Joan Osborne: Music, Dylanology & Life in the Hudson Valley

Joan Osborne is the latest multi-platinum-selling singer-songwriter to call the Hudson Valley home. But unlike some, she didn’t venture far to be here, just from her former country retreat in Sullivan County, where she has lived for the past two-plus decades. Her primary reason for the move? It’s to be nearer to the close community of artists with whom she crafts her joyful music. 

This soul-stirring singer ventured from her native Kentucky to New York City in the late ’80s not to launch a music career but to study film at NYU in hopes of becoming a documentarian. It was a dare from a “cute guy” at the corner blues bar that led her to nervously take the stage for the first time in the Big Apple and belt out “God Bless the Child.” Within a few years, she would leave her cinematic aspirations behind and score international mega-success with her major-label debut, Relish, and the global smash single and video, “If God Was One of Us.” Since then, Osborne has released 14 acclaimed albums, earned eight Grammy nominations, and collaborated or duetted with everyone from the Grateful Dead, Patti Smith, and Stevie Wonder to Luciano Pavarotti and Bob Dylan.

Her love of Bob Dylan has led her to create two albums featuring both his anthemic classics and some obscurities, 2017’s Songs of Bob Dylan and 2025’s Dylanology Live. On these albums, Joan and her band take risks that reward both new and longtime Dylan devotees, with imaginative rearrangements that make Dylan’s often spun chestnuts feel brand new.

In this exclusive interview with INSIDE+OUT Upstate New York, Joan shares insights into her early life, her career, her love of the Hudson Valley, and her ongoing Dylanology Tour, which will visit The Assembly in Kingston on August 8.

 

Joan Osborne On Dylan

INSIDE+ OUT: You’ve released two albums of Bob Dylan’s songs: a studio and a live collection. When did you first fall in love with his music? What are some of your favorite songs to sing?

Joan Osborne: I first really came under his spell when I was playing a lot in the Village. His ghost still haunts that area. You can walk down Bleeker Street past places he actually played that are still open, where people will be singing his songs. I also wanted to learn to write my own songs and to learn from the great songwriters, and you can’t go wrong with Dylan. Every songwriter has to go through a Bob Dylan phase because he advanced the form so much.

I have vague memories of hearing him on the radio as a little child. The first song I think I heard was “Lay Lady Lay.” I was just a kid, and it was a little shocking because it was an adult song. I remember thinking, “Am I allowed to listen to this?”

INSIDE+OUT: What are some of your favorite Dylan songs to sing?

Joan Osborne: So many! I always loved the album, Oh Mercy. I recorded “Man in the Long Black Coat” on my first major-label record, a song I still really love. There’s another song on that album, “Shooting Star,” that I never recorded but we’ve been doing at live shows; it’s stunningly gorgeous. We did “Tangled Up in Blue” for a long time in the show. It’s a huge, sprawling story, like “The Odyssey” all in one song. Then, of course, there are big anthemic songs like “Forever Young.” Also “Mississippi,” another amazing song to do live that I haven’t recorded. Lately we’ve been doing “Lovesick,” which is another one I truly love. The live show isn’t just the songs we’ve recorded because the catalog is so rich and huge. There are so many things to dip into that we like to go there, into deep cuts and his devotees’ favorites, to surprise the audience.

INSIDE+OUT: Many people have covered Dylan, 600 at last count, from The Byrds, David Bowie, and Johnny Cash to Janis Joplin, Willie Nelson, Cat Power, and Bryan Ferry. Did any of them influence your approach to his catalog?

Joan Osborne: I don’t think so because my north star when I’m covering anyone is to find the place where my voice and perspective offer something uniquely mine. 

INSIDE+OUT: Your 2025 album, Dylanology (Live), features unexpected arrangements of songs like “Highway 61 Revisited,” a bluesy rocker in waltz-time, and “Masters of War,” which gets a heavier rock treatment than the acoustic blues on your 2017 studio disc, Song of Bob Dylan. Are you actively reinventing these songs to match the style of the musicians you are playing with at the time?

Joan Osborne: Yes. “Highway 61” has more of a Middle Eastern influence. I was just playing around with it on the guitar, and that feel came up, and it seemed to work. I brought it to the band, and they took off with it. That’s been a staple of the live shows for a while. As for “Masters of War,” the live album is full band, and on the studio album we switched between a full band and stripped-down acoustic; on the studio album it was the latter acoustic approach. On the live album, again, we had the full band, and we wanted to lean into the grit and anger and bring out the rage and message of the song. Dylan is good at that. When he’s focusing on people who deserve that anger, he’s like nobody else.

INSIDE+OUT: With your takes on “Rainy Day Woman” and “Spanish Harlem Incident,” there’s a lot of gospel flavor. Has this genre had a bigger influence on your music in recent years?

Joan Osborne: That’s always been a place I like to go. When I first started out singing, I was listening to and trying to emulate a lot of blues, R&B, and gospel singers like Mahalia Jackson. I also worked with The Holmes Brothers, who brought a strong gospel flavor to their music. If you’re looking at any branch of American music, you’re going to find gospel in it. The soul and R&B music that we all love came out of gospel.

INSIDE+OUT: The live album features one of your longtime collaborators, Amy Helm, who is also a Hudson Valley local. What is your history with her, and that of her legendary father, Levon Helm of The Band?

Joan Osborne: I can’t really remember the first time I met Amy. I played the Barn when Levon was still living, and I think she was in the Ramble Band then. They played a set, then I played a set, and we jammed onstage together. I used to do a Mother’s Day show every year at the City Winery. I would be myself, along with other performers who were moms, and we would have different people every year. I remember she and Fiona Apple came down one year. I have known her for a long time and have great love and respect for her.

INSIDE+OUT: Your August 8th appearance at The Assembly in Kingston falls in the middle of your latest Dylanology Tour. What has the reception been so far? And are there any Dylan songs you are performing on this tour that aren’t available on the two albums?

Joan Osborne: The response has been wonderful. We do a show that’s full of Bob Dylan songs, some from the recordings and some we just want to do. People who come to the live show will get something a little different every time. I so appreciate my fans and want to bring them something fresh every show. I know how fortunate I am to still be out here doing this. We do end up doing some of my songs to balance it out. What’s gratifying is when young people come up to the autograph table after a show and say they’ve never heard Bob’s music before, or only the most popular songs. Some people say they never quite got it until they heard it with my voice, which is maybe more traditional than Bob’s. It’s very cool and quite humbling to think we are leading some younger listeners to appreciate an artist of Bob’s incredible stature.

Joan’s Origin Story

INSIDE+OUT: When did you first become interested in music, and who were your first big inspirations?

Joan Osborne: I’ve always loved to sing. I was in the madrigal choir beginning when I was 11 years old back in Kentucky, and we were doing these old English songs in five-, six- and seven-part harmony. There was something so transporting about that. I didn’t think for a minute that music was something I would do for money. I didn’t move to New York with doing music in mind; I moved to go to NYU Film School to become a documentary filmmaker. Music was a total accident.

When I was a kid, I listened to Top 40 radio, which was very varied at the time. You’d hear the Rolling Stones, The Spinners, Charlie Rich, Stevie Wonder, and more. It was through Elvis that I got an education in roots music. I loved all that, but I was thinking about becoming a filmmaker. Plus, if you told people where I grew up that you wanted to make a living in music, tour the world, and sell millions of records, it wouldn’t go over at all. 

INSIDE+OUT: What was the impetus for your shift from film to music when you got to NYC? 

Joan Osborne: There was a guy living in my building who invited me to have a drink at a blues bar on the corner of my block, the Abilene Café. After the band finished, the pianist kept playing, and this guy dared me to sing with him. I picked “God Bless the Child“ and sang. I wasn’t earth-shattering or anything. The pianist thought I was pretty good and invited me to come back for their weekly open mic. I was intimidated to sing in New York, but this was pretty low-pressure, so I started doing it there and then at open mics and jam sessions at other clubs. I started to meet a lot of musicians and found out about this rich music scene happening in New York City in the mid- to late-80s. A lot of it was roots music, with bands like The Surreal McCoys and songwriters like Chris Whitley. There was a lot going on, and I fell in love with it. It got to the point where I was spending all the money I should’ve been saving for my education on Howlin’ Wolf and Etta James records. It ended up taking over my life, and I put my own band together from the musicians I had been meeting.

INSIDE+OUT: Where did you do your early gigs?

Joan Osborne: The first gig I had was at a place called the Wonderland Blues Bar. I had taken my little rehearsal tape around to all these places, and nobody got back to me. Wonderland had a cancellation and called me, saying that if I could be there in two nights, I’d get a gig. I was terrified, so intimidated by the idea of singing at an actual show in New York. I was sick to my stomach and couldn’t open my eyes on stage. At the end of the night, they booked me again. Then we started playing other places: Mondo Cane, Mondo Perso, Nightingales, Rodeo Bar, Manny’s Car Wash, the Continental, Wetlands, and more. I played CBGB, but that was after I got a record deal, for a record release party.

INSIDE+OUT: From the Grateful Dead and Stevie Wonder to Emmylou Harris to Pavarotti, you’ve collaborated with some very heavy-hitting musicians. What are some of your fondest memories of these collaborations?

Joan Osborne: I’ve come to appreciate more and more the time I spent with the Dead. In the beginning, I spent all my time just learning the show, which, of course, changed from night to night. Now that it’s seven years behind me, I realize what a privilege it was to be with the band and in front of that audience, that great, peaceful, loving community. I remember one night at Red Rocks. It was my birthday, and I sang “Stella Blue,“ and it was one of the most transporting moments of my time on stage.

I also sang with Stevie Wonder at the Rock and Roll Hall of Fame Induction of Gladys Knight. My first album had just come out, and Paul Shaffer, the musical director, invited me up to sing with Stevie. I said no at first, then agreed. Another incredible moment.

INSIDE+OUT: Your 1995 album, Relish, and the single “What If God Was One of Us“ really skyrocketed you to international stardom. How did this impact you, both positively and negatively? And did it play a role in your taking a more independent, less corporate course in your career? 

Joan Osborne: I’m certainly very grateful that it happened; it was a wonderful thing in many ways. To have that global reach is incredibly gratifying. There were difficult parts. I’m an introvert by nature. I like my privacy and to tool around like a normal person. Stardom at that level puts you under a microscope, which can be disconcerting at times.

Actually, I was indie from the start. My first album was released on my own label. If I had come up with another global hit, I might’ve stayed corporate. But I decided I could live and be happy with a more modest version of it. The fame part of it was never something I loved.

INSIDE+OUT: Your 2022 album, Radio Waves, is a real treat for fans like me, a collection of live performances from radio stations around the world spanning 1995 to the 2010s. What was it like sifting through all these tapes to put it together? And what inspired your demo of “Real Love,“ an acapella with your stacked harmonies and a drum machine?

Joan Osborne: This was during COVID-19, when I wasn’t able to tour. So, I thought I’d give the fans something and keep myself busy. It was fun going back through all these performances, and there are still many more boxes of tapes to go through! I’m my own worst critic, but I thought these were all suitable for release.

“Real Love“ is a Toshi Reagon song. It’s somewhat similar to her approach, and I thought it would be a cool demo… so I did it.

INSIDE+OUT: Though you are widely known as a masterful interpreter of songs, you are also a songwriter with a substantial catalog of your own. Aside from Dylan, which songwriters most inspire you?

Joan Osborne: So many. Some of my favorites are Joan Armatrading, Van Morrison, Rickie Lee Jones, and The Rolling Stones. I also love the blues writers, folks like Willie Dixon and Muddy Waters. They have a style that cuts to the chase. I get ideas from other media, especially film. Film tells a story with images. I’m a huge fan of Fellini, Spike Lee, John Sayles, Fassbinder, and Truffaut, along with documentary filmmakers like Barbara Kopple.

Joan’s Hudson Valley Story

INSIDE+OUT: When did you first move to the Hudson Valley, and what drew you here?

Joan Osborne: I moved to Sullivan County in 1998, but that’s not really the Hudson Valley; it’s a different animal. I relocated to the Hudson Valley this past January. It seems all my friends, like Gail Ann Dorsey, Rachel Yamagata, and the folks in my band, are up here. It was hard to get together when I was so far away, an hour and a half away, sometimes a two-hour drive. Last night I went to the VFW Hall and saw my friend Cindy Cashdollar’s new honky-tonk band. It was an eight-minute drive home vs. 90 minutes. It’s just a more fun and less isolated place to be. It’s much easier to be part of the incredible Hudson Valley music scene than where I was before.

INSIDE+OUT: What are some of your favorite places to play and see a concert in the Hudson Valley?

Joan Osborne: I really like Opus 40 as a venue and a place to visit. It’s a really stunning place to see a show. I haven’t seen a show yet, but the Hutton Brickyards look terrific. I’ve been there to dine and hike the trails, and it seems like a beautiful spot to see a show. I really like The Assembly. The acoustics are first-rate, and it’s cool because people can just walk there from their houses if they live in Kingston. I also can’t wait to check out The Local in Saugerties. The programming seems really interesting and very adventurous.

INSIDE+OUT: Who are some of the local musicians who most inspire you?

Joan Osborne:  As I mentioned, I just saw her really cool honky-tonk band with Connor Kennedy, Will Bryant, and Lee Falco. John Sebastian sometimes sits in with them. It’s a blazing, kick-ass country band. No one in Nashville or Texas would complain about them. I also love Olivier Manchon, a wonderful composer and string arranger who has worked on many films and on my albums. 

I can’t say enough about Rachael Yamagata. She has a one-in-a-million voice and is an incredible songwriter. I first met her at the annual John Lennon charity concert in New York. I was backstage when I heard an incredible voice coming from a dressing room, and I had to head straight there to meet her. If this were the 1970s, the era of the singer-songwriter, she would be a mega-star on the level of Taylor Swift. She’s also an incredibly cool chick. You have to catch her on a recent episode of Nora Jones’ podcast, “Nora Jones Is Play Along with…”. Nora’s jaw is on the floor listening to Rachael. As I said, she’s one-in-a-million. 

INSIDE+OUT: What are some of your favorite activities and places to go in the Hudson Valley?

Joan Osborne: I love going on the hiking trails. And I’ve been on a mission to find all the great swimming holes this summer – some of which are well known, and others that are like a top secret.

INSIDE+OUT: What is the Hudson Valley missing that you wish it had?

Joan Osborne: Better parking at the Rhinecliff train station! 

INSIDE+OUT: Everyone has someone who changes how they see the world. Famous or not, who has had that impact on you, and how has it shaped your creative life? 

Joan Osborne:  My music teacher from Kentucky, Carolyn Browning. She believed in our capacity, giving young kids challenging pieces to learn in the chorus. I learned a ton about music, especially harmony singing, from her. How to keep your part when there are so many other voices singing their own notes. She singled me out and said I was talented; she gave me extra work and solos to sing. It was invaluable.

INSIDE+OUT: If you could have one superpower, what would it be?

Joan Osborne: To be able to heal people.

Photos courtesy of Joan Osborne and Laura Crosta

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