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Sydney ‘Syd’ Chaplin, older brother of famous actor Charlie, was also an actor and owned several properties in Encinitas. Photo courtesy of Lisa Stein Haven
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Sydney Chaplin’s Encinitas investment pays off

ENCINITAS — If it weren’t for Sydney Chaplin’s pursuit of a deal, the current 1st Street Bar on S. Coast Highway 101 in Encinitas may never have come to fruition.

Sydney, elder brother to famous actor Charlie by four years, apparently knew a good investment when he saw one and was clearly ahead of his time, according to biographer Lisa Stein Haven, Ph. D., professor of English at Ohio University Zanesville.

Syd Chaplin with puppies. Photo courtesy of Lisa Stein Haven

And speaking of deals, the elder Chaplin, an actor in his own right, purchased acreage in 1923 for $5,000 in Encinitas. Today, 1st Street Bar sits on that land at 656 South Coast Highway 101.

Haven wrote in her book, “Syd Chaplin: A Biography” (2010, P. 119): “Chaplin recently completed a home for himself on Victor Avenue and has given a contract for a store building on the boulevard. The business structure, which will be of the Spanish type of architecture, will be occupied by a cafe, barbershop and dancing floor.’” 

Her source she said comes via “Film Folk Buy Encinitas Sites for Residences,” Los Angeles Times (31 August 1924), p. D5.

And according to the Encinitas Preservation Association’s website, the elder Chaplin owned other properties in the area: The Sidney Chaplin Building (656 S. Coast Hwy 101) is noteworthy because its owner in the 20s was a brother of movie star, Charlie Chaplin. Sydney owned other property as well including several lots near today’s Self Realization Fellowship and property on the hillside overlooking Downtown. Charlie Chaplin also purchased property in the Downtown area. Soon after a two-story Neoclassical home was completed on Neptune Avenue in 1925, Charlie Chaplin bought it for his mother.”

Why would Sydney Chaplin buy land in San Diego County?

Haven said: “Sydney was always on the hunt for a good deal of some sort that he thought would grow into some money later.  

“He bought the property in Encinitas and held onto it for a long time — maybe until the 1950s or ‘60s,” she said. “By the time the family got rid of it, it was worth a lot of money, and he knew that was going to happen. He wasn’t even living in the state then.

“I think after his death, his wife Gypsy, was trying to get rid of the land. At that point, it was part of her inheritance. She had some trouble disposing of it, which I don’t know what about, but he left that land to her.”

1st street bar in Encinitas sits on a plot of land originally purchased by Syd Chaplin in the 1920s. Courtesy photo

Making movies, not easy

Over the course of his lifetime, Sydney Chaplin made 35 films in the 1910s and 1920s. Haven said he had a contract with Paramount Pictures in 1919 but it didn’t get completed.

By 1920, he was without a contract, so he went back to bit parts and was working his way back up in terms of reputation. By 1923-1924 he had had some successes, and by 1925, he had snagged a five-picture deal with Warner Bro. for which he was the main star.

“By then, he had quite a bit of money and he started buying land throughout California,” Haven said.

She added that Sydney Chaplin invested in a many other things besides land such as the first domestic American airline in 1919, called the Syd Chaplin Aircraft Corp.

“It was the first in this country and went from San Pedro to Catalina Island and back,” she said.

“It had a pilot school and showroom that had planes sitting in it. Most of the stuff he did, though, lost money, and it went down in a year. He also had a dress company that made gingham dresses … ”

While Sydney Chaplin did try to ride a bit on his brother’s famous coattails, he was trying to make as much money as he could, so he didn’t have to lean on his brother entirely.

“He wanted fame and he wanted money of his own,” Haven said.

Scathing scandal
Overall, Haven said Sydney Chaplin’s career was halted by scandal.

“Talk about the #metoo movement, he invented it,” she said. “He bit off the nipple of a young actress by the name of Molly Wright in London. It was a major scandal in the day … ”

But at the end of all his ups and downs, Haven said: “Sydney Chaplin was an opportunist, fine actor and street kid all rolled into one.”

A bar with history
Since the days of Chaplin, there have been several businesses on the original Chaplin-owned land including the current 1st Street Bar owned by David Kenneth Shapiro.

Prior to Shapiro buying it in 2015, it was owned by husband and wife Christine and Michael Schwartz from 1993 to 2007. They also named it 1st Street Bar and later sold it to Ty Lee Hauter who owned it until Shapiro bought it.

“It was packed from the day we took it over, people loved it,” Christine Schwartz said. “We had a good run, and we had great bands. We had 25 cent pool tables that brought people from all over … ”

Sydney Chaplin in a Warner Bros. promotional stunt. Photo courtesy of Lisa Stein Haven

She said in 1980s into the 1990s, the bar was called Ireland’s Own and in the 1970s it was owned known as the Courthouse North.

As for its current owner, Shapiro, he has a long history of working in the industry and was excited to buy the bar.

“I bar-backed at Walter Payton’s bars as a teenager, bartended Gibson’s Tempe for three years and have been managing bars ever since,” he said. “This is the first bar I have raised money for and bought.”

Shapiro said he learned of the Chaplin connection early on and thought it was fascinating.

“Encinitas is my favorite town on earth and I could not be more honored and prouder to have a little bar with a little stage right in the heart of the 101 Encinitas,” he said.

Shapiro said he didn’t want to change the name because of its long history in the city.

“If it really needed a name change, I would have done it, but it had a decent history and my goal was to just make some minor tweaks and run a good and peaceful live music room,” he said.  

Shapiro said at one time he had heard the bar was also called “Fat Cats,” “Snug Harbor,” and “Stingaree,” but wasn’t sure about dates, actual names, or owners prior to Ireland’s Own.

And what about Chaplin’s ghost, has he seen it or any?

“I don’t know of any, but if there are I would hope they are good ones,” he laughed.

Sydney Chaplin died on April 16, 1965, also Charlie Chaplin’s 76th birthday.