Greg Brown is missing from the posts above (I definitely agree with Joni, Dylan, Tom Waits, and Paul Simon though). He’s got that low soothing voice and a wonderful turn of phrase that’s simple but just so evocative and picturesque.
If songwriting duos are acceptable, then Lennon & McCartney, hands down. If I had to nominate one of the two, then I’d have to go with McCartney, though his one weakness is in writing lyrics (he’s not bad at it, but in comparison to everything else, it’s not great). Problem with both of them is their quality took a dive after the Beatles broke up - I think it’s safe to say that if they’d never met, neither of them would have made it in the music world at all, let alone become legends.
I also thought of Paul Simon, but his output varies a bit too much in quality for me. Strange thing is, the albums of his that do well are always the ones I can’t stand, and vice versa (Hearts and Bones I loved, but it was a flop commercially; Rhythm of the Saints did well, but I don’t particularly like it).
Todd yells when the need arises, but he really is an astonishing vocalist. As a songwriter, he’s been covered by a huge range of artists, and he’s been hired solely as a singer for projects like the later Bat Out of Hell.
One of the best tours I’ve seen him do was for his album Acapella, with no instruments, just vocalists.
Not sure where Ray fits in here. Ray Davies is, beyond a shadow of a doubt, one of the two, maybe three, best songwriters in rock music. This is beyond question. He is, however, pretty limited as a singer. He sounds wonderful singing his own songs, but he never really covered other writers’ stuff (and no, the Banana Boat Song doesn’t count).
Actually, upon reflection, I’m not sure I understand the question being asked in the OP. And yes, I know this thread is (or was on its way to becoming) a zombie.
I’m a big fan of the singer/songwriters. And while it would be difficult to pin down which one is the best, I really think Billy Joel is getting shortchanged in this thread.
Popular songs. Extremely versatile. Highly evocative lyrics. Melodies that stick with you. Songs that cover everything from social injustice to enjoying life’s pleasures. He even wrote several classically inspired piano pieces. Looking at his whole catalog, it’s hard to come up with anyone better.