College Preparatory School for Girls Grades 3-12

51 Years of Singing, Laughing, and Learning with Bob Tupper

51 Years of Singing, Laughing, and Learning with Bob Tupper

This story appears in the Summer 2021 issue of Doorways magazine. To read the entire magazine online, click here.

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Back in the early 1970s, beards were a symbol of the hippie counterculture, so as a new teacher Bob Tupper let his grow only during summer months and carefully removed every whisker before classes resumed. He kept up the routine for about three years and then showed up one fall with a full beard just in time for opening faculty meeting. Holton was not a politically radical kind of place, and Tupper noticed the pained expression on then-Head of School Jim Lewis’s face when he stopped into his office to say hello.

“I could tell he was about to give an executive order to remove the beard when his wife, Susan, spoke up. She said, ‘Jim, don’t you think he looks like a college professor? This place could use a little class,’” Tupper recalls. “His executive order was overruled by the Supreme Court of his family.”

Tupper never shaved again and thus ended his experimentation with marching to anybody’s beat but his own.

Now a tried-and-true trailblazer, Tupper retired in June from classroom teaching after 51 years, a school record. A longtime History Department Chair, conceiver of the innovative Core Curriculum, early supporter of Global Education, and legendary AP Government teacher, he is revered for his idiosyncratic approach to life and learning. It was common to hear the accomplished folk musician strumming his guitar and singing songs in class to make an important lesson more memorable. His rigorous yet righteous approach to his role as an educator and mentor earned students’ respect, and his willingness to be silly, humble, and present for them earned their devotion.

Outside the classroom, as the fiercely committed coach of It’s Academic, he quizzed, coaxed, and drilled generations of girls to compete at the highest level, winning multiple matches and reaching the finals during many seasons. Though his teaching was mostly limited to the Upper School, Holton’s youngest students got their first impression of him at the annual Thanksgiving assembly where he led everyone in singing “All The Good People” and “This Land Is Your Land,” both folk songs garnished with his original Holton-centric verses.


When Tupper announced his intention to retire, alumnae of classes spanning five decades rushed to respond to an invitation to share favorite memories.

Remembers Lynda Cokinos ’77, who was president of the Folk Club with Tupper serving as the advisor: “He was omnipresent and involved in both the classroom and in the halls … He laughed often and he laughed loudly, and that sense of humor along with his compassion for teenage angst truly helped me survive high school. An unforgettable teacher and mentor, Bob Tupper will always be a hero to me.”

Tupper literally fell into his first teaching job after graduating from Hamilton College in 1969. He taught for a year at Glenelg Country School and then interviewed at Holton. He was offered a position on the spot as a math teacher. But in order to avoid getting drafted by the military to serve in Vietnam, he had to apply for a deferment with the draft board in Rockville, Maryland.

“I explained that I was morally opposed to the war, and that I was not going to kill people, but since I was not a Quaker I understood I couldn’t declare myself a conscientious objector,” he says. “We had a respectful conversation and I thanked them for listening.”

On his way out the door, he clumsily stepped into a trash can and tripped. As he scrambled to his feet, he looked over his shoulder and asked, “So, do you want to put a gun in my hands or have me teach math?” As soon as the door closed, he heard the laughter and the next week he received notice of his teaching deferment.

Tupper did not major in education, nor was he an especially strong math student. But he studied nonstop over the summer, determined to emulate the qualities of the best teachers he’d had, while avoiding the habits of the worst teachers he remembered.

In the fall of 1970, he entered the halls of Holton’s Upper School as a young man not much older than his students. He’d grown up with two brothers, graduated from Landon, and went on to Hamilton, another all-male institution at the time. “When I was growing up I was as big a chauvinist as you can find,” he says. “My dad somehow figured I couldn’t get in trouble if I was surrounded by guys.”

Meeting his future wife, Ellie, as a college senior changed him. At that point, he’d achieved some local renown playing gigs as a folk musician—otherwise he doesn’t think Ellie would have considered his invitation to go out. “I had to wise up enough to court and marry this beautiful blonde who also knew every word in the English language.”

It was the dawn of the Equal Rights Amendment and Tupper was suddenly surrounded by women. “Getting to know students as people, and then as young women, it’s hard not to be an advocate for women’s rights. Chauvinists don’t last very long at Holton and aren’t very happy,” he explains. “I had some very good women mentors, especially [former teacher and later trustee] Sally Colclough Alexander ’51 who cared enough about me and my teaching to be very honest but also very supportive to praise what I was doing right and call me on what I was doing wrong.”

So what makes a great teacher? Tupper believes it’s important to keep your mouth shut, open your ears, and keep learning. “If you don’t learn from your kids, you’re not listening to them, and if you’re not listening to them, you’re not teaching,” he says. “Whether it be history or economics or world events or a whole variety of things that shape our world, people tell me I know so much. That’s because I’ve had the toughest teachers on the planet for 50 years—you can’t bullshit them.”

Tupper worked hard to reciprocate and keep students on their toes. He employed a “roll the dice” method of deciding whether there would be a pop quiz and made sure they stayed current on real and relevant issues by using The Washington Post as a textbook. Many alumnae report they’ve continued the practice of poring over the newspaper every day. In AP American Government, their reading of The Corner, by David Simon and Ed Burns, gave many girls their first insights into what it’s like to live in poverty in a West Baltimore neighborhood a short drive away. Inviting some of the real people whose stories informed the book to speak in class was even more enlightening.

One former student still marvels at the genius of an exam question: “You are hosting a salon at the time of the French Revolution. You can seat your guests in a two-person loveseat and a single chair. For each of the following trios of guests, whom would you seat where, if you do not want blood on your carpet?”

A lifelong baseball fan, Tupper cops to his competitive nature. He says coaching the It’s Academic team has helped him channel his childhood desire to become the manager of a major league franchise. Students say he made them all feel like MVPs while learning the value of practice (last year he held sessions all summer), perseverance, and joy in the face of intense pressure.

“Before every on-air taping, Mr. Tupper would be sure to say to us, ‘Just have fun.’ His reassuring presence allowed us to represent Holton and ourselves well in the midst of a very nerve-wracking experience. . . and have the time of our lives doing so,” says Kayla Moffett ’14.

Of course, there were the occasional missteps, like the time in Contemporary Problems class when Tupper was inveighing against a history of government corruption in his native state of West Virginia. He sensed some uncomfortable shifting among 10 of the 11 students in the room, until one suggested he take another look at the class roster. There was Shelley Moore ’71, daughter of Arch Moore, then governor of West Virginia (this was when Holton had boarders).

Ironically, Tupper points out, Moore was the one politician in West Virginia he felt he could support and actually campaigned for him. But to say it then would have seemed disingenuous, so he let it go. “She never said a word about it and we just moved on with our relationship. She was a phenomenal student— not a straight A student, per se, but boy she had insights,” he says. “And it’s no surprise that Shelley Moore Capito ’71 is now a U.S. Senator walking the tightest of tight lines as a thinking person from West Virginia.”

Tupper often says that being a teacher made him a better dad and being a dad made him a better teacher. His daughter, Laurie ’04, concurs. After she entered Holton in sixth grade, the two found a way to harmoniously navigate the same halls—even when Laurie reached the Upper School and helped lead the It’s Academic team. “I called him Mr. Tupper to make things less awkward,” she says with a laugh.

“Every single time we went out in Bethesda, there would be some student from three years ago calling ‘Mr. Tupper’ and my dad would remember her name and her paper. As a teenager it was excruciatingly embarrassing but also kind of awesome,” she says.

Knowing that her dad was so respected and beloved for being so uniquely himself was affirming to Laurie. “I was also kind of a character,” she says with a laugh. “A lot of places claim to be a community that values individuality, but Holton is small enough that people can really do their thing and be themselves. The faculty was full of characters, and I think modeling that as a teacher is really valuable for students. It was for me.”

Anyone who knows Tupper is well aware of his passion for beer. Growing up, Laurie traveled abroad extensively with her parents and most trips involved stops at breweries where Bob and Ellie sampled and made tasting notes with scholarly intensity. Their book, Drinking In the Culture: Tuppers’ Guide to Exploring Great Beers in Europe, was published in 2015. Over the years, Bob and Ellie worked with several breweries to create seven original brews; although they are no longer on the market, the sales paid for almost all of Laurie’s undergraduate education.

Tupper still regards his daughter as his “favorite late-night drinking buddy,” despite the fact that Laurie doesn’t drink. Their confidential talks these days often involve comparing notes about teaching.

After earning her Ph.D. from Cornell, Laurie has pursued her own career in education as a college professor. She taught at Williams and is now a statistics professor at Mount Holyoke College. She says “the magic” of connecting with students is something she learned from watching her dad.

“Teaching isn’t about getting up in front of the class and demonstrating how I know more than these people. It’s this idea that my students are going to walk into the room, and when they walk out, their brain will be different and I will have been part of that process. One of the most incredible things that you can do with another person is to help them change their mind and change the way that they can look at the world. That’s something that my dad, I think, always embraced as the heart and the purpose of his teaching.”

Two weeks following graduation and his many retirement celebrations, Tupper was already back at Holton for the Doorways magazine photoshoot, dressed in his standard short-sleeved Oxford shirt, pens in the front pocket, a red Nationals baseball cap covering his well-earned white hair.

When asked what his future looks like in retirement, Tupper answered with a chuckle and a quote from Proverbs: “Man plans, God laughs.”

He and Ellie have started taking short trips while researching a new weekend getaway guide to the mid-Atlantic they’re planning to publish. (Ellie, a professional editor, proofreads all of Tupper’s writing, including his famously detailed student comments and college recommendations.) Thankfully, he has also agreed to continue helping out at Holton on an extremely part-time basis—subbing and tutoring—for at least the next year.

For the past two decades, Tupper has adapted and sung the Woody Guthrie song “So Long, It’s Been Good to Know Yuh,” specifically for the graduating class and led the faculty in performing it at Senior Spirit Day. This year, the entire Class of 2021 reciprocated and sang their own version with lyrics written just for him.

A new chapter begins, both for us and for you
Thanksgiving assemblies we’ll all come back to
We just wanted to thank you for staying by our side
Since 1970, it’s been one crazy ride.

“It really was the perfect way to say goodbye,” he says.