Richard C. Gregory, Former Faculty

A memorial service will be held on Tuesday, June 13th at 1:00pm at St. Philip’s Episcopal Church in Easthampton (128 Main Street). All are welcome to attend a reception in the Dodge Room of the Reed Campus Center at the Williston Northampton School immediately following.  

To livestream the memorial service, please visit:

Richard C. Gregory, age 90, passed away on May 31, 2023, at Fisher House Hospice Care in Amherst, Massachusetts. Richard was born on August 5, 1932, in Providence, Rhode Island, to George E. Gregory and Catherine B. Gregory.

Mr. Gregory graduated from what was then known as Choate Academy in Wallingford, Connecticut, before matriculating to Yale, where he graduated in 1954 with a degree in English. While at Yale, Mr. Gregory was the pitch pipe for the famous male a cappella group, The Whiffenpoofs. The Whiffenpoofs continued to perform and tour well into the 21st century. Mr. Gregory also attended the Yale School of Drama from 1955-56.

After Yale, Mr. Gregory joined the United States Navy, where he was commissioned as a First Lieutenant, serving in Guam and Washington, D.C. Mr. Gregory’s service in Guam inspired some of his musical creations, most notably his arrangement “Christmas Soup,” a hilarious rendition of the “Twelve Days of Christmas” that has been played around the world.

After graduation, Mr. Gregory took a position at what was then Williston Academy in 1961, where he served through the transition to Williston Northampton School and until his retirement in 2004. While at Williston, Mr. Gregory taught fine arts, English, humanities and music. He also served as the Assistant Director of Admission; Founder and Head of Arts and Humanities Department; Head of Fine Arts Department; Director of Band; Advisor of Drama Club/Williston Theatre; Founder and Director of Caterwaulers; Founder and Director of the Widdigers; Housemaster of Ford Hall; and Director of Music.

Not content to rest on the above laurels, Mr. Gregory endowed the George E. and Catherine B. Gregory Instructorship, in memory of his parents, in 2007. Williston Northampton also has an endowed chair in his honor—the Richard C. Gregory Faculty Chair.

In addition to serving on numerous committees while at Williston, Mr. Gregory was particularly fond of—and noted for—being the longest Master of Ford Hall, the notable senior boys dormitory where numerous pranks, hijinks and general young boy behavior was to be found. Mr. Gregory could always be called on to assist with any musical production, and was noted for playing the piano to old silent movies.

Mr. Gregory was most proud of establishing the male a capella group the Caterwaulers while at Williston, a group that traveled around the world to sing to gatherings of various Williston alumni. He was also the Director and Founder of the female concert group, the Widdigers. Mr. Gregory wrote many of the tunes which the Caterwaulers delighted audiences with. The Caterwaulers fondly referred to Mr. Gregory as “Stump.”

While at Williston, Mr. Gregory, in conjunction with Ellis Baker, raised the level of the theater program to one on par with any other local professional theater. Mr. Gregory oversaw and drew the sets for countless numbers of plays, in addition to designing all of the costumes—the drawings of which are art masterpieces in and of themselves. He directed many plays both for the Williston Theater, the Valley Light Opera, and the Commonwealth Opera.

With Ellis Baker, Mr. Gregory was the founding director of the Easthampton Community Theatre Association, later known as the Hampton Players, which regaled the Easthampton Community from 1972 to 1983.

Mr. Gregory was a long-time member of St. Philip’s Episcopal Church of Easthampton, Massachusetts, where he served on many committees; sang, wrote music for, and directed the Choir; and filled in as organist.

Mr. Gregory was a renaissance man: composer, director, and designer. He was a superb pianist and played violin, baritone, and tuba. Like Mozart, his preferred instrument was the viola. Upon his retirement, Mr. Gregory continued to write music for many organizations and particularly just for himself. His enormous talent will be greatly missed.

Richard is survived by his brother, George M. Gregory Sr.; his nephews Stephen P. Gregory and George M. Gregory; and his niece, Catherine Gregory Boyle. Richard lived a long and interesting life and will be missed by many, especially all those thousands of students who benefitted from his wisdom, humor, and musical genius.

A gracious thank you is extended to Elder Care Access, LLC, and particularly Sheryl Fappiano and Brenda Gendron for their kind and attentive care of Mr. Gregory in his declining years.

In lieu of flowers, donations in memory of Dick Gregory can be made to the Richard C. Gregory Faculty Chair at the Williston Northampton School.

51 thoughts on “Richard C. Gregory, Former Faculty”

  1. Dick Gregory had such an impact on so many people including myself while attending Williston. I joined the Caterwaulers in my second year at Williston. What a great experience. It has to be my fondest memory from my Williston years. May he rest in peace.

  2. Mr. Gregory was a great teacher and motivator. He knew how to lift you up and encourage you to explore your creative side-whether it was art, playing an instrument, acting or singing. He was a true mentor, had a great laugh, and was a wildly talented singer, writer, artist and designer. May he rest in peace.

  3. Mr. Gregory had a profound impact on my experience at Williston and had a lasting impression on what I see as valuable and honorable in many aspects of life. I will always cherish the time that we had together with him as a director, a mentor and a friend…a parent to all of us, he will be missed dearly!

    1. Well said Dave. I couldn’t agree more. The thought of Mr. Gregory and our days at Ford Hall has and always will put a smile on my face.

      Ring the bell!

  4. I dearly loved Mr. Gregory because of, and in spite of, the way he would take me to task. I remember with equal fondness getting kicked out of his class for insubordination, and the pride I took in “showing him” whenever I turned in a really good paper. He motivated me to try my hardest. Despite our differences, I always knew he liked me and at that time of my life, his approval meant everything. Rest easy, Mr. Gregory.

  5. Mr. Gregory [and it was and always will be “Mr.”] I was fortune enough to have him as s teacher on the first day of 9th grade and he became a trusted advisor. He was a great teacher to generations of students.

    The ripple effect of his working a cappella alone is historic as his influence is a direct cause the of the establishment of what is now known as CASA The Contemporary A cappella Society a truly world wide organization.

    While his influence is not widely known, Mickey Rapkin, the author of the book Pitch Perfect [which was loosely the basis of the movie franchise] did write this piece about him in 2008.

    1. Thank you for posting that…this past Christmas one of Mr. Gregory’s care givers played that song for him on YouTube and he was so delighted!!!

  6. I joined the Caterwalers my second year and was the Head of the group as a senior. Dick was a mentor in every way possible. I took his music class my senior year, I acted in several plays (minor parts), I lived in Ford my junior year and spent countless hours in his apartment which felt like a home away from home. His contribution to countless students over the years simply can’t be measured

  7. I happen to be fortunate enough to be one of the first Caterwaulers. We had a fantastic group with some amazing singers and musicians. We had gigs in several New England cities, including Boston. He also took us to New York City to perform. As we were walking down the street en masse he took out his pitch pipe, gave us a note, and we began to sing. He told us nobody in New York would ever notice so go right ahead. Many of you may not know that he also wrote a operetta. It was called Artemis Undone. He brought in some musicians at the last minute and it didn’t work out so he accompanied us on the piano. Of course I was singing, so I thought it was great but we got seven standing ovation, so I guess it was OK. It was Dick Gregory and that group of guys that made our time a lot of fun.

  8. Dick was a true inspiration to so many and he pulled me into the Caterwaulers in 197-71. To this day I still sing in four part groups and cherish the time I spent with him and my fellow singers. God Bless you Dick

  9. Mr Gregory was inspiring to many people. During my ESU year at Williston I was in the Widdigers. Mr Gregory encouraged us to sing whenever we could, whether as part of the group or with friends. I remember various concerts, discussions of a singing tour to Bermuda at Spring break and singing at an old people’s home with the group.
    He was such an interesting man, and when I returned on a visit from England he was there to say hello. Rest with music in your heart

  10. I didn’t have Mr. Gregory for anything, didn’t live in Ford,(Mem) but always have this memory that maybe will make some who knew him well chuckle. Recounted from some guys who lived in Ford who were up to no good at like 2am on a Saturday night, they said even at 2am he came out of his apartment, still in his jacket and tie, shirt buttoned to the top, to admonish them, as they were all in shock that he was still in his “uniform,” like it was 2 in the afternoon. Whenever I saw him after that I always pictured that & thought, “that seems to fit.”

  11. For my ears only Mr. Gregory leaned toward me at the dinner table at a Caterwauler’s
    reunion (I was President of the first Caterwauler group!). In a hushed voice Mr. Gregory
    told me that his “favorite” group was the first Caterwauler group. I am positive that he
    told many of many fellow classmates in other groups that their group was his “favorite.”
    From my first meeting with Mr. Gregory I wanted to be just like him- a musician, a composer, an artist, a teacher. I have patterned my entire life after this giant of a man, completing my first 50 years as a music professor at Stanford University and I will continue
    to try to reach his standard of musical artistry for another 50 years.

  12. Dick Gregory changed my life on Easter Sunday morning, 1967, when he phoned telling me that Williston‘s Headmaster, Philip Stevens, had authorized him to offer me $500 more than any other offer I had been given. I took the job to escape from the hidebound Tennessean society I foundered in, never expecting to remain in the “Kingdom of the Yankee” for more than a couple of years. That was over fifty years ago. Though he pissed me off a few times, I admired and loved Dick Gregory, and always felt a deep sense of gratitude toward him.

    1. Barry– I taught drawing, photography, and printmaking at Millbrook School for 40 years and was the AD, boys varsity soccer coach as well. I am looking at two of your prints you kindly gave me many years ago. You were an inspiration to me as an artist, after my father of course., I hope you and your family have had a wonderful happy healthy life. Know that I think of you and your humor fondly. Rick

  13. Mr. Gregory was a true legend, a giver of so much of himself in countless, selfless acts that had lifelong impacts upon all those who came in contact with him, even those on the periphery. When I think back to my time on campus, as we all do especially in times of reflection like this, we all have our Mt. Rushmore of people who influenced and shaped our young lives and there is little debate with me that Mr. Gregory has a place on that list. The memories are too many to name – early in my sophomore year, standing shoeless (zero tolerance policy for cleats in the Dodge Room) during my audition after a grueling football practice while standing amongst my friends caked in dirt and sweat; the spring day my first year when he drove out to the outer fields to fetch some of my lacrosse teammates, enraged and affronted that they were late to practice (that was the last time lacrosse practice ran over); our senior year trip to Bermuda with the Widdigers was incredible; a day in a recording studio to produce a tape I still have and wish everyday I had digitized (I remember I messed up my song so badly at the start but that we kept it in the final recording and it serves as a great blooper); and being deemed worthy of being taught “12 Days” which was the highlight of any show (John Grossman and the duck call is a classic) and given the latitude to be “free” and improvise some (respectful) stage antics. There are many memories, way too many! But, most importantly and beyond any music we were taught was what Mr. Gregory helped us all, who are forever linked as Caterwaulers, learn about ourselves. I was an awkward teenager, learning daily who I was and overcoming my shyness and other teen angst, being asked to sing scales acapella in front of my friends, to be completely vulnerable in the moment which can be extremely hard for a teen. But, Mr. Gregory, who was not tall in stature but who’s presence filled a room, who’s attention to detail and philosophy of taking pride in everything you touch are lessons I never forgot, when he looked at you with his bright eyes and calm demeanor (unless you were late to practice) you just knew that you could do whatever he asked of you because he believed in you even if, in that moment, you did not. Mr. Gregory will forever be remembered by those who’s lives he touched. We are all better people for having had him in our lives as he taught us so much more than just scales and words on the page. Wum, bum, bum…

  14. My happiest memories of Williston shall forever be trying out for Mr. Gregory and ultimately joining the Widdigers. Mr. Gregory was such a kind and elegant man; a true gentleman whose knowledge of music knew no bounds. His class was a joy to be in and I remember eagerly rushing to get there.

    I waited till I was a senior to join, I guess I was nervous, and I remember him asking me, “Where have you been?” To this day, my kids will tell you the life lesson of just going for it was because of that comment and that moment and that man. I’ve repeated it to them over the years, and thank God it stuck. I am saddened at the loss and equally grateful to have known him.

  15. I too have to add that Dick Gregory was a true Renaissance man, for all his students and for all seasons. I took his music appreciation class and was lucky enough to also get tapped to sing in his brilliant operetta and over the top funny Artemis Undone. I still remember the opening chorus that precedes the marriage:
    File in splendid bridal train
    As maids and men of war unite
    To celebrate with glad restraint
    The hymeneal rite.
    What a treat would be to do a revival of this gem. I would fly from Panama to Easthampton in tribute to the memory of our beloved Dick Gregory

    1. Of course your brother Ronald was also a Caterwauler. Ron was one of my best friends while at Williston. He had a great voice, he was a Thespian and he jad such a warm personsonality I will always cherish my friendship with your brother. Such a talented guy; such a loss at an early age. But he will always be in my
      thoughts. Bill Morrison 69’

  16. Ah, Mr. Gregory! This is the passing of a giant. As a public-school kid from California coming to Williston for just one year, I knew nothing of prep school codes, traditions, or rules; of New England, the Ivy league, the Whiffenpoofs, or anything at all about Williston. In all of this, Mr. Gregory proved a grand tour guide. His quick wit, his attention to detail, his setting of high standards, his toughness – these were always on display. His generosity, his kindness, his endless devotion to his students and friends and the school — these were perhaps less obvious, but no less a part of this extraordinary fellow. And he was really, really fun.

  17. It was a great privilege to be invited to join Dicks Caterwaulers when I was an ESU exchange student in 1968. I am one of the’global members’ who returned to sing at reunions. He was inspirational and a great friend. He also pushed me into starring in ‘The Boyfriend’ which was a great success with him and Ellis Baker.
    My daughter Katie ’96’ another English exchange student adored him. He loved all things English as I think his mother was born here.
    To see him at lunch 5 years ago at our 50th was very emotional. He will be sorely missed.
    Tom Hoyle ’68

  18. In the 1970’s, I, my sister Sue Alcock, and her family enjoyed working with Dick Gregory and Ellis Baker, providing props for several productions of the Easthampton Community Theater Association. Both Dick and Ellis were easy and fun to work with as directors. Dick designed costumes, as well, incliding two for me when I played Mrs. Webb in “OurTown”, and an Irish house maid in “Life with Father”. There’s more music now in Heaven. Rest easy, Richard. ❤️

  19. In all my life, one of my greatest joys was to be a founding member of the Caterwaulers. When we started. we had no past, no book of the old favorites, no traditions, all we had was Mr. Gregory and his musical prowess and his vision. Over the years, it was wonderful to attend a few Caterwauler reunions, to see how the group has developed and flourished.

    I still sing with community choruses. It’s a simple pleasure to make wonderful music with a group of friends. I’m sorry to have lost one today.

  20. I knew Mr. Gregory (and I, like my fellow classmate and Caterwauler, Rex Solomon will always refer to him as “Mr.”) both as a student, a Caterwauler and a colleague of my father. My dad and he taught English way back in the 60s. I was fortunate to have Mr. Gregory as an influence and mentor for my four years with the Caterwaulers. A few years back, I met several members of the acapella band Straight No Chaser. We had just heard them perform in Portland, OR. They were entertained to meet one of the original singers of the somewhat more “creative” version of the Twelve Days of Christmas that Mr. Gregory penned decades ago. Straight No Chaser went on to make it famous. I will always think of Mr. Gregory when I hear it.

    1. Thomas, thank you so much for including me, but alas I can not singing, so I wound up being the unofficial Caterwauler documentarian…. I can tell you is that I sent the 12 Days arrangement to the Indiana Straight No Chaser in 1990 when the director Walter Chase asked for a copy from the CASA library that we were operating back then. However I sent him a copy missing the last page….oops…and then one of them came up with turning it into a medley with Africa… and the rest is history. When the digitized recording of their 1996 concert was placed on Youtube and it went viral, Deke Sharon reached out to me to contact Mr. Gregory as Deke immediately knew the arrangement and who wrote it… [if you don’t know who Deke is just google him] When the new SNC came to Houston I too waited to meet them and had them autograph the arrangement for Mr. Gregory, and when I got to Walter and introduced myself as we had only corresponded decades ago, his first words were “thank you!” The number of lives Mr. Gregory touched are countless and his “ripple effect” is a tidal wave.

  21. Caught in the middle of a busy day, I saw this note and literally burst into tears.
    Sometimes it takes retrospect to acknowledge the affect that a person/teacher upon you.
    I learned so much about precision, timing and disciple while singing with Mr Gregory.
    He had very clear boundaries at a time in history where standards and boundaries were less clear.
    I am sure you are humming a tune from where ever you are…

  22. Indeed it is the end of an era, and the passing of a true gentleman, inspiring teacher and eloquent scholar. A half century after being in his class, I still remember fondly his impish smile, droll wit and encyclopedic knowledge, and the eagerness to learn and excel he imparted in us all. Despite his humble and quiet demeanor he truly was larger than life and a legend in his own time.

  23. Mr. Gregory was a great man, as we can see from his achievements and testimonials. He clearly loved Williston and dedicated his life to its purpose. As a very young, recalcitrant and at times foolish student he was generous with me nonetheless, chiding me in what I see now was an undeserved and supportive way, telling me in his comment on my bs filled response to an essay question that I “obfuscated artfully.” Ill never forget that. It taught me a lesson in the best, most artful and skilled way. I miss him.

  24. As a colleague and neighbor for years, I am filled with memories of the Caterwauler and Widdiger performances and of his pride in his students.
    In my early years he invited my Great Pyrenees, Clio, to keep him company on Park St. until he found Roscoe who was devoted and refused ever to listen to him!
    Dick was a man of astounding talent and great humor. His impact on those who were part of his life is profound.

  25. As one of his students, a Caterwauler, resident of Ford, and theater performer, I am particularly saddened by Mr. Gregory’s passing. As time has passed, I realized he was part of an outsized number of my strongest memories of Williston. To this day, his “Making much out of nothing is an art, though a minor one” note on a hastily organized paper, along with him walking past me outside of Ford, on a night I was “dormed,” then ever so nonchalantly asking if was “supposed to be” in my room, regularly brings a smile to my face. On campus and well beyond it, his effect on me was fond and profound. During each of many reunion visits, I sought him out to make my trip “complete.” I very much looked forward to doing it next year at my 50th. May this mentor and friend of so many rest in peace.

  26. Arriving on a cold January day in 1967 as English Speaking Union Exchange Scholar and lodging on the ground floor of Ford House one of the first members of staff I encountered was house master Richard Gregory, I had made the mistake of travelling with my violin and he soon learnt that my skills were limited though, probably with ear plugs in place, sometimes accompanied practice sessions. He became a generous mentor and friend for the two terms I spent at Williston and I am sure many will remember him in a similar way. Requiescat in pacem.

  27. So sorry to see this news. Arriving as an English Speaking Union student for a year, joining the Caterwaulers was one of the highlights of my time at Williston. It was an amazing group and Dick’s energy was contagious. For spring break the group got the opportunity to go to Bermuda and I didn’t have the money to go – somehow Dick made it happen. I don’t know quite how. It proved an incredible trip. I suspect all of us have a tiny handful of teachers who have a profound imprint. For me Dick was absolutely one of them. He will be missed.

  28. I took Art History with Mr. Gregory my senior year. It was my first class on the topic and with him. He drew me in. Captivated my attention, and made me understand learning for passion and not just because you have to. I have always thought of him in color, vibrant and so kind, and always will. <3

  29. Mr. Gregory was certainly one of the most profound influences on my life. I was an original Caterwauler, and I also had him for 10th grade (Middler!) English and as a Ford Hall mentor. I honestly believe that he was a major force in my becoming a teacher. He was obviously brilliant academically and artistically though he had his eccentricities; yet he also had a warm and understanding side. I remember a long conversation which I had with him in his Ford apartment — while he was working to put together his harpsichord — where he described the strengths and weaknesses of my voice, how it could be used, potentially modified, and even ruined; he helped me be comfortable with what I had. Though he was generally a by-the-book strict disciplinarian, I remember sharing a “cordial” drink (alcohol!) with him and Mr. & Mrs Richmond a couple of nights before graduation. Along with folks like the Carpenters, the Couches, the Tellers, and Heppy, Mr. Gregory made Williston an on-balance good experience despite all of its 60’s failings. I wish that I had connected more with him in recent years!

  30. It was a phone call from Dick Gregory, stating that he was stepping down as Fine Arts Department Head, and asking me to please apply for the position, that led me to 15 years enjoying the fruits of Dick’s and Ellis’ labors. Dick was a true Renaissance man, and always eager to discuss our mutual passion for classical music. Though I didn’t share his love of Wagner, and particularly “Die Meistersinger”, he graciously agreed to be a guest in my music history class, and his knowledge and enthusiasm were very persuasive! He was a wonderful, generous, erudite person, revered and admired by the many people whose lives he touched.

  31. May Light Perpetual shine upon Dick as his bright star will forever shine upon all those whose lives he touched and enriched.

  32. I tried out for the Caterwaulers and was soundly rejected because I cannot sing a note to save my life. I still remember Mr. Gregory looking me in the eye, smiling, and telling me that they would “get back to me”. Thinking about that moment puts a big smile on my face! He was such a class act. I too experienced him as a man out of time. His demenor, impecable manners, perfectly tailored clothing. and love for sherry made him seem like he had just stepped out of a Victorian era time machine.

  33. Mr. Gregory was a presence on campus. Definitely a true part of the tapestry for every student. He was so genuinely interested in the success of all students and I knew that. The community was more vibrant and we were so fortunate be his students especially those learning to love the arts.

  34. Thank you, Mr. Gregory.
    Thank you for middler (sophomore) English.
    Thank you for teaching me recitatif, Beethoven, the 5 Greek columns, Manet…
    Thank you for accepting me and my son, Michael, into the Caterwaulers.
    Thank you for “Rom Boogie” and “The Twelve Day of Christmas”.
    And thank you for our European concert tour – the best three weeks ever!

  35. I did not have Mr. Gregory in class, nor was I a Caterwauler. But I will never forget his performance as the bombastic Falstaff in the the Williston Theater production of “The Merry Wives of Windsor” in the fall of 1969 (with Sarah Stevens and Lorraine Teller in the title roles.) It was a comically riveting portrayal that revealed a side of him that was somewhat at odds with his reputation on campus as a strict disciplinarian. At my 45th reunion in 2017 I sat at a table with him during a luncheon and asked him about his military service. He told me he worked in Naval Intelligence as a courier, carrying classified documents to U.S. embassies and Navy bases on the west coast and throughout Asia. His Navy career ended when one of his assignments took him to the Soviet Union. He was not allowed to re-enlist because it could not be certain he had not been “flipped” by the KGB. But the Navy’s loss was Williston’s gain. A remarkable life and legacy of service.

  36. I remember that production well; I ran Props and built sets under Hap Haven ’70. I’d entered the previous year while he was on sabbatical and knew nothing about him other than that students who did know him were glad he was stopping in to do performers’ makeup even on sabbatical. It was very easy to see him as another stuffed shirt (of which there were several on the faculty then) — especially when he’d cut a former student dead for daring to use his first name — but I also remember his delight at discovering that the Doors had recorded a song he knew from a Brecht/Weill opera, and his demonstrating “eating” his viola (noises from scraping the bow on the back of the instrument) in the music-composition class he taught in 1970-71. I also remember his patience with mostly-inexperienced actors when I was Duke Senior in _As You Like It_ (Spring 1971) and with the often-indifferent singers performing his setting of the finale.

  37. Thank you Mr. Gregory. You found a musical home for a student that didn’t fit in the Widdigers. You walked across the street to the schoolhouse and said you had a better fit for me. With you I met the Rings, chamber music, chant, and a chance to see what choral singing was to building self esteem and community. Because of you, I have continued to sing. I can proudly say that your guidance allowed me the courage to try out and succeed outside of my normal career. I’ve performed at Carnegie Hall, the Vatican, the National Cathedral as well as been in the back up choir for Barry Manilow and Michael Crawford! You helped your students find their voice. You will be missed.

  38. Dick Gregory was one of the greatest teachers I was privileged to know at Williston. He was a very conscientious and intelligent teacher. But also a sterling human being; a gentleman. My earliest memory of him – 53 years ago – was when he served as dorm-master at Ford Hall. I had just moved to Ford from Sawyer to begin my second year (1970-71). Room-mate D.F. Brown was at swim practice one afternoon, so I played the radio. Either through chance or choice I had tuned in to a classical station. Soon thereafter, Mr. Gegory happened by. He stopped to knock, or possibly the door was already open. For a moment I thought the radio was too loud. Instead, he complimented the choice of music, telling what a pleasure it was to find a student who could appreciate classical music. I think from that day, if gradually, I went for Baroque. // It was during this same year I was privileged to be in Mr. Gregory’s English class. What I remember best from this class is Mr. Gregory’s precision with words. To this day I cannot employ the word “get” without recalling him scolding its association with “beget,” which is truly one of its meanings. He also disparaged “grieve” when employed as an intransitive verb, straightened me out on “lay” versus “lie,” and other awkward or incorrect usages. But it was the impromptu speaking element of his class that bears further telling. And perhaps it shall be if the Williston Northampton School Bulletin prints the article sent them last year. But that’s for them to decide. What I will say here is that it was certainly a novel idea at the time, so very instrumental in helping many of us students learn public speaking. But, of course, he also helped with our writing. I recall Mr. Gregory’s “Remembering the Past, Ensuring the Future” in the 2003 Williston Northampton Summer Bulletin, marveling at how simply and concisely he told his story, a story spanning 42 years. It was a pleasing but also sad story because he was getting ready to retire and one was able to see what an immense contribution he had made, what a long time he’d been with the school, only to realize nothing lasts forever and his retirement would comprehend a tremendous loss. For the school’s character did not reside in its renovated buildings or polished brass, but the men and women who served, whether as faculty, administration or grounds keepers, people who became the school by being a significant part of its history. Hepworth and Phillips Stevens were those people, Doc Gow and Messrs. Coulter and Couch were, as well; Archibald, Babcock, Francis, Henchey, Teller, McClure, Wilson, Swanson, Moser, Carpenter, Culver… many names, many fine people. Certainly, Dick Gregory stands head and shoulders with all of them, remaining with the school longer than anyone I am aware of. Mr. Gregory was the school, its best part, and now with his passing, I am saddened – deeply. There was no one like Dick Gregory!

  39. As an English man, who spent only a year at Williston, there is an inherent risk of my being a fraud in the face of those who knew Mr Gregory (like so many have said before, still Mr Gregory,
    even 33 years later to a man in his 50s) for much longer, and in much greater depth. However, perhaps the fact that, despite such a brief time of knowing him, I feel moved to express my sadness speaks volumes.

    Mr Gregory embodied the best quality in a teacher; inspiration . He took an uncertain 18 year old to one side, said “give it a go”, and made life richer. My times with the theatre production,
    and with Caterwaulers and its tour to Bermuda are amongst my fondest memories of school life. Without his persuasion and encouragement, I would have known none of it. When news arrived of a snippet of academic success, I was, and remain, delighted that it was he who delivered it.

    Always effortlessly stylish, always cool (in the true sense, because he was unaware of it). Pure class.

    Rest in peace, sir.

  40. Mr. Gregory was always “buttoned up,” precise. He drew students to singing, then taught them how to sing. He challenged himself and those hundreds of Caterwaulers over the years. Oh the joy in his eyes, when we gathered in June 2022 on his porch to sign the “Old Songs!” Never have I seen such a loving gaze through the years of time as in those eyes that afternoon last June. He chose to hear us in tune. I am not sure we were in tune with anthing other than the love, respect, and admiration we had for each other. Thank you Dick Gregory.

  41. Mr. Gregory [and it always will be “Mr.”] was the most influential teacher I had at Williston, and that influence continued through college and graduate school. I was in the Caterwaulers, pitchpipe for a time, and that experience brought me into a-cappella groups at Princeton, music director of the Nassoons, and founder of the Katzenjammers. I also arranged music for those groups, and that impulse came quite directly from Mr. Gregory’s example, and his harmony course at Williston. We sang a number of his arrangements: Lazy Day, Try to Remember, and the bizarre Elf-Man were all ’68-’70 Caterwauler inventions of his that I brought to college. I also brought The Christmas Song there, and have been accused of stealing it. Not True I say! I always placed his name on copies of his arrangements , a Yale Whiffenpoof name smuggled into the depths of Princeton’s musical history (where it still resides). But the Xmas Song in particular was so good, so striking a contrapuntal confection of Christmas crudities, that it was stolen right out of the Nassoon room by a visiting group from Colgate! (I have no idea if that is true). But once it was heard on recordings, it went viral, picked up by ear no doubt, spreading all over the East Coast, even so far as the boonies of Indiana where Straight No Chaser picked it up. That’s what Gregory’s counterpoint could do, and still does to this day. You can hear it on YouTube.
    So I owe him quite a lot. I went on in music, starting groups that sang Renaissance music in Northampton, in Cambridge, and at UNH where I taught. In the 1980s Mr. Gregory had started a madrigal group at Williston, but became too busy with theatre responsibilities; I was coaching here, and took over the group for him. He had left a number of madrigals in the repertory of the group, and I, being a student of the Renaissance, was puzzled by the attributions of some of the pieces, to composers I’d never heard of. Turned out they didn’t exist; Mr. Gregory had written them all himself, and adopted Elizabethan names to cover his tracks. A “true Renaissance man” as others have said. His music and legacy lives on in so many ways.

  42. I already knew who Mr. Gregory was when I came to Williston in seventh grade, having idolized my older brother’s performances as a Caterwauler (in particular his solo on Freckles, which was just about the cleverest thing nine year old me had ever heard…). Although I came to know Mr. Gregory from two years of piano recitals as a Middle Schooler, I was surprised when he stopped me on campus as a young ninth grader and asked me to try out for the Caterwaulers. I politely refused, noting that I did not have the first clue how to sing. Mr. Gregory insisted, reassuring me that all I had to do was sing a few notes back to him that he played on the piano, and everything else would be fine. I don’t remember much about my audition in the Dodge Room, aside from the fact that the Caterwaulers that year included the captains of five varsity sports and were all seniors, except for one other guy who was, oh yeah, a 6’6 junior All American water polo star. I’m still bewildered that the coolest guys on campus accepted me as their youngest and most socially awkward member. That turned out to be the final year Mr. Gregory led the group, so I’m honored to be the very last in a long and proud lineage of original Dick Gregory Caterwaulers.

    My friendship with Mr. Gregory stretched beyond that one year in the Caterwaulers, first as my faculty advisor and art history teacher, then as an inspiration after I left Williston. I was lucky to scrape my way into Yale and luckier still to join the Baker’s Dozen a cappella group, for which Mr. Gregory had been musical director 45 years prior. Imagine my surprise when I discovered that BD concert “uniform” was blazer and khakis, and that the group ended every rehearsal with a raucous, barely comprehensible version of Nagasaki — pretty sure I’m the only BD in 75 years to know the actual words to that song before I joined!

    Mr. Gregory and I traded letters during my time in New Haven, including when I became pitch of the BDs as a junior. That year, Mr. Gregory wondered whether I would try out for yet another a cappella group I didn’t deserve to be in, this time the Whiffenpoofs. I prevaricated, noting that my voice was not nearly strong enough to be selected. Once again, Mr. Gregory insisted, suggesting that I focus on the musicianship I’d learned from years of playing the piano. His guidance was prescient, and yet again I was bewildered to be accepted into an exclusive singing ensemble. Hoarse with both liquor and excitement, I called Mr. Gregory’s Williston number as the newly minted Whiffs of 2002 gathered on Old Campus for the first time, leaving him a long and exuberant voicemail in the glooming of Whiffenpoof Tap Night. Alas, Mr. Gregory never received my message; he was many things, but a man of technology he was not.

    He spoke with my father a few days later and then sent a warm letter of congratulations. Ever the educator, he imparted one “helpful thought” to guide me through a year of concerts, carousing and globe-trotting with the Whiffs, during which, in his words, “CEOs will be thrilled to buy you drinks” and “society matrons will fling their daughters at your feet” (which I’m still waiting for, admittedly…): “It will take you all of two months to take this attention for granted and to forecast it for the rest of your lives. Don’t. It will stop the moment you place your sheet music in the hands of the Whiffenpoofs of 2003. However, do please revel in being Kings for the Day. It is fun. I’ve always told the Caterwaulers: The whole point of singing is to have fun.”

    I think about this advice all the time, my own personal “Gather ye rosebuds while ye may,” but it wasn’t until COVID that I decided Mr. Gregory actually was wrong, which I wrote to him in a letter that I wonder if he ever received, much like my Tap Night voicemail from 20 years ago. To be honest, I’ve never stopped living like a king. On the contrary, my post-Whiffenpoof life, like my time in the Caterwaulers, has been incredibly fun, in large part because it has been enriched by music and art and theater and literature, the passions that Mr. Gregory spent his life evangelizing, and that he cared to encourage in me. And although Mr. Gregory had a uniquely profound impact on the trajectory of my life, I am by no means unique in having this experience. Sitting here at my 25th Williston reunion, there is no shortage of alumni with a deeply personal story about how Mr. Gregory inspired them with his distinctive blend of erudition and conviviality, or even just a funny story about how much fun he was to be around. The whole point of singing and, perhaps, everything else in life is to have fun, and Mr. Gregory sure was.

    Thanks for the memories, Mr. Gregory. Wum bum bum bum….

  43. I remember being in his room at Ford Hall with all the other Caterwaulers when we took a record of “Lazy Day”. He listened to it and said “This should work well” He sat down at his Harpsichord and wrote his arrangement in four part harmony. What a gift he had!

    I treasure the rehearsals we had weekdays at 5:05. When we finally met his high standard he would smile and say “Nice”

    Rest in peace.

  44. Many thoughts, many memories. So much gratitude. So much affection for that man. I will always try to remember.

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