by | May 23, 2026
Bert Kreischer: Ultimate Florida Man
Free Bert star and Tampa-born comedian Bert Kreischer opens up about family, fame, stand-up and why Florida still runs through his veins.
Bert Kreischer has long insisted he’s the luckiest guy in the world.
The comedian’s rise to stand-up superstardom is well-tread territory. In 1997, his sixth year as a student at Florida State University, Rolling Stone called the Tampa native “the top partyer at the Number One Party School in the country.”
“That’s my start into stand-up,” Bert says with a child-like excitement. Bert moved to New York around 1997 and started working the door at the Boston Comedy Club in Greenwich Village. He kept letting underage NYU students inside for free, who would then respond boisterously to his set. After noticing his legion of fans, Time Out New York wrote an article on Bert’s appeal to students, which caught the attention of Will Smith and his production company, who gave him a development deal.
Bert moved to Los Angeles in 1999 and spent the next 20 years on the stand-up circuit. During this time, he broke into TV by hosting numerous travel shows on the Travel Channel but still struggled to gain a mass following. It’s at this point in his story that Bert pauses to highlight one of the most fortuitous moments of his career.
“I mean, you want to talk about luck. My special ‘Hey Big Boy’ was released March 17, 2020.” Just two days earlier, on March 15, states had started to implement stay-at-home orders due to the COVID-19 pandemic. “Everywhere in America, people were being forced to stay inside, so they had to find something to watch.”
While Bert is happy to point out this streak of fortune, he’s not entirely modest. He tilts his head, fiddles with his gray, ever-so-slightly long but still fashionable beard and adds a caveat: “I also believe you manifest your luck by recognizing and acknowledging your luck. Even at times when you find yourself unlucky, you need to try and find the luck in it.”
Travel Bert’s Way: The comedian shares six of his favorite Florida spots, from spring-fed rivers to sugar-white sand.
Three days before I spoke to Bert on a Zoom interview, his luck was put to the ultimate test when his tour bus went up in flames on the side of the road. After leaving Rochester, Minn., on March 14 for the next date on his “Permission to Party World Tour,” the vehicle’s tire blew out. Rather than waiting on the side of the road, they organized for replacement buses to complete their journey to Fargo, N.D. When Bert awoke the next day, he was told the bus had burned down and that the driver—the only person onboard—had miraculously escaped.
“I would have absolutely been asleep in that bus when it burned down. I would have 100% died without a doubt. Everyone would have died. I haven’t processed it yet. That was my home. I’ve lost my meds. I can’t even trim my beard because the trimmers are on that bus. It’s just crazy.”
A King of Comedy
Despite having to figure out how to get to Detroit from his Los Angeles home and how to continue the tour while crossing over into Canada twice, Bert remains surprisingly calm and determined. Sitting in his office behind a desk at his computer and surrounded by a printer, files and posters, Bert wears a baseball cap on his head. His low, deep voice goes from slow when considering his responses to quick when he just has to get a thought out, all while remaining upbeat and positive.
Bert’s resolutely joyous point of view goes a long way to explaining his success. Anyone who has seen his stand-up, listened to his “Bertcast” podcast episodes or simply caught a glimpse of his contagious smile and laugh will know that part of his charm is his warm, approachable, feel-good personality.
“What I liked about Bert when I first met him is that he appeared to be a meathead,” says his wife of 22 years, LeeAnn, in her thick but instantly soothing Georgia accent. “But he’s actually a deep thinker, very self-reflective and poetic in how he thinks. He’s very artistically minded.”
After providing an update on the bus blaze, the conversation turns to a more cheerful topic: Bert’s meteoric rise since Flamingo last spoke to him all the way back in September 2019. As is Bert’s wont, when he realizes how long it’s been, he uses an analogy to sum up how he’s grown during this time. “It’s like when you meet a chick and you ask her to marry you, you think you know what love is. Then you have kids. You think that’s love. Then you send them to first grade, they leave the house and your feeling of love keeps changing.” Bert stops, eager to get to his point: “The best way to describe it is, I thought I was the fucking shit when I put out ‘Secret Time,’” his first Netflix-produced comedy special that debuted August 2018 and introduced the often-shirtless comic’s swift storytelling abilities to the streamer’s subscribers.
In the eight years since, Bert has released three more comedy specials on Netflix—“Hey Big Boy,” “Razzle Dazzle” and “Lucky”—while also taking part in “The Roast of Tom Brady.” He starred in the feature film “The Machine,” based on his breakout stand-up routine about getting involved with the Russian mafia, and began the podcast “2 Bears, 1 Cave” with his friend and comedian Tom Segura. But while Bert is immensely proud of each creation and knows that they took his writing, performances and popularity to a new echelon, he also candidly says, “I don’t think I know anything.”
Bert reached this conclusion in the wake of “Free Bert,” the Netflix sitcom released in early 2026. Based on his own life in Los Angeles with his wife and two daughters, Georgia and Ila, the show depicts Bert’s struggles to fit into Beverly Hills society as his children attend an elite private school, though LeeAnn points out that their real-life kids attended public school. After amassing millions of views, a second season of “Free Bert” was confirmed by Netflix. “In its first week, ‘Free Bert’ got five times more views than any of my specials,” declares Bert. He’s delighted by the six episodes of “Free Bert” they’ve released and is excited to see where they can take the show and story. But its success has provoked a mini-crisis in his head, which the always open and refreshingly honest Bert immediately dives into.
“I’m now doing a new hour, and I’m trying to understand what the point is of doing stand-up. Stand-up is my passion. It’s the thing I love the most. But it’s always crazy, with the show and even stand-up, when I get the notes back, and people are like, ‘I love the heart. That’s why I’ve always loved Bert.’ I never intended it to have heart. I never intended empathy or love or family or vibes. I always just wanted to be funny. That was the number one thing. I didn’t understand what I was doing.”
Bert has always been able to watch his friends’ acts and know exactly what their vibe and points of view are. He uses Bill Burr as an example, pointing out that the Boston comic says the things that “frustrate all of us, that we think, but can’t say.” After a moment of contemplation, he admits, “I don’t know what I do. I just write to entertain myself, and then I hope that it entertains other people.”
Despite the success of his new Netflix series, “Free Bert,” Bert Kreischer says stand-up comedy is the thing he loves the most. Photography by Mary Beth Koeth.
Life of the Party
It’s clear that Bert has become more introspective over the last few years. While he’s often ranked as one of the highest-grossing comics in the country and has regularly performed for tens of thousands of fans in arenas since 2022, the increased exposure has led to an increase in critics too. He’s been accused of being too loud, self-centered and one-note. Bert, alongside the co-creators of “Free Bert,” Andrew Mogel and Jarrad Paul, addresses this head-on in the opening scenes of the sitcom. After being flown out to perform for Rob Lowe’s birthday party, Bert realizes all the “West Wing” actor wants is for him to take his shirt off. Lowe is so indifferent to his routine that Bert even takes refuge in a bathroom to call his wife LeeAnn (played by Arden Myrin) and complain.
“I took so many big swings at mocking myself in the way that the internet would. The whole shirtless thing, how I feel I’m seen sometimes, even things people have said to me or that I’ve read in the comments. I wanted to explore all that. I see the criticism. I hope people can appreciate that,” says Bert, who admits that the message of “Free Bert”—if there is one—is that people have to be themselves and not be influenced by what everyone else thinks and says.
This is a battle that Bert has been fighting ever since he started doing stand-up. While the Rolling Stone article undoubtedly gave Bert a spotlight from which he could introduce himself, it also gave him a reputation that he then had to grapple with, accept or subvert. Over the decades, Bert has come face-to-face with many people in the industry who have tried to push him away from his persona. He remembers being praised for his storytelling abilities, only for another comic nearby to instantly interject with, “No one wants to hear storytellers.” He’s been told countless times to keep his shirt on while onstage. People have even told him what to wear and asked him not to tell certain jokes because they mess with their set. “I was like, ‘What?’ I would never tell anyone what to say onstage.”
But Bert is able to look back proudly on being his authentic self throughout his career. Like anyone in any profession, he’s taken missteps and insists he’s paid the price for people not liking him. But at 53, and with a litany of creative triumphs behind him, he declares, “I’m really comfortable with how I’ve represented myself. I approach everything with, ‘I’m going to be exactly who I am.’” That being said, there are still things in his personal life that Bert won’t touch onstage but can’t help but tease.
The day before we talked, Bert and LeeAnn took an IQ test, the results of which are still making him belly laugh. Chuckling, Bert insists he can’t share the results, as it would almost certainly cause a fight.
I took so many big swings at mocking myself in the way that the internet would. The whole shirtless thing, how I feel I’m seen sometimes.
—Bert Kreischer
When Bert first started talking about her onstage, LeeAnn made him agree that he couldn’t make her “a bitch and it had to be funny.” She adds, “I had to understand the payoff.” Bert has regularly joked about their sex life, comparing their intimacy to putting on a 25-year-old baseball glove that still fits, all while underlining his dedication to LeeAnn—whom he met in 2002 in Los Angeles after being set up by mutual friends. “We had a group of friends who were all married. They brought all their single friends bowling. We were the only couple that came out of that. It was just some kind of divine moment,” she recalls. LeeAnn—who hosts her own podcast, “Wife of the Party”—has become so accustomed to Bert talking about her onstage that she can even recognize when he’s apologizing to her through a joke. “He’s not great at apologizing. But he’ll write a joke, and I’ll go, ‘That was my apology.’ He works through a lot of stuff out loud. I think the benefit of that is that he really just shows that he’s a regular guy.”
It’s clear Bert gets as much joy writing jokes that will be performed only for him and his close friends and family as he does from crafting bits for a stadium of fans. “Trust me, I am crying laughing, writing jokes about that fucking IQ test.”
Bert’s mantra is simple: “I want to find a giggle. I try to live in it.” You can’t help but think that, if he could, he would live his entire life giggling like a schoolgirl, a la Homer Simpson. More than that, his life mission seems to be to remind people of the importance of laughter. He cracks a smile at the thought of recently reconnecting with his group of college friends at a Florida State football game, telling old stories and laughing hysterically for hours. “I think that’s lost sometimes in stand-up.” Bert knows so many comedians who never laugh. “They’ll tell jokes and just go, ‘That’ll be funny.’ Sure, it might mathematically work as a joke. But there’s no jazz or heart to it.” Bert stops briefly, realizing that this story sums up many of the issues he’s encountered with the comedy industry. “It’s so easy to overthink this business,” he says.
One of the reasons why Bert has remained so grounded over the last nine years is that he’s genuinely envious of his fans. Ahead of one of his sold-out shows in Savannah, Ga., Bert found himself down by the riverwalk, where he saw a huge group of people partying. Upon closer inspection, he realized that they were all his fans.
“I was insanely jealous. Because that’s what I like to do. I love pre-partying for a show. I was actually sad in a way. I wish I had more time to be like them.” Bert’s deep connection with his fans is unique in the comedy community. Bert remembers fellow comic Nate Bargatze saying to him, “You’re the only guy I know that feels like he’s one of his fans.”
Whenever Bert and LeeAnn get recognized in front of their daughters, Georgia and Ila, one of them invariably asks why they don’t get annoyed at the people interrupting them. “I always say it’s because we’re all part of a community,” LeeAnn explains. “It’s like growing up in a really small town where everyone knows each other.”
In recent years, Bert has looked to forge an even closer relationship with his fans. Last spring, Bert and Segura took part in the second annual 2 Bears 5K, where the two comedians ran around the Rose Bowl in Pasadena, Calif., alongside more than 7,200 of their fans. In classic Bert style, the 2 Bears 5K began as a joke. After discussing their recent surge in popularity, as well as the fact that they’d both lost weight, Bert joked to Segura,“‘In order to have a fan base, we need them to lose weight and stay alive.’ So it was to help them, and us, stay alive. It was really a joke to my friend.” At each run, though, Bert—who has lost over 50 pounds in recent months—has been touched to see how many of his fans have changed their lives through exercise. “It was like, ‘Holy shit! This is really affecting people.’ People are coming up to us and going, ‘This is the first 5K I’ve ever run!’ Then we all get to hang out together after.”
Captain Kreischer’s Calling
Socializing with fans was the main reason Bert brought his Fully Loaded Comedy Festival to the seas for Fully Loaded At Sea. In June 2022, after completing his first arena tour and after years of being snubbed by comedy festivals, Bert realized he had the popularity to start his own eight-stop tour of outdoor venues. “I was like one of those chicks that throw their own 30th birthday party,” he says. Alongside Dave Attell, Fortune Feimster, Nikki Glaser and a score of other comedians, Bert headlined the tour and watched with delight as his fans reveled at minor-league ballparks and racetracks.
Georgia and Ila, now college students, joined Bert and LeeAnn for the first time on this tour. “We all traveled for five weeks on a bus,” says LeeAnn, 55. “We had previously not really exposed the kids to his stand-up.” While the kids needed some time to adjust to certain jokes, particularly about LeeAnn’s anatomy and their parents’ sex life, LeeAnn can’t hide her pride when breaking down how the girls grew a deep respect for Bert, his work and how he treated everyone around him. “We had a still photographer, Troy Conrad, who traveled with us. He kept capturing our kids at the side of the stage watching their dad. To see the look on their faces. They were so proud,” LeeAnn says. Watching everyone come together for Fully Loaded reminded Bert of performing on the Impractical Jokers Cruise a decade earlier. The second he made the recollection, he knew he wanted to do the same with his fans, friends and family.
He’s not great at apologizing. He’ll write a joke, and I’ll go, “That was my apology.” He works through a lot of stuff out loud.
—LeeAnn Kreischer
The first edition of Bert’s Fully Loaded At Sea cruise set sail from Miami on Friday, Oct. 27, 2023. Over the course of four nights, the Norwegian Cruise Line ship Norwegian Pearl stopped at Great Stirrup Cay and the Bahamas. The impressive array of comedians who performed on the sold-out cruise to around 2,400 passengers included Whitney Cummings, Ms. Pat and Big Jay Oakerson.
The first voyage proved to be such a hit that the second Fully Loaded At Sea will set sail this fall. Once again leaving from Miami, the boat will head to Cozumel, Mexico. “Cruising is who I am. I take my family on cruises. I love the energy. I love gambling until two in the morning and closing down bars. I love chilling on the lido deck,” Bert says. The atmosphere and partying were so raucous on the first nautical journey that the sold-out cruise broke the long-held record for alcohol sales at sea, a number Bert aims to topple this time around.
Bellies Abroad
Much like how 2 Bears 5K improved the fitness for Bert’s fans, Fully Loaded At Sea helps broaden the minds of some of his fans who never, or barely, leave the United States. Bert isn’t judging people who don’t travel, admitting, “I don’t think I was meant to travel. I don’t think I was meant to have this life. I think I was meant to be a boat salesman in Tampa, who drives everywhere and goes to Tallahassee to see football games.” After enduring various roller coasters, water rides and other unique challenges in the United States for his 2010 Travel Channel show “Bert the Conqueror,” Bert then started traveling to places like Scotland, Vietnam, Costa Rica, Japan, South Africa and Tanzania for his follow-up series “Trip Flip,” which lasted for four seasons between 2012 and 2015.
“I think I got a real blessing by witnessing things that I never should have seen,” admits Bert, with genuine sincerity. “I think it changed a bit of my DNA. I was not supposed to go to Asia or any of those places.” Bert remembers getting into numerous remarkable scenarios, including playing soccer with kids in a favela in Brazil surrounded by tenement buildings. “I just loved getting lost in the cities. My favorite memories are actually when the episodes wrapped early, and I could just walk 15,000 steps and disappear.”
Since LeeAnn—a native of small-town Bowdon, Ga.—had never left the United States, Bert made it his mission to take her to different countries. Their first journey abroad together was to Paris, where she quickly got tired of walking around. When she started to feel guilty for not visiting the city’s endless array of tourist spots, Bert calmed her down and reminded her that they were there to do whatever they wanted. “Part of traveling is about enjoying yourself. If you want to sleep in, sleep in. If you want to drink Champagne when you wake up, do it.” Bert already has a long list of places he wants to take Georgia and Ila. He’s currently planning a large trip to Greece for all of them, and has his eyes set on trips to the Cotswolds in England and a Swiss chalet. He wants them to keep traveling because he knows it’ll inform how they live life.
Maybe his roots in the sandy tourist mecca that is the Sunshine State subconsciously sparked his inner wanderlust and love of travel. Bert instantly pivots to praising his home state and breaks down why it’s one of the most popular destinations in the world. But he doesn’t highlight the usual cities and theme parks that people flock to. His preferences are floating down the Ichetucknee River on an inner tube and feeling the powdery white sand of Destin beneath his toes. The older Bert gets, the more civic pride he feels for Florida. He’s even been listening to podcasts about Florida history to help him fall asleep. “I realize more and more that I am Florida. I grew up in the ’80s when that Cuban influence was being introduced to Florida. I’ve got Ocala, Odessa, Thonotosassa, Tampa, redneck Florida running through my veins.”
Cruising is who I am. I take my family on cruises. I love the energy. I love gambling until two in the morning and closing down bars. I love chilling on the lido deck.
—Bert Kresicher
Growing up, he didn’t think that Florida had a vibe. Now he realizes that he and his shirtless antics epitomize the Sunshine State. “Someone asked me, ‘Why are you always shirtless?’ I was like, ‘Everyone does that in Florida.’ People have no idea how comfortable we are with sweating. Florida’s vibe is being shirtless and walking barefoot. I’ve been barefoot my whole fucking life.” With Georgia and Ila now out of the house, Bert has even been trying to convince LeeAnn to move to Florida, especially because the second season of “Free Bert” will once again be shot relatively nearby in Atlanta. “I can’t see myself not in Florida. There’s so much Florida in me.”
As the conversation comes to an end, Bert acknowledges, “I’m at a really weird point in my life.” With the kids on the verge of adulthood, LeeAnn believes Bert’s creative inspiration will change, as his “art has always come from living life” and his family. On the flip side, though, Bert proclaims, “You can also look at it as a rebirth.” He’s already working on his next hour-long set, which this time might focus on his 78-year-old parents.
“My father-in-law’s hearing loss is one of the funniest things I’ve experienced in my entire life,” LeeAnn says. “That guy mishears everything, and it’s always pornographic.”
Whatever’s next, Bert’s ready to put in the work, get uncomfortable and “do some really cool shit.”
