Nick Lowe.
I'm a huge fan; I've listened to his music since 1978, and seen at least one date (usually more) on every tour since 1981, and have a ridiculously exhaustive collection of audio and video by him, from sources both legit (his entire catalog) and "not so legit" (audio and video bootlegs of shows, interviews, etc.).
When he plays in my area, he usually plays to about 150 people or so. Though I've seen him open many shows in arenas, too, for bands like The Cars and Tom Petty & the Heartbreakers.