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Jack Singer just outside of Puerto Vallarta in 1973.

Grant Gallelli

Jack Singer started his business career in Calgary as an 11-year-old collecting rent on behalf of his immigrant parents, and became a starry-eyed – yet wealthy – autograph-seeker, who ended up owning a Hollywood movie studio and hobnobbing with entertainment industry elite.

Mr. Singer's larger-than-life personality and humble beginnings seem straight out of central casting.

His parents came to Canada from Poland at the turn of the 20th century, used their savings to help hundreds of Jews escape persecution before and during the Second World War, and in doing so, instilled in their son an entrepreneurial and philanthropic spirit. Mr. Singer would go on to become a real estate mogul who would help build Calgary – and beyond – and, after snapping up a flailing studio from Francis Ford Coppola, helped rebuild Hollywood.

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Known for his brash style and quick wit, Mr. Singer never lost his pizzazz.

The last time he was in Tinseltown was in 2007 for his 90th birthday bash at the Beverly Hills Hotel, complete with burlesque dancers for entertainment. Maclean's magazine, which once called Mr. Singer Canada's Howard Hughes, asked him in 2011 whether any celebrities were in attendance.

"There were some stars there," he said, "but I didn't even meet them. I was busy getting drunk."

The headline on the story: L.A.'s Unlikeliest Angel.

Jack Singer died on Feb. 2 in hospital in Calgary of natural causes. He was 95.

He was born Dec. 17, 1917 in Calgary to Bella, a housekeeper at the Palliser Hotel, and Abraham, who tried his hand working the circus circuit – the third of four children.

His mother squirrelled away savings and quietly bought rooming houses in the city. Young Jack was collecting rent from her boarding room tenants – 75 cents a week – and helped keep the books.

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According to his sons, Alan and Stephen, Jack's parents would use their money – and they were by no means well-off – to rescue hundreds of Polish Jews from the Holocaust.

"They were hard-working, building up from nothing," Alan said.

The Singers required each person they brought over to bring somebody else, ready to work. Perhaps 1,600 people now count themselves descended from Bella's "pyramid scheme," according to the Singer family.

Among them, Sid Cyngiser, who in 1949 was the last person Bella brought over, and upon arrival, lived in Calgary for a time with Mr. Singer, who became a business associate and remained a close friend for 60 years.

"She was my grandmother's sister and I was the only one in the family that survived," he said in Jack: The Biography of Jack Singer (2010).

And her son was always there when Mr. Cyngiser – or anyone, really – needed him.

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Mr. Singer was also a capable athlete in his youth.

At Central Memorial High School in Calgary he was a pitcher on the baseball team and a quarterback in football. He had a promising amateur boxing career, enjoyed a string of wins, and at age 17, he won the Canadian lightweight amateur championship.

"My late good friend and mentor, Sammy Luftspring, often spoke of Singer's natural boxing abilities," said Spider Jones, three-time former Golden Gloves champ and member of the Canadian Boxing Hall of Fame.

Mr. Luftspring, a contemporary of Mr. Singer's, was a celebrated Jewish Canadian boxer in his own right, and a Canadian welterweight champion.

"I'm a student of boxing," Mr. Jones said, "and Singer was a really good amateur fighter; a tough kind of banger."

But Mr. Singer gave it up when two perforated eardrums did him in, but would later become a fight promoter and chum around with luminaries of the boxing world, including Joe Frazier and Don King.

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While still a teenager in 1934, Mr. Singer turned to business, and found a partner in Avrum Belzberg. They formed United Management, a real estate business that continued for four decades, and at one point, held 200 pieces of property.

Along the way, he found time for love.

In 1944, Mr. Singer married Shirley Cohen – a union that came after an unlikely beginning.

Mr. Singer's friend was actually the one smitten by the beautiful young lady, but her parents did not approve of the match. Mr. Singer showed up to convince them that he was her more "acceptable" kind of date, and then planned to hand her off to his buddy.

"But it didn't end up that way," Stephen said.

As Mr. Singer recalled in his biography, "I rang the bell at Shirley's house. I was wearing a powder blue suit and I looked like a gangster. It was love at first sight."

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They quickly became a power couple of Calgary – fashionable, jet-setting party hosts.

They would remain together until Shirley died in 2001, producing two sons, Stephen and Alan.

By the 1950s and 1960s, Mr. Singer and his older brother, Hymie, were introducing Alberta to the strip mall. They would land anchor tenants such as banks and grocery stores, which would help them get financing and snap up land. They would go on to develop other commercial sites around the city, and expand their real estate empire through the West and south to California, Arizona and Texas. Mr. Singer was reported as one of Canada's richest men with assets worth more than $1-billion, and his generosity extended to Jewish groups, community associations and the arts.

But times weren't always so good. In the mid-1950s, according to his biography, Ottawa started poking around in Mr. Singer and Mr. Belzberg's finances on suspicion of tax evasion for failure to report income and property sales.

At the time, Mr. Singer believed "they had me cold" and worried he'd be sent to jail, leaving a wife and two young children at home.

A judge levied fines instead.

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When not engrossed in business or family, Mr. Singer's other passion was sports.

"My dad watched sports every day of his life," Stephen said.

In 1959, a thoroughbred race horse he co-owned named Tyhawk set a world record over six-and-a-half furlongs at one minute 14.4 seconds at Turf Paradise in Phoenix. In 1960, Tyhawk won the Highlander Stakes at Woodbine Racetrack in Toronto, matching a course record of 1 minute 10.2 seconds over six furlongs on dirt.

Mr. Singer couldn't have been more proud. Tyhawk was later inducted into the B.C. Horse Racing Hall of Fame, considered "possibly the top British Columbia sprinter of all time."

Still, Mr. Singer had one great regret: never picking up a professional sports team, though he did try.

In 1997, he attempted to hand over $70-million to help buy the Toronto Blue Jays, but his dream of owning a Major League Baseball team was blocked by an old boys club of insiders who didn't take kindly to his involvement in a 1982 lawsuit. Even though the lawsuit was filed by Mike Shapiro, who was previously thwarted, along with Mr. Singer, in their bid to buy the Kansas City Royals, baseball doesn't like anyone involved in challenging the system – especially outsiders.

As then-commissioner Bowie Kuhn said at the time: "Baseball is quarrelsome enough. It doesn't need people with a propensity for litigation."

"All that stuff, it happened 16, 17 years ago," Mr. Singer told The Globe and Mail during his failed attempt to purchase the Jays. "I was a witness [for Mr. Shapiro]. I didn't shoot baseball."

Still, baseball didn't want him or his money.

Other failed ventures included an effort to bring an NFL franchise to Los Angeles, and another to buy the Empire State Building in New York. He also tried his hand with a Calgary-based energy company and ended up flushing $75-million down dry holes.

But he famously wound up with a movie studio, thanks largely to serendipity.

In 1981, he was golfing in Palm Springs when he was asked if he was interested in touring Mr. Coppola's movie studio, where the director of The Godfather films was shooting One From The Heart. He loved movies, so Mr. Singer tagged along looking for a signature, not a deal.

But he met the director, the pair hit it off, and soon Mr. Singer injected $3-million into the film. But it was an expensive box-office flop that pushed Mr. Coppola into receivership.

In 1984, the Singers bid $12.3-million at auction for the studio. Several lawsuits followed, along with the inevitable falling-out with Mr. Coppola, who, according to the Los Angeles Times, accused Mr. Singer of "using the loan as a wedge to take away his studio." He privately believed the family was trying to ruin him, the newspaper reported in 1990.

The matter was eventually settled out of court.

For years after that chance encounter, Mr. Singer, known for delivering one-line zingers, would say, "I went there to get an autograph and I ended up owning a studio."

In doing so, Mr. Singer ended up counting George Burns, Truman Capote and Peter Lorre as among his friends, and suddenly attracted a lot of media attention himself.

For her book Controlling Interest, in which Diane Francis profiled families that owned a swath of Canadian assets, she described Mr. Singer as "pure Hollywood: large pinkie rings, open-necked shirt, hairy chest and gold chains."

She perhaps neglected to mention his ever-present cigar and mahogany-hued skin.

"My dad loved the sun," Stephen Singer said, "He would get so tanned."

Mr. Singer pumped about $20-million into modernizing the renamed Hollywood Center Studios and over the years added production stations and branched out beyond feature films into television. While he never fulfilled another dream – to make his own movie there – the studio did become home to Jeopardy, Star Search, and the children's series Pee-wee's Playhouse.

It still operates today, with son Alan, who resides in Los Angeles, at the helm.

In 2011, Los Angeles city council thanked Mr. Singer for his "vital role in the revitalization of the District of Hollywood" by creating a "world-class resource for feature film and commercial production." The special resolution declared him "an angel in the City of Angels."

Mr. Singer was too ill to travel to accept the honour. He was in hospital with a bout of pneumonia, followed by a broken hip.

Hollywood didn't forget Mr. Singer, even as he aged. Not even an old foe.

Mr. Coppola sent Alan a note upon learning of Mr. Singer's death.

"I always thought your father would outlive me," it said.

And in Calgary, where Mr. Singer's sons donated $1.5-million in 1982 to the arts on his behalf, one of the city's premier music venues bears his name – the Jack Singer Concert Hall – an especially pleasing honour.

"My father always loved publicity," said Alan. "He would love seeing his name in the paper with the concert listings."

Whatever ego he may have had, Mr. Singer never lost his sense of humour.

"Everybody said such nice things about me," he said after his 90th birthday party, "I almost started to believe them myself."

Mr. Singer leaves his two sons and four grandchildren. About 300 people attended his funeral service at Beth Tzedec Synagogue in Calgary.

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