Why did the world fall in love with Diane Keaton? Tens of millions have their theories. But to trace the origins of that charm—where it began, how it bloomed—we go back to the summer of 1967, when a young woman named Diane Hall arrived in Woodstock, New York.
That summer, theater owner Edgar Rosenblum’s star director, Harold Baldridge—an associate of Sanford Meisner at the Neighborhood Playhouse in New York City—spotted the 21-year-old graduate fresh from Meisner’s acting class. She was seeking an Equity card, a professional union membership, and Baldridge invited her to join his summer stock company at the recently revived Woodstock Playhouse.
Diane’s ascent was swift. She started in the chorus, earned a secondary role in “Kiss Me, Kate,” and soon took on Ado Annie—an offbeat and beloved part in “Oklahoma!.” After the season ended, she stayed on for “Oh, What a Lovely War” in the newly formed Hudson Valley Repertory Theater. By then, she had thoroughly impressed: The Town of Woodstock, Peter Yarrow of “Peter, Paul and Mary,” the entire Playhouse crew—and whoever first recognized the makings of “Diane Keaton,” Equity card in hand, ready for her Manhattan debut that fall in the ensemble of “Hair.”
But first, Keaton—then Hall—shared a boardinghouse near what’s now Woofstock Pet Supply with fellow apprentices including Melanie Chartoff. Costume designer Pam Knap (née Dendy), then in her early 20s, remembers her vividly.
“She was lovely, charming, guileless, genuine, and incredibly talented,” Knap said. “But modest and insecure—she never thought she was any good, although she was brilliant.”
After shows, they’d sometimes meet at Deanie’s Bar, an historic restaurant in Woodstock, uphill from what is now the restaurant Silvia. “She was going through some romantic disappointment,” Knap added, later acknowledging a connection with Peter Yarrow. “Still, she never changed. I saw her backstage on Broadway once, and she said, ‘Oh, you should have told me you were coming! Was I any good?’”
Not everyone remembered the same quiet Diane. Apprentices Jency Elliot and Fern Malkine-Falvey, local sixteen year olds at the time, recalled her as radiant and confident.
“Diane would often join us on the back steps of the Playhouse during breaks,” Fern reminisced. “I’d have my guitar, we’d be harmonizing, and she’d sing along—she had a lovely voice. She seemed so much older, so sure of herself, like she was saying, ‘Bring it on!’”
Fern never forgot her vitality: “She stood out in every way—funny, kind, spontaneous, always ready to take risks on stage. She did it joyfully. I never saw her angry or speak ill of anyone.”
According to Baldridge’s, then, leading man, William Metzo–now 88, “Diane Hall was not under contract at the Woodstock Playhouse. Rather, her intention had always been to earn Equity, assume her mother’s maiden name of ‘Keaton,’ and make a bee-line for auditions in Manhattan.”
Fittingly, Diane’s star turn in Woodstock awaited her last performance at The Playhouse: the rapid-fire complexity of Cicely in Oscar Wilde’s masterpiece, ‘The Importance of Being Earnest.”
In early rehearsal Metzo recalls helping her with a Shakespearian exit: “She had a speech that ended downstage center and then exited right. I told her, ‘Deliver the body of it, then walk to the door, turn, give the last line for the laugh–then exit. She nailed it–and the entire performance.
58 years later, our theater owner’s widow, Cornelia Rosenblum, remembers Diane to have been “nothing less than superb.”
If New York theater history is to be believed, Diane was instantly snatched away for an ensemble role in the off-Broadway sensation,“Hair: The American Tribal Love-Rock Musical.” Here, she refused the cash bonus offered any cast member who would disrobe, and soon under-studied the female lead—eventually awarded her when “Hair” landed for its historic run on Broadway. Woody Allen next auditioned her to play his leading lady in “Play It Again, Sam.” Despite her being two inches taller than Allen, Keaton got the part after which the playwright/star promptly fell in love and… the rest is herstory.
Ironically, years later, Keaton would call performing a play “night after night” her “idea of hell.” Yet those who saw her in Woodstock knew she was already practicing what Meisner had taught her: Be in the moment.
That spontaneity—the very quality that would define Annie Hall, Kay Corleone, and so many others—was forged in the blazing summer heat of a Catskills stage, two years before hundreds of confused hippies descended on Woodstock, attempting to find half a million siblings, gathered in the rain on a farm sixty miles away; a farm which borrowed the name and instilled legendary fame at “Woodstock.”
But it was here in the actual town that an unknown Diane Hall first became the unforgettable Diane Keaton.
Tad Wise is a contributing writer. Send correspondence to reporting@theoverlooknews.com.


