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Where should I start with these guys?
and then end at the end. It's all good. I'd say the 'hits' were Grace Cathedral Park, New Jersey and Drop, but all their records are great in their own right. Maybe grab Rollercoaster first. Also, Sun Kil Moon and his solo record are every bit as good, if not better.
...if not the best representation of their overall career. Fall in love with that and then get Songs for a Blue Guitar. And then dive into the early stuff - Rollercoaster and Down Colorful Hill.
Although I have to say the 4AD 'Best Of' called Retrospective is a very, very good place to start. If you get this you don't need to get Down Colorful Hill because it's got the only 3 songs you need off it anyway (24, Down Colorful Hill and Lord Kill The Pain aren't necessary. Michael, Medicine Bottle and Japanese to English most definitely are).
The get Sun Kil Moon's debut album. And then get Kozelek's solo albums and AC/DC covers and... you're in a world of beauty, my friend.