American Airlines 1704, LAX to PIT, 2:17 p.m.
It’s one thing to meet a celebrity. It’s entirely another to meet an icon: someone so famous that people from all walks of life, all ages and ethnicities, seem to lose their sense of how to behave like normal humans when they encounter him. I witnessed this personally the day I flew from Los Angeles to Pittsburgh on the same flight as Mike Tyson.
Young passengers stopped in the aisle. “No shit!”
“I love The Hangover!”
An older lady making her way to her seat simply paused as her mouth hung open, speechless. And a lot of dudes bowed down to the ultimate alpha male. “Hey, champ!” “You’re the man, Mike!” The guys raised their fists, acknowledging that they know Mike’s fist is the fist.
Tyson’s assistant, Rashad, once told me that when they visited China—one of the most strict, regimented countries on the planet—even the customs agents at the airport all left their posts to grab a photo with him. Customs agents in China are probably the last people on earth I would guess to be swayed by celebrities, but this is Mike Tyson. He’s lived a life that most of us can’t even conceive of, and most of it has been in front of our eyes: triumph, defeat, tragedy, comedy, hope, and despair all wrapped up in a pit bull’s body with an unmistakable lisp. You might have noticed that I mentioned talking to Tyson’s assistant, and you’re probably wondering how that came to be. Well, I, like all the other passengers, was fascinated by the champ’s presence, and I couldn’t help myself. More on that soon.
The first time I heard his name I was six or seven years old. I don’t remember which fight it was, I just remember my dad complaining that “this guy” kept knocking people out in the first round, and my dad was pissed that it was over so quickly.
“Shit! There goes fifty bucks. What was that, twenty seconds?”
I thought it was awesome, but it wasn’t my money spent on the pay-per-view.
I didn’t really understand why my dad wasn’t happy to have the fight end after one minute. I thought this dude was like a character that had popped out of a comic book, a superhero among us mere mortals on earth. I mean, he sure looked like one. Mike was compact and muscular. His torso looked like it was chiseled from stone. He had the most menacing eyes on his way to the ring, but hey, he wasn’t mad at me, so I loved watching him terrify other people. Later, I learned he was called “Iron” Mike Tyson aka “The Baddest Man on the Planet.” To me he looked like the baddest man on any planet. You think anyone on Mars wants a piece of Mike?
I followed the epic saga that is his life with devoted interest like when a new season of Ozark drops on Netflix. So the last thing I imagined is that I would someday have the opportunity to meet this global icon.
I shouldn’t have ever met him. When I say I should never have met him, I really mean it. I was supposed to sit in coach that day, but I was upgraded last minute at the gate. I boarded with the first few people, and at the time it didn’t seem unlike the thousands of other flights I’ve boarded. People are tired, most are dressed casually, which is a nice way of saying terribly. People used to wear suits to fly; now it looks like they’re picking up a sixer at 7-Eleven before they get back to their bonfire on the beach, wearing flip-flops and tank tops. You see the sensible business traveler, always wearing a shirt tucked in, with monogrammed luggage tags, letting people know, “I fly… a lot.” I watched this normal parade of passengers walk past me and then I saw him. I looked up, then down, but my head shot back up, realizing what my eyes had just seen. Mike Tyson walked right past me and sat one row behind me, across the aisle in the aisle seat. At the time I was in the window seat, and there was one other guy in my row, seated on the aisle. The row in front of us was completely empty, so I suggested the aisle guy move up so we could each have a row to ourselves. This was, admittedly, completely calculated on my part. I wanted to sit that much closer to Mike and increase the possibility of talking to him. The guy sitting next to me never noticed. He was a total “Justin.”
Over the next hour, I plotted how I would approach him. I had listened to the two old boners behind me force conversation with him, and it was excruciating. One of them asked him if he “remembered” one of his championship fights, because this man also remembered it. I was fuming quietly at what douchebags these guys were. The other offered him lunch the next day at his restaurant. I thought long and hard and decided I wouldn’t try to be cool. I’d just be sincere and possibly humiliated. I reached into my bag and pulled out a shrink-wrapped DVD of my first special, Completely Normal. The plan was to pass it off, like a mixtape. I got myself together, stood up, and slowly took the few steps back to Mike. He looked up at me, and I have to admit I was really nervous. Do you remember asking the girl you thought was pretty to dance in middle school? Your heart races, your throat dries out, and you stammer through the words. It’s a terrifying experience. This was like that, only this time the pretty girl was known as The Baddest Man on the Planet, and he could use his fists to kill you if he didn’t want to dance. Still, I tried to remain composed as my voice cracked a bit and my mind wondered if I was upsetting him by talking to him.
“Hey, Mike. I’m a big fan. My name’s Tom Segura and I’m a comedian. This is a DVD of my special.”
I presented my DVD to him, still shrink-wrapped. He took it and, much to my surprise, actually looked at it for a moment, then he looked at me and began speaking.
“You’re a comedian?”
“Yeah, I’m going to Pittsburgh to do shows. What about you?”
“I’m going to promote a fight.”
“Oh, cool.”
“I hate fights.”
“Oh.” I wasn’t sure how to respond or what he meant, but he elaborated.
“Fighting is so chaotic and brings up so many emotions in me. I’d rather avoid it, but I gotta pay the bills.”
One of my favorite things about Mike over the years is witnessing how self-aware, introspective, and philosophical he’d become. Here I was, getting my own little display of this, and I was loving every second of it.
“Where’s your show?”
“It’s a comedy club called the Pittsburgh Improv.”
“Where’s that?”
“I’m… not sure.” I mean I’m still not sure. I rarely know the exact location of any comedy club in the nation. I just travel to these cities and know the name of the club. The club always arranges transportation for the headlining comic, so we really never know specifics unless we’re very curious. Also, what if I did know the neighborhood? Would that actually mean something to Mike Tyson? Is he familiar with Pittsburgh’s neighborhoods? “Hey, the club is in West Homestead, across from Somerset.” Like now he’s going to say, “Oh, off 376 on the waterfront? Yeah, I love it there.”
Then he asked what might be my favorite question of our whole interaction.
“Is your show tonight?”
He asked this as we were still on a plane, close to 11:00 p.m. eastern time. What time would my show be, 2:00 a.m.?
“Uh, no. It’s tomorrow.”
“Where?”
“The… Pittsburgh Improv.”
“How do I find it?”
This one left me frozen for a second. Mike’s stare is an intense one. I watched him stare down his opponents before they fought so many times—even from my living room I could see the fear in their eyes. Now, here I was, standing above him, and I could feel a hint of that stare. Suddenly I’m Michael Spinks, and the worst moment of my life is about to happen. He had just asked me a question, and his expression said, “You’d better know the answer.” I just blurted out whatever words popped into my mind.
“Well, if you Google my name, which is on the DVD, it’ll bring up my calendar and then you can see where I’m performing. That’s probably the best way to find it.”
He thanked me and I went back to my seat. I was breathing extra hard as every ounce of me had been clearly suppressing how nervous I felt to engage him. But I did it. I was proud of myself. Just as my heart rate was coming down, I heard his unmistakable voice.
“Tooooom.”
I turned and Tyson was looking at me, casually twisting my DVD in his hands. “Were you on television recently?” I thought for a second, wishing the answer was yes, but knowing it was not. “No. Uh-uh.”
“You sure?”
“Yeah. I mean… Yeah.”
“Nothing?”
I thought for a beat and casually dropped, “I mean, I’m on Netflix.”
“Hell, yeah! I love Netflix! What’s your favorite show on Netflix, Tom?”
I tell him Breaking Bad even though I know it’s not a Netflix show. I’m nervous and I also want him to think what I watch is a solid choice. Without hesitating he says, “Yeah, my wife likes that.”
Gutted. He said it like, “Some people like the ballet.”
Then his eyes lit up. “You like Sons of Anarchy?” I was devastated. I’d heard friends and critics rave about the show for years, but I’d never seen a single frame of it. It’s just one of those things—there are only so many shows you can watch. Now I had the champ looking at me with boyish wonder in his eyes and I had to say something. Do I disappoint him more? Of course not.
“My favorite fuckin’ show.”
Mike let out a maniacal laugh. “I knew you with it! That shit’s wild!” He extended his fist, a fist that has ruined so many faces and nights for opponents. It sat there in the open space of the aisle looking like a goddamn sledgehammer. I extended my baby fist and gave him a bump. Awesome. This could not have gone any better. I not only met Mike, gave him my special and had a friendly chat, but we had a real moment. Even though I lied, it was worth it.
Now I was facing forward again and beaming, reliving the last ten minutes of this flight over and over. I was anxious to land so I could call my friends.
Just as my breathing returned to normal, I felt a strong grip on my left shoulder. It honestly felt like what I imagine a DEA agent’s grasp would feel like when they finally got their hands on El Chapo. It had big “stay right where you are” energy. I turned around expecting someone of authority to be looking over my shoulder, but it was Mike. His expression was nonchalant. This was simply a “greeter’s grasp” to him, I presume. I had no idea what was about to happen. Tyson standing over you with his hand on your shoulder is a major alpha position. My eyes widened a bit, as did my mouth, and my asshole followed. Without warning he leaned down to my left ear and gently whispered.
“I’ve been watching a lot of Netflix.”
That’s it. Then he stood up and he was looking at me like, “It’s your turn to talk.”
I stammered a bit but managed to say, “Me too. They have… so many things to watch.”
“I recognize you.” He held up the DVD I had given him. “This is the same picture that’s on Netflix.”
For a brief moment I wasn’t sure if he was fucking with me. He was showing me a picture of me that I had just given him and mentioning that it was on Netflix after I had just said that. But the look on his face was sincere, kind, and hopeful.
“Oh yeah, that’s the copy of that special.”
“I know who you are.” This was surreal. Beyond surreal, actually. This larger-than-life figure who I grew up watching knock out grown men like he was in a video game was looking at me telling me he knows me.
“What’s your phone number?
“Mine?”
Rashad, the man who had been sitting next to Mike, pulled out his phone. I gave him my number.
“We comin’ to your show tomorrow.” It was Mike’s last statement to me before returning to his seat.
Soon after, we landed and I hurried off the plane. It felt like the interaction had gone so well that any staying behind could only ruin it. I didn’t want to overstay my welcome.
On the way to my hotel I called three friends and my father. I had to tell people. All of them responded with disbelief.
“Kid Dynamite!”
“You’ve made it, Tommy!”
“Did he make you suck his dick?”
That last one came from my friend Casey, not my father.
The next morning I woke up thinking it was a dream and knowing that, as with a lot of celebs, many of whom I had encountered, I would never see him again. Sure, he said he wanted to come to the show, but everyone knows that is just something people say. And it’s not limited to celebrities. Most of the time it’s non-celebs, if I’m being honest. People constantly ask when and where your shows are and make proclamations about how they “definitely” want to come and how they’re “trying” to make it as if it’s meaningful to you, the performer, if they do or not. Little do they know, most comics not only don’t care, they sometimes dread people they actually know coming to the show.
I decided to take a chance. I was going to tell the club to maybe expect Mike Tyson to come to the show. Why not? No one would know except for the guy I was telling, and he was the manager of a comedy club, so fuck him. I called. I was nervous.

“Uh, yeah, I’m at the hotel… Yeah all good… Show’s at seven? Okay, cool… one other thing… Mike Tyson… might come to the show tonight.”
“The fighter?”
“No, the guy who founded Tyson Chicken. Yeah, the fighter.”
The manager paused. “Holyfield too?”
“Uh, I don’t think so.”
He told me if it happened they’d take care of him.
I wanted Mike to come, but more than that I wanted him to come to a great show. Most shows are fine, even good. Some are terrible beyond belief, and then some are just… magic. I was praying for one of those.
But in comedy, like life, things don’t ever go how you think they will.
The afternoon felt like the longest one I could remember. I walked to a diner, paced around a mall, went to the gym, and stared at the ceiling in my hotel room. I couldn’t believe how much the anticipation was fucking with me. I just wanted to know whether or not he’d really come to the show. Around 3:30 p.m. my phone rang.
“Tom, it’s Mike Tyson. We comin’ to your show tonight, brotha.”
“Fuckin’… really?”
“Yeah, we wanna watch you do your work.”
I was genuinely excited. “That’s fuckin’ crazy!”
He was gracious.
“It’s all love.”
I’d heard that expression before. It’s one I really enjoy. You’re simply stating that the action you are taking is all about the best thing in the world, love. In this case, brotherly love. I knew it was my turn to talk, and I wanted to say something that conveyed a similar message. I wanted to sound cool. I paused and then I said it.
“I love you.”
Fuck. I shut my eyes so hard I almost had a stroke. What am I doing? I just told Mike Tyson I love him?! There was a pause on his end.
“Aight, good luck tonight,” and the line went dead. Did I just ruin this? Was the former undefeated, undisputed heavyweight champion of the world about to come to my show, but changed his mind the moment I fell apart and professed my love to him?
The house was half full. I started and the first joke fell flat. I was distracted, looking for the champ. I kept doing my set, and then it happened. I heard a loud slapping of a table, I squinted and saw Mike Tyson about three quarters of the way back in the room. The show ended up being… fine. It was hard to concentrate because all I could think was, Is Mike laughing at this? Am I bombing? Is he going to walk out? Luckily, I couldn’t clearly see him, and I was finishing my set strong, but all I could think about was, What happens next with Mike? Do I acknowledge him and ask him to stand so 183 people can say, “Are you shitting me?” Should I wave like a kid in a commercial to one of their sports idols? Luckily for me, I didn’t have to think long. As I walked up the aisle, the audience was clapping and music played, and then I felt what I can only describe as what you might feel right before a polar bear effortlessly tears your shoulder off. Mike had slapped my back.
“Funny shit, Tom! Let’s go to the green room!”
I didn’t even say a word. I just followed Mike to my green room. He led the way, of course.
Once inside this small room, Mike and two of his crew got comfortable and Mike began smoking cigarettes. One after the other. One thing that amazed me about this was how one of the guys would light Mike’s cig as he was putting it up to his lips. He didn’t have to wait a beat. That was the first time in my life witnessing that level of… submissiveness. I mean it’s beyond “baller.” It’s a guy making sure you don’t blink between cigarettes. Something I imagine Prince Al-Waleed bin Talal would have had done for him in one of his three Saudi palaces, should the multi-billionaire investor decide to begin smoking.
The conversation with Mike was epic. I’d love to put it all in this book, but I would certainly fear for my safety and ability to chew solid foods if I divulged all the details. I can say that we talked life, boxing, and a lot of Mike’s ups and downs. One of my favorite moments that I feel like I can share is how he viewed his role when stepping into the ring. He said it wasn’t just about beating his opponent, but respecting that the audience wants to see a “show.” He was going for those knockouts, not just to win, but because he knew we wanted to see them. I loved it! He also went into detail about boxers he didn’t think respected the audience and how boring they were to watch, and I will not be listing those names here!
After about his fourth cigarette, he asked me, “You got a window in here?” I’m thinking, It’s a little late for that. You’ve been puffing for an hour. I look around and tell him, “No, no window.” And like something straight out of a movie, he took a long drag off his smoke and said, “That’s when you’ll know you’ve made it. When your green room has a window.”
I’d never heard it put that way or thought about it, but it registered right away. It also felt like someone clearly telling me, “You definitely have not made it yet.”
Mike smoked a few more cigs, then said he was going to turn in. A few hours had passed, and when I opened the door to walk him out, the entire staff of the club was lined up. They all wanted pics, and Mike obliged.
If this story sounds familiar to you, it’s because you’ve heard the stage version, one that I started telling the next day. It killed immediately. Eventually it became my closing bit on the new hour I was working on. You can see the stand-up version of it on my 2016 Netflix special, Mostly Stories. I also ended up telling it on talk shows and podcasts as it was a fan favorite. One random afternoon a few years later, I got a call from Joe Rogan. He told me to come by his studio in about an hour. When I walked in, I saw a group of people sitting in one of Joe’s green rooms.
I made my way through the small gathering to see who was on the couch. It was Mike Tyson holding court. He looked up at me.
“Man, you know people stop me all the time, asking me if that shit is true. I say, ‘Yeah, man. All that happened.’”
“Me too!”
He got up and gave me a hug, and I thought, what a cool moment. I thanked Joe and then Joe really surprised me. He leaned in and said in my ear, “Why don’t you stay and podcast with us?”
My heart almost stopped. Not only was I floored at the offer, but I was torn as well. This happened to be the day that I was supposed to be meeting up with my wife at a hotel nearby to celebrate our anniversary. I didn’t know what to say. What I felt was that even though sitting in on a podcast with Mike Tyson seemed like the coolest thing in the world, something about it made me feel like I shouldn’t put it over my wife, especially on our anniversary. It felt like the right thing to do was leave. I didn’t want to make that call: “Hey, I’m podcasting for a while so… see you later?” I told him I could stay for a little bit, but we got started and the podcast was awesome. I got to ask him something I had never remembered to ask when we hung out, which was, “What made you think you could get a tiger?” The answer was better than anything you could make up. Mike told a story about ordering his first wildcat from prison. He was on the phone with his car broker and the broker happened to mention that he could also get wild animals, so naturally Mike said, “Can I get a tiger?” And his car broker told him, “No problem.” Mike Tyson basically got a tiger because his car guy was out of Bentleys.
The energy was flowing so well on this podcast, but I kept looking at the time. I needed to make a decision: stay and have a good talk or leave. I was feeling anxious and told the two of them, “I gotta go.” And it was Mike who was pleading with me to stay.
“Come on, man. Don’t go.” Surreal. Iron Mike telling me to stay because he was having fun.
I had to.
“Wife, you know.” They both nodded.
I left Joe’s studio and had to pause.
Damn, that would have been cool to stay.
I took the 405 over the hill to the Beverly Hills Hotel. I arrived a few minutes before my wife and took her to their famous eatery, the Polo Lounge, for lunch. I tried to talk about anything else, but I couldn’t stop thinking about what had just happened.
“You’re not going to believe it. I was just podcasting with Joe and Mike Tyson. So unreal. But you know what, I left, so I could be here with you.”
“Why didn’t you stay?”
Umm, isn’t it obvious? Hello?
“I didn’t want you to feel bad that I made that a priority over meeting up on our anniversary.”
Clearly there are big-time husband points to be had here. I stopped doing what I wanted to do because I was putting her first. Isn’t that what every wife wants? For their husband to stop enjoying himself so he can have lunch with her.
“Oh… I would’ve stayed.”
“What? But we had plans to be here… now.”
“Yeah, but it’s Mike Tyson.”
GOD FUCKING DAMNIT.
