Published: August 10, 2026
First Appeared In NEA Today for NEA-Retired, August 2026
Art Garfunkel
Pop quiz! Where did folk-rock duo Art Garfunkel and Paul Simon first meet? If you guessed an elementary school production of Alice in Wonderland, then you’d be correct. Unlike the other celebrities on this list, Garfunkel became an educator after he became famous, teaching math at Litchfield Preparatory School, in Connecticut, from 1971 – 1972. “I was trying to turn my back on all of the ego that goes with show business. So it was my resting time,” Garfunkel said, in a 2017 interview with Forbes. “I would have been happy being a teacher.” He adds that he may have pursued a lifelong career in education if he had never met Simon in that fateful school play.
Billy Crystal
In the early 1970s, when Billy Crystal was performing comedy improv, he worked as a substitute teacher at his alma mater, Long Beach Middle School, in New York. Crystal’s older brother, Joel, was an art teacher. In 2004, Crystal told Oprah, “I taught everything from English to auto shop. I’d be at the front of a class saying, ‘Listen, I don’t know anything about science, but these two guys walk into a bar.’” Later that year, Crystal was offered a full-time teaching job. He turned it down to pursue his career in comedy. It was a gamble that paid off, no doubt thanks to testing out jokes on his students!
Hugh Jackman
Long before Hugh Jackman became the brooding superhero Wolverine, he taught physical education. In 1987, Jackman spent a year working at the Uppingham School, in England, before attending university. In a viral video from 2013, Jackman recognizes a former student on the red carpet. He says winkingly, “I want to know how your physical education is progressing.”
Jon Hamm
“I think teaching is one of the great professions on the planet, and I had the good fortune to do it for a year,” Jon Hamm said on the Today Show, in 2017. Hamm was a daycare teacher during his time in undergrad and, after graduating, he taught drama full time at his alma mater, the John Burroughs School, in St. Louis. One of his students was actress Ellie Kemper, who played red-headed Erin Hannon on The Office and starred in the Netflix comedy Unbreakable Kimmy Schmidt. In 2011, the former student-teacher duo appeared side by side in the hit comedy Bridesmaids.
Mark Knopfler
Dubbed one of the greatest guitarists of all time by Rolling Stone magazine, Dire Straits frontman Mark Knopfler also received the Living Legend honor from the Scottish Music Awards. So what’s so legendary about him? Beyond selling more than 100 million records with 1980s mega-band Dire Straits and launching a successful solo career, he was once a teacher. Knopfler taught English for three years at a college in Leeds, England. “I was delighted to have [the teaching job], because it proved to be a real steadying influence,” says Knopfler, in a 1979 interview for Guitar Player magazine. “I also would go out into country schools and teach little kids basic guitar and singing a few times a week.”
Sheryl Crow
You know Sheryl Crow as the Rock and Roll Hall of Famer and chart-topping singer-songwriter who blazed onto the music scene in the 1990s. But did you also know Crow was a backup singer for Michael Jackson, a writer for McDonald’s TV commercials, and an elementary school teacher? A native of Missouri, Crow graduated from the University of Missouri, in 1984, with a bachelor’s degree in education and then taught music at Kellison Elementary, in Fenton, Mo.
Roberta Flack
Grammy Lifetime Achievement Award winner Roberta Flack was a prodigy who apparently had no interest in doing things at a normal pace. By age 15, she had a scholarship to attend Howard University. By 19, she was teaching English literature in her home state of North Carolina, and by 36, she was the first artist to win the Grammy Award for Record of the Year two years in a row. In 2006, when discussing her time teaching, Flack told NPR: “For that area, it was the only Black school available. And so, I had kids from preschool all the way through twelfth grade, and I taught every one of them something musical.”
Sylvester Stallone
Who would make a better physical education teacher than Rocky Balboa? No one! A decade before Sylvester Stallone flexed his muscles on the big screen, he worked as a P.E. teacher and “dorm bouncer” at a Swiss boarding school, while studying acting at the American College of Switzerland. Stallone then moved back to the U.S. to study drama, eventually becoming the stuff of Hollywood legend.
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