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Bill Callahan gets super meta, talks about writing his song 'Writing'

5 Songs We Can't Stop Listening To is our chance to talk to artists we love about songs they love.

Listen to the whole segment below.
Bill Callahan on Bill Callahan
Bill Callahan: Photo by Hanly Banks

My guest today is Bill Callahan. A peculiar thing has been happening on 5 Songs. Normally, I ask an artist that we're playing what is one song they can't stop listening to and they pick the song. Usually, those picks are just random. It's whatever they have been listening to. But in the past couple of months, three artists have all picked different songs from the same album. That album is "Shepherd in a Sheepskin Vest" by Bill Callahan. David Gray, Kevin Morby and Adrianne Lenker from Big Thief have all picked different songs from this album they love. There is something about this album. So I figured I need to talk to the man himself and ask him what is his favorite song from his own record. My guest today is Bill Callahan.


Hey, Bill?


How are you?

I'm good. How are you?

I'm good. What's your favorite song from the record?

I think it might be "Writing." There's a certain way that a person feels when they know something that they are working on has been set free. It had been such a long time between records for me. That feeling is always a rush and an exciting time for me. But on this record in particular because it had been so long. I wrote a song to capture that feeling, so I guess it's the one that I like to hear the most. And I really like Matt Kinsey's guitar playing. It's really out of this world on that song.

"Writing" is a song that I love on the album as well. How did you get that song down onto paper and be like, "This is the song I'm going to write" not "I'm writing again, let's write about something else" but to actually write about writing?

Well, I think with this record, because there are 20 songs, I was trying to cover the story in as many different perspectives as possible. One of them was to look at who is writing the story. Turning the camera around and looking at the person writing all the songs.

Humor is such a part of this record. What role does humor play in the record?

I want some songs to have the highs and the lows all in one. Because that's basically what being alive is like. It's a mixture of those things.