Emmy-winning ‘Cash Cab’ host Ben Bailey cracks up DC Comedy Loft

WTOP's Jason Fraley chats with Ben Bailey (Full Interview) (Jason Fraley)

As you hail a cab this weekend, tell your driver that you’re going to see Mr. Cash Cab himself.

Emmy-winning “Cash Cab” host Ben Bailey performs two nights of stand-up Friday and Saturday at the DC Comedy Loft, located above the Bier Baron Tavern in Dupont Circle.

“There’s really no telling what I’m gonna talk about, but nothing political, which maybe is a good thing for D.C., I think people want a break from that,” Bailey told WTOP. “I talk about weird stuff. I talk about why we build houses for birds when they can build their own houses? All kinds of weird stuff, nothing political, nothing too offensive. It’s observational humor.”

That observational humor includes his roast of Ruth’s Chris Steakhouse in the video below:

Born in 1970, Bailey grew up in Chatham, New Jersey, but had no early dreams of stand-up.

“I had funny guys in my family,” Bailey said. “My dad was very funny and sarcastic, and my grandfather on my mother’s side was a big storyteller and very funny. I think I was inspired by those guys and I watched some stand up before I really should have been watching when I was younger. I saw some George Carlin, Richard Pryor, I always loved Rodney Dangerfield. He often gets left off the list of the all-time greats, but he’s definitely one in my book.”

After attending Old Dominion University in Norfolk, Virginia, he moved to Los Angeles in 1993.

“I just happened to fail a job interview right next door to The Comedy Store,” Bailey said. “I’d been working in hotels. There was a place right next to The Comedy Store that I applied for a job along with thousands of other people and I did not get it. I ended up talking to some guys out in the parking lot and getting a job answering phones at The Comedy Store. That’s how I got into comedy. ‘Are you a comedian? No, but I stayed in a Holiday Inn Express last night.'”

While answering phones backstage, he ultimately got his break.

“I stumbled into it,” Bailey said. “I accidentally ended up on stage. I was telling a story in the green room. … I wasn’t a comedian yet, but I had an audience by the time I was done with the story because a bunch of comics were listening. So, they all thought I was a comedian and a guy offered me a spot on his show that Saturday and I took it.”

He’ll never forget the adrenaline rush of getting his first laugh.

“That’s what I wanted to do pretty much the instant I got my first laugh,” Bailey said. “The first thing I ever said on stage, I got a laugh and I was like, ‘This is it, this is what I’m going to do.’ … I said, ‘I was nervous coming up here but I remembered from ‘The Brady Bunch’ to picture everyone in their underwear’ and I said to this big heavy guy, ‘You look great in those panties.'”

Six months later, he moved back to New York City to work the stand-up scene.

“I moved back to New York and I just relentlessly pursued stand-up for about 11 years,” Bailey said. “At that point, I was a weekend regular at all of the clubs in New York. That’s how I was making my living, bouncing around doing 10 to 12 shows in the night, trying to get by on the money the clubs in the city paid, which was not much. Then ‘Cash Cab’ came along.”

Turns out, the producers of Britain’s “Cash Cab” wanted to create a U.S. version of the game show, which quizzes unsuspecting taxi passengers on the way to their various destinations.

“I did a lot of auditions, six times,” Bailey said. “We were pretending to [drive], sitting in chairs that were set up like a cab, and they had a couple of people that would sit behind you. It went really well and they brought me back in, then I had to go to taxi school, I had to do a background check. It was a lot of hoops to jump through, it took about six weeks, then finally I got the gig.”

The hit show made him the most famous taxi driver in New York, save for Robert DeNiro.

“[Other cab drivers] would often recognize me,” Bailey said. “They would usually either try to take a picture while they’re driving and I’m like, ‘Wait until we’re stopped!’ or they would complain that people hail them, they pull over, the people look in to see if it’s me and then wave them off like, ‘Go ahead, I don’t want you. I’m looking for the Cash Cab.'”

How did he focus on the road while simultaneously quizzing riders?

“It’s a weird skill set for sure,” Bailey said. “It’s gotten easier as we’ve made more and more episodes of the show, but yeah, it’s almost like a zen thing. I just have to put it all in my head and just let it happen. It’s too much going on to focus on any one thing.”

That includes the special segments of the Red Light Challenge, Shout Outs and Video Bonus.

“Those are all pretty tricky for me,” Bailey said. “The Red Light Challenge is tough because everybody’s calling answers out. You gotta make sure we hear them all and give them credit when it’s due. The whole job is very difficult. It’s fun, but it’s not easy.”

The show originally aired from 2005-2012 on the Discovery Channel, where it was revived from 2017 to present. You can also now watch it on the DiscoveryGo streaming app.

“We made new ones last year and the year before, and nothing solid yet, but it looks like we’ll be making some new ones this year too,” Bailey said.

The show earned him three Emmys for hosting and three more for Outstanding Game Show.

“I have a collection,” Bailey said. “We’re gonna mount one as a hood ornament on the cab!”

It also lead to a guest cameo on “30 Rock” across Tracy Morgan.

“It was just the two of us,” Bailey said. “I’d known him for years, but it was super fun doing that episode. It was hilarious, he’s like ‘Slumdog Millionaire,’ he just happens to know everything from personal experience. They did a great job of writing that, I think Tina Fey wrote it.”

He’s since starred in two specials for Comedy Central, while his “Road Rage and Accidental Ornithology” is now streaming on Netflix. He also produces his own original content on his YouTube channel, including the spoof comedy “Badly Written Action Man.”

“It’s about a movie action star, but his lines are really terribly written,” Bailey said. “So they’re not these quick, concise one-liners, they’re a bit wordy and confusing. [Instead of ‘I’ll be back’] it’s like, ‘Maybe I’ll come around here another time later.’ I liked the idea so much I decided to just produce it myself, so I did and it’s out there for viewing pleasure.”

Until then, check out the well-written comedy man this weekend at the DC Comedy Loft.

“Everybody needs to laugh,” Bailey said. “Come out and I promise I’ll make you laugh until you forget about the things in your life that suck.”

Learn more on the DC Comedy Loft website. Listen to our full conversation with Ben Bailey below:

WTOP's Jason Fraley previews Ben Bailey at DC Comedy Loft (Jason Fraley)
WTOP's Jason Fraley chats with Ben Bailey (Full Interview) (Jason Fraley)

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