In his 20s, Edward Hammerman crashed the Old Town Art Fair with a dozen multi-colored globs of plastic. Mr. Hammerman, just starting out in the advertising business, had nabbed the scraps from a plastics client. He and longtime friend Joe Adler hauled the orbs from their Rogers Park apartment and set up shop on the street, posing as artists.

Mr. Hammerman knew how to sell the act, Adler said. He was a joker, but “never phony.”

Soon, Mr. Hammerman was managing much more than makeshift art. An advertising executive at Hammerman & Morse, the Northbrook resident served clients for more than 40 years — and he did it with humor.

“Not a day went by that wasn’t fun with Ed,” former colleague Donna Greene said. “He just made life fun.”

When South Holland Bank & Trust wanted to gain waste management clients, Hammerman’s firm sent boxes with the slogan, “A sample of the waste paper ready for your pick-up.” Inside was a crumpled dollar bill.

Hammerman & Morse advertising campaign | Provided photo

When an account supervisor obsessed over a WMAQ commercial featuring tap dancing women dressed as dollar bills, Mr. Hammerman got someone to pull one of the costumes out of storage. “I finally got to be a dancing dollar,” Greene said. “He knew it would be special.”

Relatives say Mr. Hammerman brought his irreverent, Lenny Bruce-style wit to every situation, no matter how sensitive. Even receiving cancer treatment at an Arizona hospital, his daughter Deborah Hammerman said, her father was making friends with the physician.

“When does social hour end?” his daughter remembers thinking. “At some point this is a doctor’s appointment.”

“There’s nothing he wouldn’t joke about,” his son said. “He was not a shy man.”

He died June 23 in Northbrook. Rabbi Ari Averbach of Congregation Beth Shalom told mourners at his funeral he reviewed Mr. Hammerman’s jokes, hoping to tell one — but none were appropriate.

Mr. Hammerman got his start in the industry during its heyday, but colleagues say his firm felt less “Mad Men,” more creative and open. “We did things you could be proud of,” Linda Lepp said.

In 1985, Mr. Hammerman opened his firm with partner Gayle Morse; accounts included Des Plaines Bank, Northwest Community Hospital and Grant Hospital. Morse said he helped pioneer a new approach concentrating radio advertisements for repeated exposure.

If clients got nervous, Mr. Hammerman was the one they called. “They’d go, ‘Well, we don’t look like everybody else [with this campaign],'” Greene remembered. “And he’d say, ‘That’s the point.'”

Edward Hammerman grew up in Dayton, Ohio. | Provided photo

He grew up in Dayton, Ohio, the son of Anne and Ben Hammerman. His mother was editor of the Dayton Jewish Chronicle and wrote a column titled, “Hammered-Out.” He graduated from Ohio State University, and had a lifelong love for the Buckeyes.

As a young man in Chicago, Adler said Mr. Hammerman had a certain “joie de vivre.” The friends would crash weddings and bar mitzvahs at the Drake Hotel and Hilton Chicago, then swing by a deli on California Avenue.

After Mr. Hammerman married Doris Newton, the couple moved to Evanston to raise their children. His daughter likened family life to a Norman Rockwell painting; after the family moved, the new owners said it took 10 years for neighbors to stop calling it “the Hammerman house.”

Ed and Doris Hammerman | Provided photo

Doris died suddenly in 1998, but Mr. Hammerman still made dinner for his mother-in-law every week, despite what his son called “experimental” cooking.

He met his second wife, Arlene Gitles, on a Jewish dating site. On their first date, he stepped into Gitles’ living room, frowned, and said: “You have cats. I’m allergic.” She was thrown.

“I wasn’t happy with him,” she said. “I thought, ‘Okay, sweetie, you can take me out to dinner and then I’ll never see you again.'”

But she did. They married in 2005 and traveled the world — China, Ireland, Mexico.

He was active in local synagogues, including Kehillat Shalom in Skokie and Beth Shalom in Northbrook, where he liked to wear Hawaiian shirts to service — because, he told Rabbi Averbach, he “liked to get people riled up.”

In retirement, he vented on his blog, “Hammerman’s Words of Wisdom” — frustration over his cancer treatment, political diatribes. “Once he had your email, unless you were willing to switch it, you were trapped,” his son said. He loved to rant, read and watch the White Sox, which he did on Tuesdays with his son.

Mr. Hammerman is survived by his wife, Arlene Gitles; children, Deborah and Joel; siblings, Stan and Miriam; one grandchild; three step-children; and five step-grandchildren. Services have been held.

Deborah, Ed and Joel Hammerman | Provided photo