In late 2001, I was a consultant working on a project in Los Angeles. I was headed to North Dakota for the holidays and rushing through the airport to catch my flight. I ran into Pamela Anderson on the way to my gate, and then plopped down on the plane next to Louie Anderson. My first thought was: Wow, that’s two opposite ends of the Anderson spectrum! My second thought was: Louie is one of my comedy heroes and I’ve got a captive audience ― he can’t go anywhere.
So I started chatting him up. The flight was delayed two hours, and we had the great Louie Anderson entertaining us the whole time! Then, once we finally took off, Louie and I talked the whole flight ― and we kept that conversation going for over 20 years.
I spent a little time as Louie’s tour manager after we met, but mostly we were close friends. Over that time we played thousands of games of pinochle (a card game favored by inhabitants of the Upper Midwest), ate hundreds of bad room service meals and watched dozens of basketball games, usually with him on one coast and me on the other. We also had some of the deepest conversations of my life. Louie taught me life lessons that I’ll always treasure and do my best to pass along to my kids. As Louie’s cancer progressed ― and after our friendship came to a natural but devastating end when he died in January ― I reflected on a number of these lessons as I worked through both grief and gratitude.
1. Be open to a new path
Louie used to have a line about sitting next to a “chatty Cathy” on an airplane. She asked what he did and he replied, “I mind my own business, that’s what I do, ma’am.” The reality is that Louie never minded his own business. He talked to everyone and anyone.
These days it’s so easy to dive into a book, do some work or scroll through your phone instead of interacting with others. If Louie or I had done that 20 years ago, a beautiful friendship would never have transpired.
During our conversation on that flight, he asked for some help on his new book, “The F Word: How to Survive Your Family,” which he was co-writing with his friend Carl Kurlander. That led to leaving my job to take over the “F Word” tour after Louie left his gig hosting “Family Feud.” Over that year or so, I saw the “funny business” up close and personal before going to business school. My life moved in a different direction based on that one conversation.
2. Everyone’s voice deserves to be heard
Over the years, I attended hundreds of Louie’s shows and saw him interact with thousands of fans. I can’t think of a single time when he was anything but gracious during those encounters ― no matter how inconvenient they may have been. He had a way of talking to fans that made it clear they were the most important thing in the world to him. Every good comedian is relatable, but Louie was also approachable.
There was the woman in St. Louis who tentatively approached him after a show to thank him for saving her life. She struggled with an alcoholic father, as Louie himself had, and during a particularly rough time, she watched Louie’s comedy special over and over to remind herself she was not alone.
There was the 20-year-old kid in Las Vegas who asked for a picture after a show. “Where are you from?” Louie asked. “I came here from Romania during my school break in hopes of meeting you,” he replied. It turns out that Louie’s cartoon “Life with Louie” was still popular in Romania, and this kid watched it as an escape from a rough childhood.
There was the older gentleman who greeted Louie after a show in Wisconsin to say that he was dying of pancreatic cancer and only had a couple of months to live. He took his daughter to the show and thanked Louie for making him laugh so hard he forgot about his devastating diagnosis for an hour or so.
Interspersed with those life-changing conversations were hundreds of everyday meetings with fans asking him to sign a butter dish, take a selfie in the bathroom or share a donut. Through every one of these requests, Louie made it clear that what his fans had to say mattered.
In Minneapolis after a show, there was an older woman at the front of the line waiting to talk to him. Louie was going through a rough patch, and wasn’t in a mood to meet people, but he always pushed through. This woman stood in front of him, and her mind went blank. She started rifling through her purse. Tissues and candy wrappers went flying. The people in line behind her were shifting in place and looking at their watches, wondering when she would finally get it together. I tried to help find her phone and get things moving. Eventually she asked for a picture, and as I snapped it, she gave Louie a big, wet kiss on the cheek before picking up every last bit of trash around her.
As the woman walked away, Louie turned to me and said: “You know, every time I’m having a tough time, my mom finds a way to reach out to me through someone I needed to help. Every single time.” There was no hint of frustration in his voice as he spoke of his mother, who died in 1990. That was Louie.
3. Be nice ― you never know what someone has been through
When Louie passed away, tributes came pouring in from so many of the celebrities he got to know over a career of more than 40 years. The remembrances were heartfelt, and needed during a difficult time. However, the tributes I think he would have appreciated most were the ones shared by an army of stagehands, theater managers, hotel clerks, waiters and flight attendants across the country. Thousands of these people had had encounters with Louie that were genuine and memorable. Some of these encounters changed their lives. This was the audience Louie always catered to. Of course, he was savvy enough to know they usually have access to the best snacks. But more importantly, he saw that they were often underappreciated or forgotten, and he wanted to make them feel seen and important.
I’ll never forget a show I joined him for in Denver. A driver from the theater picked us up at the airport. Within minutes of meeting someone, Louie could pinpoint the exact question that went to the heart of who they were as a person and the pain they felt in life. I’ve never seen anyone else with that talent. Prior to becoming a comedian, Louie was a social worker, and although he eventually quit to pursue his stand-up career, I don’t think he ever stopped doing that work.
The driver said he was a fan, and asked about a few specific bits. After hearing just a little, Louie felt he had him pegged.
“So, how many kids were in your family?” Louie asked.
“Well ― real, step, half or adopted?” the driver replied. “I didn’t have a great relationship with any of them, so don’t really keep in touch.”
The driver’s story continued to tumble out in what became a kind of therapy session.
The next day, the driver took us to a couple of media interviews and then to the show. During our time with him, we heard more of his story. On our last day, he took us back to the airport. Before we parted ways, he said: “Louie, I just want to thank you. Last night I called my dad. I haven’t talked to him in more than 10 years, and I know I wouldn’t have called him if it weren’t for you.” Louie had a bigger reserve of empathy than I had ever imagined a person could possess.
Louie won three Emmy Awards, was a New York Times best-selling author and was named one of the Top 100 Comedians of All Time by Comedy Central. However, none of these incredible honors were among the first things brought up by anyone who knew Louie well when reflecting on the impact he had on our lives.
4. Never grow up
Louie always had a childlike enthusiasm ― and he kept it right to the very end. On every one of my birthdays, I’d get a voicemail of a version of “Happy Birthday” that Louie made up. Often, when I’d be out somewhere with him, like at Whole Foods, I’d hear an “Alright!” come from the next aisle over, in the distinctive voice of Little Louie from “Life with Louie.” Walking into his house, I’d typically hear “Chip! Chiiiiipp! Chip!” in the twang of Christine Baskets, the mother of Zach Galifianakis’ character in “Baskets.” When we were on a road trip, we’d often play Keno by buying a ticket at one gas station and checking the numbers at the next rest stop down the road.
About a year before Louie passed, I got a call from him.
“Dave, how close are you to Plymouth?” he asked frantically.
I live just north of Boston, but I’d become used to games like this from Louie, and did my best to play along.
“Plymouth? Why Plymouth?” I replied.
“My family came into the country through Plymouth. I had a dream last night ― Powerball is up to $684 million and we need to get tickets. The closer you can get to Plymouth Rock, the better.”
Every time one of these games came into Louie’s head, it initially seemed completely insane to me. As the conversation went on, he would reel me in and it would somehow start to make sense. By the end of the conversation, I was thinking to myself, Well, his family did come in through Plymouth, so...
It wasn’t long before I was headed out the door to pick up a few Powerball tickets near Plymouth Rock, Massachusetts. We did not win.
5. Life with Louie
Louie was a complicated guy. I think anyone with that much talent, and that much empathy bottled up inside, is going to be complicated. I know with certainty, though, that our friendship made me a better father, husband and friend. For that I will be eternally grateful.
During one of our chats in between chemo sessions, we went pretty deep. I was going through some issues at work and was hitting middle age, so I went to my friend Louie to get his thoughts. He is the friend I always talked to when things were rough, or when I was trying to figure out something big in my life. That’s the void I especially felt on Jan. 21 of this year, when he passed, and that I continue to feel today.
“If you had it to do all over again, what would you change?” I asked Louie. He’d seen successes that played out in popular culture and on stages nationwide, but he’d also experienced periods of profound sadness ― his life was filled with the high highs and low lows inherent in any Hollywood career that lasts as long as his did.
“Dave, I wouldn’t change a thing,” he told me. “I’ve been the luckiest guy in the world. For over 40 years I was able to do exactly what I wanted to do: make people laugh, and feel their love from the stage.”
There was a long pause.
“Well, actually,” he said. “If I could go back and change one thing, I think I would become a cake delivery person. Can you imagine that? Every single person you meet would be excited to see you, and they’d probably share some cake!”
That turned out to be a great synopsis of everything Louie wanted out of life: to be loved by all, and a little cake.
Note: A shorter version of this reflection was given as a eulogy at Louie Anderson’s memorial service on Feb. 12, 2022.
Dave Gilbertson is a senior executive and adviser to numerous leading software companies. He has spent most of his career blending leadership and humor, culminating in a 2018 TEDx Talk, “Leading with Laughter: 7 Lessons in Leadership from Stand-Up Comedians.” Dave holds degrees from Georgetown University and the Tuck School of Business at Dartmouth.
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