If anyone's taste runs towards jangle pop, they might want to check out Marti Jones. She sings like an angel and she's married to the noted singer/songwriter/producer Don Dixon. Her songs are generally (tho not always) less introspective than some listed above, but they're tons of fun in their own right. She also has great (and ecclectic) taste in cover material; ranging from lots of John Hiatt, to David Bowie's "Soul Love", to Joe Tex's "You Got What It Takes (To Take What I Got"). My wife and I used the Dixon/Jones arrangement of this song for our first dance.
Her album, "Used Guitars", is a gem and her "Live At Spirit Square" is a great overview of the Marti Jones catalog (nicely recorded by Dixon, too).
Another (related) fun choice is Marti's friend Amy Rigby (they sometimes perform together as Cynical Girls, which is a Marshall Crenshaw reference, I think). Amy's very funny lyrics are worth the price of admission alone.
Marty