It didn’t matter if you had a bad day, a bad check-up, or your car and love life sputtered.

Frank Rotondo would have your drink waiting for you and maybe a little advice, if you wanted it.

Mr. Rotondo spent 48 years tending bar at L. Woods Tap and Pine Lodge and its previous incarnations at the same Lincolnwood address: the Kenilworth Inn and Bones.

One time, he also served drinks at a Pump Room gathering where Rat Packers Frank Sinatra, Dean Martin and Sammy Davis Jr. hung out.

When he started bartending, Richard Nixon was president, and customers wanted just a shot and a beer. He kept pouring ’em through the era of mixed cocktails, to umbrella drinks, to the rise of craft beer and good American wine.

“He was the best,” said Lettuce Entertain You chairman Rich Melman, who credits Mr. Rotondo for contributing to the success of the restaurant and hospitality company he founded.

Thanks to Mr. Rotondo, “people come back,” said Melman, who described him as “part therapist, part bartender, part friend.”

“People would come in just to see him,” said Mr. Rotondo’s wife Jamie.

He had kind, wise eyes that looked like he’d seen some life. At work, he wore dress pants, crisp white shirts and a black vest emblazoned with his first name.

“If you called central casting in Hollywood and said, ‘Send me a bartender,’ they’d send you Frank,” said Chicago broadcaster Bob Sirott, an investor with Lettuce Entertain You.

Mr. Rotondo died Oct. 11 at 83 at his home in Hanover Park, according to his wife, who said he’d been in failing health since suffering a stroke in July.

Bartender Frank Rotondo under the “Frank’s Tap” sign at L. Woods Tap and Pine Lodge in Lincolnwood. | Lettuce Entertain You

A child of Italian immigrants, he grew up in Paterson, New Jersey. He was driving west to meet a friend in California when he totaled his car in an accident in Chicago.

“He was going to continue to California, but he met me,” Jamie Rotondo said.

They were married in 1971. She was working at Allegretti’s Restaurant at 4124 W. Peterson at the time. Mr. Rotondo joined her there, learning to mix drinks.

He had the type of intangible quality that endears hairdressers and barkeeps to customers. “He listened well,” his wife said.

People would come in looking for him, Sirott said, asking, “Is Frank working? What are his hours this week?”

“He’d always want to talk sports and what you were doing,” said Sirott. “He was a good interviewer. He was a guy who’d always turn [the attention] back on you.”

And whether he was serving Bill Murray, actor William Devane or Chicago Bears quarterback Bobby Douglass, “He treated everybody like a VIP,” Sirott said.

“Getting behind the bar with him was like going back to school, truly,” said L. Woods manager Patrick Gallivan. “He would go out of his way to introduce me to his regulars.”

The Rotondos raised their four boys in Hanover Park. All went to college, his wife said.

Thirty-eight years ago, Mr. Rotondo was diagnosed with lung cancer. But he quit smoking and survived. And he came back in one piece from serving in the Army in the Korean War, where he drove a tank and never forgot the bitter cold.

It wasn’t easy to be on his feet behind the bar every day, but “he had good legs, he always said,” according to his wife.

In 48 years, he probably mixed hundreds of thousands of Manhattans, old-fashioneds, whiskey sours and gin-and-tonics. But he never drank at work. At home, he’d have a scotch on the rocks. He preferred Clan MacGregor to pricier scotch whiskies.

For cars, “He liked his Caddies,” said his wife. “But, as he got older, he liked to drive his Toyota RAV-4.”

Mr. Rotondo wasn’t crazy about the craft cocktail craze.

“Not long before he passed, he was complaining about the new drinks,” she said, saying “a drink doesn’t need that many ingredients.”

He is also survived by sons Chris, John, Rob and Michael, his sister Rose Lijoi, brothers Joseph, Anthony and Vince and seven grandchildren.

Because he was a bartender, “he always had cash in his pocket,” said his daughter-in-law Lisa Nitti-Rotondo. “When he saw the grandkids, he’d always fold up a $5 bill and give it to them.”

At Mr. Rotondo’s services last month, his sons tucked some Lucky Strikes and a lighter in their father’s casket. And his wife said, “Each of his grandchildren put $5 in his pocket.”