Has there been a more successful band of "dorks" than Toto?

HALF of them did.

Donald Fagen is weird looking, even slightly menacing, but I don’t think you can credibly accuse him of not looking cool.

Walter Becker did, indeed, look like the polar opposite of cool, from the first years of Dan all the way to the end.

My work here is done.

The Decemberists look like dorks. Pretty sure XTC are dorks.

While we’re at it, British prog rock Stackridge (Davis and Warren later founded The Korgis) looked dorky too.

Thank you, thank you, thank you for this.

I’m not sure if they count since they’re well known mostly because of their awfulness and the story behind them, but The Shaggs.

Ding! Ding! Ding!

On the less successful side, I cannot think of a dorkier-looking band then The Pastels, the lead singer of which often wears an actual anorak!

Hombres G were pretty dorky, dorky enough to be surprised by encountering Crocodile Girls (their name for groupies, and also one of their songs). They also sold enough records on both sides of the Atlantic to be called “the Spanish Beatles”. Their lyrics often were of the “and this is while being sober” variety.

I remember reading in a music rag in the early 80s about Elvis Costello the "hippest computer geek you’ll ever see "

Yeah, but he doesn’t count, because he was *trying *to look dorky.

The word you are looking for is “adorkable”

…will peg when you watch the ‘Rock Me Tonight’ video by Billy Squier. Hilariously horribly bad. Makes you wonder WTF somebody was thinking.

The video in question. So dorky that many people (including Squier himself) see it as having directly contributed to Squier’s career stalling out. I’m not sure if that’s really true, but a video in which you’re not-intentionally-ironically dressed like (and acting like) a teenaged girl lip-syncing to “Flashdance” in your bedroom wasn’t likely to help one’s image as a male, adult rock star.

I encourage every Doper out there to give this video a watch. It is laugh-out-loud funny!
And you’re right, it killed his career.
I’d kinda feel bad for Billy if it wasn’t so fucking funny.

Are you forgetting 50% of Cheap Trick during their peak?

I never liked his music, but I felt sorry for him after watching that. What could he and the producer have been thinking?