KITT would definitely win, because he’s a secular humanist.
Herbie is funnier and girls like him, therefore plotwise he has a distinct advantage. Funny guys that get the chicks always win.
KITT is a bit of a nerd, (it was always The Hoff that got the girls) and is therefore more likely to end up with broken glasses, in unattractive underwear and being laughed at by the same chicks. Cos that’s all nerds deserve.
On paper, KITT would walk all over Herbie, which is why Herbie can’t lose; he’s the underdog and because of that, he’ll always overcome the competition.
Lindsay Lohan in a racing jumpsuit vs. David Hasselhoff in a leather jacket.
The winner is clear.
:dubious: I like nerds. The guys that always get chased by girls don’t appreciate it.
Sure, but he wouldn’t do that, because he’s a goody-goody two-shoes Autobot.
Now, Motormaster, he’d gladly smash everyone else off the road, and stomp them into the scrapyard for extra malice.
So what’s the deal with Herbie? Is is Possessed? Computerized like KITT? Is it ever explained?
I believe he was the reincarnation of somebody, or had a soul fly in his exhaust pipe or something like that. I can’t remember exactly. It’s been a long time.
I say Herbie wins. He has actual consciousness as opposed to AI and can be sneaky in ways that KITT can’t (literally) imagine. I mean, he can talk to other cars! He can persuade any other VW or other compact car to come to his aid and block KITT’s progress.
Goddammit. That’s the only reason I was going to open this thread!
Big deal, I can talk to cars too.
The question is, do the cars respond? 
They would, if they thought you had anything interesting to say.
I vote for Kitt. He has pursuit mode which allows him to accelerate to 200 mph in about 10 seconds. He had turbo boost which allowed him to leap over obstacles like gorges. Plus, he was indestructible to anything short of a missile, and for some reason missiles always missed him. Oh, and don’t forget the LED’s in his grill. Herbie never stood a chance. Of course this is all assuming Speed and his Mach 5 don’t show up.