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It's your duty to listen to each and every show. The best/worst shows are obviously personal taste, but there was a couple threads a few months back discussing just that.
Personally I think your best bet is to start at #1 and go from there. A lot of stuff that happens in early shows is referenced throughout the 300 odd after that.
If you think you'll have trouble listening you should quit your job/leave school and get on unemployment and enjoy the show. With about 345 hours of shows to listen to if you commit 8 hours a day, 5 days a week of listening to KATG it'll only take you 9 weeks to get through them all. How can you possibly find that daunting?
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