You can both appreciate James Taylor and also think he’s not cool.
I like JT, but he (and John Denver, and Gordon Lightfoot, etc) certainly aren’t cool. Their whole point is that their songs are earnest, and earnest is the anti-thesis of cool.
Sort of. It was Taylor’s “underground” hit, released on the Beatles’ Apple label. Taylor’s first album, like most of Apple’s signings other than Mary Hopkin and Badfinger, languished in obscurity upon release, but the single of “Carolina in My Mind” did manage to dent the low end of the charts. Once Taylor moved to Warner Brothers and became a huge success with his second album, Sweet Baby James, the first one started selling on its coattails. A re-released “Carolina in My Mind” entered the charts again, this time doing significantly better (if not spectacularly). So the song gets cool points for Taylor’s being a Beatles protégé at the time, and for its being the “before he was famous” release.
Exactly
Very interesting theory. Now I have to see if I can come up with someone who is both unquestionably earnest and unquestionably cool.
Bono?
Unfortunately that don’t make it so.
I feel it’s like that episode of Futurama where someone has to inform Fry that “Dave Mathews does not ‘rock’”. You can certainly like James Taylor. But people like him because they like his bittersweet 70s soft rock singer/songwriter style. They don’t like him because they think he’s so cool.
Bob Dylan.
Well, if you live in one of the Carolinas it does make you pretty fucking murderous.
And now you got it stuck in my head, GODDAMN IT.
Mister Rogers, for the win?
James Taylor is lucky to be alive. He was in/out of psychiatric hospitals before getting famous. Then his heroin addiction throughout the 70’s. He was a messed up dude for a long time.
I respect him as a musician. He supported and helped Carole King with her early albums. He’s listed on her albums playing guitar and providing vocals. They’re still friends and did a reunion tour together in 2010 and 11.
He knows that a lot of his songs sounds almost the same. I heard him joke about it in an interview last year. No matter what he writes it ends up similar to his other songs.
Once in awhile I enjoy his easy listening style. Is it hip? Maybe not. But I find his music soothing.
Dylan is earnest? Maybe in some specific songs from his early protest period (or his Jesus period), but taken as a whole? Surely if any songwriter was ever ironic, elusive, evasive, mercurial, and contradictory, it’s His Bobness.
With his causes and affected sunglasses? Dude tries WAY too hard to be cool. Cool is effortless. Cool doesn’t care if people think it’s cool. In that way JT is cool. But not, really.
Christgau and Bangs and everybody else–was there ever a rock magazine with better writers than the Creem of the early seventies? Hell, I even bought Lou Reed’s Berlin on their recommendation. And played it once.
I don’t know if it’s fact or a longstanding Urban Legend, but supposedly when J.T. was a young, strung-out junkie, not yet famous, he was trying to score in a rough part of NYC, when another, even more fucked up druggie attacked him in an attempted robbery; There was a fight, and Taylor struck the guy in the struggle, and the would-be robber fell and hit his head on the pavement, and ended up dying from his injuries…
James Taylor was never charged with a crime, the fight being ruled self-defense.
As for cool, John Belushi was convinced that J.T. was cool enough to party with…
Too bad that hard life didn’t show up in his work. I don’t hate the guy - think he’s got a great voice, for one - but he’d have a lot more cred if he had a harder, darker edge. He wouldn’t have to leave his genre, either, just change it.
About cool: he’s not trying to be cool. That’s okay. You should either have it in you or not mess with it. What separates James from cool, probably more than anything, is his masculinity. It’s too 1970s, too just-be-yourself. He’s masculine without being manly.
Didn’t George steal the title of “Something in the Way She Moves” from him? George loses cool points for that.
Well, that’s not exactly the most ringing endorsement, now, is it? “He was a great guy to shoot up with” isn’t something you bring up about JT over the dinner table to your family. 
JT is cool to those who find self-absorbed musicians who sing mellow songs cool, or he’s a great guy to party with cool, but he was never “cool” in the sense that he became a influential trendsetter on the overall culture itself (like the Beatles, Elvis, Sinatra, mid-90s Tarantino).
Wasn’t it the Beatles/Apple Records who gave JT his big break?
Bono in 1980-83 was earnest and cool, but now he’s too old to be cool. IMHO, I don’t think you can really be “cool” after 40, other than exceptional circumstances (Obama in '08, that guy who landed the airplane in the Hudson river, you’ve walked on the moon sometime in your life and you’re still bustin’ up punk CT-ers in your 80’s, etc).
Self-absorption can be cool. In fact some degree of it is probably essential to cool.
That kind of cool takes a careful walking of the line. You have to put nonconformity in the service of conformity. Be a kind of outlaw for the status quo.
In fact I would call the Beatles anything BUT cool. Trailblazers, tastemakers, yes, but they were too just-be-yourself - too 60s in the way Taylor is too 70s. Their British proto-hippie creative play did more to expand the culture than reinforce it. Creativity is not, by itself, cool. Cool is not playful, it’s knowing. Cool is not an outlook, it’s an Attitude.
Beatles were the essence of cool in 63 Britain and 64-67 US/UK. To argue otherwise implies that we’re talking about different definitions of “cool”… or something. 
We might be. What, if anything, did the Fab Four have in common with Sinatra? with Mick Jagger? with Connery’s Bond? with Steve McQueen?
They influenced styles and fashions beyond the typical rock star “sphere of influence” of teenagers and rock musicians - just look at the development of my Dad’s hair from 1964 to 1970 and you’ll see the Beatles influence, just as looking at my Dad’s martini showed Sinatra’s influence.
Don’t watch Mad Men so have no idea how to respond to that one.