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Leo, in “Trying Times” you sing “You have to laugh just to keep from crying but it’s not so funny, these are trying times.” An almost prophetic song in view of the Covid pandemic that broke out shortly after you wrote the song in early 2020. How did you experience the beginning of the pandemic in New York?

I wrote those lines in response to what felt like an already uncertain set of conditions in America and the world at large. It’s not a political song – I’m not really a political writer – but there was an unsettled mood after the trauma of our previous political situation.

Maybe it was also a reaction to being the father of a young girl and seeing the world through my daughter’s eyes. I want to believe that things will improve in her lifetime. I want to tell her that the problems around us are not so bad and that “every little thing is gonna be alright,” like Bob Marley sang. But of course these are very difficult times in the world and it’s not necessarily going to get better. It’s a small triumph sometimes just to find a little stillness or peace.

Somehow in the face of all those feelings, I wrote a song that became the de facto manifesto for the record. Laughter and love can be the antidotes to these challenges. My father has often said to his audiences that sometimes “feeling good is a radical act”.

When Covid arrived, of course it was a shock. But I was somewhat at peace with it, almost like I had been expecting it my whole life. I was born in the mid 1970s and have often felt like mine is a lost generation – born after the cultural revolution of the 1960s and before the millennials who were raised in the chaotic freedom of the internet. I wanted to know what it was like to live through history, even if it was painful. For years we’ve heard about the potential for calamity on a global scale, so when the pandemic arrived it was strangely a relief. Not the tragic loss of life, or the ridiculousness of science deniers and politicization of public health. But living through an event that literally everyone else in the world was also experiencing at the same time was profound for me.

I was worried about what might happen with the music community, with my daughter, with my parents, with my career, with my friends around the world. Everything was unknown. However, there is something liberating in not knowing and in not being able to plan.

I remember thinking sometime early on in the pandemic that I was so grateful about the decisions I’ve made in my life. I love my family, I love where I live, I love what I do. I embraced the quiet pace, the slower tempo of life, and tried to make the most of the time by writing music, making podcasts, and enjoying a simpler life at home. I know it sounds strange, but I actually look back at those early days of the pandemic with a certain amount of nostalgia.

Being a musician and producer is a particularly communicative profession. Personal contact, interaction with other musicians and of course the audience are essential. Many artists I have spoken to in recent months have been hit hard by this global crisis. How has this forced withdrawal into the private sphere affected your work in general and the creation and themes of the new album in particular?

Music is generally collaborative and interactive, it’s true. But I have always been very self-contained, going all the way back to when I was a kid learning how to play and produce music. I have no siblings so I was comfortable spending time alone with myself from the beginning. My approach to producing can be solitary. I’ve had a studio in my house for 10 years, so my routine was already built to work at home. And my production style often involves me playing multiple instruments.

Before Covid I had cultivated a community of creative friends in New York who came to my house regularly for recording, and I also have a podcast so every week I was meeting with someone in person to do an interview. I have missed that interaction but I can feel that it’s already beginning to return, at least in New York.

On the other hand, so many musicians learned how to record themselves at home this year – it seemed like everyone who didn’t have one already bought a microphone and a portable studio setup. So musical collaborations were actually easier in a way. We lost direct human connection but we gained a lot of access to one another.

But you’re also right about the “private sphere”. As a songwriter I’m influenced by what I experience, what I think about, what I see. And this was a very internal year; it was about my wife, my daughter and a few neighbors. So the songs speak to that intimate space. Rather than thinking about an audience all around the world, I really was only thinking about my limited audience at home. Some of these songs were written to sing to my daughter before bed at night, to make my wife smile, or to capture my own feelings at the time.

And the social isolation helped me to define the sound of the record – it would be made primarily at home, and using the limited resources around me. As we know, limitations are so helpful in creative endeavours, and without those boundaries, who knows what kind of record I would have tried to make instead of this one.

In a certain way, “The Art Of Conversation” has become a family album, and not only thematically. Your wife Amanda and also your father Ben Sidran were actively involved in it. How important was this collaboration to you?

My wife is an unusual muse for me because although she is very supportive of what I do, she is also somewhat aloof when it comes to my work. She doesn’t get swept up in the details of my process. She has opinions but she doesn’t involve herself too much.

I have spent nearly two decades trying to impress her and to draw her into my creative world. I think she probably understands that it’s useful to me for her to maintain a gentle detachment because it seems to motivate me. I hate to admit that. But it might be true.

I love the way she sings; I think she has a perfect and pure voice and in fact we met in a band in the early 2000s. But I have to practically beg her to sing on my records. During Covid we were home together all the time, and she had nowhere to go so I got her to sing quite a bit!

As for my father, it’s not unusual for us to work together. I’ve been making records with him for years and we’re constantly talking about projects and sharing ideas with one another. I don’t even see what we do as collaboration. It’s more of a fact of life. My last record was a tribute to Michael Franks, as you know, and it was a little strange that my father didn’t make an official appearance on the record because it was closer to his world than anything I had done before as a solo statement. But in fact he was extremely present in the project in ways that maybe only he and I will ever fully understand.

I did try to quietly honor my dad on the Franks record by recording “You Were Meant For Me” which I first heard in the 90s when my father produced the original version for Michael. But after promoting the Franks project and thinking about his importance as an artist, I realized that I wanted to be able to do the same for my father who I think is also an important artist, so I started looking for material from his catalog that I could do. “Song For A Sucker Like You” was one of his best known songs but he doesn’t generally perform it anymore so it was a good place to start, and it was very clear to me that he should sing on it as well.

The most significant family collaborator on the record is the one you didn’t ask about: my daughter, Sol. She sings backing vocals on two songs, and she also inspired many of the others. The album opens with “Wake Up SoSo,” a song that came out of an evening improvisation for her. “This Is Night In Brooklyn” was a musical response to a drawing she made a few years ago.

When I read the name of your album, I couldn’t help thinking of “The Art Of Tea” by Michael Franks. And the title track, a bossa nova duet sung between you and jazz vocalist Kat Edmonson, has definitely a Franks’ vibe. Would you agree with that?

I completely agree with that and I am so happy you made those connections. After I did Cool School [The Music Of Michael Franks] I was not entirely sure how to follow it. I wanted to follow the story I had started to tell in my career, not only about Franks, but also about sophisticated, understated, “cool” music. Michael’s music is so deceptive because it’s hip, but it’s also commercial. He weaves in elements of Brazilian music, folk music, jazz, funk… and it all works. Looking back at it, I think I was compelled to do a project of his music in order to be able to see my own original music more clearly.

I gravitated to The Art Of Tea when doing the Franks project – the raw immediacy of that record captured my attention, the playfulness of the performances, the humor, the size of it.

As I started to think about writing new songs for this album, I was hoping to find a song or two that helped to bridge the gap between Cool School and whatever this project turned out to be and I knew I wanted to write a bossa. I’ve written variations on bossa for years and gently infused Brazilian and latin elements into my songs. That was one of my first points of connection for me to Michael’s music.

When I first heard Kat Edmonson, I absolutely loved her – she’s a fantastic songwriter and artist in her own right, her voice is so expressive and filled with personality. I reached out to her to be a guest on my podcast and we had a brilliant conversation. Immediately after she left the interview, I wrote “The Art Of Conversation”. I thought maybe Kat would consider singing it with me one day, but it was more like a dream than it was a strategy. It was my hope for the song.

Eventually I proposed the idea to her and she graciously agreed to join me on it! So I owe the title track to Michael and to Kat.

When I listened to the album for the first time, it reminded me of another great artist, Paul Simon. Would you say that Simon and his way of songwriting and playing with foreign musical elements have influenced your work as a songwriter?

Paul Simon was a huge influence on me in my early development. On every level. His singing, his lyrics, his musicality, his humor, his love of great musicians, his appetite for broad influences and willingness to experiment and absorb new elements. And his relationship with rhythm, drums and drummers (Steve Gadd, Jamie Haddad, etc.).

He managed to make all that sophistication and cosmopolitanism palpable to a pop audience. And that is not easy to do! When I first started making records, I was inclined to mention Paul Simon as an influence because it was an easy way to explain that I incorporate international elements and jazz into more traditional pop songwriting. Over time I have started to feel that while it’s convenient to casually compare oneself to Paul Simon, in fact it should not be done lightly. He’s one of our greatest practitioners of songwriting.

A song that touches me personally is “Pop”, which in a way also deals with the aging of loved ones. What inspired you to write this song?

I wrote that song about my grandfather Louis Sidran who died in 1967, almost a decade before I was born. In the family they called him “Pop”. I’ve lived my whole life with the ghost of “Pop” even though I never met him. I’ve always imagined what it would be like to explain my life to him, or to explain the world today to him. What would he think of it all? He represents something powerful and ever-present to me.

The song is also about my father, waiting to leave home. It was not always so happy in their house and the song describes a mutual dissatisfaction among the members of the family. The lyric “in the silence they created, the boy patiently waited to get out of town” is about my dad biding his time until he was old enough to leave home and start a new life. I had never written a song like that before and I knew it was special to me from the very first moment. I tried to sing it to my wife, and to my father, I couldn’t get through it without crying. Now I can sing it without tears, but it took a while to get there.

I think the song “Row On” has a special meaning for you. The original “Al Otro Lado Del Rio” by Jorge Drexler from the film The Motorcycle Diaries, which you co-produced, won the Oscar in 2005. How important was this prize for your further development as an artist?

I want to believe that those kinds of awards don’t matter, but on some level they always do. I like the way you frame the question around development as an artist rather than development as a “professional”. The award opened doors for me and gave me a level of access to the record and film worlds that I wouldn’t have had otherwise. So there was an element of opportunity that came with it.

But as an artist… it brought confusion for me at first. It won in 2005 and it took me 10 years to make a solo record after that (2015’s Mucho Leo was the next solo statement I made). I don’t think I knew exactly who I was supposed to be after the Oscar or what I had to say. I moved to New York from Wisconsin right away and started to get involved in production and scoring. I basically avoided the whole question of being an artist for nearly a decade, and one of the first songs I wrote when I started to compose again for myself was the song “Where Have I Been” which talks about that confusion (it’s on Mucho Leo).

The success of “Al otro lado…” represented a deeper truth to me also because of how it happened. I had been a huge fan of Jorge Drexler when I was in college, and when I met him we became friends very quickly. At the time it was as if my most deeply held desire was coming true: to work with and befriend him. When that ultimately led to me becoming the producer of an Oscar winning song at 26 years old, it was like the universe saying to me “Do work that you love. Do work that you think is important! What you love matters!” It was a major personal success.

But how do you follow that kind of experience? What do you make of it?

Ever since then I wanted to find a way to cover that song in my own way but I wasn’t sure how to approach it for a long time.

In your English adaptation, the song becomes an anthem of hope: “I think that I see a light, just on the other shore.” How important was it for you to convey a positive message?

It’s incredible that just before Covid, I had started to produce two songs: “Trying Times” and “Row On” and both of them were so prescient. “Trying Times” is small, intimate and familiar. “Row On” is, as you say, more anthemic.

By the time I finished the basic recording of “Row On” the pandemic had arrived, but in fact I did the English adaptation before that. I was honestly just interested in conveying as much of the original Spanish meaning as possible in a poetic way. The original lyric that you cite in Spanish translates as “I think I’ve seen a light on the other side of the river.” So it’s quite close, really.

Through some magical trick of language and arranging, even though my version is based closely on the original, something happened in translation both musically and lyrically that put a different focus on the meaning of the song. English rendered it a little less personal and a little more universal in its feeling.

I also owe a debt of gratitude to two people on that song. The first is Michael Sackler- Berner, my friend and collaborator for many years. I co-produced and co-wrote two EP projects for his solo career, and this was the first time that he returned the favor to me as a co-producer on my music. He built a studio just before Covid started, and I recorded the basic tracks for “Trying Times”, “Row On” and a few other songs with him before the lockdown. Michael encouraged me to move the rhythm of “Row On” away from the original South American folklore feeling and towards something more rooted in Americana.

Also, the great Argentine-American singer-songwriter Kevin Johansen gave me the gift of “Row On”. I had done the full adaptation of Jorge’s lyrics but I was singing “Go On”. When Kevin heard it he said to me “Why not Row On?” and it was like someone turned on the lights. That was a huge act of generosity on his part.

The song features a chorus of singers from all over the world, from jazz singer Kurt Elling to legendary rock producer Butch Vig, and even Jorge Drexler himself sings along. Tell us a little about the recording process.

Seen through the Covid lens, it was clear that the song had taken on yet another meaning. It represented hope, optimism for the future, solidarity and perseverance. I began to ask friends around the world to sing on the track. I tried to contact Jorge but he was non responsive at the time. So I reached out to many of the musicians in Spain and South America who I know because of Jorge. I wanted to pay tribute to Jorge in some way – after all “Al otro lado del rio” did change my life.

Then I started to reach out to my jazz friends, songwriting friends, people I knew through my podcast, or from my work with my father. First there were 4 people. Then 8. Then 20. Eventually 40 incredible artists from around the world sang on the chorus – they sent recordings from their phones and I mixed them in and made a video. Almost everyone I asked said yes, although there were a few who declined (I won’t say who!).

Finally Jorge emerged – he had been silent because he was sick with Covid in March of 2020. I shared the version with him and he immediately offered to sing it with me. It was, once again, the absolute best possible outcome that I could have imagined.

Also on the new album you played most of the instruments yourself. What attracts you to record the songs in this way? How important is it to you to have control over the whole recording process?

When I play all the instruments, there is something that happens. The arrangements are very defined, and the rhythm is very connected. The music begins to breathe in a certain way. And I work quickly because I don’t need to communicate it to anyone else. Also I do often have clear ideas of what I am hearing. It’s the most natural way for me to work because it’s how I’ve always worked – ever since I was a teenager. Not only the performance but also the recording and often the mixing too.

On the other hand, working with Michael Sackler-Berner on half of the songs on the record definitely changed the results, even though I played most of the instruments on those songs. Production is mysterious and sometimes just having another person in the room who you trust is enough to reorient the music.

A few years ago I co-produced a record for the Cuban-Canadian artist Alex Cuba (Healer). That’s the record that won a Grammy. I played most of the rhythm section instruments on half of the record, and on the other half I barely played any instruments. I discovered that the sound of the album was coherent even when I didn’t play on the songs – there was something in my approach to production that was happening even if I wasn’t playing.

So I don’t know how important it is to have control. I could imagine making another solo record and only playing guitar or maybe just singing.

Leo, you have mastered the ‘art of conversation’ not least as an accomplished interviewer for your successful podcast series “The Third Story”, in which you talk with musicians, artists and songwriters. Many of those who contributed to the album were already guests on your podcast. How did that come about? Was it more spontaneous or was it planned by you to involve friends and interview guests on the album?

It began in a more spontaneous organic way. Sometimes I interview my friends, and many times friendships and collaborations are established during the interviews. There’s an enormous amount of good will that is generated through the podcast conversations, and that seems to translate easily into working together.

At some point in the process of making the record I also realized what you have noticed too, that almost everyone who contributed to the record had been a guest of the podcast – and at that point I did make an effort to bring in collaborators on the record who had also been on the show. It supported the idea of the art of conversation so beautifully.

I tend to interview people who I admire, so asking those same people to contribute to my record made a lot of sense.

Your record also reflects the collaborative possibilities of social distancing that modern technology makes possible. This kind of album recording would have been unimaginable just a few years ago. Do you think the pandemic is changing the music industry and the way an album is recorded and produced even faster? What do you see as the big advantages for artists through modern technology and what will fall by the wayside in the medium term?

It is becoming harder and harder to distinguish between general “content” and a larger artistic or musical statement, like a record. Maybe it doesn’t matter anymore because most consumers are actually responding to an algorithm to help them discover new music, and the algorithm prioritizes singles and smaller pieces of content. We make long form records because that’s how the technology evolved – from 78 RPM albums with 3 minutes per side, to 3 RPM LPs with 25 minutes per side, to CDs with 70 minutes. The expectation changed with each innovation. Now with streaming we’re back to singles again.

On the other hand, I don’t feel that a world of singles necessarily fosters artistic expression or development. I think there is value in curating a collection of songs, of conceptually tying them together, making a more developed argument. But it is very possible to write a song, record it, and release it immediately and that also has its value.

My biggest concern is that we look back at a project like mine in five years and categorize it as a “Covid record”. I’m very happy to make music that reflects the times, but I don’t want that reflection to necessarily be tied to technology. The pandemic has changed many things – not only the way we make music but also the way we consume it. Concerts have been almost completely missing for a year, so not only are we recording music in solitary isolation, but we’re also listening to it in our own private bubbles.

I honestly can’t predict what will happen in the future. I probably felt more free and comfortable to contact people like Butch Vig and Kurt Elling, Becca Stevens and Camille Bertault, Will Lee and Alexandre Kassin, Louis Cato and Antonio Lizana, and ask them all to sing because I knew they were isolated and alone at the time. I wonder if I will do that again. On the other hand, I made new musical friends online this year, and I hope I continue to do that after this is over. In fact, I know that we are doing this interview because of the internet, because you discovered my Michael Franks record years ago online.

By the way, I have to tell you one anecdote. In 2018 Jorge Drexler was playing at New York’s Central Park Summerstage summer festival and I joined him on stage for a song. I had a copy of Cool School in my bag, and I ran into the great New York DJ Greg Caz backstage. I handed him the record and he said to me “Oh man, wait until Thomas Splett finds out about this!” I was so proud when I told him “Thomas already found it!”

You have been living in Brooklyn with your family for many years now. In a way, “The Art Of Conversation” sounds despite or because of its stylistic diversity like a New York album. How big, do you think, is the influence of your adopted hometown on your music?

I’m happy that you say that. I don’t know if I’m so aware of that. New York has a way of seducing people, and if you can survive here for long enough it does change you. It’s an energy, a disposition, even a shared experience of suffering. For musicians, New York is an exceptional place – not even for the opportunity, because in fact there’s less and less opportunity here now – but because of the mentality. I think maybe that’s what is coming across in the music.

This is such an innocent record in some ways and it draws from very un-edgy sources, everything from bossa to 50s doo wop. So it’s kind of funny that it feels like a New York record. Maybe it’s because there’s freedom in it and a sense of not worrying about what it is or isn’t.

What’s next, Leo? Will you present the album live?

I have a couple of shows booked locally in New York over the summer, and I’m organizing a few weeks in Europe in October with my Groovy French Band™ in France and Spain. I’d love to play in Germany as well – we’ll see what I can manage to book. I’m optimistic that by the fall, we’ll be able to tour again and I can’t wait to play these songs live.

There are also a few “orphan” songs that didn’t make it onto the record, mostly because they weren’t quite ready when I was finishing this collection – but I’m planning on releasing an extended version of the record in the fall that includes the bonus tracks as well.

Are you already working on new projects?

I have these few extra songs that I’m finishing up, and I’m really excited about them. After that, I do actually have an idea for the next record already, which will probably change but I’ll follow it wherever it leads me. I haven’t really produced a record for anyone else in over a year, and other than the podcast and my work scoring music for television and advertising, I don’t have a very clear picture of what’s coming next. But I think I learned during Covid that it’s good not to plan too much because it could change in an instant.

Leo, thank you very much for the interview!

Thank you so much Thomas, for all your work and support. You really asked beautiful questions. I’m honored to be part of your community and I feel like I know you. One day we’ll meet in person I’m sure.