I didn’t immediately enjoy it when I first listened, but I’ve recently really been digging You Look Nice Today a podcast by Merlin Mann, Adam Lisagor and Scott Simpson. It’s comedy, and depends on the very idiosyncratic senses of humor of the three friends, so I won’t necessarily recommend the podcast to everyone.
That said, if your youth was anything like mine, you’ll love The Sake Period, which is about growing up uncool, and all the bizarre ideas you develop about what you would need to do to become cool. So you have the guy who shows up at school in August with a fake British accent that he acquired over the summer, or my friend who intentionally developed a huge interest in the Spice Girls in 9th grade. I was always too chickenshit to try to reinvent myself, but if I had, I’d have been the guy sitting in Central Park with a towel on his head.
You can find the episode at the You Look Nice Today website, or on the iTunes store under podcasts.