A Crazy Rift: Barbra Streisand and Winnipeg Find Each Other Strange

Jeff Swystun
7 min readAug 15, 2024

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Let’s hop in a time a machine to 1961, the year Barbra Streisand performed in Winnipeg that marked her first appearance outside of the United States. Born in 1942, the singer was barely 19 when she traveled to the city. This was before her amazing global success.

18 Year Old Streisand in 1960

Streisand got the performing bug at age 14 when she saw her first Broadway play, The Diary of Anne Frank. Immediately she began paying her dues by jumping into community theater doing anything required from small background roles to helping backstage. For a time, she sang in a choir with a young Neil Diamond. At 16, she boldly moved out of her Brooklyn home and rented a small apartment in Manhattan’s theater district.

Streisand took menial jobs to make her pursuit of show business work. During one period, she lacked a permanent address, and found herself sleeping at the home of friends or anywhere else she could set up the army cot she carried around. Her mother was horrified and begged her to pick any other career which only strengthened her resolve, yet audition after audition went nowhere.

Streisand’s boyfriend, Barry Dennen, convinced her to enter a talent contest at the Lion, a gay nightclub in Manhattan’s Greenwich Village. She performed two songs, after which there was a “stunned silence” from the audience, followed by “thunderous applause” when she was pronounced the winner. She was invited back and sang at the club for several weeks.

Streisand was influenced by beatniks whose counter culture creativity either appealed or proved a head-scratcher.

During this time, disliking her name, she changed it from “Barbara” to “Barbra”. Streisand was repeatedly told she was too ugly to be a star and was advised to get a nose job. That advice was ignored but must have hurt. Soon though, Streisand’s audition at the Bon Soir nightclub paid off and she was signed at $125 a week opening for Phyllis Diller. She recalls it was the first time she had been in that kind of upscale environment, “I’d never been in a nightclub until I sang in one.” The year was 1960.

Streisand improved her stage presence by speaking to the audience between songs. She discovered that her Brooklyn-bred style of humor entertained. Some began comparing her to Judy Garland, Lena Horne and Fanny Brice. Her ability to charm an audience with spontaneous humor became more sophisticated and theater critic Leonard Harris wrote, “by the time she’s thirty she will have rewritten the record books.” Harris was accurate.

Winnipeg Here We Go

The provincial vehicle license plate has long claimed Manitoba to be “friendly”. So Winnipeg, as the capital, should be expected to be extra friendly. Perhaps that is why her manager booked a run at Winnipeg’s Town n’ Country nightclub in The Towers at 317 Kennedy Street. The gig was to run July 3 to 16, 1961. This meant performing three shows nightly. One could guess that this was good training and a way to grow Streisand’s following.

The Towers in Winnipeg 1960. A venue on par with leading clubs in North America.

Winnipeg historian and author, John Einarson, wrote about the club scene in his book, Heart of Gold: A History of Winnipeg Music. The Town N’ Country was perhaps Winnipeg’s top supper club in the 1950’s and the mid-60’s. It housed three levels with a restaurant on the main floor, a lounge on the second, while the top level was coined The Towers where singers and bands performed.

This was part of a new trend in the entertainment scene where you could catch dinner, a show and dance all in the same sitting. Other Winnipeg supper clubs included the Copacabana, Pierre’s, Chan’s Moon Room Cabaret, Rae and Jerry’s Scarlet Lounge, Club Morocco, The Paddock and the Constellation Room.

To fill their stages, these clubs relied on a circuit of mid-level and up-and-coming U.S. entertainers which is how Streisand, who had a Chicago-based agent, ended up in Winnipeg. She earned approximately $300 a week but Streisand had to pay her own way to the city and cover hotel room expenses.

She played to critical acclaim, but the style was new to Winnipeggers. Gene Telpner, in a favourable Winnipeg Free Press review wrote, “Miss Streisand is the type of singer you’d expect to find in the Blue Angel or San Francisco’s Hungry I. That’s why Winnipeggers may find her rather strange.” The audience watched quietly; some say it’s because they didn’t ‘get’ her but others said that they were silenced by her amazing voice. Author Einarson says she was fired after three days by the club manager over a struggle to connect with the audience.

In his column, Around the Night Clubs, Telpner wrote on July 4, 1961, “Barbra Streisand, the current attraction at The Towers, is a girl with an unusual singing style that could take her right to the top. Born in Turkey and raised in Brooklyn, she has a semi-Oriental look and a singing manner all of her own. But she seems to grow on you after you settle down to listen. Barbra sings songs off the beaten path, such as Come to the Supermarket in Old Peking, which she does extremely well. When she sings her hair flies, her hands twirl, and her whole torso gets into the act. The boys in the band think she’s terrific, and musicians are usually good judges of talent. Her closer, Lover Come Back To Me, was really worth hearing.”

“Born in Turkey and raised in Brooklyn, she has a semi-Oriental look and a singing manner all of her own. But she seems to grow on you after you settle down to listen.”

Telpner enjoyed her talent but was less a fan of her wardrobe as it came from rummage sales. That seems fitting for a young woman that was more bohemian than polished at the time. Here comes some personal research. I remember my mother mentioning Streisand’s time in Winnipeg. She recalled that those who encountered the performer were put off by her lack of hygiene which fits the bohemian theory.

If Winnipeggers didn’t get Streisand, the feeling was mutual. A subsequent television interview on The Tonight Show saw her speak of the Winnipeg gig, “I’ve worked in three places, like weird, not weird, country places. Like in Winnipeg Canada in Manitoba. This was a beautiful nightclub with three floors, very posh, except the people wore short, short shirt sleeves. They didn’t wear ties to come to the nightclub.”

“I’ve worked in three places, like weird, not weird, country places. Like in Winnipeg Canada in Manitoba.”

Johnny Carson was guest hosting and asks if Winnipeggers were nice. Streisand responds hesitantly with pauses, “…Um….yes.” It took 45 years until she performed again in Canada. Winnipeg lore says that Streisand was fired by Town N’ Country co-owner Auby Galpern and told that she would never make it as a cabaret singer. That has been disputed by former senior Town N’ Country staffers who say she was released early at the request of her agent to return to the U.S. for work. Many others say she saw out the entire contract.

Her tenure remains a debate but what we do know is that within three years, Streisand would appear on the cover of Time magazine marking her early success in film and music and signal a remarkable career. As for the supper club phenomenon, as cities around Winnipeg grew, the old entertainment circuit that had been around since the days of vaudeville disappeared.

The Towers continued until January 5, 1971, when the Winnipeg Free Press reported, “Late Sunday night, the popular Town ‘n Country Restaurant at 317 Kennedy Street was destroyed in a two-hour holocaust that reduced the night spot to a gutted shell.” In its place sprang Studio 44, Winnipeg’s largest discotheque. In 1981, it was renovated again into the Stage West Dinner Theatre. The building was torn down in 1985 to make way for the Portage Place retail development.

The closest Streisand ever got to Winnipeg again occurred in 1969 and 1970, when she dated Prime Minister Pierre Trudeau. On one occasion the two attended a performance of the Royal Winnipeg Ballet in Ottawa. During their time together Streisand appears positively regal standing in contrast to earlier days. Yet, she remains consistent if not unchanged. In 2009, Streisand said, “When I was a teenager in New York, I was buying antique clothes. I still am.”

Meeting and greeting the ballet company.

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Jeff Swystun

Business, Brand & Writing Strategies. Former CMO at Interbrand, Chief Communications Officer at DDB Worldwide, Principal Consultant at Price Waterhouse.