Ben Bailey rolls through City Winery
Question: Who’s the biggest game show nut around this motherfucker?
Question: Who will whip your stupid asses anytime there is a competition with tough questions?
Answer: me again.
For real, dawg. I will tear that ass up. Whether in Jeopardy or in some arcane Game Show Network oddity.
But for all my quiz enthusiasm, there aren’t many programs in this category that I find both challenging and entertaining. Ever since Jimmy Kimmel found much better things to do than hang out with Ben Stein, nothing has put Trebek’s top spot in real jeopardy. With one standout exception…
Cash Cab upped the ante from the first time that comedian Ben Bailey rolled down Broadway in Manhattan back in 2005. Between the clever questions, the way you get to meet contestants in a deeper way than happens in those corny 15-second intros on the Wheel, and of course the charismatic host, the show took off and drove for seven seasons.
Now, after a five-year hiatus, Cash Cab has returned to the Discovery Channel. With Bailey hitting City Winery in Boston for a stand-up show this week (yes, we’re told there will be Cash Cabernet involved), I asked my favorite TV quiz driver everything I have always wanted to know about his amazingly odd triple career as a comic, host, and chauffeur.
What was the original casting like for Cash Cab?
They auditioned a ton of people in LA, San Francisco, Chicago, New York—over 2,000 people. I didn’t expect to get a callback, but it did go really well. Something just clicked in that audition, so I thought maybe there was a shot, because we were just laughing the whole time I was in there. Sure enough I got the callback, and then I went back and did it again. I did that again four more times, so six times I went, and then they were like, “We want you to host the show, we just want you to go and do this background check and pass the test and get an actual taxi license.” They were keeping other possibilities open just in case I didn’t pass one of the standards or something.
How long did it take for you to get acquainted with the whole driving-while-hosting-a-TV-show thing?
I was pretty familiar with New York City already. I had driven around there a lot; I had been a limo driver. I’ve been driving to make my living since I was able to drive, delivering whatever—pizza, flowers, prescriptions, sandwiches, people.
Can you write jokes while you’re driving? Is it a good job for a comic?
Yeah, it is. I like driving. You’re working for somebody, but you’re out there on your own.
How has traffic changed? Does technology come into play? Or does none of that really matter since you’re filming a television show?
Yeah, we don’t really mess with Waze or anything—just the old-fashioned way. Traffic’s pretty terrible, though.
How does that affect the rhythm of the show?
We’ve actually kind of figured out a way to work around it. We start at a particular time of day, and we have a few spots where we start. We’ve gotten pretty strategic. We don’t play the game while we’re sitting in traffic, so we just kind of sit there and chat. It can take two hours to go 20 blocks.
Yes, these are the things that we wonder about at home. Did you have an inkling that there was going to be a comeback? Where did everything leave off last time that you did the show?
People were clamoring for us to make it again since we cancelled it, and I don’t know—it was as much of a surprise to me as it was to anyone else that just all of a sudden the network was like, We’re going to make it again.
What was the first creative thing that you wanted to do after the first stint of “Cash Cab” ended?
I always wanted to do more acting—I love acting. I was planning to be a filmmaker, but I got into stand-up comedy, which then led to Cash Cab instead. I’m not trying to get myself back on that track, but I’m happy to be hosting, I’m happy to be doing stand-up.
Is your act different when you’re touring pegged to Cash Cab?
I talk about weird things regardless. I’ll talk a little about Cash Cab, maybe do a Red Light Challenge.
What are some of the questions you get asked the most about the show? How do you avoid crashing the car?
Have you ever crashed the cab? Have you ever been robbed in the cab? What’s the weirdest thing that ever happened? Did anyone ever throw up in the cab? I get that last one often.
Has it happened?
It has never happened. Thank goodness.
I’m sure that you have been asked this a million times, but how conscious are you and the producers about making sure that the Cash Cab doesn’t discriminate against certain types of riders?
We’re pretty conscious.
You kind of fit into the same conversation with Sacha Baron Cohen, like, How fucking long can this go on for without everybody knowing who they are? Do you get away with it because the passengers are looking at the back of your head when they get in?
Sometimes people know, but the biggest thing we have on our side now is that people didn’t know that we’re doing the show again. They weren’t expecting it.
BEN BAILEY W/ JIM MCCUE AT CITY WINERY. FRI 8.31. CITYWINERY.COM