This is What Happens When Ben Bailey Gets Pulled Over While Driving The ‘Cash Cab’

Just as the Cash Cab is about to pull out of its parking spot on the east side of Second Avenue on the Upper East Side in New York City…an Uber pulls right up in front of it, double parking and blocking the cab’s exit. Host, driver, and comedian Ben Bailey sighs, explaining just how often this happens, as we watch the female passenger exit the vehicle. The Uber doesn’t move, but Bailey’s got this. He’s an expert driver, not just because he knows how to maneuver his way around New York City, but that he’s able to do so while quizzing passengers on random trivia for their chance to win money on their way to their desired destination.

Cash Cab returns tonight to its new home on Bravo, airing after Watch What Happens Live with Andy Cohen, and as Bailey told me, “I’m super excited. More than I have ever been. Something just feels great about this. I think they’re the best ones we’ve ever done. There’s a new levity and fun about it.” And for $50….he’s right! (JK, he’s not getting money for his answers during our interview.) Cash Cab and WWHL is the perfect pairing for Bravo and for pop culture fans, though that doesn’t mean Bailey was always so sure about returning. “Leading up to it, I was like, I can’t believe I’m gonna do this again. There’s a lot going on driving this thing around and hosting a show, but as soon as I got in here I was like, oh right, I can do this. And it’s fun, I like doing it. It’s like putting on a suit that I made for myself because I created a lot of what it is that I do, and it just feels natural and fun.” 

Also natural to Bailey is driving — and yes, he drives the cab himself. “I’ve always been a driver,” he said. “Literally from the day I got my driver’s license I was driving to make money. I delivered everything all over the town that I grew up in. I delivered prescriptions, pizzas, sandwiches, eventually people. Cash Cab and I fit together right from the beginning and it’s just getting better and better.” Though when he’s not driving around with excited passengers in the backseat and flashing lights overhead, he drives in complete silence, noting that it’s one of the only times when he can actually think. 

I ask what it’s like navigating the streets of New York City and if fellow cabbies are nice to him or yell at him. “Well, both of those are definitely true,” he says with a knowing smile. “They’re generally very nice to me, they seem happy to have some good PR for New York cabbies because they get a bad rap. But they also get annoyed because people always get into their cabs and say, ‘Is this the Cash Cab?!’ and they’re like, nope. Sorry, just a regular old cab.”  Ultimately, Bailey said, ” Generally it’s pretty good but you definitely get into some things with people on the road, it’s impossible to avoid.”  

I also ask if he’s ever been pulled over in the cab and Bailey gives me a quick, “Oh, yeah.” And would you make your passengers use their winnings to pay for your ticket? “Absolutely!” he laughed. “I was distracted, you’re the reason I got pulled over so you pay the fine!” But in reality, Bailey admits, “I haven’t been pulled over in a long time. Early on, we seemed to get pulled over more.” And in his own form of winning, he tells me that he’s never gotten a ticket while driving the Cash Cab. “Most of the time if they pull me over they’re like, can we get a picture? They’ve been good to us, they’re nice to us. They’re happy that we’re out here, I think,” he says of the NYPD. 

Popping up in the Cash Cab this season are many Bravo stars including Cameran Eubanks and Shep Rose of Southern Charm, Captain Sandy from Below Deck Mediterranean, and Ryan Serhant and Fredrik Eklund of Million Dollar Listing New York. And while Bailey tells me his dream celebrity guest would be Bill Murray, if he weren’t already busy driving and doling out trivia questions, would he want to play the game himself? “I would and I wouldn’t,” he admits. “It would be fun but I’m a little bit afraid of how I would do because people would have such high expectations. They would expect me to know everything and I don’t. I might do okay. I’d like to see how I would do, but not have anyone else be able to see.” I get it, it’s scary. You want to prove to be the trivia master we all believe we are, and as I would be playing a round of the game myself in just a few moments (the ideal kind, where no one will be able to see how I do), I knew exactly what he meant. But Bailey was certainly being a bit modest. He admits to being a “trivia nerd” and loving Trivial Pursuit and watching Jeopardy with his parents when growing up. 

After hosting over 450 episodes of the show when it was originally on Discovery Channel, Bailey admits, “I do have a lot of random ridiculous information crammed in my head. But I like that.” Though he’s conscious of not being annoying about it, he does share that’s he’s dropped a fun fact or two on his friends at a party after learning it on the show. And it’s not all useless information. “Believe it or not, through Cash Cab, I have a much broader understanding of history than I ever did before. I realized I didn’t get that much history out of school, but I’ve pieced together a timeline in my head, I have a perspective of how things have happened that I didn’t have before.” 

Another important lesson he’s learned is that you truly can’t judge how much a contestant will know just by glancing at them as they get into the cab. “You really can’t,” he says earnestly. “I learned that years ago from doing this show, you can’t tell what people are gonna know by looking at them. And I think that’s part of what people like about the show watching at home, which is cool, I’m happy that you can’t judge people by how they look.” 

When he finally gets the cab around the idling Uber, I know we’re about to play the game, but that doesn’t make the music, and the lights and him stating “You’re in the Cash Cab!” any less exciting. But I was nervous: I didn’t want to be a Cash Cab failure! Luckily, I breezed through the first $50 question about the actor behind the @actuallynph Twitter handle (Neil Patrick Harris) and model Karlie Kloss’ sister-in-law (Ivanka Trump), before Bailey was forced to pull over to let a police car with sirens go by. We resumed the game with my first missed question, about the monarch of Monaco who demanded a $2 million dollar dowry before marrying actress Grace Kelly. The answer was Prince Rainier III, a person I had to drop a “Sorry to this man” on because I had never heard of him in my life (I didn’t even know how to spell his name as I wrote this), but as Bailey told me, “You won’t forget it if you miss something.” I’ll now know the name of that dude for the rest of my life. “Don’t feel bad,” Bailey assured me, as I’d already racked up $150 in fake cash, and we moved along to a question about Ashton Kutcher’s favorite brand of trucker hats (Von Dutch), an easy grab for me, an early 2000’s pop culture expert. I didn’t ever think that info in my brain would come in handy, I admitted, as Bailey threw out a great slogan for the game show, “Making useless knowledge useful.”  

As we rounded the block, my final question was coming up. “It’s all come down to this,” Bailey said in his famous game show host voice. “Remember, there’s nothing on the line. There are no stakes at all,” he laughed.

“My own self-esteem is on the line!” I reminded him. Luckily, I nailed the last question about an Oscar-winning actress in back-to-back Best Picture winners (Octavia Spencer), exiting the cab with $350 fake dollars, but a real sense that I, a trivia master, just took the best cab ride in New York City.

Cash Cab premieres Monday, October 7 at 11:30pm ET/PT on Bravo. 

Where to stream Cash Cab