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I'm probably the only guy on obner who has everything he's released, so here goes:
Bobby Conn (1997, Truck Stop) - Conn's self-titled release is more a collage of his influences wrapped up in his self-styled antichrist persona than an actual album perse. Really a labor of love by Conn, his girlfriend Julie (aka Monica Boubou) and DJ LaDuce. It's all here, his Jackson 5 side (Never Get Ahead), his Jon Spencer side (The Sportsman) and his dirtier, jammier, grittier side (most of the rest of the album. It's my favorite of his, but it's certainly a grower and not an entry point I would strongly recommend, although the two singles are among his catchiest songs ever.
Rise Up! (1998, Thrill Jockey) - Here the sound is more streamlined and the antichrist persona just as amplified. Significantly cleaned up in terms of execution, this set of songs is a concept album about religion and state. An all star cast provides the backing band (Jim O'Rourke on lead guitar, anyone???), and the material is essentially soul-infused hard rock with riffs galore. I recommend this album as an entry point.
The Golden Age (2001, Thrill Jockey) - His most subdued work. Post millenium Conn dropped the anti-christ schtick. This is essentially just a collection of songs, and although it's good, it's not quite as good as his other three albums.
The Homeland (2004, Thrill Jockey) - Concept album about the war in Iraq, basically a sister album to Rise Up! and arguably just as good, although the band doesn't have quite the all-star caliber. Several great tracks. I recommend this one just as much as RU or more.
Live Classics, Vol. 1 (2005, Thrill Jockey) - A live album recorded at Wall to Wall Studios in the summer of 2004. I was there, Phil was there too. Amazing shows. A good retrospective of his best material, and not a bad entry point at all. Definitely captures the energy of his phenomenal live show!
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