When The National was first starting out, guitarist Aaron Dessner used to save up his vacation days to promote his band’s fledging releases. Fortunately, he had a lenient boss who also happened to be a founder of the Red Hot Organization, the people responsible for the definitive 1990s charity compilation No Alternative.

Shortly after The National 2005 breakout CD Alligator hit stores, the guitarist and his brother/bandmate Bryce Dessner began working on a benefit record for Red Hot of their own and, this past February, those tracks finally surfaced as Red Hot’s twentieth release, Dark Was the Night. The resulting album features original material, unique collaborations and rare covers from a pool of artists that includes the likes of David Byrne, Feist, Ben Gibbard, My Morning Jacket, Arcade Fire, Yeasayer, Bon Iver, Sharon Jones and the Dap-Kings, Spoon, The New Pornographers, Sufjan Stevens, Yo La Tengo, Iron and Wine, Conor Oberst, Gillian Welch and, of course, The National. On May 3, many of the musicians featured on Dark Was the Night will also come together for a benefit concert at New York’s Radio City Music Hall, marking The National’s return to the historic room for the first time since opening for Arcade Fire in 2007. Shortly before Radio City, Aaron Dessner discussed the benefit concert and compilation with Relix/Jambands.com and explored The National’s own overlooked roots in the jamband scene.

I worked for Red Hot’s sister company for a longtime, Funny Garbage. It is this weird, funky design company located downtown, and I worked there from 1999-2005. Everyone used to help out with Red Hot projects, and the guy who founded Red Hot, John Carlin, was my boss at Funny Garbage and a good friend. He was always very tolerant when I would sneak away to play music and, as The National got more popular and I could finally afford to quit my job, he was really supportive. He also said that it would be great to one day make a Red Hot record togetherI just didn’t think it would be so soon! But Alligator did well, and we toured a ton on that record and met so many people at a time when all these independent rock people were getting into the Billboard charts for the first time.

It just kind of clicked that we could really do a record focused on this scene. And when I say “scene” I say it with a grain of salt because the music on this record is so diverse that it is not meant to be a document of any one particular genrebut there is some shared audience. So I convinced The National’s label Beggers to sponsor the project, and my brother and I just started collecting tracks for two-and-a-half years.

It must have been a daunting task to jump into this project. Who was the first artist you approached?

At first we started recording our musician friends and people who were easy to access and then we went after people we didn’t know. Working with Red Hot made it easy because so many people were so familiar with the No Alternative album from the 1990s. It had Pavement and Sonic Youth and a secret Nirvana track on it, so people where aware of that album. It was just a really slow process. Sometimes we would get a few tracks in one month and then months would go by where we didn’t get any tracks.

The first person who we approached was Sufjan Stevens. He lives in my neighborhood, and I lent him a banjo back in 2005 [laughter]he’s a friend. We kind of used him as a carrot to help convince people that the project would be viable and, shortly after, we got in touch with 10 or 15 artists. It was actually pretty easy getting in touch with artists and getting them to commitwhat was hard was getting people into the studio and getting something down.

_Dark Was the Night_offers a mix of covers, collaborations and other exclusive tracks. How many songs on the album were recorded specifically for the benefit CD?

I would say 90% of the album was recorded specifically for the project. There are a few cases where a band really wanted to contribute or we really wanted artists to be part of the project but where they weren’t in a recording cycle. So the Arcade Fire track is from the time of [2004’s] Funeral and the Spoon track is older. But, for the most part, everything was recorded for the project.

In terms of the album’s collaborations, in most cases did you and Bryce try to pair the artists yourselves or did those moments develop organically?

Most of the ideas stemmed from discussions Bryce and I had with the people at Red Hot about what might work. They came together in all different ways. For instance, I had heard from a friend of mine who plays with David Byrne that he really likes the Dirty Projectors, and David happened to come see us play at the Brooklyn Academy of Music. He came backstage, and we kind of cornered him and proposed the idea [laughter].

Some of the collaborations were just with our friends, like my track with Bon Iver. When it came to my brother collaborating with Antony, he is just a friend and such an amazing artist so Bryce proposed doing something together and he agreed. Feist put together her own collaboration with Ben Gibbard. She agreed to be part of the record and was working on a track and decided to record it with Bensame with her collaboration with Grizzly Bear.

Benefit and charity albums are tricky to put together and don’t always sound as cohesive as Dark Was the Night. Did you look to any compilation albums in particular for inspiration?

I think in general we looked to the many Red Hot albums because they have such a legacy to them. They were always something more than the grab bag of odds and ends that so many charity compilations are. We really wanted this album to be something of that quality and to have tracks that are exclusive recordings, not cast-offs. But we did not want to make a theme album or an album of covers. We wanted to do something in the spirit of our community, which is really focused on songwriting and craftsmanship. All these artists have an attention to detail, so we really left it up to the artists to decide what they wanted to do. Occasionally we would offer suggestions or give our input on whether or not a cover might clear legally, but we weren’t trying to force a concept on people. So we really just kept our fingers crossed that they would be cohesive and have some sort of shared sensibility. Luckily, that ended up being the case, but it could have been a train wreck.

Let’s talk about The National’s contribution to the record “So Far Around the Bend.” Can you walk us through the composition of that track?

We wrote two songs with this record in mind and “So Far Around the Bend” ended up being the one we felt was the strongest and the most appropriate for the record. We were actually on tour in Europe in late 2007. It was this super dark, cold time and I was just recording lots of little ditties for Matt with this little acoustic guitar on the tour bus and that was the one that worked. It is just kind of a simple, four-cord folk-shuffle, which is usually not the basis for a song off a proper National album. More often than not we usually gravitate toward either rock songs or ugly ducklings that are sort of odder or more intricate in terms of the music. So this song felt like it wouldn’t be part of the next National album, but we all really liked the melody and felt the lyrics were really strong, so we decided to use it for the album. We sent the music to our friend Nico Muhlywho is this really talented arrangerand twenty minutes later he sent back that arrangement, so it was this great Mozart moment where it came out perfectly scored. The chorus was already really catchy but he sort of perfected it with the clarinet and flutes.

We recorded in Williamsburg and did a lot of tracking at my house and then we sat with it for a few months and realized that it was boring us, so we went in started messing around with it again. That always happens with usit usually takes us at least six months to turn a song into something we all feel is finished, so we ended up mixing this track three times before we felt it was done.

Were you happy with the track after all that work?

Well, it is not perfect. I still have issues with it, but I think it is pretty good.

You and your brother also appear on Sufjan Stevens’ track.

It was an amazing experience for my brother and to play on Sufjan Stevens’ amazing, sprawling “You Are The Blood.” We recorded the guitar and bass in his studio in DUMBO, and I remember being like “What is this?” but, as always, he had this much larger arch in his mind that he turned into this great piece that is over 10-minutes long with all these great textures and moods.

It was just an amazing experience: my brother has played in his band and, as I said earlier, he was the first artist we asked to be part of the project. So to go out there and help him make it was a great experience.

Was the live show based around Dark Was the Night always part of your initial vision?

It think we always felt it was important to try and create some sort of live event around the album to kind of sell it and raise money for the organization. Just to get so many artists who are on the album together in that beautiful hall is going to amazing. We are going to do some of the songs on the album and some songs that aren’t on the album and hopefully some collaborations that are in the spirit of the record. The idea is really to create a live experience based around the album. We also are hoping to do one or two more of these events over in Europe.

Kind of like the modern Last Waltz

Speaking of The Last Waltz, we are trying to get Garth Hudson down to play that huge pipe organ they have in Radio City. That would be pretty epic, so we will see.

The National features two sets of twins. Can you talk a little bit about playing music with your brother in this context?

We like to play a lot of non-rock music together and collaborate on all sorts of projects. It is always fun to get inside other people’s minds when it comes to making music. They have all these different habitsSufjan is such a musical mind that whenever you have an opportunity to collaborate with we have to take him up on it.

I know your tastes have changed a bit over the years and there was a time when you and Bryce played a lot of jamband music.

We grew up in Ohio which isn’t too far from places like Deer Creek where Phish used to play a lot. I’ve been to a few Phish concert and many Allman Brothers concerts, who I love. One of the reasons my brother and I started playing guitar was because of the song “Jessica.” My dad had all their albums and my sister’s name was Jessica so she said, “You guys should figure out how to play that song.” My dad was a drummer, actually, so that was part of our impetus for learning how to play guitar when we were 12 years old. [The National’s] Bryan and Scott Devendorf have been to many, many Grateful Dead and Phish shows. They have a long association with that music, especially the Grateful Dead.

I learned to play guitar at camp in North Carolina when I was little and a lot of the counselors were old hippies and those were the songs they taught us. My brother and I eventually became the soloists on the guitar, and it was basically “Eyes of the World” into “Franklin’s Tower” and we learned how to play all these Neil Young songs, which definitely had an influence on us. Oddly, the National is pretty far from that type of thing, though when we play live there is definitely an element of spontaneity and they take on a different quality and the songs can go on for a while more like a jamband. But, for some reason, I am not as interested in guitar solos these days. Maybe it because I grew up playing solos all the time [laughter].

*I definitely can’t see [National singer] Matt Beringer enjoying Phish, but I know some of the guys in The National dragged him to a show once.*

It was Matt, Scott and Bryan and they had to drag Matt to Deer Creek, and I think he was completely miserable the entire time. He listened to one song and then went and hid in the car. Weirdly, Bryan had taken my car without asking. This was in high school and he did not have a car and it was only much later that I found out that they were tailgating in the lot of the Phish show at Deer Creek. It is a legendary National story. Matt can still not understand at all how any of us can stomach Phish. He just can’t stand it at all [laughter].