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Tracy Chapman started writing songs when she was in grade school. She got her hands on a $20 guitar and sang about what she read in the newspaper: “People were finding out about asbestos and Andrew Young was in some sort of controversy, and I had something in there about flying saucers…” she told Rolling Stone in 1988.

She won a scholarship to attend Wooster School, an Episcopalian prep school in Danbury, Connecticut for high school. Here’s what her time there was like.

Tracy Chapman, Amnesty International, Wembley Stadium, London, 2nd September 1988
Tracy Chapman | Rob Verhorst/Redferns

Tracy Chapman didn’t always feel comfortable at school

Along with Chapman, about a quarter of the students at Wooster at the time were financial-aid recipients. The singer told RS that, sometimes, she didn’t exactly feel at home.

“Even though almost everything was paid for — my books and my transportation to and from vacations — you’d end up on shorter vacations where you couldn’t really go home and you couldn’t stay at the school,” she said. “So you’d have to go to someone’s house, and often they were people I didn’t know. And you did get the sense that they felt like they were doing charity work.”

What Tracy Chapman was like in high school

According to the school’s dean of students at the time, Sid Rowell, Chapman was ” a strong B, B-plus student.”

According to the chaplain and soccer coach, Reverend Robert Tate, she was also a gifted athlete. And, of course, she was very musical.

David Douglas, the head of the music department, said Chapman wasn’t involved in the music department. From the beginning, she was a solo artist. He told the publication he remembers seeing her “playing her guitar and sitting on the white fence outside her dorm building or taking advantage of the acoustics in the small, high-ceilinged chapel.”

“I remember her as, on the surface, a very quiet, somewhat shy person,” said Tate, “But once you got to know her, the person that comes through in her music — deep thinking, passionate, very concerned about other people and about issues — that person came through.”

Tate was actually thanked on Chapman’s first album. He organized a collection in order to buy her a better guitar during her first year at school. He told RS they raised the money “in about 10 minutes.” But Rowell said Tate donated “a good portion of the money” himself.

Tracy Chapman’s senior yearbook quote

Even though Chapman spent much of her time at Wooster writing music (including “Talkin’ ‘Bout a Revolution”), she didn’t select song lyrics for her senior yearbook quote like most of her peers. She chose a quote from Black feminist poet Nikki Giovanni.

There is always something to do. There are hungry people to feed, naked people to clothe, sick people to comfort and make well. And while I don’t expect you to save the world I do think it’s not asking too much for you to love those with whom you sleep, share the happiness of those whom you call friend, engage those among you who are visionary and remove from your life those who offer you depression, despair and disrespect.

Nikki Giovanni
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The class of 1982 yearbook also featured predictions about the future of the senior class.

“Tracy Chapman will marry her guitar and live happily ever after,” read one prediction.