Tiffany Woolf with longtime family friend Larry King.
Tiffany Woolf with longtime family friend Larry King.

Saying so long to Larry King, a family friend I interviewed last year

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Throughout his 63-year career in broadcasting, talk-show legend Larry King shared his insatiable curiosity with an audience of millions, first on his overnight radio show, then on television and more recently for on-demand digital platforms.

King, who died Jan. 23 at age 87, conducted more than 60,000 interviews with celebrities, royalty and heads of state among many other personalities. Though he arguably missed his true calling as a Borscht Belt comedian, he left an indelible mark on the cultural landscape.

Like many others who grieved his loss, I, too, have been a lifelong member of the Larry King fan club. But I had the good fortune of growing up with Larry King in my actual living room. My father, the late Bob Woolf, a pioneering sports and entertainment attorney, started representing Larry around 1978. Thus ensued a decades-long loving friendship, a co-mingling of families and a whirlwind of larger than life moments.

Larry sat at the head table of life, yet he always made sure to pull up extra chairs for the rest of us.

After my dad negotiated Larry’s contract with CNN in 1985, it took both of them to a whole new level, as Larry interviewed everyone from Richard Nixon to Frank Sinatra, Mikhail Gorbachev to Donald Trump, Muammar Gaddafi to Ronald Reagan, Margaret Thatcher to Marlon Brando … and countless others. Larry and my father were like two kids in a candy store, filled with childlike wonder that they were able to rub shoulders with such giants — kicking themselves over how they could have been so lucky.

They were also there for each other in tougher times.

When Larry had heart surgery in 1987, my dad was the first one at the hospital and the last one to leave. In fact, Larry ended up recuperating at our house in Florida for two weeks, with strict orders from my mother that we weren’t allowed to bring anything with salt into the house and that pastrami sandwiches from Pumpernick’s Deli were strictly forbidden.

For Larry’s 60th birthday, my father and sister threw a “50th Anniversary of Larry King’s 10th Birthday” party. It was a throwback to 1940s-era Coney Island, featuring a makeshift boardwalk of jugglers, clowns, hot dogs and popcorn machines, attended by some of the biggest names in Washington and Hollywood.

Former Speaker of the House Tip O’Neill showed up in a Red Sox uniform. “Wonder Woman” star Lynda Carter chatted with John Kerry and CNN founder Ted Turner over cocktails and cotton candy. Larry’s childhood friends, including his oldest and dearest friend Herb Cohen, gathered in a corner proudly sporting matching Brooklyn letterman jackets from the old days.

An artist made a puppet in the likeness of Larry, and Larry gave it to my father. He loved it so much that, to insure it remained intact, he got an extra seat for it on his flight back home to Boston.

Ten days later, my father died suddenly of a massive heart attack. I was 22.

That night on Larry’s broadcast he concluded with a tribute to my dad and to their friendship. He told viewers how he lost one of his best friends and about the party my family had thrown for him just a little over a week before.

There was a clip from the event in which you could see my dad laughing while holding the puppet. Larry choked up. “God he loved that puppet. God I loved him.”

My father’s funeral was so crowded that stereo speakers had to be set up outside the temple for fans and well-wishers to listen in on the service. Inside, the sanctuary was filled with famous faces: world-renowned athletes, entertainers and statesmen … with yarmulkes on.

a woman sits in a chair in the background; in the foreground, she is seen in a live feed on a monitor
Tiffany Woolf on set for her series “Coming of Age.” (Photo/Courtesy Silver Screen Studios)

After the rabbi spoke, Larry walked up to the bimah and looked out at the crowd.

“I’m Larry King,” he began. “I’m the Larry they put on hold when the other Larry calls Bob’s office.” With impeccable timing, he nodded toward Larry Bird, one of my father’s other famous and beloved clients.

Then, for 15 minutes he gave the best stand-up performance ever to be witnessed at our temple, or any other for that matter. He joked about my dad’s fascination with one-hour photo processing, his notoriously bad driving and the way he would so lovingly eat a sandwich. He set the stage and others followed, a treasure trove of stories and slapstick — just what my father would have wanted.

I overheard one mourner leaving the temple saying, “Wow, that was the best funeral I have ever been to!”

Prior to losing my father, I had never really experienced grief before, and the pain of his passing was almost unbearable. I was suddenly untethered from the life I had known, and woke up to a harsh and unwelcome new reality that was heavy and directionless.

Not longer after, my mother died at age 62. Having lost both my parents at relatively young ages (Dad was 65), I desperately craved their connection, advice and comfort. To fill the hole of their absence, I befriended older adults and created an array of beautiful surrogates, role models to help navigate life’s major milestones as I grew older. I’ve always had an affinity for our elders; in college, I ran the bingo program at a nursing home.

In a contemporary culture rife with ageism that too easily writes off seniors, Judaism offers a framework of spiritual edicts regarding the way that young people relate to their elders. This is perhaps best expressed in a passage from Leviticus 19:32 that reads in part, “You must rise up before the aged, and honor the face of the older person.”

To this day, I want nothing more than to talk to my parents, to get their perspective on the state of the world, to introduce them to their grandchildren and to bask in the unmistakable feeling of familial bonding that we all desperately need right now.

Since I no longer have that luxury, a few years ago I decided to make it my mission to seek out and interview inspiring Jewish seniors across the country and around the world.

If my parents weren’t here, I could at least spend time with older role models and be the recipient of their advice and wisdom. Perhaps I could capture their stories before it was too late.

With the invaluable support of the Jewish arts and culture nonprofit Reboot and PBS producer Steve Goldbloom, I created Silver Screen Studios, an oral history media platform that would capture the stories of people in their 70s, 80s, 90s and beyond. In Judaism, bubbe and zayde are sacrosanct.

I envisioned the project as a symbolic continuation of the awe-inspiring experiences that Larry and my father shared, and of the celebrated personalities they brought into my childhood home.

So I set out across the country, filming older role models both in and out of the public eye. I was building a library of wisdom, advice and encouragement; a chronicle of daily hopes and misgivings from the greatest generations.

When Covid-19 spread in early 2020 and the world went into lockdown, I knew that my work had to continue, even if I was no longer able to travel. Together with Emmy-winning producer Noam Dromi, the head of Reboot’s content studio, I launched “Dispatches from Quarantine,” a digital series featuring short interviews with older luminaries.

It gave them a platform to talk about how they were navigating stay-at-home orders and to share their insights on a moment in time that has proven to be especially detrimental and isolating for older people.

My primary goal was to inspire people to pick up the phone or use technology to call their loved ones during the quarantine. I sent out prompts and calls-to-action to encourage everyone I knew to capture the stories of their older loved ones in real time, without excuse or delay.

As I learned from the deaths of my parents, tomorrow is promised to no one.

But it’s hard to compete in the cluttered media landscape of Netflix, TikTok and PS5. So I decided to reconnect with some of the legends I knew from the past in the hope that I could interview them and give the project some much-needed star power.

My first phone call was to Larry last April.

He answered the phone right away and we spoke as if no time had passed. I asked him if I could interview him for my little show. “Sure,” he said. “Do you want to do it now”? I thanked him and said I would call him the following week so I could prepare.

When we finally did the interview, he dropped countless Larry-isms, gems that I will hold in my heart forever.

In talking about his litany of health issues, he was equal parts nostalgic and acerbic. “The toughest part of being 86 is that friends die,” he said. Quoting baseball great Mickey Mantle, he said, “If I thought I would live this long, I would have taken better care of myself. But I made it, Tiffany.”

Even in the face of his mortality, he approached it all with his customarily sanguine outlook. “When you take away complaining from a Jewish guy, what do you have left? We love to complain. Sometimes I look at myself [in the mirror] and think, ‘Did that happen to him?’ I’ve got a lot of blessings.”

Mostly, Larry wanted to talk about my dad, certain that he’d have gone a bit nuts in lockdown since he was such an extrovert.

“I miss your dad,” he shared with authentic emotion and longing. “We used to speak every day. I wonder what he’d think if he saw me today. You had such great parents.”

Reflecting on my father’s joie de vivre, he recalled that “everything Bob saw was the best thing ever. He would have a glass of water and say this is the best glass of water I’ve ever had.”

As I grieve, I’m reminded that what I set out to do in creating Silver Screen Studios is more important than ever. We never know what tomorrow will bring, especially in these times.

It’s a time of reflection, forgiveness and healing, and recording the stories of older generations is a vital part of this process.

The Tag Institute for Jewish Social Values summarized the critical significance of honoring our elders in a 2012 academic paper titled “Jewish Perspectives on Ageing Enrichment.”

A sample: “There is no age limit for this process of enrichment. Judaism values elders, and views them as leaders and as a repository of knowledge. They must be held in high esteem and treated with respect. Older people have gained from their life experience and have much to share with the next generation.”

So take this moment and capture your family stories. Don’t make excuses. Just do it. If you’re not sure where to start and need some help, reach out to me at to learn more.

After hearing the news of Larry’s passing, I went back and watched some of the footage from our time together. At the end of the interview, Larry said, “We have to do a follow-up call. I’ll come back with lots of jokes. I’ll make you laugh, Tiffany, that’s what we’ll do. You say when and I’ll be there.”

We never had that follow-up call, but I can only imagine he was saving those jokes for my dad. Two best friends, catching up and laughing over pastrami sandwiches and marveling at the extraordinary lives they lived.

The views and opinions expressed in this article are those of the author and do not necessarily reflect the views of J.

Tiffany Woolf
Tiffany Woolf

Tiffany Woolf is co-creator and executive producer of Silver Screen Studios and its original series “Dispatches from Quarantine,” in association with Reboot. Woolf lives in Pacifica with her husband and kids.