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Jenny Lewis

Jenny Lewis knows a thing or two about running from the past. The irony is that — while trying to run from it — she ended up running toward it and embracing the past in a strange way. It took the 10th anniversary of the album "Rabbit Fur Coat" for her to realize that.
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21: Matisyahu and Reggie Watts

Matisyahu helps me work through some serious issues on a very special anniversary — namely whether or not to shave my beard. I also talk to improvizational musical comedian Reggie Watts. Not about beards, but also about identity and defining yourself.
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Reggie Watts

There's only one Reggie Watts. Not just because his act is unique, but because there are very few people in the world as sure of themselves and as affable — much less in the world of show business.
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Matisyahu

Matisyahu knows that facial hair isn't so trivial. You might even think it's insignificant at first glance, but you might reconsider after hearing this conversation with the formerly-bearded, formerly-Hasidic rapper.
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20: Sadie Dupuis of Speedy Ortiz and the Duplass Brothers

Sadie Dupuis of Speedy Ortiz talks about egalitarianism in music and how she went from math major to major label employee. Mark and Jay Duplass discuss the positives and negatives of being successful filmmakers and family men.
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Sadie Dupuis of Speedy Ortiz

Speedy Ortiz frontwoman Sadie Dupuis has experienced a lot of transition over the last year. The idea of transition is a recurring theme throughout this conversation, whether it's regarding her former life as a math major or her newfound flamboyance as a frontwoman.
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Mark and Jay Duplass

Mark and Jay Duplass usually field film and TV projects involving family and identity. As it happens, they've built a small empire by focusing on those two things. It's no surprise those topics came up in earnest during this conversation.
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19: Craig Finn and Mike Birbiglia

Craig Finn talks about the difference between making music with The Hold Steady and making music on his own, as well as how his attitude has changed relative to those creative endeavors. Mike Birbiglia talk about his life story, because he wrote a story about his life — and turned it into a movie.
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Mike Birbiglia

This interview with Mike Birbiglia is not for the faint of heart. I'll just go ahead and say that you shouldn't listen to it if The Backstreet Boys make you sick to your stomach.