Delaware shaped Grammy folk hero Loudon Wainwright III during teen years, he says

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The film "Dead Poets Society" is famously tied to St. Andrew's School near Middletown. But there are a bunch of Hollywood movies that many Delawareans don't know are linked to the school.

This includes "The 40-Year-Old Virgin," Martin Scorsese's "The Aviator," Tim Burton's "Big Fish" and "Jacknife" with Robert De Niro. There are also TV shows like "Parks and Recreation" and "M*A*S*H."

Unlike "Dead Poets Society," which was partially filmed at the school, those other projects are all linked to St. Andrew's because they feature acting credits from its former drama student: Loudon Wainwright III.

The Grammy-winning folk legend/actor wrote the 1970s song "School Days" inspired by his time at St. Andrew's.

Wainwright, 77, said he'll probably perform the nostalgic tune when he headlines the new Elkton Music Hall in Maryland, on Saturday, Nov. 4.

How did Loudon Wainwright III end up in Delaware?

Wainwright was born in North Carolina and grew up in Westchester County, a suburb of New York.

His dad sent him to St. Andrew's for high school where he graduated in 1965. But Wainwright initially wasn't thrilled about getting shipped off to a boy's boarding school, which St. Andrew's was until the 1970s.

"I kind of was pissed off," he explained. "I kind of wanted to go to high school where kids were dancing, and there were girls there. [That] seemed, at least from the outside, to be a much freer environment than a boy’s boarding school."

A rebel at heart in Middletown

Loudon Snowden Wainwright III performs during Rufus Wainwright 50th Birthday Celebration at The Montauk Point Lighthouse on July 13, 2023 in Montauk, New York.
Loudon Snowden Wainwright III performs during Rufus Wainwright 50th Birthday Celebration at The Montauk Point Lighthouse on July 13, 2023 in Montauk, New York.

Freedom was a theme of the early 1960s. Major events like the Vietnam War and issues like segregation were happening while Wainwright was in the Middletown area.

During his teenage years, women also were thirsty for Hollywood bad boys like Marlon Brando and James Dean.

Wainwright wanted to be like them, which he noted in "School Days," instead of going to school in a shirt and tie.

"It was a disciplined, kind of repressed place," Wainwright said about St. Andrew's. "On the other hand, I got an education. I don't regret having gone there."

Delaware led Loudon Wainwright III to Hollywood

Musician Loudon Wainwright III poses with Best Traditional Folk Album award for 'High Wide Handsome: The Charlue Poolo Project' in the press room during the 52nd annual Grammy Awards held at Staples Center on Jan. 31, 2010, in Los Angeles.
Musician Loudon Wainwright III poses with Best Traditional Folk Album award for 'High Wide Handsome: The Charlue Poolo Project' in the press room during the 52nd annual Grammy Awards held at Staples Center on Jan. 31, 2010, in Los Angeles.

The acting bug bit Wainwright at St. Andrew's.

"One of the things I liked the best was being in the school plays, the drama club," he said. "That's kind of where I decided that I wanted to be an actor."

After graduation, he attended the drama school Carnegie Mellon University in Pittsburgh. That didn't last long.

"I dropped out, I guess, my sophomore year and went to San Francisco. I became a hippie," he explained. "Again, it's that theme of wanting to be a blaspheming, booted, blue-jeans rebel guy."

Acting break comes with 'M*A*S*H'

His first acting break came in the military sitcom "M*A*S*H," in which he appears in three episodes.

"M*A*S*H" writer Larry Gelbart cast Wainwright after seeing him perform a concert at the famous Los Angeles nightclub the Troubadour around 1974.

"He had an idea of a character who was a surgeon, but who also played the guitar and wrote songs and sang. So that's how that happened," Wainwright explained.

Wainwright III still loves acting & music

Over the years, Wainwright's music and acting career continued to blossom. He won a Grammy, followed by two more Grammy nominations, and recorded over two dozen musical projects.

The folk legend has appeared in about the same number of films and TV shows as records he's released, according to IMDB.

Wainwright is a father of four and three of his children are working musicians. His most famous child is singer-songwriter Rufus Wainwright.

The elder Wainwright, who has a new 1-year-old granddaughter he adores, is working on new music.

Fans and former classmates might hear those songs when he gigs at Elkton Music Hall on Saturday, a venue that's only about 35 minutes from St. Andrew's.

The impact that the school's drama club had on him still inspires him to act. He's down to make another movie if he gets the right call.

"I'm always ready. If Steven Spielberg wants to give me a call, I'm ready to go."

Elkton Music Hall (107 North St., Elkton, Maryland) at 8 p.m. Saturday, Nov. 4. Ticket is $50. Visit elktonmusichall.com. 

If you have an interesting story idea, email lifestyle reporter Andre Lamar at alamar@gannett.com. Consider signing up for his weekly newsletter, DO Delaware, at delawareonline.com/newsletters.

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This article originally appeared on Delaware News Journal: Loudon Wainwright III explains how Delaware played big role in career