Author Bill Zehme, whose subjects included Sinatra, Hugh Hefner, Leno and Andy Kaufman, is dead at 64

CHICAGO — Name a star or celebrity of the last 40 years and it’s likely that person was the subject of Bill Zehme’s keen mind and artful writing, in such magazines as Rolling Stone, Playboy, Vanity Fair and Esquire, and in bestselling books in collaboration with Jay Leno and Regis Philbin, and about Andy Kaufman and Frank Sinatra.

“Bill was a great writer but he was an even greater person,” said Tom Dreesen of suburban Harvey, for years Sinatra’s opening act. “Humble about his writing skills, and more interested in knowing about you than you knowing about him.”

Zehme was diagnosed a decade ago with colorectal cancer. Ever upbeat through it all, he was never strong enough since to write more than a bit for magazines or to complete his long-brewing biography of Johnny Carson.

He was riding a medical roller coaster of hope and despair that ended on shortly after noon on Sunday, when the 64-year-old Zehme died in Weiss Memorial Hospital on the North Side. He had been hospitalized there since early March.

“It was very hard,” said actress Jennifer Engstrom, with whom Zehme lived and who had been his constant companion for more than a decade. “There were many times during this month when we thought death was coming. He was not eating or drinking but he was fighting. He was so courageous, this month and over the last decade, and that helped get me and his sister through all this. It was inspiring. He always hated deadlines and I think he wanted to wait until his sister and I were both there in the room before he said goodbye. He was a gentleman to the end.”

Said his younger sister Betsy, “We never mentioned the word cancer. Never. This is a tragedy for all of us but when you consider that he beat the odds, living far longer than he should have with this disease, it goes to his spirit. We always told him he had superpowers even until the very end. Which he confirmed daily during his last days. Let’s just say, he definitely did it his way, and we were privileged to be part of it. He was always trying to uplift us. He was the strongest person I’ve ever known.”

Zehme was born in 1958, the son of Robert and Suzanne Zehme, owners of Clemensen Florists in Flossmoor, a business that began in South Shore where Suzanne Zehme’s father arrived from Denmark to help landscape the color-splashed Columbian Exposition in 1893.

A self-described “geek” at Thornwood High School in South Holland, Zehme attended Loyola University, majoring in communications and graduating in 1980. He began his career here, writing for local magazines and newspapers, including the Tribune, before being discovered by editors on the national scene. With a distinctive style that was impossible to imitate, he would become an inspiration for a generation of writers and as admired, prolific and successful as any nonfiction writer of his generation.

He was large in stature (at 6 feet, 5 inches), and in charm and personality.

“I first met Bill ages ago when he interviewed me for Success Magazine,” said Bob Sirott, longtime media fixture and morning host at WGN-720 AM. “We became fast friends and bonded on the ridiculousness of showbiz. He was a regular on some of my television shows.

“I loved that Bill would talk about the things guys usually don’t talk about — like feelings. I’ll forever cherish my text thread with him. That was his main means of communication in recent years. But it sparkled with the same unique flair, insight and humor as his many magazine stories, books and dinner conversations.”

As his stories came at a furious pace, he began to write books, the first being a humorous 1991 collaboration with fellow writer David Rensin called “The Bob Book.” Soon came his collaboration with Philbin in 1995′s “I’m Only One Man!,” followed the next year with Jay Leno’s “Leading with My Chin.”

His Sinatra book was next in 1997. “The Way You Wear Your Hat” grew out of the last extensive interview given by Sinatra, the first he had granted to a reporter in more than 25 years. It was a hit.

What many argued was Zehme’s best book came next. “Lost in the Funhouse: The Life and Mind of Andy Kaufman” was six years in the making and a book about that one-of-a-kind comic.

He was busy into the new century, dabbling in TV as an on-camera personality and lively guest; writing 2001′s “Hef’s Little Black Book,” an illustrated packed of advice and philosophy; and publishing in 2002 a collection of some of his magazine work, “Intimate Strangers.” He won the 2004 National Magazine Award for profile writing for his Esquire magazine piece about former Tribune columnist Bob Greene.

The next year he was deep into what he would refer to as “Johnny world.”

Johnny Carson had given Zehme the only interview he conducted after retiring in 1992 as host of the “Tonight Show.” The resulting story, which appeared in Esquire magazine’s May 2002 issue, pleased Carson so much that he wrote Zehme a note thanking him. A book deal was inked and Zehme got to work.

No one could have imagined the extent of that work.

One night in 2013, Zehme walked into Twin Anchors, the venerable Old Town tavern and restaurant famous for its ribs (and that Frank Sinatra ate them whenever he was in town). Zehme once wrote, “I love no place quite like I love this place. It is everything Chicago is supposed to be: familiar, old, neighborhoody, friendly …”

There he talked about the Carson book, tentatively titled “Carson the Magnificent: An Intimate Portrait.”

“In ‘Johnny world,’ one thing leads to another, one person to another,” he said.

He had spent all the money advanced by his publisher and still had work to do. NBC planned to make a miniseries biopic based on Zehme’s book.

“Now I just have to finish the thing,” Zehme said.

He packed his car with research materials and drove up to a secluded cabin to write. There, he began to experience terrible stomach pains and returned to Chicago where he was diagnosed by a doctor friend — he did not have health insurance.

I chronicled his fight with colorectal cancer in 2016. That was a bright moment but darkness came and the ensuing years were filled with all manner of health troubles and cancer’s insidious spread. He kept in touch with some close friends. He told me, “One thing I have realized through all of this is that you better laugh every day of your life.”

Caring for him through all of this was his younger sister Betsy, who he called “my sunshine bomb” and Engstrom, whom he called “my everything. ”

Now, as she deals with the pain of loss, she must decide what to do with his vast collection of materials gathered during his star-studded career.

He had told me that museum curators and art dealers have expressed interest in purchasing his vast collection of stuff. There is so much: books, papers, photos, artwork, tape recordings, a carousel horse and all the other stuff accumulated (and none discarded) during his busy life at the center of show business. It is a treasure trove, an amazing do-it-yourself museum, a haunted house.

He said, “It looks like the movie set made for a mad professor of popular culture.”

His words defined an era and he once tried to explain how he went about the business of interviewing the celebrated. He said, “I try to find why a certain person touches the rest of us, the essence of why we care about this person.”

In addition to his partner and sister and her husband Bill and their son Luke, Zehme is survived by an adult daughter Lucy from a long ago marriage. A memorial service is being planned.

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