The star of TV’s Cash Cab visits Chicago’s Up Comedy Club May 9-10

By Trent Modglin

No doubt you’ve seen the show. Unsuspecting people hail a taxi in New York City, and as they hop in, lights suddenly flash on the ceiling of the cab as the smiling driver, Ben Bailey, turns around to congratulate them and announce that they’re part of a game show in which they get to answer trivia questions for cash prizes during the drive to their desired location.

Cash Cab, though canceled by the Discovery Channel in 2012 after a seven-year run, continues its life through syndication, and Bailey, who has performed on The Tonight Show and in his own special on Comedy Central, continues his busy life as a world-traveled comedian and actor.

Bailey, who visits Chicago’s Up Comedy Club May 10-11, chatted with The Real Chicago recently to discuss his worst gigs ever, awful drivers and the difference between Chicago and New York.

For ticket information, visit www.UpComedyClub.com or www.TheRealBenBailey.com

Q: I have to tell you, my wife and her friend love Cash Cab. I’m always interested in the trivia, but they get excited about the people’s reactions when the lights go off on the ceiling.

A: You know, I had a really great time doing it. There’s a lot going on with that show, a lot to do and to remember. I’ve always been driving for a living. That part was second nature. But things will happen on the road or in the show that caused me to pull over sometimes. Especially in a city like New York.

Q: I imagine it’s hard to concentrate with some of the bad drivers out there.

A: It is insane. Awful drivers. Oblivious is the word I’d use. They’re e-mailing or texting or iChatting. You just assume they’re drunk. Instead, you get up next to them and realize, nope, they’re typing. Or maybe watching a movie while they drive.

Q: What’s the most annoying aspect of your average city driver?

A: That’s a tough question. Probably not paying attention to what they’re doing. They’ll ride right up on you and just sit there. Mindlessness. Everywhere. They get up and sit right on you. “What are you going so slow for?” “Well, maybe it’s because you came up on me going 90 when I was going 40. Ever think of that?”

Q: It was funny, earlier this week I was on vacation in the Cayman Islands, and what comes on TV when we got back to our hotel at 1 a.m.? Cash Cab. I had to tell my friends that I was interviewing you in a few days.

A: Ha, that’s funny. I’m sure they were impressed. I’ll bet you turned that shit off after five minutes (laughs).

Q: No, it was longer than that I swear. We watched it for a bit.

A: … It would be cool to open a bank account in the Caymans. But just only have to put 40 bucks in it. Then tell everyone about your Caymans account, but no one would have to know (how much is in it). That would be great.

Q: (Laughing) Yes, I guess it would. … You’ve had some odd jobs while making a name for yourself on the comedy circuit. Tell me about your days as a limo driver when you were just starting out.

A: I definitely did some of that. I remember one time there was this older couple on their way to a Harvard benefit dinner, and we started talking on the way into the city and they found out I was a comedian and that I had a show that night. And they said screw the dinner and came with me that night (laughs). They made me stop so they could go into a deli so they could get a six-pack and could party in the car before my show. Then I took them to the dinner afterward. It was just funny to see this mid-to-late 60s couple blow off their stuffy Harvard dinner to come see my show. … They had a good time that night. They went to their thing afterward and told everybody the story. They were pretty funny and were still partying, and I had to take them to get more booze on the way home after all of that. Maybe he was an alcoholic (laughs), but they sure had a good night.

Q: Can you describe the life of a comedian? What is it like out there on the road, especially now that you’re established?  

A: First of all, it’s really fun. It’s a great way to make living, and I feel really lucky that I get to make money this way. You’re in a different town every week. And there’s always nice people to greet you and take care of you. It’s great. Really an awesome way to spend my life because you get to meet all kinds of cool people from all over the place, and everyone is really nice.

Q: Are they treating you a lot nicer now that you’re at the level you’re at, or has it always been that way?

A: No, it’s different now. Nobody used to give a shit about me at all (laughs).

Q: So I’m guessing you didn’t have someone waiting for you at the airport in Omaha back in 2002?

A: No, I sure didn’t. I had to get myself everywhere, and then when I’d get there, they’d be like (in bored voice), “Oh, hey.” Now they pick me up and they’re (in an excited voice) “Hey, Mr. Bailey.” It’s very different now with the car service and the nice dinners and nice hotels, but the other side of it is that I’m away from home a lot. And when all the shows are all done, it’s 1 or 2 a.m., and I’m in a hotel room somewhere — even if it’s a nice hotel room — and it’s kinda like, you know, it would be nice to be home. So there’s a little bit of a lonely road shock, I think, for everyone and at every level. Unless you’ve got a private jet and you can fly home whenever you want. … It’s great and it is glamorous, but there is that other side to it where you’re away from home a lot.

Q: Every comedian has a good story about the worst club they played or a rough crowd. Got one you’d like to share? Or one you can share?

A: Sure, the first one that comes to mind is when I once got this call on a Saturday afternoon. It pays $300, and it’s in the Poconos, which is like a three-and-a-half-hour drive from where I was living at the time. Which basically meant I had to get in the car right then and go. Someone had canceled, and it was a last-minute thing. And I was trying to get in with this (booking agent) and didn’t want to turn down the first thing they offered me, so I said sure. So I get up to the Poconos and I walk into the room, and there’s about 500 people in there, and all of them are either eight years old or younger or 70 years old or older. And I’m a New York City nightclub act — I don’t have anything I can say to these people. I’m running through my material in my head, and I don’t have a damn joke I can do with this crowd. I can’t even remember what I said (on stage), but it was awful.

Q: Was it a grandparent-grandkid retreat or something?

A: I don’t know how it ended up like that. I think it was a thing where they hired the same guy every year, or a couple of guys had done it a lot (previously). Maybe a clown. I don’t know who could have done the gig. Maybe a guy with puppets or I don’t know what. I just know I was screwed as soon as I walked through the door.

… I can’t even begin to tell you about what I was talking about up there, and then this guy stands up, this old guy, and goes (in an old man’s voice), “I’ve been coming up here for 30 years for this thing, and you are the worst performer I have ever seen!” And I said, “Well thank you very much, sir, that I just spent three and a half hours driving up here so you could tell me that.” What a nightmare (laughs). A rough gig. It was the really only bad gig I ever had where I was filling in for someone like that. The only really nightmarish gig where I ended up in a situation that was not right and I shouldn’t have been there at all. I’m sure everyone has had a gig like that where they walk in and ask, “Oh jeez, what the f—k am I doing here?”

… I’ve done a show where I had to climb on a bar, or a few without microphones or speakers. One time I had a room with like 300 people in it, and they didn’t think I would need a microphone. It was like this little amphitheater, so I figured if I spaced myself away from the crowd and talked into the back, bottom center of the big curved amphitheater, everyone could here me OK. So I did my show seated, facing the back wall so the people behind me could hear me. They were basically like, “If you don’t do the show, we can’t pay you,” so I went and found a good place to get an echo in the back and just sat there and talked to the crowd so I didn’t have to yell the whole time (laughs). That was at a college in upstate New York somewhere.

Q: So going back to your single days, do you believe the old adage where women say they’ll take a sense of humor over looks or money?

A: Yeah, I would look back more to when I was growing up (to notice women) appreciating a sense of humor. Not all of them, but it feels good to laugh, you know? Few things feel better than a real good laugh. … It definitely depends on the woman, but there’s something to it.

Q: What you like best about Chicago when you play here?

A: The crowds are always great in Chicago. I’ve never had a show where the crowd wasn’t really into it. And that’s enough all by itself. I love city, too. I don’t know it all that well, but when I’m roaming around I always enjoy it. The architecture is phenomenal, and the history — I learn a little bit more each time I go. It’s just a great city. A lot of great food, cool things to see and great crowds.

Q: I know you’re a New York guy, so I’m curious how you’d compare the two cities.

A: A lot of big cities feel pretty much the same, but New York and Chicago definitely have their own vibe. It’s interesting to me that I can get downtown (Chicago) without going through a tunnel or over a bridge. Chicago, I think it’s the people. That Midwestern mentality is different than the East Coast. New York moves at a slightly quicker pace. In Chicago, there’s always a lot of people out doing things, but it’s not quite at the insane rate New York is. And I kind a like it for that because you still have everything, it’s just not so frantic. Love the elevated trains too. They’re cool.

Q: Can you share any secrets about your upcoming show? A little preview, if you will?

A: I won’t give you a preview, but I will say that it’s completely new. My next (TV) special is in the works, and the set is very close to ready. It’s a brand-new set that I’m really enjoying doing right now. It’s a good time to come see me if people are thinking about it (laughs). Right now, I’m kind of on the cusp. The last few weeks, it’s all come together really well.

Q: What is the easiest target in comedy? The easy target in society, or the consistent thing that can always get a laugh or finish a show on a high note?

A: There are always go-to things, but as far as a big closer, my writing is all over the place. I don’t work on anything topical. I just close with whatever I love most at that time. … I tend to do a lot more improv lately because I’m trying to expand on stuff I’ve got. … Whatever comes to me as a good bit, it sticks, and that’s what I end up with. I do have a balls bit that I go to sometimes.

Q: I would imagine if you do a little improv and it’s a hit, the next week you could easily filter it into your show.

A: Yeah, I’m always looking for fodder. I do my best writing on stage. I’ll just delve into idea or something that comes up and play with it. I go into the crowd a little bit. I used to really only go into the crowd if I had to, like if they weren’t listening or were distracted or whatever. But now I like it. I go in and just play with answers they give me and end up getting some good inspiration that way. And spontaneity is tough to compete with.

Q: Agreed. Messing with that audience member who deserves it can be a beautiful thing.

A: Oh yeah. I tend to get a little carried away with that sometimes. Only for my own taste. Usually people say that was their favorite part of the whole show, but I feel bad if I really reamed the guy.