The first time I tried Dr. Zed, I got my ass handed to me. It is outrageously hard unless you are the correct level, though I don't remember what it is. Moxxi is probably the worst, and you can kinda judge for yourself how much time you want to spend with it, so I'd say start there. I haven't tried clap trap yet, but it sounds like it wraps things up a bit, so maybe end there.
Both the Jet Set soundtracks (Radio, Radio Future) are amazingly good if you like quirky hip hop. A little hard to find now, but worth it. They aren't original scores, but great licensed music, very unique.
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