I've been listening to episodes of "This American Life" recently and I've found that it's a conversational dead end. Talking about the show at parties is like talking about reading ancient Greek plays: everyone knows they're supposed to be great, but nobody has read enough of them to really comment. If you listened to an old episode of "This American Life" every day for a full year, you'd still have 50 episodes to go.
"A Life Well Wasted" is similarly great, but there are only four episodes. And it's about video games and swearing.