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Between her singing success in California and New York, Chippewa Falls native Judy Henske has seen a lot of what show business has to offer — the good and the bad.

“During that time, I met some of the best people, and also some of the worst,” she said. “Just the meanest, meanest people.”

As Henske’s full-throated voice and exuberant personality made her more popular, she was offered a role in the 1963 film, “Hootenanny Hoot.” She very much enjoyed her role, being able to perform two songs: “Wade in the Water” and “The Ballad of Omie Wise.”

“I really loved singing that song,” she said of “Wade in the Water.”

That same year, she was also offered a role as a regular on CBS-TV’s “Judy Garland Show.” Henske couldn’t pass up a chance to work with the famous singer and actress she admired as a child.

“She was something,” Henske said of Garland. “She was very nice … and I was just dazzled by her.”

At that time, though, she noted it was obvious that Garland’s addictions were overtaking her, and it seemed as if no one was trying to help her.

Henske’s time on the show was short-lived, as she hated the scenes and dialogue she was given. The show’s writers wanted to paint the Wisconsin girl as a flamboyant rube who was calling for the hogs.

“I told them this isn’t funny, it doesn’t have anything to do with being from a small town. I’m not going to do it,” she said. (Coincidentally, Garland was born in a small town in rural Minnesota.)

Henske then moved to New York and found considerable success in the burgeoning Greenwich Village folk music scene. She recorded her first two solo albums with record executive Jak Holzman, whose label Elektra Records also signed such famous musicians as The Doors and Carly Simon.

Henske sang extensively in clubs around the city, including the well-known jazz haven The Village Gate. She became a favorite for her humorous — and just a bit bawdy — performance style, which she modeled after the lively radio performers she loved listening to as a child.

“I liked when people were engaged, and they show it with laughter and not just clapping,” Henske said. “It didn’t sound like people just sitting lifeless in their seats, admiring you. It was alive.”

Because of her style, she also performed many times with an up-and-coming comedian at that time: Woody Allen.

The two dated for a while, which sparked much talk about her influence on Allen’s 1977 hit movie, “Annie Hall.” The title character, Annie, is an aspiring singer from Chippewa Falls, and even brings Allen back home to meet her parents.

There has been speculation that Henske was the inspiration for the character of Annie Hall. However there has been similar speculation directed toward the actress who played Annie and was the character’s namesake, Diane (Hall) Keaton. She also dated Allen for a long time.

“I had not seen it for years,” Henske said of the film. “It was actually things we did (in some scenes). What’s cool about it is that it puts Chippewa Falls on the map.”

But Henske’s favorite person in New York was the famous poet and author Shel Silverstein.

“I could talk about Shel all day. He was my best friend,” she said. “He was so talented; he was the world’s greatest cartoonist, and a great singer.”

Silverstein even had a hand in helping Henske write the song, “Oh, You Engineer,” which was on her second solo album, “High Flying Bird.” He also wrote a liner note for that album, where he explores what life would be like if he gave in and married Henske.

But while she experienced a lot of success in New York, Henske never really felt at home among the towering buildings and urban sprawl.

“I was very depressed there,” she said. “I needed more elbow room.”

Henske, her musician husband Jerry Yester (a member of the Lovin’ Spoonful, the New Christy Mistrels and the Modern Folk Quartet), and their young daughter Kate moved back to California in the mid-’60s. As a duo, she and Yester made two albums, “Farewell Aldebaran” and “Rosebud,” before Henske retired from professionally performing to focus on raising Kate.

She then married her second husband, noted piano player and session musician Craig Doerge, and the two are celebrating their 40th anniversary this year. Though Henske was done performing, she still actively wrote songs with Doerge.

“Craig is a wonderful piano player, a wonderful composer, and a wonderful husband,” Henske said.

When writing a song, Henske likes to tell a story with her lyrics. She is especially influenced by narrative poetry, which was a big part of her family and her upbringing.

But Henske wasn’t quite done singing yet. She returned to performing in the 1990s and released two more albums, “Loose in the World” in 1999, and “She Sang California” in 2004.

Henske’s current focus is on enjoying her retirement with her husband, writing a book about her life and career, and crossing activities off of her “bucket list.”

One of those goals will be accomplished when she’s back in Wisconsin. Henske plans to go musky fishing up in the Chippewa Flowage near Hayward.

She’s also happy to have a chance to come back to her hometown and showcase some of her most famous songs, along with a couple of newly-written ones, such as “T’was God that Killed Virginia Woolf.”

“I’ve done pretty well in my life, and it’s been very fun,” Henske said. “I followed my bliss.”

Next: The Chippewa County Historical Society introduces classic Chippewa Valley musicians to a new generation.

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