The Pickle Barrel restaurant was the brainchild of Leo Osher who operated a number of Jewish-style restaurants and delis in the Chicagoland area from 1950 until his death.
A native of Chicago, Mr. Osher grew up on the West Side and graduated from Roosevelt High School. After serving in the U.S. Army during World War II, he opened the Corned Beef Center, a small deli at 3352 Broadway at Roscoe Street in 1950. It remained in business for 10 years.
He opened the Pickle Barrel in 1960. The quirky restaurant was right at home on the popular streets of Chicago's Old Town (50+ photos). The walls were decorated with oddities and antiques. Guests were greeted with a barrel of pickles for snacking, a bucket of popcorn, and small barrels of kosher dill pickles on each tabletop.
The Pickle Barrel, in an average week, would go through 10 fifty-pound barrels of pickles (26,000 lbs a year)—each barrel containing about 1,200 pickles, and 400 pounds of popcorn (20,800 lbs a year). The menu featured deli sandwiches, and decidedly non-Jewish deli fare like ribs, fried shrimp, and sloppy Joes. Balloon artists entertained the kids and pitchers of beer entertained the adults.
In 1964, Leo Osher was named the Pickle Man of the Year. "He was a natural candidate," said William Moore, retired executive vice president of the Pickle Packers International, then a national trade association, which bestowed the award on Mr. Osher. As the owner of Chicago's popular Pickle Barrel restaurant in Old Town at 1423 N. Wells Street. Osher played along good-naturedly with the publicity stunt, which, mercifully, only went so far. "I don't think he had to wear a banner or tiara," said his daughter-in-law, Ellyn Osher.
Osher opened four more Pickle Barrel locations, including one on Oak Street and one at Howard and Western.
Success did not come without risks, however. In March 1964, two armed bandits robbed the Pickle Barrel, making off with $2,000. The two men forced four male patrons into a walk-in refrigerator until the crime was complete, Mr. Osher told police, according to a news report at the time. "He just said that was a terrible thing," said an employee of 21 years, Sue Glaser, manager of the Barnum & Bagel restaurant in Skokie Illinois. "He never really talked a lot about it after that."
"They hit a niche. It was a simple menu with high energy and a lot of fun and value," said restaurateur Richard Melman, founder, and chief executive officer of Lettuce Entertain You Enterprises.
In the late 1970s, Osher sold the Pickle Barrel restaurant chain.
Osher was a resident of Skokie. He and his son Michael opened the Barnum & Bagel restaurant at 4700 West Dempster Street in Skokie. They briefly considered naming it, "20th Century Lox."
Osher died Tuesday, April 20, 1999, of complications from heart surgery at a hospital in California where he had a second house. He was 79.
The Pickle Barrel Restaurant, Old Town, 1423 N. Wells, Chicago, IL
The Pickle Barrel Restaurant, 7574 N. Western Street, Chicago, IL
The Pickle Barrel Restaurant, 50 E. Oak Street, Chicago, IL
The Pickle Barrel Restaurant, Park Forest Plaza Shopping Center, Park Forest, IL
The Pickle Barrel Restaurant, 240 Skokie Highway, Northbrook, IL
Compiled by Dr. Neil Gale, Ph.D.