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Libby York

Vocalist Libby York will be performing at Winter’s Jazz Club June 19th along with pianist Jeremy Kahn and trombonist Russ Phillips presenting a show called “Three For The Road: Traveling Light” featuring songs of travel to favorite destinations, both terrestrial and celestial.


We thought we would catch up with Libby and talk about how she got started in music, her influences, living and performing in New York, Chicago and Key West and how she conceptualizes her music.

1  When you were growing up tell us about how you were first drawn to music?  Did you grow up in a musical home? 


Although they were not professional musicians, my parents both played piano and sang and loved the Great American Songbook. I heard a lot of Sinatra, Rosemary Clooney, Benny Goodman, Art Hodes played around the house. I still have many of my Dad’s great 78’s. They were both Northwestern grads and Dad wrote a nightlife column for the Purple Parrot, the NU mag, which is great to read now with accounts of every famous band coming through town and all the many clubs in the 30’s and 40’s.

He would occasionally sit in & sing with the big bands that came to NU. The family story is Dad & friends who grew up in Winnetka were the inspiration for Bob Crosby’s “ Big Noise from Winnetka”, when they caused a commotion at the Huddle in Evanston. I always got the feeling from my parents that this music was to be treasured and the musicians to be admired and respected.

2  Was there a person or experience that drew you to start singing? 


I suppose I was given the gift of a natural voice because I was chosen early on to be in school musicals. My first “promo shot” was singing at O’Keefe Grade School on the south side. I remember auditioning in class and being kind of surprised they picked me. While I was at Sullivan High School, I’d go after school to a record store on Morse Avenue, near the old Asheknaz where we’d hang out every day, and in addition to the rock & roll I was buying, I somehow got a hold of Frank D’Rone’s first album. This made a huge impression on me and set the bar really high for how this music was to be done. I’m so grateful to eventually become friends with Frank & Joan D’Rone which enabled me the chance to tell Frank how much his music meant to me. Singing duets with him at the Jazz Showcase was a dream come true. Also in high school I got June Christy’s Something Cool album and I was hooked. Played both these albums over and over.  I also always loved Johnny Mathis…. still do! Of course, then listened to Ella, Sarah, Betty, Joe Williams… all the greats.

Winters Jazz Cub

3  Did you go to school for music?


I graduated in Political Science at American University in Washington DC. There weren't many college jazz programs then and I didn’t start singing professionally till I was 35. Before then I taught for awhile in DC and then opened a restaurant, The Back Porch Cafe in Rehoboth Beach, Delaware, now in its 45th year.  My music education really began on the bandstand. I had taken piano lessons with Yehuda Guttman, a classical pianist and Juilliard scholar, who lived in Key West. He was a wonderful teacher and really taught me how to work. “Slow is fast” one bar at a time, separate hands, then put both hands together. Even though I had very basic piano, sight reading training I loved playing simple Chopin Nocturnes, Bach Inventions, etc.  After I moved to New York and was playing gigs, I had to double back and take some voice coaching on how to use my voice if I was going to perform regularly. One memorable teacher who lived near Lincoln Center heard me and said “Oh, you're a crooner.” And I thought, yes I guess that’s true . I attended workshops for sight reading, accompanying myself on piano, etc. But my main training has been on the bandstand in front of an audience. Trial by fire.


4  Who were some of your musical influences and why?


There was a wonderful singer’s workshop down on Great Jones Street in Manhattan run by Cobi Narita. I was one of the “New Discoveries” of 1980 -something.  Our accompanying trio was Harold Mabern, piano, Jamil Nasser, bass and Frank Gant on drums! One of our teachers was the great Abbey Lincoln. She and I became friends and she was a huge influence on me, as she was to so many. Our styles are not alike but the honesty and soulfulness of how she approached a song sent a strong message.  I love Rosemary Clooney’s comment “I’m a singer of fine songs who works with jazz musicians.” What she does is so deceptively simple, imbuing every word with meaning. I’m not a scat singer…actually don't enjoy hearing it except from the best…but improvising with phrasing is endlessly fascinating. I had a memorable lesson with Kitty Margolis in San Francisco once. She suggested I “try putting the lyric in a bar where it doesn’t belong.”  This is something I’m still having so much fun with, improvising with phrasing. I’m a firm believer of giving the song its due and singing it more or less as written one time through before you begin improvising.  Being present in the moment with the lyric is vital. And it’s got to swing.


Green Mill Jazz Club

5  Was there a specific performance or moment that you had which helped you turn music into a career?


Interesting question since it’s been a process, not a moment, for me.  I very much see myself as part of the band, and working with wonderful musicians is such a joy. In terms of performance, there are moments when I’m playing in a club when the sound is good, the band is in sync and the music becomes effortless …that high that I get really reaffirms the essential reason why we do this.  I learn something every time I perform about connecting with an audience, staying in the pocket, living the lyric, etc. 


Early on in New York, being featured vocalist with Barry Bryson’s 8 piece band “Swing Street”  was a great learning experience. I answered an ad in the Village Voice, sent in my recording, a cassette in those days, and got the gig! We played all around town for dancers, parties and big events including the opening of South Street Seaport and a big party for Jim Henson at the famed Starlight Roof of the Waldorf. That band had great players including Doug Lawrence, saxes, Bill Moring, bass, James Chirillo, guitar, Matt Finders, trombone.  I also had a steady gig at Cousins in Brooklyn with Tardo Hammer, Ted Kooshian, Lynn Seaton, John Hebert and Neil Miner. That was great experience. I also sang in LA with Jack Sheldon which was very memorable.  I remember he said “Libby, I’ll keep it clean for you!”  


Recording and producing my 4 CD’s has also been an amazing creative experience. From the moment you conceive the theme, choose the repertoire, think through the arrangements, schedule the band and studio, go over each day’s recording meticulously, oversee the graphics, choose radio and press PR, it’s really a creative project like no other…not to mention writing the checks and figuring out how to pay for it. You are in control as much as circumstances will allow. Thousands of decisions.  Lots of waking up at 4 AM with ideas or fears, but when the finished product goes out on the airwaves around the world it’s an exhilarating experience. I have a new project in the works so just the thought of going through all that again is frisson- making. 


I think the validation of having my performances and recordings appreciated by musicians I admire and respect helped in forming my self awareness that yes, this is who I am and what I do. There’s something to be said for having done it long enough to feel I’m kind of starting to get the hang of it. My first recording Blue Gardenia was done here in Chicago for Southport Records and I learned a lot working with wonderful Joanie and Sparrow.  My next release Sunday in New York (Blujazz) was recorded in New York with Frank Wess, Renee Rosnes, Todd Coolman and Billy Drummond and Neil Tesser wrote the liner notes. This was kind of a breakthrough and got lots of airplay, made the JazzWeek charts, etc.  Recording and producing the next two albums Here With You at Bennett Studios with Howard Alden, Russell Malone, Warren Vache with liner notes by Adam Gopnik of the New Yorker, who became a friend, and my latest, Memoir with Russell, Warren, Martin Wind, and John DiMartino, and Greg Sergo was a joy.  I’m so glad Greg was able to come to New York to record because he passed not all that long afterwards. Connecting with jazz radio folks around the world is one of my favorite things…talk about a labor of love on their part!


210 Live Jazz Club

6  Your repertoire seems deeply rooted in the Mercer, Van Huesen and Gershwin songbooks. What is it about those composers that connects with you?

I’m drawn first to the lyric. Johnny Mercer is definitely one of the composers I feel most simpatico with…. the cleverness of his lyrics and that southern Savannah feel. I also love the freedom of just doing songs I like. Lately I’ve added a song written by Pulitzer Prize winner Kazuo Ishiguro “Remains Of The Day” and Jim Tomlinson that Jim sent me from his recording with his wife, the great singer Stacey Kent. I have songs in my repertoire by Irving Berlin, Truman Capote, Noel Coward and Donald Fagen. I tend to stay away from the “woman as victim” lyrics and love a little humor when possible.  The poignancy of “Something Cool” or Peggy Lee’s “Cloudy Morning” grabs me too.

7  You not only live in Chicago but you also have a residence in Key West and you perform regularly there during the Winter. How did end up in Key West and what is the music scene like?


Key West has been home base for many years. When we opened the Back Porch Cafe we had winters off so someone suggested Key West.  I fell in love with the historic wood frame conch houses, swimming in the aquamarine sea, riding my bicycle everywhere, and all the fascinating artists and writers who live there. Perfect home base for the winter, easy flights to NYC. I still work quite a bit there. Last winter The Studios Of Key West mounted a “Remembering Lenny” production to celebrate Bernstein’s time in Key West which I was happy to be a part of.  He hung out down there and I was fortunate to sing with the great maestro at a dinner party one night. For a two mile by four mile island the very cosmopolitan, international community there is pretty amazing. I also love doing concerts at the Truman Little White House, where Harry Truman spent so much time. It’s now a museum run by the State of Florida, and they occasionally open up the living room for the ultimate house concert. Jeremy Kahn, Andy Brown, Howard Alden have all been down to work with me there. There isn't as much of a jazz scene on the island as there used to be, but I still perform at The Gardens Hotel, Little Room Jazz Club, The Tennessee Williams Theater, private parties, etc.

8  You also have a strong presence in New York.  How did you establish yourself in New York and is there a difference between the Chicago jazz audience and New York jazz audience?


I moved to New York in 1981 and stayed for about 15 years, with a lot of time back there since then. That’s really where I learned to sing, to work with a band. The struggle of living in New York, always having some part time job to make ends meet, my most notable was a short stint as PA, production assistant, on Saturday Night Live. Living in New York I was surrounded by so many of the best players in the world who formed my vision of how the music should sound. Early on in New York, someone told me “there are always going to be singers who you think are better than you.”  This helped me a lot in dealing with the feeling of competition. You kind of get over yourself and always support the fellow musicians you admire. Chicago is a great jazz town with incredible musicians who I love working with. The city has also some very loyal fans who love the people who have been here for many years, while also being open to excellence wherever they find it.  It’s really wonderful to see the sold out house recently at Studebaker Theater for the CJO with my friend Paul Marinaro, or an enthusiastic full house for Jazz at Symphony Center or one of the fine clubs. Of course the Chicago Jazz Festival and Jazz Institute of Chicago are world class as well. The musicians and audiences are here!


I’m kind of in a funny place, since even though I was born and raised in Rogers Park because I lived on the east coast for so long I’m still building an audience here. Up until my partner, drummer Greg Sergo, passed in 2014, I hadn't kept a residence in Chicago for quite a while.

Hyde Park Jazz Society Room 43
Hunters Jazz Jam Session
Libby York
Libby York
Libby York

9  Tell us about your upcoming performance at Winter’s Jazz Club coming up on June 19th.  Who are the musicians performing with you and what will the repertoire be for that evening? (feel free to expand on the musicians you are playing with, how long you have known them, etc.)


It’s been so much fun putting the songs together for June 19th. The show is called “Three For The Road: Traveling Light” and Jeremy Kahn, Russ Phillips and I are presenting songs of favorite destinations, both celestial and terrestrial, I just like saying that!  Travel has always been a passion for me ever since my grandfather, florist Otto Amling of Amling’s Flowerland, would travel the world for business and bring back gifts from far flung places.  We’ll swing songs such as “Mountain Greenery”, “Rhode Island Is Famous For You”, “The Summer We Crossed Europe in the Rain”, the great Dave Frishberg tune “Do You Miss New York”, “Paris Blues”, “Corcovado" and of course, “Chicago”.  Pianist Jeremy Kahn is really my right hand man on Chicago stages for his wonderful, inventive, sensitive, swinging playing and he always has my back!  What a talent! This will be just the second time I’ve had the chance to work with the wonderful Russ Phillips, even though he and Jeannie Lambert have been friends for years. I love the beautiful, mellow tone he gets on his trombone. Since Russ sings too, we have a couple of special vocal duets on tap. It promises to be an especially fun night & I hope folks will come out! 


Sunday June 17the  and 9pm l I’ll be live in the WGN studios with Rick Kogan on his After Hours show. We’ll chat about the Winter’s date, and whatever else we come up with.  Talk about a Chicago treasure always love being with Rick.



10  What do you have coming up after your performance at Winter’s Jazz Club on June 19th?


I look forward to returning to Mezzrow NYC August 28 with Michael Kanan, piano, and Neil Miner, bass. Spike Wilner has created the closet thing to the old Bradleys, an intimate listening room and wonderful hang.


Before that, July holds several Chicago dates with great musicians: July 6 Music By The Fountain concert at the Fourth Presbyterian Church with Andy Brown on guitar, July 19 Marie’s Pizza with JoAnn Dougherty and Larry Kohut, July 25 WDCB night at Parker’s, July 30 Serbian Village with Tom Muellner’s group, I’m headed to California early August….gig dates soon. And it’s become something of a tradition for me to celebrate my birthday at the Jazz Showcase, so I’ll be back there in September to mark my 74th trip around the sun. That will be one of the last Chicago dates till spring as I’m singing in Paris in October.


Details for all dates at   A recent reviewer said I was “a keeper of the flame of jazz singing.” I’ll take it. I still find it endlessly fascinating, challenging, creative and joyful. Heaven knows, we need the music now more than ever.  There’s nothing I’d rather do and I’m grateful for the chance to live this jazz life. Jazz musicians and fans are the most fascinating people!

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