I grew up in a household full of cops—both my brothers, my dad, all my uncles, and nine of my cousins are cops. Honestly, I probably would have become a cop too, but then I learned about background checks, and I thought, “You know what? Maybe not.” My upbringing in such a big law enforcement family had a big influence on me. 

Humor was a survival skill for me because I had older brothers who would often beat me up. Comedy became a way to take the edge off and diffuse tense situations. I was surrounded by funny cops in my family who told a lot of dark jokes. I heard countless street jokes, like the classic, “Two guys walk into a bar.” Being half Polish and half Sicilian, I was also exposed to a lot of Polish jokes and Italian street jokes about the mob as I was growing up. 

This environment of humor drew me toward comedy as a kid. Joking around became a form of currency for me, helping me get out of trouble. I wanted to emulate the funny people around me because it seemed like a cool thing to do.

It's funny to think about how I not only took the long way but also had passengers along for the ride. Many people in showbiz take the long route, but few do it with others in the backseat. As a cab driver, I discovered that driving a cab is excellent training for hosting a talk show in two key ways.

First, everyone who gets in my cab becomes a guest for the duration of their trip—whether they’re heading to the airport or coming home from a bar. Each time the door opens, I’m introduced to a new guest. I was an outgoing driver, so most people would engage in conversation. What I found interesting is that for many passengers, I became a sort of affordable therapist. They knew they weren’t going to see me again, so they felt free to share all sorts of personal stories, conspiracy theories, or details about their love lives. 

The tricky part is that sometimes, you do run into these same people again in the city. Then it becomes awkward to pick up where you left off, like, "Oh, hey, the cowboys are back in the saddle, or, still doing that thing with the GI Joe." 

However, this dynamic allows for a level of candor that you wouldn’t usually get, as people feel comfortable sharing because they believe they won’t see you again. It’s like the original form of social media! Passengers would share information that I would then pass along to others throughout the day. For instance, the first passenger might say, "Hey, did you see what the mayor did?" By the end of the day, I might have developed my own opinion on it just from what I heard throughout the shifts. It was like experiencing Facebook or Twitter in person—something I’m not suggesting we should do, but that was my experience. I love that.

Here we go. I was driving a cab during the day and doing stand-up at night. If you establish yourself as a stand-up comedian in this city, meaning nobody knows who you are but you’re performing at various clubs, you often get invited to work on peripheral projects. For example, I was invited to punch up a movie script.

My first writing job was for a TV show called "Gotham Comedy Live," which was filmed and aired on Comedy Central at the Gotham Comedy Club. My role was to write celebrity monologues for the show. They would hand me names like William Shatner or Pamela Anderson, and I had to create a 10-minute joke monologue for them to use on stage.

Now, I mention this because it was the first time I appeared on Fox News. A booker had seen me perform at Gotham and invited me to be on Fox the next night. So, of course, the first time I hit this network, I found myself in a taxi double-parked on Sixth Avenue with the trunk open and the hazards on. That’s how you avoid a parking ticket in Manhattan. If you represent that you’re running inside to grab something, the cops usually give you about 20 minutes of leeway.

When I first appeared as a guest, I was walking out front with Kennedy, and I told her, "I have to go get my taxi." She replied, "Don't worry about it; there’s nobody in it." I clarified, "Oh no, it is mine. If you need a ride home, it is my taxi."

At that point, I had appeared once as a guest and been booked back a few more times. Eventually, there was an opening for a writer. I mentioned that I had a small writing job before this and that they liked me as a guest. They hired me as a writer.

I essentially started as an employee at Fox, working on a business show, which allowed me to appear more frequently around the building. My profile began to rise, and I’m pretty sure it was because everyone thought I had dirt on them from that taxi ride in my previous life—but that’s irrelevant. The point is, here we are.

Definitely environmental. A lot of the jokes I tell are observations about my current life. Early on, it was all about taxi passengers and New York driving experiences. As I moved into news, the focus shifted to news figures and media personalities. Now, on tour, I often share how my life has changed since the audience last saw me—like in Seattle, where I’ve gone from being “the guy they semi-know from Fox” to “the guy with his own show.” Audiences have come along for that ride, which is fascinating.

Comedy isn’t about boasting; it’s about self-deprecation. Take Rodney Dangerfield—his whole bit was “I get no respect.” He was wildly successful, yet his persona was far from “alpha.” When people know you’re doing well, it’s harder to play the underdog. For instance, I used to go on stage and say, “I’m a cab driver” and throw in some self-deprecating humor, but now, having my own show, I have to approach it differently. I’ll say something like, “Sure, I’m on a successful channel, but I’m still the guy people ask for change.” I want to keep that connection with my audience.

I approach everything with realism. I don’t look like a TV star; I look like the guy who installed your TV. That relatability is my superpower. I’m not coming from a political or intellectual background—I’m sharing news in a way that feels familiar to my audience. I stick to that approach because it’s unique in cable news; you don’t often see someone like me—a guy who dresses like a figure skater who let himself go. That’s my vibe.

The biggest impact on me as a stand-up comedian came from Rodney Dangerfield. He was the first established professional comic I looked up to. I learned that every successful comedian has their own unique persona. Rodney's persona was that of a likable loser. He would share stories about how things went wrong in his life, saying, “I’m doing all right, but last week, I was in bad shape.” He demonstrated the importance of changing the energy in the room. 

There’s a phrase people use: “read the room.” But in stand-up comedy, it’s not about reading the room; it's about leading it. You’re the only person with a microphone, and you're responsible for establishing the mood and defining the boundaries of the conversation. If you're going to take the discussion to unexpected places, you need to do so confidently and without malice. As comics, our job isn’t to abuse the First Amendment; it’s about disarming the potential for disaster with any topic we tackle.

These were my key influences: Rodney showed me the necessity of having a hook for my act. In my case, it was, “Hey, I’m this cab driver you’ve never heard of, and nothing’s working out in my life.” While it’s not exactly “I get no respect,” it definitely reflects the world I inhabited when I started.

Another significant influence was my fifth-grade teacher, Mrs. Pascana. She encouraged me to go home and watch The Tonight Show with Johnny Carson, saying, “Ask your parents to stay up till 11, because I honestly believe you could host one of these shows someday.” At the time, she may have said that because she realized I had no other options in life. However, I watched it from that fifth-grade year until today, and I was crazy enough to believe I would achieve that dream. That belief helped me push through countless long, exhausting taxi shifts where I had little motivation to pursue any ambition.

Teachers can have a profound impact on young kids when they genuinely believe in them. So, in addition to Rodney Dangerfield, I owe a lot to Mrs. Pascana, who doesn’t get enough credit. People often talk about comedy greats like Seinfeld and Chappelle, but no one ever shouts out for Mrs. Pascana. Where’s the justice in that?

The big challenge is making it accessible. For instance, if you’re making a political joke, you know that 50% of your audience won’t agree with the point. To make the joke work, I try to establish that I’m coming from a place of good faith as a comedian, not an activist. I approach it with a “smiley, good-time guy” vibe. The trick is to use contrast—comparing the point to something non-political or universal. For example, when one candidate avoids interviews, I might compare it to someone setting you up on a blind date without mentioning if the person’s good-looking. It’s a way to make the joke about the shared experience, not the politics. You want the punchline to be about humor, not ideology.

Here’s another example: I talk about attending both Trump and Kamala rallies. I explain the contrasts, and people love it. Even if they don’t agree politically, they can appreciate the humor in the differences. It’s all about showing them that I’m paying attention to the people, not just the politics, and unifying the room by being with the audience, not a particular viewpoint.

From my time as a cab driver, consuming media all day, I became very mindful of how media affects the audience. I see myself as a force multiplier of positive energy. If you’re angry for three hours on the radio, you multiply that anger in your listeners, who then spread it. I aim to be a force multiplier of good energy. I want to know that, in my limited time on such a huge platform, I’m having a positive impact. So, even on my Saturday show, I say, “Comedy doesn’t have a political party; comedy is a party.” Whether people agree with me or not, I want them to feel good.

In the beginning, when you’re developing stage presence, you’re very attuned to audience laughter. As you get more experience, you start anticipating what will work and what won’t. The real skill is in self-awareness. Knowing that you might look like you feel a certain way about a topic, but actually having a different perspective allows you to navigate tricky areas without losing the audience’s comfort. My stand-up special on Fox Nation is called They’re Just Jokes, and I often remind the audience that there’s a difference between a joke and a hate crime. It’s about keeping the perspective that this is comedy, and we’re here to escape, not add to our problems.

I’d love for the election to just end already! But on a serious note, I’m going on another stand-up tour and launching two new comedy series on Fox Nation. Bigger than any individual project, though, I want us to remember that everyone in this country has “American privilege.” People used to get in my cab from JFK and cry because they’d made it to America. I feel we’ve lost that perspective over the years, and I want us to have fun again. Regardless of who wins the election, there’s no rule that says we can’t enjoy life. I just want to take people off the hot playground and bring them for some ice cream.

I’d take that role! And yes, I want people to enjoy themselves. 

Well, I’d say, if you want to help the world, we don’t need more Republicans or Democrats; we just need fewer jerks. Be a Republican, be a Democrat, but don’t be a you-know-what. That’s my lane. I think everyone should try to enjoy the journey because no matter what it says on your business card, we’re all in the fun business. If you died tomorrow, you’d wish you’d had more fun today. So, for me, it’s about staying positive and enjoying every mile of the ride.

They can follow me on Twitter at @JimmyFailla. My stand-up tour tickets are available at Fox Across America dot com, where they can also find my New York Times bestselling book, A Cancel Culture Dictionary. And yes, I return my own messages—just look out for all the grammar errors.