WEBVTT 00:00:00.000 --> 00:00:01.860 Welcome back to the Deep Dive. You've given us 00:00:01.860 --> 00:00:03.779 the sources and we're here to pull out the most 00:00:03.779 --> 00:00:07.320 fascinating, need -to -know stuff. That's the 00:00:07.320 --> 00:00:09.820 plan. Today, we're diving deep into the career 00:00:09.820 --> 00:00:14.359 of Douglas Steven Benson, comedian, actor, host. 00:00:14.960 --> 00:00:18.050 It's quite a ride. It really is. We're looking 00:00:18.050 --> 00:00:20.510 at this arc, you know, from being an extra on 00:00:20.510 --> 00:00:23.910 classic movie sets through reality TV and then 00:00:23.910 --> 00:00:26.609 really hitting his stride in the kind of early 00:00:26.609 --> 00:00:29.449 days of podcasting and weed culture commentary. 00:00:29.690 --> 00:00:32.170 Exactly. And this isn't just about listing credits. 00:00:32.270 --> 00:00:35.289 It's about a whole brand, right? A career built 00:00:35.289 --> 00:00:37.770 on, yeah, the comedy, observational, satire, 00:00:37.770 --> 00:00:40.890 sarcasm, all that. But it's fundamentally linked 00:00:40.890 --> 00:00:44.869 to his very public, very open advocacy for recreational 00:00:44.869 --> 00:00:47.270 drug use. That's key. And what's really interesting 00:00:47.270 --> 00:00:49.810 is how he used that persona, that specific angle, 00:00:49.869 --> 00:00:53.649 to become this central figure in comedy podcasts 00:00:53.649 --> 00:00:55.950 when they were still pretty niche. Yeah, pioneer 00:00:55.950 --> 00:00:58.710 almost. Totally. And then translating that super 00:00:58.710 --> 00:01:02.270 specific brand to TV, even ending up with a legally 00:01:02.270 --> 00:01:04.530 binding court show. It's kind of wild when you 00:01:04.530 --> 00:01:07.129 lay it all out. A real study in mastering a niche. 00:01:07.310 --> 00:01:10.030 So our mission for you, listening in, is pretty 00:01:10.030 --> 00:01:12.900 straightforward. We want to synthesize all this 00:01:12.900 --> 00:01:15.840 diverse work, but, you know, go deeper than just 00:01:15.840 --> 00:01:18.120 the surface level. We're connecting the dots. 00:01:18.299 --> 00:01:20.819 How do you go from being a face in the background 00:01:20.819 --> 00:01:24.599 in, like, 80s movies to launching multiple hit 00:01:24.599 --> 00:01:27.939 shows focused on very specific things and dominating 00:01:27.939 --> 00:01:30.640 panel shows? It's the details. Exactly. We're 00:01:30.640 --> 00:01:34.019 zeroing in on the specific projects, the strategic 00:01:34.019 --> 00:01:37.459 moves, the little details that make his whole 00:01:37.459 --> 00:01:39.859 body of work so unique in comedy. Okay, let's 00:01:39.859 --> 00:01:47.400 do it. Okay, let's untap. All right, so the basics. 00:01:48.340 --> 00:01:51.319 Douglas Stephen Benton, born in San Diego, California, 00:01:51.500 --> 00:01:55.560 July 2, 1962. So he's 63 now. Okay. And the family 00:01:55.560 --> 00:01:57.480 background. It's kind of interesting given where 00:01:57.480 --> 00:01:59.579 he ended up. His mom was a pharmacy clerk. His 00:01:59.579 --> 00:02:02.219 dad was an English teacher who later went into 00:02:02.219 --> 00:02:04.640 sales. So pretty grounded middle class background. 00:02:04.879 --> 00:02:07.700 Very much. Southern California upbringing, which 00:02:07.700 --> 00:02:09.699 makes his later sort of counterculture persona 00:02:09.699 --> 00:02:11.919 stand out more. And even back in high school, 00:02:12.000 --> 00:02:14.259 Grossmont High, he was already creating stuff, 00:02:14.360 --> 00:02:16.259 right? Not just acting. Yeah, that's a great 00:02:16.259 --> 00:02:17.639 point. He was in the drama department. Sure, 00:02:17.759 --> 00:02:20.060 that's common. But the thing that jumps out is 00:02:20.060 --> 00:02:22.719 him making these like eight millimeter action 00:02:22.719 --> 00:02:25.759 and thriller short films. With a friend. Wow. 00:02:25.840 --> 00:02:29.319 OK, so hands on filmmaking. Right. Junior, senior 00:02:29.319 --> 00:02:31.800 year. He wasn't just performing. He was thinking 00:02:31.800 --> 00:02:35.419 about structure, storytelling, the whole cinematic 00:02:35.419 --> 00:02:38.639 process. Even then. Which maybe explains his 00:02:38.639 --> 00:02:40.780 later obsession with movie details and rules. 00:02:41.099 --> 00:02:43.479 I think it connects directly. It shows he came 00:02:43.479 --> 00:02:45.520 into the entertainment world with not just a 00:02:45.520 --> 00:02:48.819 performer's view, but also thinking about like 00:02:48.819 --> 00:02:51.409 the mechanics of media. How things are put together. 00:02:51.509 --> 00:02:53.689 We totally see that later with his podcast games. 00:02:53.889 --> 00:02:55.849 And speaking of mechanics, there was that personal 00:02:55.849 --> 00:02:59.009 health detail. Something about his eyes. Yeah, 00:02:59.009 --> 00:03:01.069 this is interesting. As a kid, he apparently 00:03:01.069 --> 00:03:03.949 struggled with vertigo and had poor depth perception. 00:03:04.250 --> 00:03:06.710 So it was because his eyes are close set. Huh. 00:03:06.889 --> 00:03:09.509 So literally seeing the world a bit differently. 00:03:10.009 --> 00:03:12.710 Possibly, yeah. Having to navigate with maybe 00:03:12.710 --> 00:03:15.979 a slightly skewed or flatter... visual field. 00:03:16.240 --> 00:03:18.819 You wonder, does that difficulty with spatial 00:03:18.819 --> 00:03:22.080 stuff maybe push someone towards more analytical, 00:03:22.120 --> 00:03:24.599 structured thinking? Like creating really complex 00:03:24.599 --> 00:03:27.599 trivia games instead of relying on, say, physical 00:03:27.599 --> 00:03:30.259 comedy. Could be. It might partly explain why 00:03:30.259 --> 00:03:32.280 his biggest successes are built around these 00:03:32.280 --> 00:03:35.240 intricate, detail oriented. Game structures. 00:03:35.439 --> 00:03:37.759 It definitely leans into the intellectual side 00:03:37.759 --> 00:03:39.800 of things. So after Grismont College, he does 00:03:39.800 --> 00:03:42.120 the classic thing, Moose to L .A. to act. Yep, 00:03:42.199 --> 00:03:45.120 the 1980s Hollywood hustle. Taking those stand 00:03:45.120 --> 00:03:47.939 -in jobs, extra work, trying to make rent while 00:03:47.939 --> 00:03:50.319 looking for actual roles. And those gigs put 00:03:50.319 --> 00:03:52.240 him right in the middle of some iconic films. 00:03:52.479 --> 00:03:54.979 Absolutely. He worked as a stand -in a lot, but 00:03:54.979 --> 00:03:58.080 also popped up as an extra or in tiny parts in 00:03:58.080 --> 00:04:00.629 huge movies from that era. We're talking Blade 00:04:00.629 --> 00:04:03.469 Runner. Wow. Fast Times at Ridgemont High. Right. 00:04:03.550 --> 00:04:05.990 About last night. This period is crucial. It's 00:04:05.990 --> 00:04:08.050 where he soaked up all that film trivia, learned 00:04:08.050 --> 00:04:10.449 about production, credits. The stuff that literally 00:04:10.449 --> 00:04:13.550 becomes the basis for Doug Love's movies. Exactly. 00:04:13.629 --> 00:04:16.730 That deep, almost obsessive knowledge of how 00:04:16.730 --> 00:04:18.850 movies are made and who's in them. And the weirdest 00:04:18.850 --> 00:04:21.629 detail from that time. The Disney thing. Oh, 00:04:21.649 --> 00:04:25.430 yeah. Captain EO. 1986. He was apparently a backup 00:04:25.430 --> 00:04:29.209 dancer in this huge 3D Michael Jackson sci -fi 00:04:29.209 --> 00:04:31.170 musical attraction at Disneyland. Directed by 00:04:31.170 --> 00:04:34.310 Coppola. That's wild. It really is. From the 00:04:34.310 --> 00:04:39.350 grit of Blade Runner to sparkly MJ choreography 00:04:39.350 --> 00:04:43.230 in 3D, it just shows the sheer variety of gigs 00:04:43.230 --> 00:04:45.069 you had to take to survive in Hollywood back 00:04:45.069 --> 00:04:47.610 then. Total adaptability. But the acting wasn't 00:04:47.610 --> 00:04:49.670 the thing that clicked career wise. It was stand 00:04:49.670 --> 00:04:52.449 up. Right. And kind of by accident. Yeah. The 00:04:52.449 --> 00:04:55.350 stand up origin story is classic. Age 22. Wasn't 00:04:55.350 --> 00:04:57.290 like a burning desire apparently. He and two 00:04:57.290 --> 00:04:59.449 buddies dared each other to try it. And the friends 00:04:59.449 --> 00:05:01.610 bailed. Pretty much. One didn't show the other 00:05:01.610 --> 00:05:03.410 signed up too late. But Benson actually did it. 00:05:03.430 --> 00:05:05.990 Got on stage. Did what he called three minutes 00:05:05.990 --> 00:05:07.970 of whatever. And people laughed. Yeah. He said 00:05:07.970 --> 00:05:09.790 people actually laughed. And that's often all 00:05:09.790 --> 00:05:11.649 it takes. Right. That little bit of validation 00:05:11.649 --> 00:05:14.310 to turn you from someone watching comedy to someone 00:05:14.310 --> 00:05:16.860 doing it. But the whole stoner comic thing, that 00:05:16.860 --> 00:05:19.199 wasn't immediate. That's the key timeline thing 00:05:19.199 --> 00:05:22.430 people miss. Crucial point. He was doing stand 00:05:22.430 --> 00:05:26.189 -up for like six years before that persona really 00:05:26.189 --> 00:05:29.889 formed. He became a dedicated stoner, as he puts 00:05:29.889 --> 00:05:32.649 it later, around age 28. After smoking with other 00:05:32.649 --> 00:05:34.870 comics? Yeah, apparently after a week of hanging 00:05:34.870 --> 00:05:37.189 out and smoking pot after gigs with Brian Posen 00:05:37.189 --> 00:05:39.790 and Greg Proops. So it wasn't like some teenage 00:05:39.790 --> 00:05:42.629 discovery. It was an adult choice. Right. And 00:05:42.629 --> 00:05:45.129 he later folded that lifestyle choice into his 00:05:45.129 --> 00:05:47.290 comedy. It wasn't the reason he started comedy. 00:05:47.569 --> 00:05:50.399 Exactly. It fit his style, that observational 00:05:50.399 --> 00:05:52.519 kind of analytical approach. And then he just 00:05:52.519 --> 00:05:55.079 leaned into it hard, turned a personal habit 00:05:55.079 --> 00:05:57.709 into a whole media identity. So while that identity 00:05:57.709 --> 00:05:59.870 was forming, he was still grinding away, getting 00:05:59.870 --> 00:06:03.389 TV spots. Those late 80s, early 90s appearances 00:06:03.389 --> 00:06:05.470 on Comedy Central shows like The A -List, Two 00:06:05.470 --> 00:06:07.970 Drink Minimum, Building Credits. And The Writing 00:06:07.970 --> 00:06:10.389 Work. Important, too. Wrote for that MTV game 00:06:10.389 --> 00:06:13.050 show Trash to 94. Again, you see the interest 00:06:13.050 --> 00:06:14.769 in game structure, learning how to burn those 00:06:14.769 --> 00:06:17.250 mechanics. Foreshadowing. Totally. And he was 00:06:17.250 --> 00:06:19.689 in Joel Hodgson's pilot, The TV Wheel, after 00:06:19.689 --> 00:06:22.850 MST3K. Part of that alt -comedy scene. And all 00:06:22.850 --> 00:06:24.370 this kind of comes together with the marijuana 00:06:24.370 --> 00:06:26.250 lugs, right? That seems like a big step. Huge 00:06:26.250 --> 00:06:28.810 step. Co -creating and performing that stage 00:06:28.810 --> 00:06:31.910 show with Arch Barker and Tony Kamen. It ran 00:06:31.910 --> 00:06:35.189 for a long time, toured. That really cemented 00:06:35.189 --> 00:06:38.009 his public connection between comedy and cannabis. 00:06:38.129 --> 00:06:40.430 It set the stage perfectly for what came next. 00:06:40.649 --> 00:06:42.529 Okay, so this is where things really explode 00:06:42.529 --> 00:06:44.889 for him, right? The move into podcasting. This 00:06:44.889 --> 00:06:46.750 feels like the turning point. Absolutely. Around 00:06:46.750 --> 00:06:49.350 2006, he launches I Love Movies with Doug Benson, 00:06:49.529 --> 00:06:52.769 quickly becomes Doug Loves Movies, DLM. And back 00:06:52.769 --> 00:06:56.310 in 2006, podcasting was... Different, much more 00:06:56.310 --> 00:06:58.629 of a Wild West. Oh, yeah. Very niche. And what 00:06:58.629 --> 00:07:00.970 he did was smart recording it live, usually at 00:07:00.970 --> 00:07:03.829 UCD in L .A. That gave it an energy, that live 00:07:03.829 --> 00:07:06.329 comedy club feel that a lot of early, you know, 00:07:06.329 --> 00:07:08.889 recorded in a closet podcasts didn't have. The 00:07:08.889 --> 00:07:10.889 format seems simple on the surface. Talk about 00:07:10.889 --> 00:07:13.970 movies, have comedians on. Right. But the execution, 00:07:14.149 --> 00:07:16.430 the structure, that's where the genius is and 00:07:16.430 --> 00:07:18.930 the absolute core of it. The thing that's driven 00:07:18.930 --> 00:07:21.689 it for, what, nearly two decades now? The Leonard 00:07:21.689 --> 00:07:23.829 Moulton game. Okay, break this down for anyone 00:07:23.829 --> 00:07:25.810 who hasn't heard it. It's more complicated than 00:07:25.810 --> 00:07:28.129 it sounds. Definitely. People call it Name That 00:07:28.129 --> 00:07:30.350 Tune With Movies, which is kind of right. But 00:07:30.350 --> 00:07:33.850 way nerdier. Way nerdier. Needs super deep film 00:07:33.850 --> 00:07:36.709 knowledge. So, Benson reads bits from a movie 00:07:36.709 --> 00:07:38.930 review, usually from Leonard Moulton's old guides. 00:07:39.389 --> 00:07:42.430 The guests then have to wager. Wager on what? 00:07:42.550 --> 00:07:45.230 On how many names. Read from the bottom of the 00:07:45.230 --> 00:07:47.449 cast list upwards. It'll take them to guess. 00:07:47.500 --> 00:07:49.920 the movie. Okay, so the lower the bid, the harder 00:07:49.920 --> 00:07:53.040 it is. Exactly. If you bid, say, five names, 00:07:53.199 --> 00:07:56.480 he reads the fifth to last actor credited. Usually, 00:07:56.540 --> 00:07:59.079 as someone pretty obscure, if you bid one name, 00:07:59.259 --> 00:08:01.560 you're banking on recognizing the movie just 00:08:01.560 --> 00:08:03.959 from the very last credited actor, often like 00:08:03.959 --> 00:08:06.579 Man Hashtag 2 or something. It rewards that insane 00:08:06.579 --> 00:08:09.759 recall for character actors and bit parts, the 00:08:09.759 --> 00:08:11.579 kind of knowledge he probably picked up being 00:08:11.579 --> 00:08:14.980 a stand -in. Precisely. It taps into that deep 00:08:14.980 --> 00:08:17.519 cinephile knowledge base and it creates these 00:08:17.519 --> 00:08:20.100 like legendary moments on the show. Like the 00:08:20.100 --> 00:08:22.279 negative names thing. That sounds impossible. 00:08:22.540 --> 00:08:25.459 Right. Sean Sakame, a fan who won an auction 00:08:25.459 --> 00:08:27.600 to be on, won the Tournament of Champions in 00:08:27.600 --> 00:08:31.519 2013. Then to qualify the next year, he guessed 00:08:31.519 --> 00:08:34.460 Titanic in negative names, meaning he guessed 00:08:34.460 --> 00:08:36.600 it correctly just from the review before Benson 00:08:36.600 --> 00:08:38.879 even read any names from the cast list. Just 00:08:38.879 --> 00:08:41.519 pure deduction and confidence shows the level 00:08:41.519 --> 00:08:43.710 of obsession the game inspires. And there's the 00:08:43.710 --> 00:08:46.210 big annual championship, the Christmas special. 00:08:46.289 --> 00:08:49.389 Yeah, the 12 Guests of Christmas, huge two -hour 00:08:49.389 --> 00:08:51.870 elimination -style game with a dozen or more 00:08:51.870 --> 00:08:54.090 comics. It's like the DLM Super Bowl. And there 00:08:54.090 --> 00:08:56.549 are rivalries, recurring champs. Oh, yeah. Scott 00:08:56.549 --> 00:08:58.330 Aukerman won the first one, then won again years 00:08:58.330 --> 00:09:01.370 later in 2015. Graham Elwood had a dominant run 00:09:01.370 --> 00:09:03.610 for a couple years. Rikki Lindholm had a big 00:09:03.610 --> 00:09:06.570 win over Jimmy Pardo in 2014. It creates this 00:09:06.570 --> 00:09:09.409 whole meta -narrative within the L .A. comedy 00:09:09.409 --> 00:09:12.490 podcast world. But DLM isn't just the Maltin 00:09:12.490 --> 00:09:15.250 game. He invented a ton of other segments, right? 00:09:15.529 --> 00:09:18.309 That speaks to his creativity, too. Absolutely. 00:09:18.370 --> 00:09:21.490 The sheer number and variety of games show his 00:09:21.490 --> 00:09:25.110 knack for structure and, frankly, absurdity. 00:09:25.429 --> 00:09:27.610 We don't need to list all 20, but some are just 00:09:27.610 --> 00:09:30.169 brilliant concepts. Like Lincoln or Bane. Perfect 00:09:30.169 --> 00:09:32.730 example. He reads a quote. You have to say if 00:09:32.730 --> 00:09:34.529 it was Abraham Lincoln or Bane from The Dark 00:09:34.529 --> 00:09:36.570 Knight Rises. Because they both have that kind 00:09:36.570 --> 00:09:39.769 of slow, formal delivery. Exactly. The juxtaposition 00:09:39.769 --> 00:09:44.850 is hilarious. Or now Buscemi, now you don't. 00:09:44.850 --> 00:09:46.909 Which is. It's like the shell game, but with 00:09:46.909 --> 00:09:48.389 pictures of Steve Buscemi because, you know, 00:09:48.389 --> 00:09:50.250 Buscemi's in everything. It's a running commentary 00:09:50.250 --> 00:09:52.929 on character actors. So it's trivia mixed with 00:09:52.929 --> 00:09:55.889 meta commentary. Totally. And doing lines with 00:09:55.889 --> 00:09:58.590 Mark Wahlberg, just quoting Wahlberg movie lines. 00:09:59.689 --> 00:10:02.070 ABCD's nuts. He's constantly finding ways to 00:10:02.070 --> 00:10:04.710 twist movie trivia into reputable, funny formats. 00:10:05.009 --> 00:10:07.090 And the closing catchphrase saga is fascinating, 00:10:07.309 --> 00:10:10.490 too. The Willem Dafoe thing. Oh, man. Yeah. For 00:10:10.490 --> 00:10:13.470 years, he ended every show with, as always, Willem 00:10:13.470 --> 00:10:16.070 Dafoe is a shithead. Which was pure satire, right? 00:10:16.129 --> 00:10:19.129 Like, Dafoe is so respected, it's absurd to attack 00:10:19.129 --> 00:10:22.409 him. That was the joke. Benson thought it was 00:10:22.409 --> 00:10:25.519 the most random, illogical thing to say. But 00:10:25.519 --> 00:10:27.720 a lot of listeners didn't get the satire at all. 00:10:27.820 --> 00:10:30.080 They thought he genuinely hated Willem Dafoe. 00:10:30.240 --> 00:10:33.460 Yeah. He got confused emails, people asking what 00:10:33.460 --> 00:10:35.960 Dafoe ever did to him. The joke just didn't land 00:10:35.960 --> 00:10:38.120 universally. So he had to explain it over and 00:10:38.120 --> 00:10:40.259 over. Right. Eventually, he kind of retired it, 00:10:40.320 --> 00:10:44.159 let Dafoe rest. But the concept lived on for 00:10:44.159 --> 00:10:47.379 a while until 2019. The runner -up in the Malton 00:10:47.379 --> 00:10:49.879 game got to name their own shithead as a consolation 00:10:49.879 --> 00:10:52.220 prize. A little moment of catharsis for losing. 00:10:52.519 --> 00:10:55.580 Pretty much. But that ended. Now the closing 00:10:55.580 --> 00:10:58.360 is positive energy. Which is a tribute. Yeah, 00:10:58.419 --> 00:11:00.299 a direct tribute to his friend, the comedian 00:11:00.299 --> 00:11:02.620 Brody Stevens, who passed away and used that 00:11:02.620 --> 00:11:05.840 phrase a lot. So it shifted from absurdist satire 00:11:05.840 --> 00:11:08.679 to something more genuinely causative. It shows 00:11:08.679 --> 00:11:10.899 evolution. Yeah. And beyond his own show, he 00:11:10.899 --> 00:11:13.919 became like podcasting royalty, guesting everywhere. 00:11:14.379 --> 00:11:18.419 Oh, absolutely. Comedy bang. Bang. WTF, Joe Rogan, 00:11:18.440 --> 00:11:20.559 nerdist. If you had a comedy podcast, you wanted 00:11:20.559 --> 00:11:23.080 Benson on. He was reliable, quick, knowledgeable, 00:11:23.220 --> 00:11:25.360 brought that energy. He became a connector in 00:11:25.360 --> 00:11:28.519 that whole scene. The cannabis -centric media, 00:11:28.679 --> 00:11:30.620 documentaries, talk shows, and legal rulings. 00:11:31.100 --> 00:11:33.840 Okay, so DLM gives him this huge dedicated audience. 00:11:34.120 --> 00:11:37.000 And that platform lets him really dive into the 00:11:37.000 --> 00:11:39.779 media that fully embraces the cannabis brand. 00:11:40.379 --> 00:11:43.299 Starting with Super Jaime. 2007 release, right? 00:11:43.399 --> 00:11:45.519 The title obviously playing on Supersize Me. 00:11:45.659 --> 00:11:48.460 Exactly. Morgan Spurlock ate McDonald's for 30 00:11:48.460 --> 00:11:51.279 days. Benson's experiment was 30 days no marijuana, 00:11:51.519 --> 00:11:54.259 then 30 days smoking as much as possible. A pretty 00:11:54.259 --> 00:11:56.940 bold public experiment. Totally. Part comedy 00:11:56.940 --> 00:11:59.679 stunt, part personal advocacy. And the results, 00:11:59.740 --> 00:12:01.580 at least as presented in the film. Minimal negative 00:12:01.580 --> 00:12:04.360 effects, right? Yeah. Based on his tests, cognitive 00:12:04.360 --> 00:12:06.200 checks, general health monitored in the doc, 00:12:06.399 --> 00:12:08.440 the conclusion was that the heavy use period 00:12:08.440 --> 00:12:10.960 didn't really harm him significantly, which was, 00:12:10.980 --> 00:12:12.960 you know, a big statement against the prevailing 00:12:12.960 --> 00:12:15.220 anti -drug messaging at the time. It gave the 00:12:15.220 --> 00:12:17.559 pro -legalization side a kind of funny, relatable 00:12:17.559 --> 00:12:20.240 data point, even if it was just one guy. Right. 00:12:20.320 --> 00:12:22.820 Look, I did this, professionally documented it, 00:12:22.840 --> 00:12:25.419 and I'm fine. It resonated. But things got messy 00:12:25.419 --> 00:12:27.320 after the film's success. There was a lawsuit. 00:12:27.679 --> 00:12:30.059 Yeah, that happens. The other producers wanted 00:12:30.059 --> 00:12:33.179 to release a sequel, Super High Me Redux, using 00:12:33.179 --> 00:12:36.220 leftover footage. Benson sued them around 2014, 00:12:36.519 --> 00:12:39.759 2015 to stop it. So clearly some friction there 00:12:39.759 --> 00:12:41.980 about control and maybe how the original is being 00:12:41.980 --> 00:12:44.259 exploited later. Then came the talk show, Getting 00:12:44.259 --> 00:12:46.759 Dug With High. This feels like the ultimate expression 00:12:46.759 --> 00:12:49.279 of his brand at the time. For sure. Ran from 00:12:49.279 --> 00:12:52.860 2013 to 2019. weekly show on YouTube, streamed 00:12:52.860 --> 00:12:55.480 live, usually Wednesdays at a very specific time. 00:12:55.659 --> 00:12:59.000 4 .15 p .m. Pacific. Yep. Setting up the main 00:12:59.000 --> 00:13:01.899 event. The 4 .20 smoke session. Exactly. The 00:13:01.899 --> 00:13:04.759 core ritual. He'd have guests on, huge names, 00:13:04.980 --> 00:13:07.820 Snoop Dogg, Sarah Silverman, Cheech Marin, Jack 00:13:07.820 --> 00:13:09.700 Black, tons of comics, and they'd all light up 00:13:09.700 --> 00:13:13.200 together right at 4 .20 PST during the live stream. 00:13:13.220 --> 00:13:15.559 And talk. Yeah, talk about whatever. Usually 00:13:15.559 --> 00:13:19.139 cannabis -related comedy movies. Very relaxed, 00:13:19.279 --> 00:13:21.789 obviously. How did they handle the live audience 00:13:21.789 --> 00:13:25.269 shows? Couldn't exactly hotbox the venue. Good 00:13:25.269 --> 00:13:28.190 question. They adapted. Often used vaporizers, 00:13:28.330 --> 00:13:31.029 with guests inhaling from those big bags of vapor. 00:13:31.230 --> 00:13:34.370 It kept the ritual intact, visually, without 00:13:34.370 --> 00:13:37.669 violating venue rules or smoking laws. A smart 00:13:37.669 --> 00:13:39.990 workaround. And the ending. The magic trick. 00:13:40.230 --> 00:13:43.240 Always. Every single show, no matter who the 00:13:43.240 --> 00:13:45.879 guest was or how high they were, ended with Benson 00:13:45.879 --> 00:13:48.659 making them watch a magic trick. Just pure, delightful 00:13:48.659 --> 00:13:51.980 Benson weirdness. Totally. A signature, absurd 00:13:51.980 --> 00:13:54.840 little flourish. Okay, but the absolute weirdest, 00:13:54.940 --> 00:13:57.879 most ambitious project has to be the High Court. 00:13:58.440 --> 00:14:01.440 2017, Comedy Central. This one is fascinating. 00:14:01.620 --> 00:14:04.139 It's a court show. Yeah. Like Judge Judy or People's 00:14:04.139 --> 00:14:06.679 Court, standard format. The judge is Doug Benson, 00:14:06.840 --> 00:14:09.740 and he's high, openly. Yes, that's the entire 00:14:09.740 --> 00:14:12.580 premise. He's the judge. ruling on cases while 00:14:12.580 --> 00:14:14.639 admittedly under the influence of cannabis during 00:14:14.639 --> 00:14:16.860 the taping. Now, the crucial detail here, the 00:14:16.860 --> 00:14:18.360 thing that makes it more than just a sketch, 00:14:18.559 --> 00:14:21.120 the cases were real. Absolutely real. These were 00:14:21.120 --> 00:14:23.720 actual small claims disputes. And his rulings 00:14:23.720 --> 00:14:27.759 were legally binding. Yes. That's the mind -bending 00:14:27.759 --> 00:14:30.620 part. It worked like binding arbitration. The 00:14:30.620 --> 00:14:33.059 people bringing their cases, signed contracts, 00:14:33.159 --> 00:14:35.919 agreeing to accept Judge Doug's decision, whatever 00:14:35.919 --> 00:14:39.269 it was, high or not. So real legal consequences 00:14:39.269 --> 00:14:42.169 decided by a comedian who's openly stoned on 00:14:42.169 --> 00:14:44.669 camera. Pretty much sums it up. Yeah. And the 00:14:44.669 --> 00:14:46.610 show played into it. There'd be segments where 00:14:46.610 --> 00:14:49.830 Judge Doug and the bailiff would retire to chambers, 00:14:50.090 --> 00:14:52.350 which meant they'd go smoke weed while deliberating 00:14:52.350 --> 00:14:55.389 the case. It's performance art meets actual legal 00:14:55.389 --> 00:14:58.110 process. It's kind of brilliant commentary, actually. 00:14:58.330 --> 00:15:00.610 It really is. Pushing the boundaries of comedy, 00:15:00.789 --> 00:15:05.429 reality TV and the justice system all at once. 00:15:05.529 --> 00:15:08.230 And quickly. The Benson interruption. That started 00:15:08.230 --> 00:15:10.370 live, too. Yeah, long -running live show where 00:15:10.370 --> 00:15:12.269 he'd literally interrupt other comedians during 00:15:12.269 --> 00:15:14.590 their sets. Very confrontational, funny stuff. 00:15:14.789 --> 00:15:16.730 Got a TV version on Comedy Central for a bit. 00:15:16.850 --> 00:15:20.129 One season in 2010. But then, naturally, he spun 00:15:20.129 --> 00:15:23.750 it off into a podcast in 2011. Audio only, longer, 00:15:23.929 --> 00:15:27.269 unedited sets and chats. Again, adapting a successful 00:15:27.269 --> 00:15:30.429 live concept for the podcast medium he knew so 00:15:30.429 --> 00:15:33.610 well, Consistent Pattern. So we've seen the podcast 00:15:33.610 --> 00:15:36.570 The Weed Shows. But we also need to talk about 00:15:36.570 --> 00:15:39.230 his sheer output of traditional stand -up. He's 00:15:39.230 --> 00:15:41.669 released, what, 10 comedy albums? At least 10, 00:15:41.769 --> 00:15:43.789 yeah. Starting with Professional Humorudian back 00:15:43.789 --> 00:15:47.870 in 2008. And he has this specific goal with the 00:15:47.870 --> 00:15:50.389 albums, right? The timing. Yeah, it's very deliberate 00:15:50.389 --> 00:15:52.529 branding. He aims to record a new album every 00:15:52.529 --> 00:15:54.970 April 20th. Naturally. Naturally. For a release 00:15:54.970 --> 00:15:57.409 later that summer, he wants to keep that streak 00:15:57.409 --> 00:16:00.159 going for as long as possible. It's smart. It 00:16:00.159 --> 00:16:01.960 ties his stand -up directly to the 420 date, 00:16:02.039 --> 00:16:04.379 reinforces the brand, creates anticipation. He 00:16:04.379 --> 00:16:06.679 becomes the official comedic chronicler of that 00:16:06.679 --> 00:16:09.019 date, in a way. And the titles reflect the brand, 00:16:09.080 --> 00:16:11.740 too. Potty Mouth, Smug Life. Smug Life is a great 00:16:11.740 --> 00:16:14.019 one. Very self -aware of his stage persona. Then 00:16:14.019 --> 00:16:16.820 Gateway Doug. Gateway Doug 2. Forced fun and 00:16:16.820 --> 00:16:19.159 promotional tool. He's definitely in on the joke 00:16:19.159 --> 00:16:21.639 about his own marketing. Absolutely. He knows 00:16:21.639 --> 00:16:24.740 the game. But beyond his own albums... He was 00:16:24.740 --> 00:16:27.220 also making waves in mainstream TV competitions 00:16:27.220 --> 00:16:29.340 and panel shows. Right, last comic standing in 00:16:29.340 --> 00:16:31.440 2007. He was actually a contestant. Yeah, fifth 00:16:31.440 --> 00:16:34.000 season. And he did really well. Got significant 00:16:34.000 --> 00:16:36.779 exposure. Made it pretty deep. Finished sixth 00:16:36.779 --> 00:16:39.620 overall, I think. So his niche comedy style could 00:16:39.620 --> 00:16:42.059 play to a broader audience. It showed it. It 00:16:42.059 --> 00:16:44.179 could translate, yeah. And he was a regular on 00:16:44.179 --> 00:16:46.940 VH1's Best Week Ever for years doing that pop 00:16:46.940 --> 00:16:49.440 culture commentary thing. The dry, sarcastic 00:16:49.440 --> 00:16:52.860 take. Exactly. Plus that G4 special in 2009, 00:16:53.019 --> 00:16:55.320 The High Road, following him and Graham Elwood 00:16:55.320 --> 00:16:58.320 on tour. More proof people were interested in 00:16:58.320 --> 00:17:00.600 him as a personality, not just a performer. But 00:17:00.600 --> 00:17:02.720 his biggest competitive stage was probably at 00:17:02.720 --> 00:17:05.220 midnight, right? The Comedy Central show. Oh, 00:17:05.220 --> 00:17:08.259 he owned that show. It ran from 2013 to 2017, 00:17:08.480 --> 00:17:10.660 all about rapid fire jokes based on Internet 00:17:10.660 --> 00:17:12.900 stuff. Perfectly suited for his quick wit. And 00:17:12.900 --> 00:17:16.299 his record was insane. Unmatched. He holds the 00:17:16.299 --> 00:17:18.160 record for both the most appearances and the 00:17:18.160 --> 00:17:20.980 most wins on the show. Like by a lot. He was 00:17:20.980 --> 00:17:22.740 the undisputed champ. To the point where they 00:17:22.740 --> 00:17:26.019 basically built a week around him. Yeah. January 00:17:26.019 --> 00:17:28.779 2016, they did the Benson Bowl, a whole week 00:17:28.779 --> 00:17:31.400 of competition, and lots of the games were specifically 00:17:31.400 --> 00:17:34.480 tweaked to have weed themes. It showed how central 00:17:34.480 --> 00:17:36.779 his persona was, even to that fast -paced format. 00:17:36.980 --> 00:17:40.059 The show literally adapted to him. And all this 00:17:40.059 --> 00:17:42.319 time, he's still popping up in acting roles occasionally. 00:17:42.599 --> 00:17:45.579 Kept his hand in, yeah. Small parts, but on huge 00:17:45.579 --> 00:17:49.160 shows. Mr. Show, Friends. Friends, really? Yep. 00:17:49.460 --> 00:17:51.240 Curb Your Enthusiasm, How I Met Your Mother, 00:17:51.380 --> 00:17:54.490 Sarah Silverman Program. Yes, dear. just steadily 00:17:54.490 --> 00:17:56.710 working, showing up in the background of major 00:17:56.710 --> 00:17:59.329 sitcoms. And more recently. Trailer Park Boys, 00:17:59.589 --> 00:18:02.289 you're the worst, did voice work on Bob's Burgers. 00:18:02.369 --> 00:18:04.910 And the voice of Bane in the Lego movie. Right, 00:18:05.009 --> 00:18:08.410 the Lego Batman movie in 2017. Full circle back 00:18:08.410 --> 00:18:10.869 to movies, using that distinctive voice for a 00:18:10.869 --> 00:18:13.910 major villain parody. Kind of perfect. Okay, 00:18:13.990 --> 00:18:16.500 so we've tracked this huge... successful, very 00:18:16.500 --> 00:18:18.619 specific career. But if we're looking at the 00:18:18.619 --> 00:18:20.460 whole picture, we absolutely have to talk about 00:18:20.460 --> 00:18:22.599 the red eye incident. March 2009. This feels 00:18:22.599 --> 00:18:24.579 like a major bump in the road. It's more than 00:18:24.579 --> 00:18:28.259 a bump. A really stark example of how comedy, 00:18:28.380 --> 00:18:30.720 especially satire, and that kind of deliberately 00:18:30.720 --> 00:18:34.200 ignorant persona can just crash headlong into 00:18:34.200 --> 00:18:37.559 real world tragedy and politics. With serious 00:18:37.559 --> 00:18:40.240 consequences. So the setup. He's on Greg Gutfeld's 00:18:40.240 --> 00:18:42.240 show, Red Eye, on Fox News. They're talking about 00:18:42.240 --> 00:18:44.859 Canada's military. Yes, specifically a comment 00:18:44.859 --> 00:18:47.599 by a Canadian general, Andrew Leslie, who'd suggested 00:18:47.599 --> 00:18:49.960 the Canadian forces might need a year -long break 00:18:49.960 --> 00:18:53.140 after their mission in Afghanistan ended in 2011. 00:18:53.519 --> 00:18:55.559 And Gutfeld started with jokes about them doing 00:18:55.559 --> 00:18:58.019 yoga and painting. Standard stuff. Playing on 00:18:58.019 --> 00:19:00.259 stereotypes. But then Benson chimed in. And his 00:19:00.259 --> 00:19:02.220 comments were... First, I didn't even know they 00:19:02.220 --> 00:19:04.190 were in the war. Then... I thought, that's where 00:19:04.190 --> 00:19:06.650 you go if you don't want to fight. Go chill in 00:19:06.650 --> 00:19:10.630 Canada. Oof. Okay. Playing dumb, but... Playing 00:19:10.630 --> 00:19:12.710 dumb at the worst possible moment. The timing 00:19:12.710 --> 00:19:15.329 was just catastrophic. Why? What had just happened? 00:19:15.569 --> 00:19:18.289 The segment aired, or at least hit YouTube, just 00:19:18.289 --> 00:19:20.390 three days after four Canadian soldiers had been 00:19:20.390 --> 00:19:23.410 killed in Afghanistan. Oh, wow. Okay. That changes 00:19:23.410 --> 00:19:26.720 everything. Completely. It transforms the joke 00:19:26.720 --> 00:19:29.720 from maybe slightly lazy satire into something 00:19:29.720 --> 00:19:32.759 deeply disrespectful, appearing to mock a nation 00:19:32.759 --> 00:19:35.440 actively grieving its soldiers. And Canada's 00:19:35.440 --> 00:19:37.859 role wasn't minor, right? They were heavily involved. 00:19:38.240 --> 00:19:40.079 Critically involved. Yeah. They were leading 00:19:40.079 --> 00:19:42.759 the NATO mission in Kandahar province, the Taliban's 00:19:42.759 --> 00:19:45.339 heartland. Sources say Kandahar had some of the 00:19:45.339 --> 00:19:47.460 highest casualty rates for coalition forces. 00:19:47.700 --> 00:19:49.440 So for Benson to say, I didn't even know they 00:19:49.440 --> 00:19:52.289 were in the war. looked like profound, willful 00:19:52.289 --> 00:19:54.930 ignorance of real sacrifice. Exactly. And the 00:19:54.930 --> 00:19:57.950 reaction in Canada was furious, immediate. Official 00:19:57.950 --> 00:20:00.170 reaction, too. Oh, yeah. The Canadian defense 00:20:00.170 --> 00:20:02.690 minister, Peter McKay, personally demanded an 00:20:02.690 --> 00:20:05.869 apology from Fox News, called the comments despicable, 00:20:06.069 --> 00:20:09.109 hurtful, and ignorant. This wasn't just online 00:20:09.109 --> 00:20:11.390 chatter. It was a diplomatic incident. And it 00:20:11.390 --> 00:20:13.970 hit Benson directly. Canceled shows. Yep. He 00:20:13.970 --> 00:20:16.490 had gigs scheduled in Edmonton, Canada. The club 00:20:16.490 --> 00:20:19.099 owner canceled them, citing threats of Bodily 00:20:19.099 --> 00:20:21.460 injury against Benson. Real serious backlash. 00:20:21.720 --> 00:20:24.579 So how did Benson respond? To his credit, he 00:20:24.579 --> 00:20:26.940 seemed to grasp the severity pretty quickly. 00:20:27.099 --> 00:20:30.220 Yeah. He went on Canadian TV, CTV News, and gave 00:20:30.220 --> 00:20:33.299 a direct, seemingly sincere apology. What did 00:20:33.299 --> 00:20:35.720 he say? Admitted he was ignorant about the situation 00:20:35.720 --> 00:20:38.380 in Afghanistan. Said the timing was completely 00:20:38.380 --> 00:20:40.019 out of line. He didn't try to hide behind it. 00:20:40.039 --> 00:20:42.819 It was just a joke. He owned it. Seemed to. Said 00:20:42.819 --> 00:20:45.259 things like, I honestly said things in retrospect 00:20:45.259 --> 00:20:48.099 I completely regret. and he vowed he'd never 00:20:48.099 --> 00:20:50.720 appear on Red Eye again. It was a full mea culpa, 00:20:50.940 --> 00:20:53.380 a real wake -up call about the limits of edgy 00:20:53.380 --> 00:20:55.740 comedy when it bumps up against raw national 00:20:55.740 --> 00:20:59.640 pain. Hashtag have DJ Z -Sive. Outro. Okay, so 00:20:59.640 --> 00:21:01.759 let's try and wrap this up. Looking back at this 00:21:01.759 --> 00:21:03.940 whole deep dive on Doug Benson, what are the 00:21:03.940 --> 00:21:05.900 big takeaways? For me, it's that incredible consistency, 00:21:06.220 --> 00:21:08.920 the prolific output, 10 albums, the super long 00:21:08.920 --> 00:21:11.319 -running podcast, the cannabis shows, all very 00:21:11.319 --> 00:21:13.759 focused, very structured. Definitely the focus. 00:21:13.799 --> 00:21:16.400 And his ability to fuse that pop culture knowledge 00:21:16.400 --> 00:21:19.400 with the personal advocacy, making his unique 00:21:19.400 --> 00:21:21.960 selling proposition. He really rode the wave 00:21:21.960 --> 00:21:24.420 of new media. Podcasts, especially. Yeah, he 00:21:24.420 --> 00:21:27.240 mastered that space. But the career also shows 00:21:27.240 --> 00:21:30.119 maybe the power of finding that very specific 00:21:30.119 --> 00:21:33.099 niche, right? Absolutely. Marrying comedy with 00:21:33.099 --> 00:21:35.160 a lifestyle choice built him this incredibly 00:21:35.160 --> 00:21:38.359 dedicated fan base. But as the red eye thing 00:21:38.359 --> 00:21:42.589 showed, there are real world lines. Satire has 00:21:42.589 --> 00:21:45.210 boundaries, especially when it touches on things 00:21:45.210 --> 00:21:47.789 like national sacrifice or tragedy. You can't 00:21:47.789 --> 00:21:49.789 always play dumb. It highlights the responsibility 00:21:49.789 --> 00:21:51.930 that comes with having that platform, even if 00:21:51.930 --> 00:21:54.710 your platform is built on being irreverent. Right. 00:21:54.990 --> 00:21:56.950 Which leads us to that final thought, something 00:21:56.950 --> 00:21:59.690 for you, the listener, to chew on. It ties back 00:21:59.690 --> 00:22:02.390 to the high court. The legally binding rulings 00:22:02.390 --> 00:22:05.009 from the high judge. Exactly. Considering he 00:22:05.009 --> 00:22:07.930 actually had the power to make real legally binding 00:22:07.930 --> 00:22:11.730 decisions in that community context. What responsibility 00:22:11.730 --> 00:22:14.349 does a comedian take on when their persona, their 00:22:14.349 --> 00:22:16.930 act, crosses over into roles usually reserved 00:22:16.930 --> 00:22:19.970 for serious authority figures? Even if the whole 00:22:19.970 --> 00:22:22.369 thing is presented as comedy, does the context 00:22:22.369 --> 00:22:24.470 erase the responsibility that comes with the 00:22:24.470 --> 00:22:26.509 power? Yeah. What stands out to you about that 00:22:26.509 --> 00:22:29.740 blurring of lines? The comedian as judge. Literally. 00:22:29.759 --> 00:22:32.099 Where does the performance end and the real world 00:22:32.099 --> 00:22:34.619 impact begin? Something to think about. Definitely. 00:22:34.779 --> 00:22:37.519 How media keeps playing with those boundaries 00:22:37.519 --> 00:22:40.599 between entertainment and authority. Always evolving. 00:22:41.200 --> 00:22:43.259 We'll catch you next time for another deep dive.