Bert Kreischer

THE MACHINE BREAKS FREE

by Randy Mastronicola

with Molly Headley | portraits by Storm Santos

BERT KREISCHER IS DOING THE ONE THING everyone tells you to give up by middle age: stop being the biggest beast at the party. Onstage, on tour, and now in the spirits aisle, he’s still the shirtless legend who inspired Rolling Stone to crown him “The Number One Partier in the Nation” back in 1997, loosely inspiring National Lampoon’s Van Wilder.”

THESE DAYS, The Machine (the moniker he earned when partying and robbing a train with Russian gangsters during a Florida State University class trip in the mid-1990s) is also a dad, a producer, and co-founder of Por Osos vodka with fellow comedian Tom Segura. And just in case reality wasn’t wild enough, he and his wife, LeeAnn, a former screenwriter who now runs Berty Boy Productions, created a scripted Netflix series based in part on their lives. Free Bert, premiering this month, follows what would happen if the pro partier was forced to “put on a shirt” and survive bougie Beverly Hills with his wife and kids.

Off-camera, he’s still sprinting: touring, podcasting, and chasing his own redemption story, which unsurprisingly features a through line with vodka. The magic formula is somehow working. Kreischer seems to be walking a perfectly buzzed line straight into his biggest chapter yet. We recently sat down with Bert (and even had a spontaneous aside with the formidable-in-her-own- right LeeAnn) to chat about all the good things on the horizon.

Randy Mastronicola: Let's talk about Free Bert premiering on Netflix this month. How did it come about?

Bert Kreischer: I think my white whale has always been a sitcom. When we started, everyone said you've got to do something with your family, because my stand-up is my family, and I resisted that forever. I never wanted to be the comic that talked about his kids and wife. I was like, that's so lame. But that's where I landed organically.

Judd Apatow came to me early and was like, I would love to do Hurt Bert, like a work thing with this guy who does crazy adventures and then juxtapose it with your family. We went through a lot of versions of what this show could be, and we landed on this period in my life when I was lost. It was 2016, I was fired from Travel Channel, fired from this, fired from that. No stand-up. My wife wanted me to get a vasectomy. My life was falling apart. I didn’t really know who I was as a comic. Then I figured it out. This rebirth is exactly that, encapsulated in a guy going, well, who the fuck am I? Then at the end, I find out who the fuck I am.

I'm really excited for people to see Free Bert. I think the number one thing you'll see is, holy shit, Bert can act.

Are you still that guy from Florida State University? Or have your tastes changed?

I was a beer and chewing tobacco guy until I was probably 29. Then I had a cigar. Growing up in Florida, cigar smoke is super familiar. I used to go with my dad to court, and they'd be smoking cigars, in his old office on Bird Street. When you walked in, it just smelled like cigar smoke. I was six years old, so 1977, 1978. Everything always smelled like cigars. You went to a restaurant, guys were out front having Cubans.

There's a cigar shop right next to the Comedy Store by the Improv and V Cut, and one day when I was 29, I walked in and said, “Maybe I'll get into cigars.” I got a Cubano and cigars that I couldn't afford. I sat in my house, Cecil B. DeMille's old house, with the doors open, overlooking Hollywood and Highland. One of the most beautiful views.

I had a cigar, and I enjoyed it so thoroughly, I said, “I think I'm in.” From that moment on, I became a cigar guy. Around that time, I got signed by Jameson Irish Whiskey to do a tour. Then I turned into a spirits guy. From there, I graduated, and I started trying new things. I remember going to dinner with my uncle. My uncle, who's always been a big wine guy, said to me, “You always start dinner with a martini. You get a dirty martini, blue cheese olive.” Now, I'm 53. I don't think I've ever started a dinner without a martini.

That early connection of cigars and spirits clicked for you–a lifetime of appreciation.

100 percent. I remember when I was on tour in South Africa, we were doing one theater every night for one month. The bar there, God, one of the most beautiful bars in the world. They'd open up every bay window, and the wind would come off the ocean. Every night, I got a Cuban cigar and a glass of Jameson.

I know there's a part of me that, because I'm from Florida, feels a tether to the cigar industry. Then it wasn't until the first time I quit drinking—we did Sober October—where I started really looking forward to a cigar and going, “I'm going to get up early and go get an espresso and a cigar at the cigar shop.”

I've been in some of the best goddamn conversations I've ever had in a cigar shop.

Absolutely. There's that camaraderie, connection. Every year on January 23, I celebrate Winston Churchill. I do a thing called Winston Churchill

Day where I dress like him, and I live like him. I wake up at 7:00 a.m. and I get breakfast served in bed, soft Scotch eggs, bacon, toast, jam, fruit,

coffee, orange juice, and a cigar. I smoke a cigar in bed. I will tell you, in my experience, there is no better cigar to ever be had than in your bed,

with a soft Scotch egg at 9:00 in the morning, with a paper in front of you.

[laughs] That’s a non-starter in my household.

Oh, there is no better manly feeling than a cigar in your own bed.

What a way to start the day. Do you have the little ding- a-ding-ding bell, like the queen used to signal Winston Churchill when his time was up?

LeeAnn: Do you?

Bert: Do you want to answer that?

LeeAnn: Yes, you do.

Bert: Yes, I do. [laughs]

LeeAnn: I bought all the stuff. Winston Churchill Day, it's one day, so I leaned in.

Bert: She bought me all the fine cutlery, all the things to hold the toast. This thing to hold the butter, she bought all of it.

[laughter] Nice. It's good to have that kind of support.

Here's the deal with cigars. When Tom and I started our booze, Tom wanted to do whiskey. I said, “Tommy, we're never going to convince anyone to change their whiskey.“ That's the truth. Whiskeys are like cars. I can tell you what kind of car you should get, but you're going to pick the car you want. When it comes to whiskeys, people have been doing it for so many generations that to change their mind in 2025, I don't think it can be done. “Let's go into vodka,” I said. It’s the same with cigars.

Go where the road takes you.

Yes. When it comes to starting my own brand of cigar, I go, “You know what? I’m going to leave it to Tatuaje. I’m going to leave it to Padrón. I’m going to leave it to La Gloria Cubana. I’m going to leave it to Oliva.” That’s how I feel. I’m super passionate about this.

It was interesting that you took that route because so many guys want to do brown spirits or Mezcal, which they view as badass-ish. It's interesting that you went with vodka. You're very secure.

I know what I like. I think, truthfully—this is going to sound really silly—my brand, really, is recovery. People go, “Your brand's partying.” It is, but it’s actually recovery because if I don't recover, then I just look like an alcoholic. I got up this morning, did a workout with my trainer for 45 minutes, sauna’d, came over here.

I took my testosterone. I took my BPC-157. I took my pills, my blood pressure medicine. I journaled. My brand ultimately is recovery because I love to party. This is one of my favorite booze stories: I've always been a beer guy on a plane. A beer, you can measure your buzz. No one looks at you like you're out of control drinking beer. I'm flying from New York to LA. I'm next to this beautiful guy, jawline, great head of hair. That's not me. Lady comes up and says, “What do you want?” I say, “Heineken.” The guy next to me says, “Can I get a double Tito's and soda?” It's early, so I go, “Interesting. Vodka with soda in the morning?” He looks at me and says, “It's in my contract. I'm a high-end male model. I'm only allowed to drink if I drink vodka. I found that Tito's is the least bloating of them and the healthiest. So, yes, I allow myself a double Tito's and soda every now and then. It keeps you slim.” The lady comesback with a Heineken. I go, “You know what? I think I'll switch to a double Tito's and soda.”

In 2016, Tom Segura, my business partner, starts fat-shaming me. We start a weight loss competition. I say to him, I'm going to lose more weight than you by New Year's Day and I will drink every fucking night. I drank Tito's and soda. I lost, I think, something like 40 pounds in two months. It was crazy. I drank every single night.

Then we went on Joe Rogan. I started talking about Tito's on that. Tito's hears about it. They hit me up. They're like, “Yo, dude, thanks for mentioning us on Rogan.” Then they start sending me bottles of Tito's. I didn't pay for a Tito's from 2016 until we started Por Osos. I reached out to Tito's. I said, “Yo, it seems like we're a good partnership. I would love to do something with the company. I'd love to be a brand ambassador.” They told me in no uncertain terms, “Go fuck yourself.” I was like, “Tommy, let's start our own vodka.”

Sincerely, I’ve made a clear profit on this vodka just because I haven't paid for vodka in two years. I went to Harvard Business School to speak

about marketing and branding and advertising. They had AI try to figure out my brand. AI was like, this doesn't make sense. He's into MMA. He's into track and field. He's into 5Ks and marathons and alcohol and marijuana and cigars and partying and NASCAR and pro wrestling. They're like, who is this fucking guy? I really think vodka, for me, came about because I felt healthier. I woke up in the morning and I didn't feel bloated. I didn't feel out of shape. I felt like it was a clean in and out drink.

Are you happy with where the brand is right now?

There are always miles to go. Tom said to me when we started, “Is this something that we want to do for the rest of our lives or is it something we're just trying to make a profit off of? Personally, I'd like this to be our company and I want to do it forever.”

Right, and there's something to hand off to the next generation.

Comedy is so big right now that all of us feel like it can't last forever. I can't do arenas for 10 years. This can be a job for us that we really enjoy, and it can be a thing we do into our 70s, into our 80s. We can be like Sammy Hagar. Sure, he plays music, but when you think of Sammy Hagar, you think of his tequila.

Tom said, “Then if that's our move, we've got to really commit to getting out in front of this.” We do these bar takeovers. We were at this place called Clayton's in Indianapolis. I was standing on the bar pouring vodka into girls' mouths from 6 feet up in the air for two hours as a country music band played on stage, and I sang into the microphone. It was the most insane evening of my life. It's fun for us because it's a reason for us to hang out as friends, and we're working, but we're not working. We do a bottle signing at an ABC or at a local retailer, and then we go and do a bar takeover.

Tom gets drunk. He never gets drunk. He’s a one-drink kind of guy. When we do these bar takeovers, he gets lit, and we have a blast. Work hard. Play hard. I think our branding's pretty beautiful. Our bottle's bespoke. It's gorgeous. I'm proud to show people our bottle. We helped design it top to bottom. Everything. The only thing I wish we had stuck with was that we initially had two bears butt-fucking that I wanted to do a limited release of, and we were going to make the cap a butt plug. They were like, “I think this is a bad idea.” I thought, but that’s the fun of this. We’re comedians. We don’t give a shit. That’s because comedians have a license to kill. Por Osos…I'm drinking it neat? Vodka soda? Martini with

blue cheese? I always say vodka soda. As a vodka drinker, there are certain vodkas I can't stomach. I won't say their names. When we did this vodka, I said, run me through all the flavor profiles. I landed on what I would consider a very non- intimidating vodka. My toughest vodka I'll ever drink is going to be 7 in the morning at LAX, and I got to fly to fucking London. I'm afraid of flying, so I have to drink. I always say I want a vodka to whisper. I don’t want it to yell in my ears. I don’t want it to go, “we're drinking this morning.” I want it to be like, “Hey, I'm with you. I got you.” Never at any point with our vodka do you go, “too much vodka.”

Partying, family life, career. How does that all come together for you?

Oh, it's LeeAnn. If my horse starts to buck too wild, LeeAnn will take the reins. Trust me, there's been times where she has said, “Hey, I think we're going to slow down.” If she says that, it's really time to slow down. She knows how to steer a ship. She has always been a voice of reason. When I was on the road, she held it together with the girls. When I come up with a crazy idea, she forwards it. She was an executive producer on my TV show. She runs Berty Boy Productions. We have a cruise. She has her own podcast. She runs my podcast. She's savage.

What do we need to know about your life right now that you haven't already shared?

Fuck, I've shared so much. I keep thinking about this. You always hear comeback stories. Today, I was watching a surfing video. There's a thing in surfing called a double up, where you're on a wave, but that wave takes over another wave and gets bigger. I think I'm on the double up portion of my career. I think I've been riding this really crazy, insane wave. At times, I'm pumping to make sure that I can catch that double up and I get to ride it all the way to shore. That's the vodka. That's Free Bert.

Bert, thank you for being so open with us.

My pleasure, Randy.