofs that are really just lame borrowings (you know, how a show will make a reference to some '80s show or commercial and expect us to laugh at the reference, even though nothing funny has happened), this was simultaneously a tribute to cheesy pop culture and an implied criticism of it -- as in, wouldn't a couple of terrible shows like Diff'rent Strokes and Webster have been better with some brass knuckles added. And it provided the opportunity for commentators and readers to take their useless pop-culture knowledge and apply it in creative, and often twisted, ways.