Zapp is arrogant and clueless but he’s not cool. Confidence is part of being cool, but he goes to pieces when Leela calls his bluff. Kiff couldn’t be any less cool.
For that matter, most of Bill’s henchpeople/former henchpeople are cooler than Bill himself.
The manga drags something horrible, too. Hueco Mundo has pretty much become the new Namek.
I don’t even know these people, but your truth stands on the names alone.
Right. Was a blunder.
He is ridiculously overconfident in other matters, though. And he has a sort of style.
I don’t know what you’re smoking but Zapp is Kirk cranked to 11, he’s the epitome of confident. Who else would say, “If it’s one thing I don’t need, it’s your “I-don’t-think-that’s-wise” attitude!”.
Montrose; Archibald Cunningham, played by Tim Roth in “Rob Roy” (1995).
Yeah, but it’s all an act. Whenever he’s in true danger, he falls to pieces. So, he may seem cool, but he’s a total fraud. This is what makes Kiff such an empathetic character, instead of just plain pathetic.
Yes, yes, we all love Kif, but he isn’t cool.
Zapp is cool despite the fact that he is a fraud! He doesn’t lose cool points for wearing a girdle, he gains cool points for speaking of it as if it’s nothing to be ashamed of, since it is on his own amazing physique! He doesn’t lose cool points for being the dummy with no pants, he gains them for not even considering for a moment that he, the great Zapp Brannigan would have to wear pants like the rest of us. He oozes cool man. I can’t believe you can’t see it.
Eh. I may be overstating just to be contrary. He wasn’t exactly oozing cool. But he was cool. In his way.
If you love him so much, why don’t you marry him? 
Well whatever he is he’s certainly cooler than Kif. Kif is the epitome of pathetic loser. Sympathetic? Maybe. But I’m straining to think of even a single “cool” moment or line he has throughout the entire series.
Wormtongue was cooler than Saruman.
Preahps you’ve forgotten that he once retained Dazzler. 
Sleeping with Amy? Of course, even Fry gets to do that… She’s a total space-slut.
New versions make Shredder the main villain because Shredder is an actual character from the original comics, unlike Krang, who was just loosely based on the TCRI aliens/utroms in that they were brains walking around in the stomachs of robot bodies. They were mostly benevolent, or maybe neutral, though, not evil.
When licensing the new cartoon, Peter Laird didn’t want characters like Krang, Rocksteady, or Bebop to be used because they weren’t actual TMNT characters, they were just made up for the cartoon. This also is why Baxter Stockman doesn’t turn into a fly and April isn’t a reporter in newer versions.
Pffft. The TV show was probably way better than the original comics anyway. Krang was awesome.
The Toad – I mean the version from the 1960s X-Men comics, not the movies – was a sniveling sycophant to Magneto, but still way cooler. The original-version comic-book Magneto was never cool, just constantly angry, and without any of the tragic depth of Doctor Doom. No lackey ever out-cooled Doom.
That’s nothing. In one silly comic, he had Aunt May as a Herald; “Golden Oldie”. She fed him pastries.
I saw an internet rumour before Ep III, that General Grevious was going to be a rebuilt cyborg version of Darth Maul (based on the fact he had similar eyes). That would’ve been much cooler than what Lucas came up with (not particularly difficult).
Dick Cheney was sort of cooler than George Bush. Also not particularly difficult.
Those are fighting words, on a level somewhere between “your momma wears combat boots” and “we’re going to show a depiction of Mohammed”.