Mike Love and pretty much everyone else from the Beach Boys.
Kim Deal (the epitome of cool rock chick) vs Frank Black (great musician, but not … cool)
Bjork vs Einar
Yes, but the Tambourine Rule is in effect. Nobody can be cool while playing the tambourine. Try to picture Steve McQueen playing the tambourine. It can’t be done, the cognitive dissonance is too strong.
I was going to nominate Valerie Brown over Melody Valentine for this thread, possibly the sole exception to the Tambourine Rule.
Winner.
Unfortunately, I have to disagree with Sitnam’s observations of Wham! - consider:
Andrew Ridgeley: spends his mornings surfing or playing golf, goes to the pub, then goes home to Karen from Bananarama.
George Michael: every year seems to bring another embarrassing story in the tabloids - crashing cars while under the influence, George’s seemingly insatiable desire for weed etc.
I would also say Brian cool, roger lam. Brian went back to Uni to get his PhD in astronomy, while Roger mainly walks around with too hip sunglasses.
ps good username/post combo
Brian Eno and Bryan Ferry, Roxy Music.
Eno is still the epitome of cool. Ferry lost it at some point in the late 70s and has been getting uncooler ever since.
King Crimson: Robert Fripp (cool), Ian McDonald (ended up in Foreigner)
Jefferson Airplane: Jorma & Jack became Hot Tuna & stayed cool. The rest became friggin’ Starship.
I take it you are unfamiliar with Ian Brown and Bez, then…
Just to pick a nit: Brian May and Roger Taylor aren’t former bandmates…they’re still current bandmates. Freddie’s gone, and John Deacon’s retired, but Brian and Roger are still recording and touring as Queen (with Paul Rodgers, up until earlier this year).
It’s not clear to me that The Who have disbanded, and I have a 25-year-old t-shirt from their final tour that supports my opinion. Sure, they no longer have Entwistle’s amazing bass, but they replaced Moon and survived. OTOH, the only reason they stayed together past the turn of the century was to rock the shit out of NYC and to get John Entwistle some income.
I think that Roger Daltrey’s relative un-coolness is actually mucho cool. He saw what happened to Keith and cleaned up his act to where he does gigs on children’s TV shows. Entwistle died about as cool a death as you could ask for (nearly 60 years old, in bed with a stripper), but you know what? Past a certain point, coolness just isn’t worth it.
+1
.
Nobody wants to be Peter Criss, not even Peter Criss.
George Michael is gay, whats Ridgeley’s excuse for being in Wham!?
He was young, and he needed the money? 
Dennis was cool. He was the cool guy Brian used as inspiration to write the surf songs of early Beach Boys.
Al Jardine, on the other hand, looks a bit funny.
I agree since Garfunkel sang most of the lead vocals so one assumed he’d have the big career. But he only wound up with one top ten hit on his own while, Paul Simon had hit after hit in his solo career
Women.
(a far better excuse, IMHO)
Andrew Ridgley had no purpose other than to be a front. Both Michael and Ridgely later said, that Andrew Ridgely did virtually nothing in the band. All the stuff he was credited for was made up. Be he and Michael were friends so Ridgely was in and that was that.
It reminds me of an old interview I saw with Olivia Newton-John, it was Mike Douglas and Karen Carpenter and Olivia were on (they were very good friends in real life) and Karen said her solo album was shelved because Richard felt it stoled too much from the Carpenters’s sound. And Olivia said “What do you mean? You (refering to Karen) ARE the Carpenter sound. Without you there’s nothing.”)
Maybe less so now, but back in the 1980s, Mike Mills of REM always stuck out like a sore thumb in band photos as being especially geeky-looking. It looked like he’d stumbled into the rehearsal room by mistake while looking for chess club, or something.
Exhibit A, with Bill Berry for comparison purposes.
Exhibit B. He’s trying hard, bless him, but those shades are fooling no-one.
Exhibit C. Own up, who brought their little brother along to band practice?
Exhibit D. Even with the chef’s trousers, Stipe is still only the second-worst-dressed member.
Exhibit E. Mike, your hair is really letting down our look, dude.
And that’s only from the first couple of pages of Google Images… 