I gave Toad the Wet Sprocket a shot, even though the Python reference was obscure even by my standards. But some bands just can’t be taken be seriously. Something about the name conveys arrogance or perhaps desperation. Or perhaps they just sound like some Gen Y snark dealers.
I’ll add to this list as memory kicks in. The list is …
- G. Love & Special Sauce (could you try a little harder to be hip)
- Death Cab for Cutie
Mostly Modern Media 
* And You Shall Know Us By The Trail of Dead
* Squirrel Nut Zippers
* The Soundtrack of Our Lives
I’m sure there will be many others …
One weirdly named band that I did like a lot was Camper van Beethoven, and more specifically I liked their tendency to name their albums with 4-word nonsensical phrases, such as “Telephone Free Landslide Victory” and “Vampire Can Mating Oven” …
P-man
You sort of bring up an interesting point here. When are bands being fun or clever, and when are they just being pretentious? It’s subjective, I think.
The trick for any band name is to sound timeless, and there’s a higher degree of difficulty there when you choose a pop culture reference. Like “Toad the Wet Sprocket” or the Toronto Raptors, you’re bound to sound dated. (Though “Duran Duran” did okay…)
Personally, I’ll take pretentious band names that smack of desperation just for the variety. There are no more good band names that follow the format “The [Plural Word]”.