@mitchagain, great stuff! The 1st and 2nd Graham Parker albums feature the playing of a couple members of Brinsley Schwartz (the band), including Brinsley himself. Speaking of that band, Nick Lowe, himself a member, said they were trying to sound as much like The Band as they were capable of. Another member was Ian Gomm, who is also a relatively-unknown real good artist.
Dwight Twilley (the group) is a particular favorite of mine, especially when drummer/singer Phil Seymour was a member (the first two albums). Their Sincerely debut album is in my all-time Top 10 list. It's really, really good.
John Hiatt is very well known, and his Bring The Family breakthrough album is unbelievably great. Not just great songs and singing, but also the playing of Ry Cooder, Nick Lowe, and Jim Keltner. I saw that line-up live, and it was a high point of my musical life.
Loudon Wainwright III is known, but not as well as he deserves. A great, great songwriter, his Last Man On Earth album is particularly good. By the way, early in his career he wrote a song memorializing the birth of his son Rufus, "Rufus Is A T*t Man" ;-) .
I hope everyone knows all about Marshall Crenshaw, who has made a lot of great albums. He plays almost all the instruments on his #447 album, which is packed with great songs.
Another relatively unknown working in the singer/songwriter style is Michael Kelsh, whose Bill Halverson (Clapton, Hendrix, Albert King, Neil Young, Beach Boys, Cream, C, S & N, hundreds of others) produced Well Of Mercy is fantastic. The album was executive-produced by Rodney Crowell, who I hope everyone knows of.