That’s when James Taylor was married to Carly Simon (which is also when she was in her prime). Being the S.O. of a hot woman will always increase your coolness.
Still, to give credit where credit is due, J.T. was cool enough to have Elvis cover one of his songs (“Steamroller Blues”).
As for me, I think most of James Taylor’s songs are bland, inoffensive, and forgettable. I do like “Fire and Rain” however.
I love James Taylor’s music, every bit of it.
And I think it’s cool that he didn’t try to fight his body when it came time for his hair to say “farewell.”
I dunno if he’s cool, but I’d give three thousand dollars to be able to sing like him.
mmm
I’ll see your three and raise you a thou.
I have figured out a bunch of his songs over the years; did the same with Jim Croce and Paul Simon, too - and sure, John Denver back in the day (his plane went down about a mile from my parents’s house - big news at the time). JT isn’t particularly cool, but he’s good and some of his songs are great.
To be fair, he was one of the pioneers of whiny fucked up rich kid emo, I’ll bet that counts as cool in some circles. If he came out today, he’d have tons of tats, hair in his face, and a legion of teenage cutter fans.
You forgot to mention Sean Connery in this regard. But the truth of the matter is that when your over 40 you usually don’t give a flying fig about what’s supposed to be cool, at least not the way you did when you were 20. It’s sort of like being cool and lame at the same time. 
As someone said above (Simplicio, I think) not being cool doesn’t mean that none of his music was worthwhile. I like a lot of his songs (Fire and Rain is moving as hell…) but I never thought he was cool. So what? Being cool doesn’t elevate your talent. I LOVE a lot of Jim Croce’s music, but I don’t know if anyone would call him “cool” either. (Maybe he was, in a sort of 70’s, Starsky and Hutch kind of way…) Sorry, this has gotten off-topic from the OP. I think it was not uncommon to think JT wasn’t cool.
This.
Jim lost any cool points he may have had, along with his career, when he left New York. Unless Hollywood is calling, you never leave New York.
If he came out today nobody would be surprised. 
Hell yeah he was cool! Not only was he on The Simpsons, but he also starred in one of the greatest films ever made!
O.P. here (so I guess I’m in charge). Feel free to go off-topic. I’m interested in the whole “cool” thing.
My favorite JT songs are Wandering and Lighthouse, which has harmony by Crosby, Stills, and Nash. Were CS&N cool?
I think that many great artists fall outside of the cool bucket.
In the 70s, I thought there were different strata of coolness. In my various circles, James Taylor was cool compared to Carpenters type music among my high school friends, not cool in the groups that listened to Janis Joplin, Grateful Dead etc. Part of the criteria seemed to be whether they smoked pot or not (or it was assumed they did).
what is this obsession with ‘cool’ ?
who cares except those who are not ‘cool’ ?
They both come off as assholes, but Lester Bangs wins this. By a lot.
Doesn’t having an attribute that isn’t something you bring up over the dinner table to your family increase coolness?
Yeah, I like a lot of his stuff, but it would never occur of me to think of him as “cool”.
You have to admire a writer who reviews an artist by fantasising about stabbing them in the gut with an off-brand soda bottle. The man simply did not give a fuck until it really mattered: when he wrote about the music he loved, he was beautiful, profound and moving:
Lester Bangs shaped the music I listen to more than any other writer or critic, because he believed that music truly mattered: even when he was angry, especially when he was angry, it was at what he saw as something falling short of what it ought to be. And the man wrote like a god.
Plus he was played by Phillip Seymour Hoffman. That’s a rare honor.
Young Elvis Presley was cool. He’s the only musician I can think of who actually was cool. Others may or may not be entertaining, but they are never, ever really cool. The most they manage is to chisel off a little of The King’s coolness. So, no, I guess James Taylor isn’t cool.
I went to college in the 70’s and a few people I knew were huge James Taylor fans. They were all, each and every one, as uncool as it is possible to be. Even I, a nerdy science student, could freely tease them about their lame music. Of course that just made them turn up the volume on their whiney music so even more people could hear how sad and misunderstood they were.