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Remembering Robert Shy - Friends Share Their Memories of the Legendary Chicago Jazz Drummer

Updated: Dec 15, 2018


Photo by Bill Klewitz


On November 8th Chicago lost a jazz legend, drummer Robert Shy. Known for his hard driving swinging feel, his attention to detail on and off the bandstand and his wonderful encouraging personality, Robert Shy was always someone that helped to lift the music to another level.


We thought we would reach out to musicians and friends who knew Robert Shy so that they could share their memories and pay tribute to a man that meant so much to the legacy of Chicago Jazz music.



From Marlene Rosenberg

Photo by Bill Klewitz


I am so very saddened by Robert’s passing. I can barely believe you’ve left this realm. That’s why I haven’t written anything especially coming on the wings of Roy Hargrove’s passing. I still can hardly believe you’re gone to a place where many have recently gone. What a swingin band it is “there!”... I was going to call many times just to say “hey” …but I didn’t. How many times have we heard this comment and have I done this? I’m trying to do better…

...Robert, you have enriched so many lives with your calm and cool and loving demeanor, musical energy, colorful solos, swingin’ medium grooves, quircky and silly sense of humor and funny repeated Robert Shy- (“but I’m not”...”Shy”)-isms.


I have a long list of Shy-isms- for instance- you putting your fingers up on your head like “Horns” of a Ram or Bull, because I was Aries, and you were Taurus and we both were, well….kind of stubborn..lol and somewhat fiery when we played music. Or…at least, the music made us, or you, and me feel the “fire”, and inspired to do the best we could.

Robert would ask about my daughter Samantha Hey…”how’s little bit?” (when she was younger)- just funny little ways of saying things and explaining your thoughts.


I remember a time we went to the drum shop on Wabash to check out cymbals, and you taught me how you listened to the pitch, tone and harmonics of each one to see how they might fit into the music you heard in your ear. I’ll never forget this moment as we went from cymbal to cymbal. I was in awe. Truly ear opening! Drummers’ forth have me listening to all the resonance of the cymbals they’ve chosen. Of course the sticks and mostly the player has much to do with the music from the chosen “tools”, but never the less, I feel like I’ve been “let in” on the little “secret” regarding drums and cymbals and ALL the tones and sounds that can be chosen.


The world is a bit less swingin’, vibrant, musical, humorous and warm now that you’ve passed... Your rhythms have left an impression that I will eternally miss and am thankful for. You were 100 Plus percent supportive of me, and many along the way. You worked so hard to provide a comfortable and loving life for your family as you continued to pursue your love for the music.


A life well lived, I believe. I hope you felt this way before you left Robert, I really do. Thank-you so much.


You will be missed!


My sincerest condolences to your wife Florence, and your children and family.


Rest in Peace and Music Robert.


Marlene Rosenberg

From Larry Gray


I am blessed to have a history of playing with Robert that spans 43 years, and there were many wonderful, and often amazing, musical moments in between. For me, meeting and first playing with Robert as I turned 21 was pivotal, and it forged a memorable relationship with him over the next four decades. I am so grateful that I was able to play a final gig with him this past August at the Chicago Jazz Festival where we performed in celebration of the musical life of the great Willie Pickens.


There is a consistent thread to my memories of Robert Shy. In short, Robert had a beautiful and positive spirit. He was extremely balanced and had a fantastic sense of humor. Some of his jokes, totally silly on the surface, still make me laugh whenever I replay his delivery in my mind. I can’t help but smile when I recall the many wonderful moments shared at jazz festivals and on jazz cruises with Robert and his wife Florence, along with my wife Karolyn and daughter Soffia. Those will always be cherished memories.


Robert had fortitude, and that was particularly inspiring. While holding down a full time job driving a semi truck during the day (which began, I understand, after getting off the road with Rahsaan Roland Kirk), Robert would show up every night and play 2 or 3 sets of hard jazz at an extremely high level. I would occasionally “pick his brain,” and it was clear that there was a very powerful inner strength in Robert. I know he listened and practiced in his mind all day long and, clearly, he was ready for the gig. I don’t ever remember him saying he was tired; he was pretty amazing all in all. To think that his whole musical concept was clearly built upon creativity, formed and founded in improvisation, makes it even more remarkable. Thinking back, his focus, especially given his day-to-day schedule, was nothing short of extraordinary.


As a musician, Robert focused on presence and connection. He brought a buoyant energy to every gig. He had a strong individual identity, and his sound and approach to the drums was, despite obvious influences, completely his own. I had a sense that he heard music a little “differently,” and I found that both fascinating and intriguing. This individual identity, voice, and sound was always there, no matter the gig. He extended this careful connection to sound and texture to his relationship with his instruments. He was always working on the drums, deciding about tuning or the like within the context of the date. As great as his time playing, group sound, and feeling was, he was also a most powerful and compelling soloist, whether trading with horns or playing an extended solo.


I have many musical memories of Robert, and they often involve our time together at the Jazz Showcase. In fact, I recall him coming to the Showcase to listen to a gig I was on with pianist Benny Green. Benny had brought his own drummer, and we were playing the last night of a six-night engagement. Robert was invited to sit in along with the wonderful guitarist Henry Johnson. I will never forget, aside from how terrific and unique Robert sounded right away, the way Benny Green responded to Robert’s presence. Benny looked at me with a kind of “who is this guy” look combined with “wow!” Immediately, Benny’s harmonic approach and feel changed, clearly inspired by Robert.


One of Robert’s favorite lines, which I’m sure most Chicago players know well, was “we’ll pick up right were we left off,” which is the best way to think about Robert. He was always moving forward,on to the next gig. For me, memories of Robert Shy will always live brightly and his legacy of musical gifts will continue.


From Dave Jemilo

Robert Shy performing with Ed Peterson, Brian Sandstrom, Eric Schneider and Willie Pickens (not pictured) New Year's Eve 2013 at the Green Mill.


Robert Shy will be sorely missed by all, especially the Green Mill family. Robert was an original Green Mill All Star beginning in 1986. He was to play this upcoming New Year's Eve at the Green Mill with two of the remaining All Stars, Ed Petersen and Brian Sandstrom. When talking details about the gig with Robert a couple weeks before he passed, he said his standard line, "We will pick up where we left off." I loved that about him. He said that every Friday before and after Green Mill All-Stars gigs. We are sad that the circle has been broken. Hopefully, Robert will toast us on NYE with Willie Pickens from above.

From Stu Katz


About 50 years ago, Chubby Jackson, the wickedly witty bassist best known for his long tenure with Woody Herman, is reputed to have lamented “They can put a man on the moon – yet nobody knows where ‘one’ is.” If he had ever heard him play, Chubby would have added “. . . that is, except for Robert Shy.” Steeped in the bebop tradition, Robert had his own distinct approach which made his playing unique among Chicago jazz percussionists. He was an impeccable jazz drummer with a committed respect both for time and for melody (I can remember walking into Joe Segal’s Jazz Showcase on more than one occasion in the middle of a Robert Shy solo and quickly being able to identify the song the band was playing). I was one of the fortunate Chicago rhythm section pianists to have been afforded hundreds of opportunities to work with Robert in multiple settings over the years, most recently this past September 1 at the Millenium Park tribute to Willie and Irma Pickens. Every time I worked with Robert was a joyous occasion, as were our personal interactions over our decades-long friendship. His death is a profound loss to the Chicago jazz scene.


From Eric Schneider


Those who heard Robert knew he was a very fine drummer, but might not have realized he was an even greater human being.


With his soft-spoken nature and arid sense of humor it's almost incongruous that at a certain tempo he could swing and groove as hard or harder than anyone.  Some nights it was almost surreal, and we (the other musicians) would be giddy.


"You know that's right" was one of his favorite phrases, and he would go to great lengths to make sure they were indeed right.  I'm unaware of any other drummer who cared as passionately about getting the "right" sound out of a drum set as Robert. 


Every year we did two or three nights (usually the latter) at The Green Mill.  The Mill has drums, apparently of a high enough quality I've never heard of other drummer who didn't use them.  Robert would bring his own.  He'd get there way early, set them up and tune them until satisfied.  After playing his buns off (sweating buckets) at the end of the evening he'd dry off and then tear them down---and repeat the procedure the following day.  This added at least an hour to his evening, and even longer on opening and closing nights.


He had a physically and mentally demanding day job and did it for decades, which says a lot about his discipline, determination and focus.  That he could do that job and then play drums until all hours of the night and do his job the following day is testament to his indefatigable nature.


I will miss this gentle soul. 



From Joan Hickey

Dave Urban, Joan Hickey, Edwin Williams, Pete O’Neill, Robert Shy, Jim Cox


So many beautiful things have already been said by fellow musicians, but I would like to say a few words about Robert. He contributed so much to the musical community.  Robert was a real student of life, always watching and listening. Such a wonderful balance of class, earthiness, and humor. He was a gentle soul, but always commanded respect.


His drum sound had a unique quality. Even while playing intricate ideas, you could hear each drum and cymbal individually. Crystal clear. So he never covered anyone up. I don't know how he did it, or how to really describe it. Joel Spencer used to say that Robert Shy was the only drummer that "scared" him when he first moved to Chicago, he was so good. And he always played the "head" on his last chorus of a drum solo. It was beautiful.  I felt a true musical kinship with him, and he always treated me as an equal even though I was just starting out on the scene. He, Eddie DeHaas and I were in the "Volvo Club" together. Robert had a charming sense of humor and I used to love that when saying goodbye, he would bend his head down and whisper "We'll pick up where we left off."

From Dee Alexander


I had the honor of working with Robert along with Kenny Prince and Jon Weber at the Other Place on 75th and King Drive for 3 months on Wednesdays and Thursdays during the summer sometime in the 90s. Robert was the consummate professional who always greeted me with a smile, a joke, encouragement and advice whenever I asked for it! He was so cool and I always called him the “cool cat”!!! He, in return, called me the “catette”!!! Good times we had and I will miss him dearly......now he’s chillin on the other side!!

From Tom Muellner


I’ve had the great pleasure to have played with Robert over the years. He was always kind and the consummate gentleman. He also happened to be one of the greatest drummers I’ve ever known. I also heard Robert play countless times with many legendary musicians too numerous to mention. I never heard anyone say a disparaging word about Robert. Everybody loved Robert. He didn’t even use curse words and would say things like “that’s a bunch of bull crap” instead. I will always remember Robert, and he will be sadly missed.

From Solitaire Miles


Joshua Ramos, Solitaire Miles, Willie Pickens, Robert Shy, Ari Brown at the Jazz Showcase


I had the pleasure and honor of working with Robert Shy often over the past 25 years in combos  with other beloved Chicago greats like Von Freeman, Willie Pickens, Eddie Higgins and Jodie Christian.  Not only was Robert a great musician but he was a wonderful friend and band mate.  He was kind and nurturing to so many young Chicago jazz musicians and singers, and he would patiently and very kindly answer any question you had.  I never wrote out complicated arrangements when Robert, Willie and I recorded because I knew that the two of them would work it out naturally in the studio, all I had to do was give them a chart in my key.  Not only was Robert a wonderful musician but he was a great listener, and he paid close attention to what everyone was doing on stage so that he could compliment our ideas.  Our first recording to make the jazz charts "Baltimore Oriole"  was an oddball piece written by Hoagy Carmichael, and Robert held the tune together with his signature style, which was at the same time laid back and sizzlin' on the beat - keeping me, Willie and Marlene Rosenberg all together with a down home,  Chicago groove. 


I will miss Robert for his wonderful ears and his playing, but I will also miss Robert as my friend even more.  I would call him on the phone to discuss a recording project or a gig and he always took a lot of time with me like I was one of his children, no matter what was going on, and at the end of every conversation we had he would always remind me, "Be cool Solitaire, be cool..."    Robert was cool, all of the time, under any circumstances, and Chicago Jazz will never be the same without him. 

Solitaire Miles Podcast Interview with Robert Shy



From Eric Hochberg

Rich Fudoli, Robert Shy and Eric Hochberg


Robert Shy was a gem. A nicer man and more musically giving player I haven’t come across. We first started playing together around 1982 in Rich Fudoli’s Quintet at our regular Tuesday night gig at the Piano Man Lounge near Wrigley Field. Robert came in the band as Paul Wertico’s sub/replacement after Paul got the Pat Metheny gig. Of course, Robert fit in to our free-wheeling exuberance straight off, contributing all the swing and creativity he was known for. I loved playing with him right from the get-go!  We also played together in Howard Levy’s Quartet a bit and Robert also played dates with my band. In a time of so many recent drumming losses including Rusty Jones, Mo Jennings and Charlie Braugham, it was heartbreaking to hear the news of Robert’s passing. 


From Frank Russell

Robert Shy, Frank Russell, Willie Pickens


The late great Robert Shy was a bebop drum encyclopedia. Every time I played on stage with him and the late great piano genius Willie Pickens I felt I was taking a journey of the highest order! He was so musical and had great instincts and knowledge of the music plus he was a humble kind gentleman just like Willie. I felt very privileged and blessed to be a bass guitarist and play with these bebop jazz legends. I began to weep when I heard of Roberts passing just as I did when I heard the great Willie Pickens passed because I knew it was the end of a Chicago era. And they were just kind kind human beings and treated me like an equal. RIP to both!!

From Margaret Murphy-Webb

The first word that comes to my mind when I think of Mr. Robert Shy is "gentleman".  From the moment I was introduced to him, he always and only had positive words of encouragement.  I had the pleasure of working with him on one of Von Freeman's gigs when I was just starting out.  I had no sense of time and though Von was working hard with me, for some reason that night I could not find the "one" to come in after a solo.  Mr. Shy reinforced the solo endings with a hard hit, a smile and a nod giving me my cue to sing. That young singer is now an older singer and I will always remember his smile. 

From Pat Mallinger

He a sweet and kind man, a Chicago Jazz legend that devoted his life to the Chicago Jazz scene.  Dedicated to the extent of choosing to stay in town driving a truck for several decades to take care of his family, and lugging his drums to countless venues. Outside of jamming with him at the Bop Shop, the Get Me High, and hearing him perform at the Green Mill and the Jazz Showcase throughout the years, I had the great pleasure of recording and performing with him over the last couple decades with Art Hoyle's band.  One thing I recall distinctly about his playing is his reverence to the melody. He would always recapitulate the theme at the end of his solos, bringing the band and the audience back to where it’s all about, the melody.