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How Diligence Pays Off: Isaac Gillespie on antiflolk, smashing guitars, and jamming with Mickey Hart | July 2011

Photography by Louisa Marie Summer

Isaac Gillespie is an interesting man. His wry humor and knack for melody often produce sincere, obtuse songs one can only classify as antifolk. The New York Citydweller recently put together a dream team of young musicians to create The Due Diligence, and orchestrated I Will Wreck Your Life, one of the most pleasurable albums of the spring. Soon after the album was released, Isaac chatted about his musical starts on a boat with one of the Dead and how he met his favorite musical contemporaries.

The Due Diligence

What have you been up to?

All spring we had a series of incredible shows and then the album release at the end of March. Basically, the whole spring was one crazy sprint towards releasing this album. Every show got better, and they were all at these venues like Death By Audio and Cake Shop. Ever since then… to be honest, getting the next one together (laughs).

As The Due Diligence?

That’s an interesting question… I haven’t told anyone, including the people in the band, but I’m kind of considering renaming the band, just because The Due Diligence of the record I Will Wreck Your Life is such a sprawling affair, almost a collective. I guess since the beginning of 2011, we’ve been doing this trio thing, myself, Alex [P], and Charles [Goold], like a classic 60’s power trio. It is the most fun ever, us rocking really loud. It feels different from I Will Wreck Your Life; it’s much more streamlined.

The Due Diligence

How long have you known all the players?

I was up in Boston, staying at this kind of commune, where it’s affiliated with Harvard. It’s where the Magnetic Fields first lived and practiced. I’m trying to play music and I couldn’t find the group of people I was looking for. I said, “Fuck it. I’m going to New York. Music isn’t working; I’m going to try film.” I don’t know why I went to Boston to do music, but I went to New York to do film. I landed at a great, nonfiction production company. I worked in TV! I was at the company for two years. I did development, coming up with the next TV show, and I produced a few episodes of A&E Biography, Justin Timberlake and N’Sync.

I came up with an idea to do a travel show hosted by Mickey Hart of The Grateful Dead. He was going to go around in this bus, using his experience traveling back and forth across the country; he could clue you in on the greasy spoon, the whacky corners of the continent. We pitched it and he got really excited. He came out to New York for a pitch video.

I wasn’t really playing music at this time, a little bit for myself. But of course, Mickey Hart’s in town. We shot this thing and the last day, we’re on this boat in the Hudson River and I brought my guitar and some drums. I start playing. He starts playing. We’re jamming together. It’s really fun.

The Latin clave, it’s the central rhythm to Latin music. People know it as the Bo Diddly Beat. Mickey’s playing this on the bongos. I start playing these different Grateful Dead songs, but to the Latin clave. He’s getting a kick. Some Grateful Dead are already in it, like “Not Fade Away”, but then he starts throwing curve balls. “Do ‘Box of Rain’,” songs that don’t easily lend themselves to this rhythm. I’m like, OK, going trough the whole catalogue.

He says, “Keep playing,” and pulls out his phone. He dials; it goes to voicemail, and he goes, “Hey, Bob, I found a kid that can play all The Grateful Dead songs in the Latin clave!” He calls up Bob Weir. In the course of that, off the cuff, he says, “Hey, man, that’s diligence.”


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