Sherry Winston has entertained us with her magical flute for over three decades. The Grammy-nominated artist who has entertained presidents and dignitaries is a dynamo who made playing the flute her life’s work.  Despite a few odds, she grabbed the reins of her career and pulled them in a direction that gave her life purpose, promise, and her reward has been an enviable career.

The petite force to be reckoned with who has worked with some of jazz’s creme de la creme artists has now also added to her repertoire a cookbook, For Lovers Only–A Cookbook and More.  

The musician, writer, lecturer, composer, and businesswoman chatted with entertainment writer, Leon Goodman, about her brilliant career and about what looms on the horizon.

50BOLD: I’d like to start at the beginning. Actually, you were recently inducted into the Connecticut Women’s Hall of Fame. What are your thoughts about the prestigious award?

Sherry: Well, I was totally excited when I found out about the award. You know, I think many artists are a little incredulous when first informed that their accomplishments are being honored. When I finally realized I was being honored, I was thrilled that the experiences that have brought me to this point were being recognized. I think any artist would feel humbled to be recognized for their work. So now that I am receiving awards from various organizations, I feel as if I’ve been blessed by God.

Sherry and Leon Goodman at the Connecticut Women’s Hall of Fame

50BOLD: Let me also express how thrilled I was to be at the awards ceremony. It was just an amazing experience.

Sherry: Well, it was so wonderful to have you there as well; I will never ever forget all of your efforts on my behalf.

50BOLD: Let’s now discuss how did you develop your affinity for the flute?

Sherry: I really wanted to be a drummer. I was a tomboy and wanted to bang on something. So when we were lined up at junior high school for musical instrument selections, it was done alphabetically. By the time it was my turn to select an instrument, the only ones that were left was a tuba and flute. So the teacher pointed to a tuba that was sitting in a corner. It was big, ugly and monstrous looking. It was also on the rusty side and looked bigger than I was at the time.  So, the tuba was out! I selected the flute instead.

When I began trying to blow into the flute’s mouthpiece I couldn’t produce a sound to save my life; it was a bit embarrassing ego-wise. I asked the teacher if I could take the flute home and at least try to produce a sound from it. So, I took it home and spent hours trying to produce a sound then finally, it came! I kept playing the flute because I never wanted to be the worse music student.

One summer I attended a camp, it was African American, and took my flute along. Anyone who attended the camp will always remember that all I did was practice playing the flute. I was supposed to be there having fun and enjoying myself. So, I developed a passion about playing the flute from the very beginning.

50BOLD: Did you grow up in Queens, New York?

Sherry: Yes, I grew up in Queens in the Corona section. Queens is where I spent all of my youth and teenage years before heading off to Howard University.

50BOLD: Have you had a lot of doors closed in your face because you are a female?

Sherry: I don’t know that they were closed in my face. I don’t think they were ever opened in the first place! So here was my dilemma, where do you go playing flute? You head towards trying out for an orchestra, regional or national.   I knew about some of the larger orchestral organizations like the Los Angeles Philharmonic. Although there were not a lot of African Americans who were accepted into the larger symphony orchestras because of prejudice.

I have a classical music degree from Howard. When I attended the university, I entered talent contests. The Howard shows were similar to New York City’s Apollo Theater, if they didn’t like you’d get the axe. So a performer had to get themselves together before attempting to perform for a Howard crowd. So a musician getting up on stage and playing classical music would not last three minutes, they’d get booed off. So during my earlier years, I had to play something funky from like Motown, whatever was popular at the time.

When I stepped onto the stage and folks saw my flute, everybody started laughing. When the guy who I was playing with began playing this funky riff, everyone was taken aback in a good way.  The audience loved what they heard coming from my flute. So I went in the direction of jazz and participated in more contests. It was such a wonderful experience, being around African Americans, and being judged for my talent rather than for the color of my skin.

50BOLD: What inspired you to create your own Love Note record label?

Sherry: Love Note is actually my newsletter and Flying Flute Records is my label. When I was signed with these record companies, I received national airplay and recognition around the country. What I eventually discovered, however, was that I was being ripped off financially by a few of them. One day, a record label employee let it slip out of the bag how many records I had actually sold. A record executive then stated how the numbers I was quoted were not accurate. I was not receiving my true royalties. I grew tired of putting in all of this work, then not getting paid for it—RIDICULOUS! So I decided to create my own label and to distribute my own music. Luckily, when I was signed with record companies, I would never allow anyone to produce me. I always produced all of my records and selected all of the songs, musicians, and decided what the tunes were going to sound like. I just wanted to have complete control over my product.

50BOLD: Did you work in the recording industry as a marketing director? How did you build momentum in your career?

Sherry: I was technically a Director of Jazz Promotion but this is not how I started out in the industry. I began working as a receptionist at a record company and did not know diddley squat about the recording business. I couldn’t start out as an executive even though I had a degree in music, but one thing has nothing to do with the other. So I began answering phones for different record companies. I came in contact with a lot of very well known pop artists.

The label I worked for decided to add a jazz division to its roster. Even though I worked as a receptionist, my ego did not want me to remain in the position. I decided I had to leave my job. So then I became a secretary at the label for one executive. After about a month, I worked for several record execs. And I would eavesdrop to learn how do you promote a record to radio stations. After about a year or so of working as a secretary, I was asked to do some college radio promotion to push the records that were produced by the label. In my role, I was traveling a lot, and not making any more money than I was as a secretary but I had a little title.

Another record company heard about what I was doing, and asked me to come and work for them for double my salary. So this kind of how you try to build a reputation and then there are those next steps. So I kept doing promotion until I wound up with about thirty-five jazz artists, some of the biggest names in the industry. My job was very stressful, taxing, there was a lot of competition in that field I had to deal with and the role took a toll on me. It really did.

50BOLD: You wanna name drop, maybe mention a couple of jazz greats you worked with during your stint at the various labels?

Sherry: Sure! I worked with artists like Miles Davis and Herbie Hancock; there were quite a few.

50BOLD: So when you were ready to make the transition from business professional to performer, you had already laid the groundwork to propel your career forward.

Sherry: Well, not exactly. While I was working for record companies, whenever I would come across a gig, I would try to put musicians together to play at these little clubs. Eventually, I wound up at a pretty famous club in New York City, and started playing there without even having a recording.

Before Columbia Records, I was actually making recordings on the side and I was doing so at night. I’d go into the studio and self-finance these recordings with my record company salary. And sometimes we’d work until two or three in the morning. I’d only get a few hours sleep and then get up for work. I always made sure, I was on time. I finally had a period where I was laid off and began doing independent promotions out of my house. I had a lot more freedom. I could play at night, nobody would be looking over my shoulder and then record. And when Columbia Records heard about my departure from my record company, one of the vice presidents called me and stated, how they wanted me to come in and work for them. I told them I had a record and was getting ready to drop another one. I didn’t know if I wanted to make the move.

I was in a very tenuous position because I never knew what my finances were going to be from one week to the next. I was also self-financing my recordings. So I called the VP and laid it on the line, I told him that I was a recording artist. The exec told me to come in for a conversation and I did. I had a gig like a couple of days after my meeting. An Epic Records executive heard me play at the gig and this was my professional break. The man approached me after my set, stuck his card in my pocket and started raving how he wanted to record with me. He also wanted me to produce some artists; I almost had a heart attack; I was so excited but had already accepted another job.

50BOLD: Nothing like a few conflicting decisions, huh?

Sherry: Well, it was big-time drama. So when I went in to see this executive and he mentioned the amount of money they were willing to fork over. It was like huge compared to what I was making and I was like, Oh my god! Well, I mentioned how I was a recording artist first. And the exec actually said that I would have to stop playing! Well, I told him, “I’ll see you later, goodbye!” He told me, “Wait a minute! Wait a minute!”

I asked the record exec to listen to my recordings in particular, my first CD, Do It For Love. And he told his secretary to hold his calls. He actually listened to the entire record until it was finished. I couldn’t believe he gave me that kind of time. So when the album finished playing in its entirety, the exec sat there looking at me, and said, “ I can’t ask you to give that up, that would be crazy!” I responded, “Yeah, that would be like cutting off my right arm!” We agreed that I would not play when I was supposed to be promoting an artist. I understood.

I accepted the job but then I got an offer from another record company. Things got a little ugly involving my second offer so I stuck with my first and stayed the course with my desire to record. There was no way folks were going to keep me from making another recording. So at night when I would leave the record company I worked for then head straight to the recording studio. The schedule was again, so grueling. I was getting home really late, 3:00 am to 4:00 am and then getting to work at 10:00 am.

I always went to the gym first to kind of wake myself up and to get my brain going. So I would get to the gym around 8:00 am and then be at my desk by 10:00 am. So when my recording was released, my boss and my boss’s boss noticed it on charts like Billboard and Cashbox. Soon, all of these music industry magazines were taking about Sherry Winston, and my bosses wondered, was it me they were raving about. They did not know I had been recording.

So I was called to the carpet and accused of promoting myself instead of artists like Wynton Marsalis whose album lagged behind mine. I defended myself to my accusers and explained how I had hired my own team to handle my promotion. I was accused of lying. The situation got ugly; I was fired and and escorted off the record label’s premises by an armed guard. It was all so shocking but the negativity fueled me to keep working at making my dream happen!

50BOLD: How would you categorize your musical style?

Sherry: I would say funky, melodic and some of it is very romantic. So I would say my has classical influences; it’s true jazz fusion. It’s a mix of several influences.

50BOLD: So you try to cover all the genres.

Sherry: It’s not that I try to do anything, it’s what my heart puts out there musically. It’s like something that I recently heard up in Canada, and I’m preparing to learn it. If something touches me musically I go with it, and that’s how I’ve been able to select all of my music. And when I write music I think God is whispering in my ear because he gives us gifts. So I acknowledge him in that he speaks to me through music.

Sherry and Stevie Wonder

50BOLD: How did you get to perform with Stevie Wonder?

Sherry: Well Hal Jackson who was a beloved radio personality at the famed New York City radio station, WBLS, had interviewed me several times. He was so supportive of my music. So the radio station would hold these events at the Apollo Theater and I played for many of them. I would be the only jazz artist present. There were all of these R&B artists like Melba Moore and other folks at the event and there I’d be playing flute. So Hal’s wife, Debbie, wanted to throw a surprise birthday party for her husband’s 97th birthday, and asked if I would attend. Stevie was also invited but Debbie was not sure if he would show up. She said if I came to the affair, I could rehearse with Stevie’s band and if he showed up, I should be ready to play at the drop of a hat. I thought she was kidding!

I practiced with Stevie’s band that WBLS had put together. The band was smoking. I had sent the band an MP3 file of a song and they learned it. So we practiced the song. I was excited about possibly performing it. The party was in full swing with celebs all around and artists that Hal was very instrumental in helping career wise. All of a sudden there was a commotion, Stevie Wonder had arrived at the event. Everybody started screaming and the women were jumping up and down, and all over Stevie. I couldn’t even see him because there were so many women surrounding him.

Hal’s daughter, Jewel, was one of my biggest supporters; she had hired me to play for a 100 Black Women affair. Jewel knew I was supposed to play for Stevie. So Debbie came over to me and the band and said, “Start playing the song, start playing the song!” So we started playing Past Time Paradise and all of these women kept trying to talk to Stevie and tug on him as they attempted to take pictures. So Jewel went right over and was able to move these women out of the way so that Stevie could pay attention and listen to me. All of a sudden, Stevie jumped up and turned his head back and forth to determine where this music was coming from. Jewel came up to me and said, “Go down the aisle girl, go down the aisle,” she was wonderful. So I playing and walking towards Stevie, he then reached for his harmonica and just spontaneously began accompanying me. So we’re performing the song together and I thought I would die! I kept hoping that I wouldn’t mess up the song. Performing with Stevie was the most incredible night of my life.

Stevie was so fantastic! After the performance, he came over to say how he wanted to record with me. Stevie’s aide gave me his number. I kept calling Stevie’s aide the next day. I bugged this man for months but Stevie’s aide never returned my phone calls. I bet the aide never even told Stevie that I had even called! It was all so disappointing because Stevie was so excited about recording with me.

50BOLD. You have performed with other Iconic artists do you want to name drop?

Sherry: Grover Washington is on one of my CDs. I’ve also worked with Patrice Rushen, Kurt Whalum and Jon Lucien.

50BOLD: You have performed for some dignitaries as well at the White House.

Sherry: Yes, I played for Bill and Hillary Clinton when he was first elected into office. I so wanted to perform for the Clintons and tried to get an in via connections. So, I made one of my yearly trips to Barbados and when I got back home, I heard this on my answering machine… “This is the White House, and this is the 2nd time we’re calling you to perform. And if you don’t call us back by today we’re going to take the offer off the table!” I almost wet myself; I swear to God! So I immediately called back and was told that I could only bring acoustic instruments. I couldn’t bring a drummer. I couldn’t bring my base player because he didn’t have a stand up base. My keyboard player couldn’t bring his electric keyboards because there was some association with bombs and sneaking it one in via a piano or something. Oh, the entire situation became so complicated but in the end, I played for the President and First Lady!  I also played for the former president George H. Bush in New York City.

50BOLD: Do you want to talk about Sherry Winston the author?

Sherry: Sure, this is a lesson in sticktoitiveness with whatever you choose to do! It took me 19 years to actually get my book out. And the reason it took so long was because I sent it out to agents and then directly to publishers and it kept getting rejected. I felt as if I was being told, “You’re not a trained chef. You don’t work in a big restaurant. You don’t even own a restaurant. Who do you think you are? What do you know about entertaining.” So, the rejections were a real put down for me as a person. Rachel Ray doesn’t have any culinary credentials either and she has her own TV show and is incredibly successful. So I put the book project down for five years. The book literally sat on my desk, and I continued recording and performing. I was busy all the time and wasn’t focusing on the book.

One day, as the Lord will do, he directed my eyes onto this huge manuscript just sitting on my desk. I looked at this book, a project that I had dedicated so many late night hours to and there it was just sitting on my desk. So I decided to work on it again. I began calling around for a referral to a great editor who had just retired. I was able to hire her, along with a photographer who was a classmate of mine at Howard and so we all went to work on the book.

50BOLD: And the name of the cookbook is…?

Sherry:  For Lovers Only–A Cookbook and More and it comes with my romantic CD that can be played as you’re entertaining. The CD addition was kind of an afterthought but it works!

50BOLD: What is your favorite recipe from the book?

Sherry: I personally like the chicken wings on the front cover with black beans and rice. The wings have a mustard-based garlic sauce. You can cook the rice in advance. You can also cook the black beans in advance and then heat them up within 10 minutes. I would say cook the chicken wings right before you serve them.  My other favorite recipe is veal piccata.

50BOLD: What is the one thing you’re truly passionate about?

Sherry: Scuba diving! I love it! Being under water you get to see all of God’s creatures down there and the most beautiful fish in the world. I’ve been to Fiji, the Hawaiian Islands, Indonesia, Tahiti and the reefs are stunning! When I surface from the water, no matter how many times I’ve scuba dived, I just shake my head in amazement.

50BOLD: What’s next for Sherry Winston?

Sherry: Well, I want to record just a few more songs again because people are buying less CDs. Perhaps I’ll produce a simpler and less extensive recording that can be played at Pandora and Spotify. I would love to receive a Grammy, this would be wonderful. I’d like to also play bigger stages, perform concerts at larger venues.

50BOLD: Can your music be found on Pandora?

Sherry: Yes it can be fond on Pandora and it’s pretty much on every platform that you can go to including Spotify and CD Baby. Folks can also visit my website to order my CDs and cookbook from there.

50BOLD:  By the way, what is your favorite Sherry Winston song?

Sherry:  I like the song Do It for Love which I consider to be the ultimate love song!



Author Leon Goodman hosted the Lou Rawls Parade of Stars for several years. A retired human resources executive, he is currently an actor who has appeared on such TV shows as Blacklist and Bull. Leon can be seen in the upcoming feature films, John Wick 3: Parabellum starring Keanu Reeves and Halle Berry, as well as The Drummer starring Danny Glover.