WEBVTT 00:00:00.000 --> 00:00:02.359 All right, welcome back to the Deep Dive. You 00:00:02.359 --> 00:00:04.019 know the drill, we take a huge pile of info, 00:00:04.160 --> 00:00:07.040 something really fascinating, and basically boil 00:00:07.040 --> 00:00:09.759 it down for you. Concentrated knowledge, no overload. 00:00:10.060 --> 00:00:12.900 And today, yeah, we're tackling a career that's, 00:00:12.900 --> 00:00:15.439 well, pretty unique in TV. We're going to get 00:00:15.439 --> 00:00:17.760 into the cab, metaphorically speaking, and take 00:00:17.760 --> 00:00:21.839 a deep dive into the dual life of Benjamin Ray 00:00:21.839 --> 00:00:24.059 Bailey. Ben Bailey. Yeah, when you picture a 00:00:24.059 --> 00:00:25.940 New York City taxi, you know, the yellow cab, 00:00:26.039 --> 00:00:28.420 it's usually anonymous, right? Just part of the 00:00:28.420 --> 00:00:30.820 background. A space where people kind of share 00:00:30.820 --> 00:00:33.200 random bits of their lives. Maybe they're late, 00:00:33.280 --> 00:00:36.719 stressed out, whatever. But for some folks, if 00:00:36.719 --> 00:00:39.960 they happen to flag down his cab, well, that 00:00:39.960 --> 00:00:43.579 anonymity just vanished. Poof. Gone. Suddenly 00:00:43.579 --> 00:00:45.659 there are cameras, flashing lights, trivia question. 00:00:45.659 --> 00:00:47.340 That speaks. Right in the back there. Exactly. 00:00:48.380 --> 00:00:50.460 Our sources today, they really help map out this 00:00:50.460 --> 00:00:53.219 incredible path he took. Our mission really is 00:00:53.219 --> 00:00:55.740 to understand how a guy who was, and this is 00:00:55.740 --> 00:01:00.460 key, a licensed, actual New York City taxi driver. 00:01:00.719 --> 00:01:03.380 Managed to become a three -time Emmy -winning 00:01:03.380 --> 00:01:07.019 game show host, a touring stand -up comic, and 00:01:07.019 --> 00:01:09.640 even pop up in serious acting roles. It's about 00:01:09.640 --> 00:01:12.439 figuring out that range, you know, and how he 00:01:12.439 --> 00:01:14.780 made it last. Okay, so let's lay out the basics 00:01:14.780 --> 00:01:18.209 first. Ben Bailey, born 1970. He's an American 00:01:18.209 --> 00:01:21.590 comedian, actor, and, yeah, most famously, the 00:01:21.590 --> 00:01:23.829 host and executive producer of Cash Cab, the 00:01:23.829 --> 00:01:26.290 U .S. version. Been active since 93, roughly. 00:01:26.549 --> 00:01:29.629 Yeah, 93. And he's constantly juggling things. 00:01:29.790 --> 00:01:32.310 He's a proper touring stand -up headliner, which, 00:01:32.430 --> 00:01:34.329 I mean, that's a demanding job on its own. Oh, 00:01:34.390 --> 00:01:37.709 absolutely. Grueling. And at the same time, he's 00:01:37.709 --> 00:01:40.359 hosting this massive TV hit, Cash Cab. Which 00:01:40.359 --> 00:01:42.719 ran for, what was it, 14 seasons? Mm -hmm. Over 00:01:42.719 --> 00:01:44.700 a long stretch. It's that combination that's 00:01:44.700 --> 00:01:46.319 just fascinating. Think about stand -up comedy. 00:01:46.459 --> 00:01:48.319 What do you need? You need, like, razor -sharp 00:01:48.319 --> 00:01:50.939 observation skills. And timing. Split -second 00:01:50.939 --> 00:01:52.599 timing. So where do you practice that in the 00:01:52.599 --> 00:01:55.819 real world? Driving a cab in New York City. Exactly. 00:01:56.040 --> 00:01:59.140 High pressure. Hundreds of different people every 00:01:59.140 --> 00:02:02.659 week. It's like a lab. He took that raw experience. 00:02:03.790 --> 00:02:05.590 You know, the hustle, the quick wit you need 00:02:05.590 --> 00:02:07.670 just to deal with passengers, the weird intimacy 00:02:07.670 --> 00:02:10.969 of being in a cab. Right. And he fused it into 00:02:10.969 --> 00:02:14.669 this completely new, really authentic TV format. 00:02:15.069 --> 00:02:18.449 And it worked big time. So we got to trace how 00:02:18.449 --> 00:02:20.949 he got there starting way before the cab. OK, 00:02:21.030 --> 00:02:23.129 let's unpack that journey, because his early 00:02:23.129 --> 00:02:25.469 life where he grew up and started out, it's kind 00:02:25.469 --> 00:02:27.560 of all over the map. geographically speaking. 00:02:27.719 --> 00:02:31.120 It is, yeah. So, Benjamin Ray Bailey, born October 00:02:31.120 --> 00:02:35.159 30, 1970, but not on the East Coast, down South. 00:02:35.629 --> 00:02:37.669 Bowling Green, Kentucky. Kentucky. Okay. Didn't 00:02:37.669 --> 00:02:39.789 expect that. Nope. But he didn't stay long. He 00:02:39.789 --> 00:02:41.930 was raised up north in Chatham Borough, New Jersey. 00:02:42.090 --> 00:02:44.069 Ah, New Jersey. That makes more sense maybe for 00:02:44.069 --> 00:02:46.210 the observational comedy style later. That whole 00:02:46.210 --> 00:02:48.590 NYNJ vibe. Definitely. It gives you material, 00:02:48.689 --> 00:02:50.689 right? He graduated from Chatham Borough High 00:02:50.689 --> 00:02:52.729 School in 88. And here's a little fun fact. He 00:02:52.729 --> 00:02:54.969 was in the borough's last graduating class before 00:02:54.969 --> 00:02:57.479 they reorganized the schools. Hmm. After high 00:02:57.479 --> 00:03:00.180 school, he went south again, briefly. Attended 00:03:00.180 --> 00:03:02.560 Old Dominion University down in Norfolk, Virginia. 00:03:02.780 --> 00:03:05.419 Virginia, okay. But the big move, the one that 00:03:05.419 --> 00:03:07.639 kind of kicked off his entertainment career officially, 00:03:07.860 --> 00:03:13.240 was in 1993. He heads west. Los Angeles. The 00:03:13.240 --> 00:03:16.199 classic go west story for performers. Pretty 00:03:16.199 --> 00:03:18.259 much. That's the year our sources point to as 00:03:18.259 --> 00:03:20.560 the start of his active career. And this is where 00:03:20.560 --> 00:03:23.159 that almost legendary stand up origin story comes 00:03:23.159 --> 00:03:25.300 in. Right. It wasn't like he was grinding at 00:03:25.300 --> 00:03:28.280 open mics for months. Not exactly. No. The story 00:03:28.280 --> 00:03:31.659 goes he was just hanging out after hours at the 00:03:31.659 --> 00:03:34.319 comedy store in L .A. Which is like hallowed 00:03:34.319 --> 00:03:37.159 ground for comedians. Totally. A real institution. 00:03:37.219 --> 00:03:39.240 And he wasn't even there to perform apparently. 00:03:40.409 --> 00:03:42.270 Shooting the breeze. Yeah, basically just telling 00:03:42.270 --> 00:03:44.370 stories, probably about his day, observations, 00:03:44.710 --> 00:03:46.310 whatever, to the other comics who were done with 00:03:46.310 --> 00:03:48.610 their sets, just relaxing. Okay. But his way 00:03:48.610 --> 00:03:50.590 of telling these stories, his natural timing, 00:03:50.770 --> 00:03:53.949 the humor he found in everyday stuff, it caught 00:03:53.949 --> 00:03:57.030 the ear of Skippy Lowe. Skippy Lowe, the MSC 00:03:57.030 --> 00:03:59.780 there. A pretty well -known figure. A very notable 00:03:59.780 --> 00:04:03.460 figure, yeah. And Lowe heard him just talking, 00:04:03.560 --> 00:04:05.219 telling these anecdotes, and basically thought, 00:04:05.280 --> 00:04:07.580 this guy's naturally funny. He's got stage presence 00:04:07.580 --> 00:04:10.580 without even being on stage. Wow. So Lowe basically 00:04:10.580 --> 00:04:12.900 just offered him a spot, said, hey, you should 00:04:12.900 --> 00:04:15.250 get up there and do a proper set. That's incredible. 00:04:15.389 --> 00:04:19.389 Like zero formal audition, just pure raw talent 00:04:19.389 --> 00:04:22.290 being spotted in conversation. It's a great story. 00:04:22.370 --> 00:04:24.850 It shows that his comedic voice was already there, 00:04:24.970 --> 00:04:27.089 you know, before he even maybe thought of himself 00:04:27.089 --> 00:04:29.709 as a professional comic. So he gets this break 00:04:29.709 --> 00:04:33.360 in L .A. But he doesn't stay. Nope. Eventually, 00:04:33.360 --> 00:04:36.720 he heads back east to New York City. And that's 00:04:36.720 --> 00:04:38.220 where he really starts to build his reputation, 00:04:38.360 --> 00:04:40.560 starts getting popular in the comedy clubs there. 00:04:40.759 --> 00:04:42.839 Which is a whole different beast. The New York 00:04:42.839 --> 00:04:45.939 scene is notoriously tough. Oh, yeah. Super competitive, 00:04:46.160 --> 00:04:49.339 fast -paced. You've got to be sharp, constantly 00:04:49.339 --> 00:04:52.199 writing, constantly evolving. And his style. 00:04:52.670 --> 00:04:55.790 You said observational. Yeah. Our sources consistently 00:04:55.790 --> 00:04:58.529 label it observational comedy and satire. He 00:04:58.529 --> 00:05:00.889 talks about everyday stuff, you know, marriage, 00:05:01.290 --> 00:05:04.410 poking fun at himself, life's little annoyances, 00:05:04.410 --> 00:05:07.829 pop culture, things everyone can kind of relate 00:05:07.829 --> 00:05:10.850 to. Makes sense. That kind of humor plays really 00:05:10.850 --> 00:05:12.930 well in those dense urban environments like New 00:05:12.930 --> 00:05:15.540 York. Totally. If you can get a New York crowd 00:05:15.540 --> 00:05:18.680 laughing about like the subway or dating apps, 00:05:18.779 --> 00:05:20.519 you're doing something right. And clearly he 00:05:20.519 --> 00:05:22.699 was because he didn't just stay a club comic. 00:05:22.800 --> 00:05:25.860 He became a headliner. A touring headliner. Yeah. 00:05:26.079 --> 00:05:29.600 By 2019, he'd reached that status, playing major 00:05:29.600 --> 00:05:32.040 festivals like Just for Laughs in Montreal, which 00:05:32.040 --> 00:05:35.240 is huge. Wow. And even the Edinburgh Fringe Festival 00:05:35.240 --> 00:05:37.839 over in Scotland. Big international stages. So 00:05:37.839 --> 00:05:40.180 the takeaway here is he was a legit, established 00:05:40.180 --> 00:05:43.199 professional stand -up long before Cash Cab ever 00:05:43.199 --> 00:05:45.860 hit the airwaves. Absolutely crucial point. That 00:05:45.860 --> 00:05:48.060 TV fame didn't come out of nowhere. He had years 00:05:48.060 --> 00:05:51.060 of stage time under his belt. His first big special, 00:05:51.240 --> 00:05:53.180 Comedy Central Presents Ben Bailey, that came 00:05:53.180 --> 00:05:55.800 out in 2006. Right around when Cash Cab was starting 00:05:55.800 --> 00:05:59.160 to take off. Exactly. So he wasn't some TV personality 00:05:59.160 --> 00:06:02.279 trying comedy. He was a comedian who found this 00:06:02.279 --> 00:06:06.480 amazing TV gig. And he used that TV fame to boost 00:06:06.480 --> 00:06:08.920 his stand -up career, naturally. He put out more 00:06:08.920 --> 00:06:11.920 specials after that. Oh, yeah. In 2011, he released 00:06:11.920 --> 00:06:14.779 a two -parter. The titles kind of tell you his 00:06:14.779 --> 00:06:17.680 focus. Road Rage and Accidental Ornithology. 00:06:17.959 --> 00:06:20.720 Road Rage. I can see the connection to the cab 00:06:20.720 --> 00:06:22.959 driving. Accidental ornithology. Yeah, it's just 00:06:22.959 --> 00:06:26.339 that thing of like noticing weird, specific, 00:06:26.579 --> 00:06:29.420 funny details in the middle of everyday chaos. 00:06:29.660 --> 00:06:32.100 You know, the accidental discoveries. Classic 00:06:32.100 --> 00:06:34.379 observational stuff. Gotcha. Then there was Ben 00:06:34.379 --> 00:06:37.000 Bailey live and uncensored in 2016. Right. And 00:06:37.000 --> 00:06:40.540 he's kept at it. Just this year, 2024, he put 00:06:40.540 --> 00:06:42.540 out a new special, Please Tell Me What I Said, 00:06:42.660 --> 00:06:44.779 directly onto his YouTube channel. So using modern 00:06:44.779 --> 00:06:47.839 platforms too. Adapting. Yeah, it proves stand 00:06:47.839 --> 00:06:50.430 -up wasn't just... a phase or a way to get noticed. 00:06:50.529 --> 00:06:52.230 It's like the core of what he does. It's his 00:06:52.230 --> 00:06:54.750 foundation. And that foundation, that quick wit 00:06:54.750 --> 00:06:57.370 honed on stage, led straight into the role that, 00:06:57.449 --> 00:06:59.350 let's be honest, most people know him for. Yeah. 00:06:59.410 --> 00:07:02.149 The defining one. Absolutely. Cash Tab. He is 00:07:02.149 --> 00:07:05.470 the face of the American version. Host, executive 00:07:05.470 --> 00:07:08.610 producer, the whole package. Such a simple concept 00:07:08.610 --> 00:07:10.470 when you think about it, but brilliant. Totally. 00:07:10.629 --> 00:07:14.889 A game show inside a moving taxi in New York 00:07:14.889 --> 00:07:18.959 City. He drives. He asks questions. Unsuspecting 00:07:18.959 --> 00:07:20.939 passengers try to win money before they reach 00:07:20.939 --> 00:07:23.360 their destination. Mostly aired on Discovery, 00:07:23.740 --> 00:07:26.019 some on Bravo, too. And it wasn't just a flash 00:07:26.019 --> 00:07:29.139 in the pan. That show had serious legs. Incredible 00:07:29.139 --> 00:07:33.389 longevity. The first run. 2005 to 2012. Seven 00:07:33.389 --> 00:07:36.250 solid years. That's huge for any show, especially 00:07:36.250 --> 00:07:38.629 a cable concept like that. And even then, it 00:07:38.629 --> 00:07:40.589 wasn't really over. Nope. It got brought back, 00:07:40.769 --> 00:07:43.370 successfully revived from 2017 right through 00:07:43.370 --> 00:07:45.970 2020. And Bailey hosted the whole time, all 14 00:07:45.970 --> 00:07:48.189 seasons of that main run. Every single one. He 00:07:48.189 --> 00:07:50.209 was the show. Indispensable. There was that short 00:07:50.209 --> 00:07:52.129 spinoff too, wasn't there? Cash Cap After Dark? 00:07:52.170 --> 00:07:55.670 Yeah, briefly. Back in 2007, 13 episodes. Didn't 00:07:55.670 --> 00:07:57.470 quite stick like the main show, but it showed 00:07:57.470 --> 00:07:59.980 they were trying variations early on. But the 00:07:59.980 --> 00:08:02.540 main show's resilient surviving network changes. 00:08:02.639 --> 00:08:05.959 Yeah. That long break, the shifting TV landscape. 00:08:06.060 --> 00:08:09.040 It really speaks to how strong that core idea 00:08:09.040 --> 00:08:12.620 was. Yeah. And his hosting. Absolutely. Which 00:08:12.620 --> 00:08:15.240 brings us to maybe the most critical detail in 00:08:15.240 --> 00:08:18.100 this whole story. The so what that elevates it. 00:08:18.199 --> 00:08:20.800 Ben Bailey isn't just playing a cab driver. He 00:08:20.800 --> 00:08:23.899 is a licensed New York City taxi driver. Like, 00:08:23.899 --> 00:08:26.540 for real. Has the medallion license and everything. 00:08:26.800 --> 00:08:28.819 That is monumental. Like you said, it changes 00:08:28.819 --> 00:08:30.800 everything. Fundamentally, he's not an actor 00:08:30.800 --> 00:08:33.519 pretending. He's part of the city's actual infrastructure. 00:08:33.919 --> 00:08:36.200 Yeah. Imagine the authenticity that gives the 00:08:36.200 --> 00:08:38.100 show. Yeah, for the viewers, but also for the 00:08:38.100 --> 00:08:41.190 contestants. They get in a real cab. Driven by 00:08:41.190 --> 00:08:43.389 a real cabbie who suddenly turns into a game 00:08:43.389 --> 00:08:45.250 show host. Exactly. And think about the skills 00:08:45.250 --> 00:08:47.710 involved. He's genuinely navigating New York 00:08:47.710 --> 00:08:50.250 traffic, which is insane, while simultaneously 00:08:50.250 --> 00:08:52.690 running a game show, managing the clock, the 00:08:52.690 --> 00:08:55.690 questions, the contestants' reactions. That real 00:08:55.690 --> 00:08:58.450 -world competence, the driving skill, combined 00:08:58.450 --> 00:09:00.769 with the comedic timing, you can't fake that. 00:09:00.850 --> 00:09:04.529 It made the whole thing feel so immediate, visceral. 00:09:04.690 --> 00:09:07.250 It grounds it completely. He's not just reading 00:09:07.250 --> 00:09:09.269 questions in the studio. He's doing two high 00:09:09.269 --> 00:09:11.409 -pressure jobs at once. And that authenticity, 00:09:11.549 --> 00:09:14.570 that unique blend of skills and format, it turned 00:09:14.570 --> 00:09:17.429 Cash Cab into an awards magnet, especially at 00:09:17.429 --> 00:09:19.269 the daytime Emmys. They were nominated a lot, 00:09:19.330 --> 00:09:21.669 weren't they? A ridiculous amount. Bailey himself, 00:09:21.889 --> 00:09:24.330 for Outstanding Game Show Host, nominated seven 00:09:24.330 --> 00:09:27.110 times consecutively. Seven years in a row. Wow. 00:09:27.289 --> 00:09:31.850 Every single year from 2007 through 2013. Think 00:09:31.850 --> 00:09:34.590 about the legends in that category. He was consistently 00:09:34.590 --> 00:09:37.009 right there with them year after year. That's 00:09:37.009 --> 00:09:39.230 incredible dominance for such an unconventional 00:09:39.230 --> 00:09:41.710 show. And he didn't just get nominated. He won 00:09:41.710 --> 00:09:44.809 three times. He took home the Emmy for Outstanding 00:09:44.809 --> 00:09:48.190 Game Show Host in 2010, 2011, and again in 2013. 00:09:48.429 --> 00:09:51.679 Three Emmys for hosting. That's serious validation 00:09:51.679 --> 00:09:54.399 from the industry. They clearly recognize that 00:09:54.399 --> 00:09:57.019 his style, that fast grounded in the moment style, 00:09:57.259 --> 00:09:59.620 was something special. Totally different from, 00:09:59.679 --> 00:10:02.500 say, the polished studio hosts. He wasn't behind 00:10:02.500 --> 00:10:05.000 a podium. He was right there, inches away, driving 00:10:05.000 --> 00:10:07.159 the car, sharing the space. It was intimate, 00:10:07.279 --> 00:10:10.740 spontaneous, kind of chaotic sometimes. And the 00:10:10.740 --> 00:10:13.549 show itself got major love, too. Cash Cab won 00:10:13.549 --> 00:10:15.789 the Emmy for best game show three years, running 00:10:15.789 --> 00:10:19.710 2008, 2009, 2010. Three best game show Emmys. 00:10:19.830 --> 00:10:23.529 Yep. And in 2010, it also won most outstanding 00:10:23.529 --> 00:10:26.029 game audience participation show. Okay, so putting 00:10:26.029 --> 00:10:28.230 it all together, this wasn't just some quirky 00:10:28.230 --> 00:10:30.470 hit or a gimmick that went viral. Not at all. 00:10:30.509 --> 00:10:33.590 The Emmys prove it. Consistent recognition year 00:10:33.590 --> 00:10:36.570 after year for both the host and the show's format. 00:10:36.750 --> 00:10:39.870 It was acknowledged as quality television, a 00:10:39.870 --> 00:10:42.590 genuinely well -executed concept with a uniquely 00:10:42.590 --> 00:10:44.950 skilled host. It cemented his place, really. 00:10:45.049 --> 00:10:47.750 A top -tier game show host, but one who operated 00:10:47.750 --> 00:10:50.190 completely outside the usual studio system. Which 00:10:50.190 --> 00:10:52.350 then begs the question, right? Once you've reached 00:10:52.350 --> 00:10:54.929 that peak, won those awards in such a specific 00:10:54.929 --> 00:10:58.610 niche, how do you translate that success elsewhere? 00:10:58.649 --> 00:11:01.309 Can you break out of the cab? Exactly. That's 00:11:01.309 --> 00:11:03.470 the logical next step. You've got three Emmys. 00:11:03.470 --> 00:11:05.470 You're a household name. Surely other doors open 00:11:05.470 --> 00:11:07.809 up. And they did for Bailey. He definitely branched 00:11:07.809 --> 00:11:09.990 out, tried other hosting gigs. Yeah, he landed 00:11:09.990 --> 00:11:12.789 a big one, actually. Hosted a show on NBC called 00:11:12.789 --> 00:11:14.970 Who's Still Standing. This was around 2011, 2012. 00:11:15.370 --> 00:11:17.769 Oh, I remember that one. Let it trap doors. That's 00:11:17.769 --> 00:11:20.649 the one. High concept. Answer trivia. Get it 00:11:20.649 --> 00:11:22.769 wrong. Boom, you drop through the floor. Visually 00:11:22.769 --> 00:11:25.190 dramatic, for sure. But it didn't last long, 00:11:25.250 --> 00:11:27.750 did it? No, it didn't. And this is really interesting 00:11:27.750 --> 00:11:29.990 for anyone listening, thinking about the TV business. 00:11:30.529 --> 00:11:33.129 Despite having Bailey, an Emmy -winning host, 00:11:33.350 --> 00:11:36.529 despite being on a major network like NBC, the 00:11:36.529 --> 00:11:39.309 show got canceled after just one season. It wasn't 00:11:39.309 --> 00:11:41.090 renewed, and the reason cited in our sources, 00:11:41.389 --> 00:11:45.269 production costs. It was just too expensive to 00:11:45.269 --> 00:11:48.570 make. Ah, those elaborate sets, the mechanics 00:11:48.570 --> 00:11:52.659 for the trap doors, safety. All adds up. Astronomically 00:11:52.659 --> 00:11:55.299 expensive compared to sticking some cameras in 00:11:55.299 --> 00:11:58.139 a taxi you already have access to. It was a harsh 00:11:58.139 --> 00:12:00.759 lesson, really. Even a proven host in a flashy 00:12:00.759 --> 00:12:03.039 concept can't survive if the numbers don't work 00:12:03.039 --> 00:12:05.059 for the network. Your Emmy doesn't automatically 00:12:05.059 --> 00:12:07.659 guarantee a show's survival if the budget's out 00:12:07.659 --> 00:12:10.519 of whack. Good point. So besides hosting, he 00:12:10.519 --> 00:12:12.840 used his voice too, right? Narration. He did. 00:12:12.960 --> 00:12:15.440 He narrated a Discovery Channel show called Smash 00:12:15.440 --> 00:12:18.399 Lab. You know, blowing things up, testing engineering 00:12:18.399 --> 00:12:20.580 limits, kind of fits the Discovery. brand he 00:12:20.580 --> 00:12:22.580 was already associated with. Makes sense. And 00:12:22.580 --> 00:12:24.480 he did some stuff for early online platforms, 00:12:24.580 --> 00:12:27.960 too, like Shovio .com's Talkback TV, exploring 00:12:27.960 --> 00:12:30.179 different avenues. But the acting roles. Yeah. 00:12:30.399 --> 00:12:32.379 That's where you really see the range, I think. 00:12:32.399 --> 00:12:34.259 It's kind of surprising how diverse they are. 00:12:34.360 --> 00:12:36.940 It really is. He pops up in some serious dramas, 00:12:37.019 --> 00:12:40.740 like way back in 2003, before Cash Cab Mania, 00:12:40.740 --> 00:12:43.480 he was on Law & Order, Special Victims Unit. 00:12:43.860 --> 00:12:47.980 SVU. What role? Get this. Transit Sergeant Ambrose. 00:12:48.000 --> 00:12:52.100 A transit cop. So even back then, connected to 00:12:52.100 --> 00:12:55.210 New York City transportation. That's uncanny. 00:12:55.330 --> 00:12:57.769 Isn't it? Sort of foreshadowing his whole public 00:12:57.769 --> 00:13:00.129 image. And he returned to that procedural world 00:13:00.129 --> 00:13:03.289 later. He was on Blue Bloods in 2021 as a character 00:13:03.289 --> 00:13:06.330 named Emmett Fells. Okay. And Unforgettable in 00:13:06.330 --> 00:13:08.710 2016, playing Lorenzo Abrelli. These are often 00:13:08.710 --> 00:13:10.870 quick, sharp roles playing believable, professional 00:13:10.870 --> 00:13:13.049 New Yorker types. But then he flips to comedy, 00:13:13.129 --> 00:13:15.370 too. Totally. He was on Hope and Faith back in 00:13:15.370 --> 00:13:18.549 2004, The Knights of Prosperity in 2007. And 00:13:18.549 --> 00:13:20.710 then The Ultimate Sign, you've made it in pop 00:13:20.710 --> 00:13:23.389 culture, playing yourself. He appeared as Ben 00:13:23.389 --> 00:13:26.470 Bailey driving the cash cab on 30 Rock in 2010. 00:13:26.750 --> 00:13:28.870 Oh, that's brilliant. That's when you know the 00:13:28.870 --> 00:13:31.409 persona is iconic. Absolutely. And maybe the 00:13:31.409 --> 00:13:34.610 most unexpected acting credit, a recurring role 00:13:34.610 --> 00:13:37.870 on a soap opera. A soap opera? Which one? One 00:13:37.870 --> 00:13:40.730 Life to Live. He played a character named Haskell 00:13:40.730 --> 00:13:44.090 for four episodes back in 2005. Wow. From stand 00:13:44.090 --> 00:13:46.889 -up to cab driving to One Life to Live, that's 00:13:46.889 --> 00:13:50.059 flexible. Talk about range, right. He also did 00:13:50.059 --> 00:13:52.299 some film work, appeared in a movie called Bad 00:13:52.299 --> 00:13:55.100 Parents in 2012. Okay. And here's a fun bit of 00:13:55.100 --> 00:13:58.929 trivia. He actually filmed a scene for the 2012 00:13:58.929 --> 00:14:02.309 Spider -Man movie. No way. Yeah, but it got cut 00:14:02.309 --> 00:14:04.049 from the final film. Happens all the time, but 00:14:04.049 --> 00:14:06.690 still cool. He also popped up, uncredited but 00:14:06.690 --> 00:14:09.629 as himself, in the Vince Vaughn movie Delivery 00:14:09.629 --> 00:14:12.490 Man in 2013. So the cash cab identity just kept 00:14:12.490 --> 00:14:15.330 following him, even into scripted stuff. It became 00:14:15.330 --> 00:14:18.570 a shorthand, definitely. Like in 2019, he did 00:14:18.570 --> 00:14:21.330 a proper cameo, again as himself, driving the 00:14:21.330 --> 00:14:24.129 cab, in that show Perpetual Grace, LTD. So other 00:14:24.129 --> 00:14:26.250 shows were literally writing the - cash cab into 00:14:26.250 --> 00:14:28.549 their scripts yeah it shows how enduring that 00:14:28.549 --> 00:14:31.230 brand became he also leaned into the smart guy 00:14:31.230 --> 00:14:33.509 trivia aspect appearing on brain games a couple 00:14:33.509 --> 00:14:36.129 of times and even deadliest catch the bait in 00:14:36.129 --> 00:14:40.350 2016 his persona was just recognizable and fit 00:14:40.350 --> 00:14:42.669 different contexts plus the commercials right 00:14:43.500 --> 00:14:45.419 That's always a sign of mainstream appeal. For 00:14:45.419 --> 00:14:48.639 sure. He did ads for DTE Energy, the utility 00:14:48.639 --> 00:14:52.320 company, and also for ALDI Supermarkets, reaching 00:14:52.320 --> 00:14:54.519 a broad audience. And hitting the talk show circuit 00:14:54.519 --> 00:14:56.919 hard during the peak years. Oh, yeah. All the 00:14:56.919 --> 00:15:00.100 big ones. The Tonight Show, Today Show, Oprah, 00:15:00.539 --> 00:15:03.460 Rachel Ray. He was everywhere for a while. Cemented 00:15:03.460 --> 00:15:06.360 that transition from club comic to national TV 00:15:06.360 --> 00:15:09.200 star. It really takes a specific kind of personality, 00:15:09.480 --> 00:15:12.620 doesn't it? To be believable, doing stand -up, 00:15:12.659 --> 00:15:15.200 driving a cab, hosting a game show, and showing 00:15:15.200 --> 00:15:17.860 up convincingly in Law & Order. Yeah, that grounded, 00:15:17.940 --> 00:15:20.360 quick -witted, but somehow still relatable New 00:15:20.360 --> 00:15:23.200 Yorker thing. It clearly resonated across a lot 00:15:23.200 --> 00:15:24.879 of different formats. He built a lot of trust 00:15:24.879 --> 00:15:27.220 with the audience. So even with all that TV work, 00:15:27.279 --> 00:15:29.860 the hosting, the acting, he never really stopped 00:15:29.860 --> 00:15:31.580 doing stand -up, did he? It seems like that was 00:15:31.580 --> 00:15:33.620 always the constant thread. Absolutely not. It 00:15:33.620 --> 00:15:35.440 was clearly fundamental to him. We mentioned 00:15:35.440 --> 00:15:38.600 the 2006 special, the 2011 two -parter. Road 00:15:38.600 --> 00:15:41.320 Rage and Accidental Ornithology. Those titles 00:15:41.320 --> 00:15:43.639 really capture that observational core, right? 00:15:44.039 --> 00:15:46.460 Road Rage, obviously tapping into the stress 00:15:46.460 --> 00:15:48.539 of driving, something he knew intimately. And 00:15:48.539 --> 00:15:52.000 Accidental Ornithology. That sounds like finding 00:15:52.000 --> 00:15:54.279 the weird, funny little details you notice when 00:15:54.279 --> 00:15:56.379 you're stuck in traffic or just observing life. 00:15:56.840 --> 00:15:59.379 That's his sweet spot. Then came Ben Bailey. 00:15:59.899 --> 00:16:02.899 Live and uncensored in 2016. Yeah. Probably letting 00:16:02.899 --> 00:16:05.539 him talk more about his life after becoming famous. 00:16:05.700 --> 00:16:07.919 Likely, yeah. Addressing the elephant in the 00:16:07.919 --> 00:16:10.600 room, or rather, the cab. But what's really impressive 00:16:10.600 --> 00:16:13.379 recently is how he adapted when things got weird 00:16:13.379 --> 00:16:15.519 for everyone. You mean during the COVID lockdowns? 00:16:15.539 --> 00:16:18.940 Exactly. Live comedy shut down. TV production 00:16:18.940 --> 00:16:21.639 ground to a halt. what does bailey do what did 00:16:21.639 --> 00:16:24.320 he do he creates this completely new show streams 00:16:24.320 --> 00:16:26.639 it directly to youtube called work from home 00:16:26.639 --> 00:16:28.980 okay like a lot of people were doing zoom shows 00:16:28.980 --> 00:16:31.179 right yeah but this sounded pretty diy the sources 00:16:31.179 --> 00:16:33.320 say he filmed it literally in his basement in 00:16:33.320 --> 00:16:36.779 his basement wow totally grassroots and get this 00:16:36.779 --> 00:16:39.960 his girlfriend acted as co -host and producer 00:16:39.960 --> 00:16:43.100 just the two of them making a show from home 00:16:43.470 --> 00:16:45.470 That's fantastic. Talk about resourcefulness. 00:16:45.730 --> 00:16:48.429 It really is. It shows you the core appeal was 00:16:48.429 --> 00:16:51.350 him, his personality, his humor. It didn't need 00:16:51.350 --> 00:16:53.769 the fancy set or the network budget, especially 00:16:53.769 --> 00:16:57.129 not during a crisis. He just found a way to connect. 00:16:57.289 --> 00:17:00.250 Great lesson for anyone listening about adaptability. 00:17:00.610 --> 00:17:03.629 Definitely. And his recent work also shows that 00:17:03.629 --> 00:17:06.730 the cash cab idea itself still has life, even 00:17:06.730 --> 00:17:09.490 outside Manhattan. Right. He did that spinoff 00:17:09.490 --> 00:17:12.380 concept, money grabbing the cab. This was 2022, 00:17:12.819 --> 00:17:16.039 2023. Money grabbing the cab. OK, similar premise. 00:17:16.240 --> 00:17:18.680 Very similar, but with a specific twist. Instead 00:17:18.680 --> 00:17:21.119 of random city dwellers, he was driving around 00:17:21.119 --> 00:17:23.299 picking up farmers. Farmers. OK, that's different. 00:17:23.400 --> 00:17:25.359 Yeah. And the goal was specifically charitable. 00:17:25.640 --> 00:17:28.359 The farmers had 10 minutes to answer trivia questions, 00:17:28.599 --> 00:17:31.079 just like cash cab. But the money they won went 00:17:31.079 --> 00:17:33.819 to their local FFA chapter, Future Farmers of 00:17:33.819 --> 00:17:36.160 America. Ah, so taking the format and applying 00:17:36.160 --> 00:17:38.480 it to a different community for a good cause. 00:17:38.759 --> 00:17:41.789 Exactly. It cleverly leveraged. his famous persona 00:17:41.789 --> 00:17:43.869 and the game show mechanics, but gave it a whole 00:17:43.869 --> 00:17:46.690 new context and purpose. It showed the core idea 00:17:46.690 --> 00:17:49.130 Ben Bailey asking trivia in a moving vehicle 00:17:49.130 --> 00:17:52.410 works anywhere, not just NYC. Smart way to keep 00:17:52.410 --> 00:17:55.289 the brand relevant, but fresh. Yeah, shifted 00:17:55.289 --> 00:17:58.150 the focus from the city to the charity. And finally, 00:17:58.309 --> 00:18:01.450 a recent marker of his status had appearance 00:18:01.450 --> 00:18:04.369 in that 2023 documentary, The Game Show Show. 00:18:04.529 --> 00:18:07.650 Oh, yeah. He was featured in that. He was. Being 00:18:07.650 --> 00:18:09.910 included in a historical look back at the whole 00:18:09.910 --> 00:18:13.250 genre alongside the icons, that basically cements 00:18:13.250 --> 00:18:16.089 your place. It's official recognition of his 00:18:16.089 --> 00:18:18.950 impact as a unique Emmy winning host who really 00:18:18.950 --> 00:18:21.339 did change the game. Literally took it out of 00:18:21.339 --> 00:18:23.240 the studio. Okay, so we've covered the career 00:18:23.240 --> 00:18:26.460 highs, the awards, the different roles. To get 00:18:26.460 --> 00:18:28.460 the full picture, maybe touch briefly on his 00:18:28.460 --> 00:18:30.819 personal life, just for context. Sure. It helps 00:18:30.819 --> 00:18:32.599 round things out. He definitely seems connected 00:18:32.599 --> 00:18:35.380 to his roots. Still lives in New Jersey, Morristown. 00:18:35.380 --> 00:18:38.200 Right, where he grew up, partially. Yeah. And 00:18:38.200 --> 00:18:40.759 interestingly, he met his ex -wife, Lawrence, 00:18:41.000 --> 00:18:43.990 right there in Morristown, back in the 90s. In 00:18:43.990 --> 00:18:46.269 a pub, the story goes. So a local connection. 00:18:46.509 --> 00:18:49.710 Mm -hmm. They got married in 1997. Now think 00:18:49.710 --> 00:18:52.289 about that timing. That's right when he's seriously 00:18:52.289 --> 00:18:54.309 grinding it out in the New York comedy clubs. 00:18:54.450 --> 00:18:56.369 Yeah, trying to make a name for himself. And 00:18:56.369 --> 00:18:58.849 then their marriage spanned that whole initial 00:18:58.849 --> 00:19:02.910 intense seven -year run of Cash Cab. Wow. That 00:19:02.910 --> 00:19:04.910 must have been a wild ride for both of them. 00:19:04.970 --> 00:19:08.170 You'd imagine so. They divorced in 2012. And 00:19:08.170 --> 00:19:11.930 they have two children together. Hmm. 2012. That 00:19:11.930 --> 00:19:13.750 date stands out. That's right when the first 00:19:13.750 --> 00:19:16.630 cash cab run ended. Exactly. And it's also when 00:19:16.630 --> 00:19:21.150 Who's Still Standing got canceled. So a period 00:19:21.150 --> 00:19:23.809 of major professional upheaval coinciding with 00:19:23.809 --> 00:19:25.710 the end of his marriage. It doesn't explicitly 00:19:25.710 --> 00:19:28.650 say one caused the other. No, but it paints a 00:19:28.650 --> 00:19:30.690 picture, doesn't it? It hints at the immense 00:19:30.690 --> 00:19:33.730 pressure involved in juggling a top tier TV career, 00:19:33.890 --> 00:19:36.690 a stand up career that requires travel and a 00:19:36.690 --> 00:19:39.420 personal life. It's a reminder of the human side 00:19:39.420 --> 00:19:42.160 behind the Emmys and the laughs. Yeah, good point. 00:19:42.420 --> 00:19:44.259 OK, so let's try and synthesize all this. What 00:19:44.259 --> 00:19:46.200 are the big takeaways from Ben Bailey's career? 00:19:46.400 --> 00:19:49.180 I think the main thing, the absolute core, is 00:19:49.180 --> 00:19:51.779 how he leveraged authenticity. He wasn't just 00:19:51.779 --> 00:19:53.720 a comedian who got lucky with a hosting gig. 00:19:53.880 --> 00:19:56.180 Right. He was the real deal, a licensed cabbie. 00:19:56.559 --> 00:19:59.740 That real world experience, that specific, unique 00:19:59.740 --> 00:20:02.319 perspective of driving a cab in New York City, 00:20:02.460 --> 00:20:04.779 that wasn't just a gimmick. It was the engine 00:20:04.779 --> 00:20:07.599 of his television success. It infused Cash Cab 00:20:07.599 --> 00:20:09.720 with a reality that you just couldn't replicate 00:20:09.720 --> 00:20:12.119 in a studio. And his skill was blending those 00:20:12.119 --> 00:20:14.950 two worlds, right? The comedy. And the cab driving. 00:20:15.089 --> 00:20:17.589 Exactly. The synthesis, taking the timing, the 00:20:17.589 --> 00:20:20.869 wit, the crowd work from stand up and applying 00:20:20.869 --> 00:20:23.289 it to the high stress, unpredictable environment 00:20:23.289 --> 00:20:25.910 of a game show happening in moving traffic. That 00:20:25.910 --> 00:20:28.589 fusion. That's what the Emmys recognize. That's 00:20:28.589 --> 00:20:31.210 why he dominated that category for so long against 00:20:31.210 --> 00:20:34.170 more traditional hosts. So it's a lesson in finding 00:20:34.170 --> 00:20:37.039 your unique intersection. He found where comedy 00:20:37.039 --> 00:20:39.599 met commercial driving and just owned that space. 00:20:39.720 --> 00:20:41.859 Absolutely. He carved out a niche nobody else 00:20:41.859 --> 00:20:43.759 could really occupy because nobody else was a 00:20:43.759 --> 00:20:47.059 touring comic and a licensed NYC cabbie. And 00:20:47.059 --> 00:20:49.099 he managed to sustain it, keep the standup going, 00:20:49.240 --> 00:20:52.359 adapt with things like the YouTube show that 00:20:52.359 --> 00:20:55.259 shows incredible drive. That authenticity tied 00:20:55.259 --> 00:20:57.980 to a specific place like New York just proved 00:20:57.980 --> 00:21:00.210 incredibly valuable. So, yeah, that pretty much 00:21:00.210 --> 00:21:02.609 wraps up our deep dive on Ben Bailey. It's quite 00:21:02.609 --> 00:21:04.750 a story when you lay it all out. It really is. 00:21:04.829 --> 00:21:06.789 Let's just quickly hit those standout facts again 00:21:06.789 --> 00:21:09.549 for everyone listening. Remember, his comedy 00:21:09.549 --> 00:21:12.109 career basically started because Skippy Lowe 00:21:12.109 --> 00:21:14.450 overheard him telling stories after hours at 00:21:14.450 --> 00:21:16.970 the comedy store. Just amazing. And that foundational 00:21:16.970 --> 00:21:20.509 fact, he wasn't playing a cab driver. He was 00:21:20.509 --> 00:21:23.190 one. Licensed and everything. That changes the 00:21:23.190 --> 00:21:25.769 whole dynamic of Cash Cab. And the sheer range. 00:21:25.990 --> 00:21:28.670 Going from law and order dramas to a soap opera, 00:21:28.829 --> 00:21:31.710 one life to live, hosting high stakes game shows, 00:21:31.809 --> 00:21:34.789 and all the while still releasing stand -up specials. 00:21:34.809 --> 00:21:37.329 That's serious versatility. Yeah, truly rare. 00:21:37.509 --> 00:21:40.049 We saw how he basically figured out that a taxicab, 00:21:40.049 --> 00:21:42.450 this everyday space, is actually a goldmine for 00:21:42.450 --> 00:21:46.029 spontaneous human interaction, weird facts, funny 00:21:46.029 --> 00:21:48.269 moments. Right. And turned that insight into 00:21:48.269 --> 00:21:50.920 a TV franchise that ran for years. and won multiple 00:21:50.920 --> 00:21:53.920 Emmys. He literally changed the setting for game 00:21:53.920 --> 00:21:55.920 shows. So here's something to chew on as we wrap 00:21:55.920 --> 00:21:58.900 up. Bailey's success came from finding the hidden 00:21:58.900 --> 00:22:01.559 expertise and entertainment value in a job most 00:22:01.559 --> 00:22:04.960 people see as just ordinary. Driving a cab. Think 00:22:04.960 --> 00:22:07.940 about other everyday jobs. You know, the barista 00:22:07.940 --> 00:22:10.099 who hears snippets of a thousand conversations, 00:22:10.440 --> 00:22:13.259 the librarian who knows the weirdest research 00:22:13.259 --> 00:22:16.539 request, the postal carrier who sees the rhythm 00:22:16.539 --> 00:22:18.480 of a neighborhood up close. Yeah, places where 00:22:18.480 --> 00:22:20.160 people are constantly encountering unexpected 00:22:20.160 --> 00:22:23.339 information or insights just by doing their job. 00:22:23.599 --> 00:22:26.500 So what other mundane setting could be hiding 00:22:26.500 --> 00:22:29.440 the next great game show or the next deep dive 00:22:29.440 --> 00:22:32.039 format? Where else is that hidden knowledge accumulating, 00:22:32.059 --> 00:22:34.039 just waiting for someone with the right perspective? 00:22:34.119 --> 00:22:36.559 to tap into it. What's the next mobile deep dive 00:22:36.559 --> 00:22:39.299 driven by someone's unique everyday expertise 00:22:39.299 --> 00:22:41.819 that's happening right under our noses? Good 00:22:41.819 --> 00:22:43.759 question to ponder. Definitely something to think 00:22:43.759 --> 00:22:46.319 about. Until next time, keep digging. We'll see 00:22:46.319 --> 00:22:47.359 you on the next deep dive.