Kim vs Erin
(First, let me say that looking for images of Kim Possible and Erin Esurance has been, well, enlightening. It's like the Tijuana Bibles all over again, with Flash animation.)
What happens when two cartoon adventurers clash, even though they're not likely to ever meet each other in reel life? A red-haired jailbait cheerleader/world-famous super-hero and a pink-haired spy/car insurance agent, going at it? I think we're all in trouble, to be honest, this could get ugly.At first, I would say Erin has all the advantages. She's what, ten years older than Kim? Even if she started a bit later in the adventurer game, that still gives her years of experience and training. She also seems a bit taller and heavier, although both characters have waists that seem like a strand of cartilage holding their torsos together. Erin polishes off her opponents in the few seconds allowed her during a commercial, while Kim takes the twenty-odd minutes of an episode to do the same.Erin usually operates alone or with the minimal help of that nondescript guy with the sideburns. Kim relies on her team of Ron, Rufus and Wade. Even when they're getting in the way more than helping, their morale boost is important to her. I can see Kim losing some of her enthusiasm and confidence if she had to work completely unassisted. So it seems likely that in a few minutes, Erin would have Kim unconscious and tied up (at which point, the slash writers would unleash their feverish imaginations).
Even with all the advantages, I think Erin would lose the deathmatch. A little research about by Kim would show Erin's psychological weak spot -- her obsessive, psychotic desire to sell insurance. As they're trading kicks and punches, Kim suddenly says, "My dad's going to buy me a car for senior year. You think I should go to Geico for insurance?" And Erin drops her guard, pulls out a wad of policy forms and goes into her spiel. "See, it's so easy. Quote, print...THUMP!" as Kim decks her with a sucker punch.
And an unrelated comics scans, as to my shame I have not posted here in so long that I forgot...