WEBVTT 00:00:00.000 --> 00:00:03.439 Welcome back to the Deep Dive. Today we are opening 00:00:03.439 --> 00:00:07.200 up a file that is, frankly, massive. It's a story 00:00:07.200 --> 00:00:09.900 that sits right at the intersection of pop culture, 00:00:10.060 --> 00:00:12.720 business history, the sexual revolution, and, 00:00:12.779 --> 00:00:15.660 well, some truly dark, complicated controversy. 00:00:15.859 --> 00:00:18.379 It really does. We are talking about the man 00:00:18.379 --> 00:00:21.260 in the silk pajamas, the pipe -smoking philosopher 00:00:21.260 --> 00:00:24.589 of the centerfold, Hugh Hefner. It is a massive 00:00:24.589 --> 00:00:27.030 file indeed. And I think for most people, the 00:00:27.030 --> 00:00:29.410 image of Hefner is so cemented. You know, the 00:00:29.410 --> 00:00:31.850 mansion, the bunnies, the captain's hat. Totally. 00:00:32.170 --> 00:00:34.429 The whole persona. Exactly. And it's easy to 00:00:34.429 --> 00:00:36.909 miss just how profoundly he influenced and really 00:00:36.909 --> 00:00:39.590 reflected the 20th century. Right. We're not 00:00:39.590 --> 00:00:41.350 just looking at a magazine publisher here. We're 00:00:41.350 --> 00:00:43.810 looking at a figure who, I mean, he just encapsulates 00:00:43.810 --> 00:00:46.070 the complexities and the contradictions of American 00:00:46.070 --> 00:00:49.670 culture from the 1950s all the way to the 2010s. 00:00:49.670 --> 00:00:52.409 Exactly. And our mission today is to move past 00:00:52.409 --> 00:00:54.590 that caricature. We want to unpack the source 00:00:54.590 --> 00:00:56.719 material. And we have a lot of it. We've got 00:00:56.719 --> 00:00:58.840 biographical records, corporate histories, and 00:00:58.840 --> 00:01:01.439 then the very recent, very critical documentaries 00:01:01.439 --> 00:01:04.680 and memoirs. We want to understand how this guy 00:01:04.680 --> 00:01:08.140 actually happened. How did a conservative boy 00:01:08.140 --> 00:01:11.840 from the Midwest build an empire that sparked 00:01:11.840 --> 00:01:14.760 a revelation? And then leave behind a legacy 00:01:14.760 --> 00:01:17.620 that is, to put it mildly, deeply polarized. 00:01:17.939 --> 00:01:20.439 That is the key tension we need to explore. I 00:01:20.439 --> 00:01:22.219 mean, you're right. We have sources ranging from 00:01:22.219 --> 00:01:25.980 the official historical record of his civil rights 00:01:25.980 --> 00:01:28.319 advocacy. Which is significant. Very significant. 00:01:28.420 --> 00:01:30.159 And then on the other end of the spectrum, you 00:01:30.159 --> 00:01:32.840 have the allegations that surfaced in the Secrets 00:01:32.840 --> 00:01:35.540 of Playboy docuseries after his death. Right. 00:01:35.620 --> 00:01:38.060 So we're covering the rise, the philosophy, and 00:01:38.060 --> 00:01:40.379 the disturbing criticism. That's a whole package. 00:01:40.540 --> 00:01:43.090 And to get us hooked. I found one detail in the 00:01:43.090 --> 00:01:45.750 research that just, it just blew my mind. The 00:01:45.750 --> 00:01:48.909 entire Playboy empire, the mansion, the brand. 00:01:49.709 --> 00:01:51.769 The cultural shift. Yeah. It might never have 00:01:51.769 --> 00:01:54.090 happened if a young copywriter in Chicago had 00:01:54.090 --> 00:01:56.549 just been given a $5 raise. It's the butterfly 00:01:56.549 --> 00:01:59.769 effect in action, isn't it? That $5. It really 00:01:59.769 --> 00:02:02.170 represents one of the most significant pivot 00:02:02.170 --> 00:02:05.549 points in media history. It really is. But before 00:02:05.549 --> 00:02:07.430 we get to that $5, let's go back even further 00:02:07.430 --> 00:02:10.069 because the expert context here is surprising. 00:02:10.069 --> 00:02:12.349 Oh, yeah. You'd think the man, synonymous with 00:02:12.349 --> 00:02:16.110 sexual liberation, came from some wild bohemian 00:02:16.110 --> 00:02:18.990 background. But the sources say it was the... 00:02:18.990 --> 00:02:21.530 exact opposite quite the opposite i mean if you 00:02:21.530 --> 00:02:23.750 look at his origins hugh marston hefner was born 00:02:23.750 --> 00:02:27.650 in chicago april 9 1926 his parents glenn and 00:02:27.650 --> 00:02:30.370 grace were from nebraska okay and hefner himself 00:02:30.370 --> 00:02:32.909 described the family atmosphere in just three 00:02:32.909 --> 00:02:38.069 words conservative midwestern methodist conservative 00:02:38.069 --> 00:02:40.889 midwestern methodist that is a far cry from the 00:02:40.889 --> 00:02:43.430 grotto at the playboy mansion a very far cry 00:02:43.979 --> 00:02:45.860 It sounds like a house where fun went to die. 00:02:46.000 --> 00:02:48.340 It was incredibly strict. And it goes deeper 00:02:48.340 --> 00:02:51.520 than just being strict. Get this. He was actually 00:02:51.520 --> 00:02:54.240 a direct descendant of William Bradford. The 00:02:54.240 --> 00:02:56.479 Plymouth governor. The Plymouth governor. We 00:02:56.479 --> 00:02:59.120 are talking about literal Puritan lineage here. 00:02:59.259 --> 00:03:01.419 We aren't just using Puritan as an adjective. 00:03:01.539 --> 00:03:04.340 It's in the bloodline. And his mother, Grace, 00:03:04.639 --> 00:03:07.219 she actually wanted him to be a missionary? A 00:03:07.219 --> 00:03:09.960 missionary? Well, I guess in a weird way he became 00:03:09.960 --> 00:03:12.199 one. You could say that. Just for a very different 00:03:12.199 --> 00:03:14.620 religion. He was proselytizing a lifestyle, for 00:03:14.620 --> 00:03:18.060 sure. But despite the religious pressure, there 00:03:18.060 --> 00:03:20.520 was clearly an intellectual engine running there 00:03:20.520 --> 00:03:23.009 from the start. We see in the records that he 00:03:23.009 --> 00:03:25.509 had a very high IQ. Yeah, I saw that. It's often 00:03:25.509 --> 00:03:28.370 cited around a 1 in 52. But even if we stick 00:03:28.370 --> 00:03:30.830 just to the academic record, he was incredibly 00:03:30.830 --> 00:03:33.530 efficient. He graduated from the University of 00:03:33.530 --> 00:03:36.169 Illinois at Urbana -Champaign in just two and 00:03:36.169 --> 00:03:38.930 a half years. Two and a half years. That's fast. 00:03:39.210 --> 00:03:40.969 He must have just been powering through those 00:03:40.969 --> 00:03:45.210 credits. He was. He graduated in 1949. And look 00:03:45.210 --> 00:03:49.039 at his degree. A Bachelor of Arts in Psychology 00:03:49.039 --> 00:03:52.259 with a double minor in Creative Writing and Art. 00:03:52.400 --> 00:03:54.580 Okay, if you were trying to build a CEO for a 00:03:54.580 --> 00:03:57.060 lifestyle magazine in a lab. Those are the three 00:03:57.060 --> 00:03:58.620 ingredients. Those are the three ingredients 00:03:58.620 --> 00:04:01.419 you would pick. Totally. Psychology to understand 00:04:01.419 --> 00:04:03.699 what men want, creative writing to give it a 00:04:03.699 --> 00:04:06.599 voice, and art to make it look good. Exactly. 00:04:06.800 --> 00:04:08.620 And we shouldn't forget his time in the service. 00:04:08.879 --> 00:04:11.560 He was in the Army during World War II from 1944 00:04:11.560 --> 00:04:15.400 to 1946. But he wasn't, you know, on the front 00:04:15.400 --> 00:04:17.759 lines holding a rifle. Right. The records say 00:04:17.759 --> 00:04:19.759 he was a writer. She served as a writer for a 00:04:19.759 --> 00:04:22.689 military newspaper. And this is crucial because 00:04:22.689 --> 00:04:25.470 it shows that his inclination toward publishing 00:04:25.470 --> 00:04:29.009 and shaping a narrative was there early on. He 00:04:29.009 --> 00:04:32.050 was observing, writing and editing long before 00:04:32.050 --> 00:04:34.449 he had a business plan. He was learning how to 00:04:34.449 --> 00:04:36.910 communicate with men in uniform, which, you know, 00:04:36.910 --> 00:04:38.730 became a huge part of his early demographic. 00:04:39.029 --> 00:04:40.990 That makes so much sense. OK, so let's fast forward 00:04:40.990 --> 00:04:43.170 to the moment that changed everything. The catalyst. 00:04:43.410 --> 00:04:46.370 Yeah. It's 1952. He's back in Chicago. He's working 00:04:46.370 --> 00:04:48.850 as a copywriter for Esquire magazine. The big 00:04:48.850 --> 00:04:50.920 one. Which was the big men's magazine. of the 00:04:50.920 --> 00:04:54.100 time. Esquire was the titan. It was sophisticated, 00:04:54.519 --> 00:04:57.540 literary, the absolute ceiling for men's journalism. 00:04:57.959 --> 00:05:00.579 Hefner was just a cog in the machine. Very small 00:05:00.579 --> 00:05:03.360 cog. A very small cog. But the magazine was moving 00:05:03.360 --> 00:05:06.319 its offices to New York and Hefner was willing 00:05:06.319 --> 00:05:08.980 to go, but he did the math on the cost of living 00:05:08.980 --> 00:05:11.839 difference between Chicago and New York. He was 00:05:11.839 --> 00:05:14.839 practical. Very. So he went to his bosses and 00:05:14.839 --> 00:05:17.079 he asked for a raise to cover that difference. 00:05:17.379 --> 00:05:20.209 A $5 raise. Five dollars. Just five dollars. 00:05:20.470 --> 00:05:22.769 And they denied it. Can you imagine being the 00:05:22.769 --> 00:05:26.069 guy who said no to that? Sorry, Hugh. Five bucks 00:05:26.069 --> 00:05:28.870 is too rich for our blood. And because of that, 00:05:28.970 --> 00:05:33.290 he quits. He quits. And this is a classic entrepreneurial 00:05:33.290 --> 00:05:37.269 pivot fueled by rejection. He decides if he can't 00:05:37.269 --> 00:05:39.550 work for the best men's magazine, he'll create 00:05:39.550 --> 00:05:42.269 his own. Right. But he was broke. He didn't have 00:05:42.269 --> 00:05:45.810 a fortune. The financing of Playboy is a story 00:05:45.810 --> 00:05:48.189 of just scrapping together pennies. I love this 00:05:48.189 --> 00:05:49.709 part of the research. It wasn't some venture 00:05:49.709 --> 00:05:52.430 capital firm writing a massive check. He took 00:05:52.430 --> 00:05:55.290 out a $600 mortgage on his furniture. A risky 00:05:55.290 --> 00:05:58.569 move. If it failed, he loses his couch. Extremely. 00:05:58.569 --> 00:06:00.870 And then he went around raising money from anyone 00:06:00.870 --> 00:06:05.009 he could find. He got $8 ,000 total from 45 different 00:06:05.009 --> 00:06:07.470 investors. That is a lot of door knocking, a 00:06:07.470 --> 00:06:10.709 lot of pitches. It is. But there's one investor 00:06:10.709 --> 00:06:14.290 that stands out. His mom. Grace Hefner, the woman 00:06:14.290 --> 00:06:16.649 who wanted him to be a missionary. She gave him 00:06:16.649 --> 00:06:20.370 $1 ,000. That was a huge chunk in the seed money. 00:06:20.529 --> 00:06:23.110 A massive chunk. And there's a quote from Hefner 00:06:23.110 --> 00:06:25.709 later in life, I think he told E! back in 2006, 00:06:26.069 --> 00:06:28.569 where he said, not because she believed in the 00:06:28.569 --> 00:06:31.050 venture, but because she believed in her son. 00:06:31.610 --> 00:06:34.509 That is such a powerful distinction. She likely 00:06:34.509 --> 00:06:36.430 disapproved of the content. I mean, you have 00:06:36.430 --> 00:06:39.569 to remember, this is the Puritan Methodist mother 00:06:39.569 --> 00:06:41.730 who probably viewed this as sinful. Absolutely. 00:06:41.990 --> 00:06:44.689 But the bond with her son overrode the moral 00:06:44.689 --> 00:06:47.949 objection. That $1 ,000 was the difference maker. 00:06:48.209 --> 00:06:50.850 So he has the money. He has the idea. Originally, 00:06:50.889 --> 00:06:53.560 he was going to call it stag party. Which implies 00:06:53.560 --> 00:06:56.420 a very different tone, doesn't it? Stag party 00:06:56.420 --> 00:06:59.399 sounds underground, maybe a bit seedier, like 00:06:59.399 --> 00:07:01.139 something you hide in the garage. Yeah, a bit 00:07:01.139 --> 00:07:03.600 more like a backroom thing. Exactly. Playboy 00:07:03.600 --> 00:07:05.899 suggests something more sophisticated, more about 00:07:05.899 --> 00:07:08.339 a lifestyle. It suggests you are out in the open, 00:07:08.379 --> 00:07:10.740 enjoying the finer things. It's aspirational. 00:07:10.879 --> 00:07:14.800 Very. So, December 1953, issue number one hits 00:07:14.800 --> 00:07:17.759 the stands. We have to talk about the cover. 00:07:18.000 --> 00:07:20.480 You can't tell the story of Playboy without talking 00:07:20.480 --> 00:07:23.040 about Marilyn Monroe. But the context here is 00:07:23.040 --> 00:07:25.839 often misunderstood. Right. Hefner didn't commission 00:07:25.839 --> 00:07:28.259 a shoot with Marilyn for the first issue. Right. 00:07:28.319 --> 00:07:30.319 They never even met. Correct. They never met. 00:07:30.680 --> 00:07:33.699 Hefner found a nude calendar shoot she had done 00:07:33.699 --> 00:07:36.620 back in 1949 when she was struggling and working 00:07:36.620 --> 00:07:38.800 under a pseudonym. So this was old material. 00:07:39.120 --> 00:07:41.699 Very old material. He bought the rights to those 00:07:41.699 --> 00:07:44.189 photos from the calendar company. So Marilyn 00:07:44.189 --> 00:07:46.430 Monroe was the face that launched the empire, 00:07:46.730 --> 00:07:50.209 but she wasn't paid a dime by Playboy or Hefner 00:07:50.209 --> 00:07:53.269 for that specific usage in the magazine. That 00:07:53.269 --> 00:07:55.550 feels like a foreshadowing of the criticisms 00:07:55.550 --> 00:07:58.670 we'll get to later profiting off women without 00:07:58.670 --> 00:08:01.029 them necessarily having control or fair compensation 00:08:01.029 --> 00:08:03.500 in the moment. It certainly establishes a dynamic. 00:08:03.839 --> 00:08:06.720 It was arbitrage, you know, buying a distressed 00:08:06.720 --> 00:08:09.279 asset, which were the old photos, and repackaging 00:08:09.279 --> 00:08:12.319 them as a premium product. But from a business 00:08:12.319 --> 00:08:15.139 perspective, it was lightning in a bottle. There 00:08:15.139 --> 00:08:17.339 is a fascinating detail about that first issue. 00:08:17.800 --> 00:08:20.420 It didn't have a date on the cover. Because he 00:08:20.420 --> 00:08:22.560 didn't think there'd be a second one. Precisely. 00:08:22.839 --> 00:08:25.860 He was confident enough to launch, but realistic 00:08:25.860 --> 00:08:27.759 enough to think this might be a one and done 00:08:27.759 --> 00:08:30.819 failure. He produced it on his kitchen table. 00:08:30.899 --> 00:08:33.620 On his kitchen table. Yes. And instead, it sold 00:08:33.620 --> 00:08:37.100 more than 50 ,000 copies. Wow. The empire was 00:08:37.100 --> 00:08:40.019 born essentially overnight. So Playboy arrives. 00:08:40.379 --> 00:08:43.159 And suddenly, Hugh Hefner isn't just a copywriter 00:08:43.159 --> 00:08:46.460 anymore. He's a publisher. But he didn't just 00:08:46.460 --> 00:08:49.419 want to sell nudity. I think that's a misconception 00:08:49.419 --> 00:08:51.779 people have if they only know the brand from 00:08:51.779 --> 00:08:54.279 the stickers on cars. That's a huge misconception. 00:08:54.440 --> 00:08:57.039 He was selling a philosophy. This is where we 00:08:57.039 --> 00:08:59.379 need to widen the lens. If you look at the source 00:08:59.379 --> 00:09:01.799 material, specifically the Playboy philosophy, 00:09:02.000 --> 00:09:04.340 which was a sprawling series of editorials he 00:09:04.340 --> 00:09:07.820 wrote, Hefner saw himself as a crusader for individual 00:09:07.820 --> 00:09:11.539 rights. A crusader. Yes. He wasn't just a pornographer 00:09:11.539 --> 00:09:13.419 in his own mind. He was a libertarian activist. 00:09:13.519 --> 00:09:16.019 He wrote thousands upon thousands of words arguing 00:09:16.019 --> 00:09:18.480 against censorship and for personal freedom. 00:09:18.700 --> 00:09:20.799 And he used the magazine to push that. He expanded 00:09:20.799 --> 00:09:22.960 into multimedia really quickly, too. Almost immediately. 00:09:23.340 --> 00:09:25.639 With Playboy's Penthouse in the late 50s and 00:09:25.639 --> 00:09:28.759 Playboy After Dark in the late 60s, these were 00:09:28.759 --> 00:09:31.519 TV shows where he'd host parties, and the vibe 00:09:31.519 --> 00:09:34.500 was very bon vivant. Paul Vivant is the perfect 00:09:34.500 --> 00:09:38.240 term. He was curating a lifestyle of jazz, conversation, 00:09:38.720 --> 00:09:41.779 and sophistication. It was aspirational. He was 00:09:41.779 --> 00:09:44.019 telling men, this is what your life could be. 00:09:44.139 --> 00:09:46.500 You can be this cool. You can be this cool. But 00:09:46.500 --> 00:09:48.720 what's fascinating, and what really gets lost 00:09:48.720 --> 00:09:51.259 in the shuffle, is how he used that platform 00:09:51.259 --> 00:09:53.980 for civil rights. This is a part of the legacy 00:09:53.980 --> 00:09:56.080 that often surprises people. Yeah, let's talk 00:09:56.080 --> 00:09:58.090 about Dick Gregory. Dick Gregory, the legendary 00:09:58.090 --> 00:10:01.250 comedian and activist. In 1961, the entertainment 00:10:01.250 --> 00:10:04.230 world was still largely segregated. Very segregated. 00:10:04.549 --> 00:10:07.330 Hefner saw Gregory performing at a bar, the Herman 00:10:07.330 --> 00:10:10.629 Roberts Show Bar in Chicago. He was blown away 00:10:10.629 --> 00:10:13.269 by the set. He hired Gregory to work at the Chicago 00:10:13.269 --> 00:10:15.490 Playboy Club. And that was a big deal. It was 00:10:15.490 --> 00:10:18.450 a huge deal. Gregory himself attributed the launch 00:10:18.450 --> 00:10:21.389 of his massive career to that night. Hefner put 00:10:21.389 --> 00:10:23.330 him in front of a predominantly white audience, 00:10:23.450 --> 00:10:25.830 which was a significant, somewhat radical move 00:10:25.830 --> 00:10:29.470 in 1961. And it wasn't just comedians. The Playboy 00:10:29.470 --> 00:10:33.000 interview became a serious... journalistic institution. 00:10:33.320 --> 00:10:36.399 A very serious one. And there is one interview 00:10:36.399 --> 00:10:39.740 that stands out as maybe the most audacious thing 00:10:39.740 --> 00:10:42.860 a magazine editor could do in the 1960s. The 00:10:42.860 --> 00:10:45.059 interview with George Lincoln Rockwell. This 00:10:45.059 --> 00:10:47.379 is a critical moment in media history. I mean, 00:10:47.399 --> 00:10:48.899 you have to remember who this guy was. George 00:10:48.899 --> 00:10:50.960 Lincoln Rockwell was the founder of the American 00:10:50.960 --> 00:10:53.919 Nazi Party. A hateful, dangerous figure. Absolutely. 00:10:54.259 --> 00:10:56.820 And Hefner wanted to interview him to expose 00:10:56.820 --> 00:11:00.220 his ideas. But he didn't send a white reporter. 00:11:00.879 --> 00:11:03.399 He sent Alex Haley. The author of Roots. Before 00:11:03.399 --> 00:11:06.519 Roots was published, yes. A black man sent to 00:11:06.519 --> 00:11:09.299 interview the head of the Nazi party. Just imagine 00:11:09.299 --> 00:11:11.460 that room. The tension in that room must have 00:11:11.460 --> 00:11:13.580 been suffocating. The sources say Rockwell was 00:11:13.580 --> 00:11:15.399 shocked when Haley showed up. He only agreed 00:11:15.399 --> 00:11:17.460 to the meeting after ensuring Haley wasn't Jewish. 00:11:17.720 --> 00:11:20.279 Wow. But get this. Rockwell kept a handgun on 00:11:20.279 --> 00:11:22.220 the table throughout the entire interview. A 00:11:22.220 --> 00:11:24.440 gun on the table. And Haley just sat there and 00:11:24.440 --> 00:11:26.759 did the job. He did. And Hefner published it. 00:11:26.860 --> 00:11:29.379 It demonstrates Hefner's absolute commitment 00:11:29.379 --> 00:11:32.460 to a very specific interpretation of the First 00:11:32.460 --> 00:11:35.259 Amendment. Right. He believed that bad ideas 00:11:35.259 --> 00:11:37.299 should be dragged into the light and debated, 00:11:37.539 --> 00:11:40.820 not hidden. He felt that if you let a hateful 00:11:40.820 --> 00:11:43.399 man speak long enough, he would reveal his own 00:11:43.399 --> 00:11:46.419 ignorance. He applied that to LGBTQ rights, too, 00:11:46.519 --> 00:11:48.580 way before it was mainstream. There's the story 00:11:48.580 --> 00:11:51.000 of the crooked man. Yes. A science fiction story 00:11:51.000 --> 00:11:54.419 by Charles Beaumont. It was 1955. And you have. 00:11:54.480 --> 00:11:56.960 to put yourself in the context of 1955 America, 00:11:57.360 --> 00:12:00.620 the story depicted a world where homosexuality 00:12:00.620 --> 00:12:03.120 was the norm and straight men were the ones being 00:12:03.120 --> 00:12:05.379 persecuted. A total flip of the script. A total 00:12:05.379 --> 00:12:07.799 flip designed to show the cruelty of prejudice 00:12:07.799 --> 00:12:11.419 and Esquire rejected it. Esquire said no again. 00:12:11.559 --> 00:12:13.820 They really missed out on a lot of cultural milestones. 00:12:14.120 --> 00:12:16.419 They did. Hefner said yes. He published it in 00:12:16.419 --> 00:12:19.139 Playboy and naturally the angry letters poured 00:12:19.139 --> 00:12:22.200 in. Oh, I'm sure. Subscribers were furious. But 00:12:22.200 --> 00:12:24.950 Hefner's response to those letters is, classic 00:12:24.950 --> 00:12:27.850 Playboy philosophy. He wrote, and this is a direct 00:12:27.850 --> 00:12:31.190 quote, if it was wrong to persecute heterosexuals 00:12:31.190 --> 00:12:33.629 in a homosexual society, then the reverse was 00:12:33.629 --> 00:12:35.909 wrong, too. That is surprisingly progressive 00:12:35.909 --> 00:12:39.190 for 1955. It is. It shows that he was willing 00:12:39.190 --> 00:12:41.889 to alienate his own customer base to make a point 00:12:41.889 --> 00:12:44.330 about individual liberty. He wasn't just following 00:12:44.330 --> 00:12:46.409 the market. He was trying to lead it. But of 00:12:46.409 --> 00:12:48.730 course, his version of liberty also got him into 00:12:48.730 --> 00:12:51.649 legal trouble. He was arrested in 1963, right? 00:12:51.769 --> 00:12:55.129 He was. The charge was promoting obscene literature. 00:12:55.309 --> 00:12:57.870 It was an issue featuring Jane Mansfield. And 00:12:57.870 --> 00:13:00.450 the photos, they showed her in bed with a man 00:13:00.450 --> 00:13:02.470 present, which was apparently the line crosser 00:13:02.470 --> 00:13:04.389 for the authorities at the time. That was the 00:13:04.389 --> 00:13:06.919 problem. Not the nudity itself. It was the contest, 00:13:07.000 --> 00:13:09.700 the implication of sexual activity. The case 00:13:09.700 --> 00:13:11.539 went to trial and it resulted in a hung jury, 00:13:11.679 --> 00:13:14.299 but it solidified his image as a martyr for the 00:13:14.299 --> 00:13:16.399 First Amendment. He spun the arrest into gold. 00:13:16.519 --> 00:13:19.620 Absolutely. He became the face of the fight against 00:13:19.620 --> 00:13:21.299 censorship. And he put his money where his mouth 00:13:21.299 --> 00:13:23.600 was. He started the Hugh M. Hefner Foundation 00:13:23.600 --> 00:13:27.559 in 1964. Right. And here's a fact I bet most 00:13:27.559 --> 00:13:30.100 listeners have no idea about. We talk about the 00:13:30.100 --> 00:13:33.559 sexual revolution. But Hefner's foundation actually 00:13:33.559 --> 00:13:36.220 funded the prototype for the rape kit. It's a 00:13:36.220 --> 00:13:38.919 detail that often gets lost. It's so contradictory 00:13:38.919 --> 00:13:42.399 to the later image. But yes, a woman named Margie 00:13:42.399 --> 00:13:44.500 Goddard developed the prototype to help gather 00:13:44.500 --> 00:13:47.019 evidence for sexual assault cases, and the Hefner 00:13:47.019 --> 00:13:49.220 Foundation provided the funding to make that 00:13:49.220 --> 00:13:51.799 happen. So strange. It's a very complicated piece 00:13:51.799 --> 00:13:53.840 of the puzzle, considering the accusations we'll 00:13:53.840 --> 00:13:56.659 discuss later, but it is a matter of record that 00:13:56.659 --> 00:13:59.019 the foundation supported that development when 00:13:59.019 --> 00:14:01.320 others wouldn't. And on a lighter note, he also 00:14:01.320 --> 00:14:04.360 saved the Hollywood sign. Twice, actually. In 00:14:04.360 --> 00:14:07.379 the late 70s, the sign was crumbling. He organized 00:14:07.379 --> 00:14:10.100 a gala at the mansion. He auctioned off the letters. 00:14:10.200 --> 00:14:13.480 He bought the letter Y himself for $27 ,000. 00:14:13.980 --> 00:14:16.940 The Y in Hollywood is his. It is. He really saw 00:14:16.940 --> 00:14:18.779 himself as the guardian of Hollywood dreams. 00:14:19.159 --> 00:14:21.899 He loved the mythology of Los Angeles almost 00:14:21.899 --> 00:14:23.960 as much as he loved his own mythology. So we 00:14:23.960 --> 00:14:26.799 have the public figure, the crusader, the publisher, 00:14:27.019 --> 00:14:30.039 the guy buying the Y on the Hollywood sign. But 00:14:30.039 --> 00:14:32.480 we have to talk about the man himself, the guy 00:14:32.480 --> 00:14:35.019 in the mansion. Yeah. Because the Hef persona. 00:14:35.710 --> 00:14:39.289 the pipe, the silk pajamas, that was a carefully 00:14:39.289 --> 00:14:42.049 constructed image. It was a uniform. Just like 00:14:42.049 --> 00:14:44.750 a general wears a uniform, Hefner wore the pajamas. 00:14:45.110 --> 00:14:47.250 It signaled that he was always at leisure, yet 00:14:47.250 --> 00:14:49.549 always in control. It blurred the lines between 00:14:49.549 --> 00:14:53.269 work and play. And then in 1975, he moved his 00:14:53.269 --> 00:14:55.769 operations from Chicago to Los Angeles permanently, 00:14:56.110 --> 00:14:59.049 establishing Playboy Mansion West. And the relationships. 00:14:59.429 --> 00:15:01.330 Wow. The source material here is like a soap 00:15:01.330 --> 00:15:03.429 opera. It starts with Mildred Williams, his first 00:15:03.429 --> 00:15:05.690 wife. And this relationship really explains the 00:15:05.690 --> 00:15:08.250 psychology of the bachelor era. Mildred and Hugh 00:15:08.250 --> 00:15:10.509 were college sweethearts. They were the typical 00:15:10.509 --> 00:15:13.690 1940s couple. The ideal. The ideal. But before 00:15:13.690 --> 00:15:15.370 the wedding, Mildred confessed something that 00:15:15.370 --> 00:15:17.870 broke him. She had an affair while he was away 00:15:17.870 --> 00:15:20.049 in the army. He called it the most devastating 00:15:20.049 --> 00:15:23.970 moment of my life. Right. And out of guilt, Mildred, 00:15:24.049 --> 00:15:26.009 who we should remember was also trying to navigate 00:15:26.009 --> 00:15:28.730 a very conservative marriage, she allowed him 00:15:28.730 --> 00:15:30.809 to sleep with other women. She allowed it. She 00:15:30.809 --> 00:15:32.850 allowed it. She thought it would balance the 00:15:32.850 --> 00:15:34.870 scales and save the marriage. That sounds like 00:15:34.870 --> 00:15:37.679 a recipe for disaster. It was. They divorced 00:15:37.679 --> 00:15:41.360 in 1959. And experts and biographers suggest 00:15:41.360 --> 00:15:44.159 this betrayal launched Hefner into his bachelor 00:15:44.159 --> 00:15:46.720 era. It was almost a reaction to the failure 00:15:46.720 --> 00:15:49.460 of the traditional romantic ideal. He swung the 00:15:49.460 --> 00:15:51.820 pendulum. He swung the pendulum to the absolute 00:15:51.820 --> 00:15:54.779 other extreme. If the good girl could hurt him, 00:15:54.860 --> 00:15:57.000 he would surround himself with bad girls and 00:15:57.000 --> 00:15:59.700 control the environment completely. And he admitted 00:15:59.700 --> 00:16:02.240 to being involved with 11 out of 12 months worth 00:16:02.240 --> 00:16:04.580 of planates in some years. It was a production 00:16:04.580 --> 00:16:07.860 line in a way. He even experimented with bisexuality, 00:16:07.879 --> 00:16:10.159 which he acknowledged in 1971. He was trying 00:16:10.159 --> 00:16:12.779 everything. He was consuming life and people. 00:16:12.879 --> 00:16:15.200 He was running at 100 miles per hour, fueled 00:16:15.200 --> 00:16:18.879 by Pepsi and other things. But the party hit 00:16:18.879 --> 00:16:23.120 a wall in 1985. He had a stroke at age 58. The 00:16:23.120 --> 00:16:25.419 stroke seems like a major turning point. A huge 00:16:25.419 --> 00:16:27.940 one. He tones it down. He hands over the business 00:16:27.940 --> 00:16:30.500 operations to his daughter, Christy, and then 00:16:30.500 --> 00:16:32.659 he does something unexpected. He gets married 00:16:32.659 --> 00:16:36.039 again. To Kimberly Conrad. And there is a 36 00:16:36.039 --> 00:16:38.539 -year age gap there. But for a while, the Playboy 00:16:38.539 --> 00:16:41.080 Mansion turned into a family home. Really? Yes. 00:16:41.240 --> 00:16:43.580 The tennis courts were used for tennis, not parties. 00:16:43.720 --> 00:16:45.860 There were toys on the lawn. He tried to play 00:16:45.860 --> 00:16:48.019 the role of the traditional father, but they 00:16:48.019 --> 00:16:51.480 separated in 1998. And that ushered in the era 00:16:51.480 --> 00:16:53.960 that a lot of our younger listeners might recognize. 00:16:54.320 --> 00:16:57.139 The Girls Next Door era. The reality show. Holly 00:16:57.139 --> 00:17:00.159 Madison, Bridget Marquardt, Kendra Wilkinson. 00:17:00.240 --> 00:17:04.000 This was a pop culture resurgence. In the 2000s, 00:17:04.000 --> 00:17:06.839 Hefner became this sort of lovable, eccentric 00:17:06.839 --> 00:17:09.980 grandpa figure on the E! Network. But looking 00:17:09.980 --> 00:17:12.759 back, the dynamic was so strange. Incredibly 00:17:12.759 --> 00:17:14.519 strange. He was living with up to seven women 00:17:14.519 --> 00:17:16.960 at once, but the show focused on the main trio. 00:17:17.039 --> 00:17:19.900 It was branded as fun and campy, but the power 00:17:19.900 --> 00:17:23.599 dynamic was incredibly skewed. And finally, the 00:17:23.599 --> 00:17:26.759 last marriage to Crystal Harris. The runaway 00:17:26.759 --> 00:17:29.769 bride incident. Oh, the timing was excruciating 00:17:29.769 --> 00:17:32.849 for them. Crystal broke off the engagement five 00:17:32.849 --> 00:17:35.950 days before the wedding in 2011. The problem 00:17:35.950 --> 00:17:39.130 was the July issue of Playboy had already been 00:17:39.130 --> 00:17:41.869 printed and shipped. And the cover said, Mrs. 00:17:42.049 --> 00:17:44.329 Crystal Hefner. Introducing America's princess, 00:17:44.670 --> 00:17:47.599 Mrs. Crystal Hefner. You couldn't write a more 00:17:47.599 --> 00:17:49.779 awkward script. They did eventually reconcile 00:17:49.779 --> 00:17:53.180 and married on New Year's Eve 2012, staying together 00:17:53.180 --> 00:17:55.640 until his death. Okay, so we've seen the rise, 00:17:55.900 --> 00:17:58.859 the philosophy, the personal relationship. But 00:17:58.859 --> 00:18:01.880 now, now we have to turn the page to the section 00:18:01.880 --> 00:18:04.660 of the file that is much harder to read. Because 00:18:04.660 --> 00:18:07.720 while Hefner views himself as a liberator, there 00:18:07.720 --> 00:18:09.759 are plenty of people who viewed him as an exploiter. 00:18:10.109 --> 00:18:12.049 And this is where the conversation shifts from 00:18:12.049 --> 00:18:14.569 legacy to liability. The criticism isn't just 00:18:14.569 --> 00:18:16.769 a footnote. It is central to understanding the 00:18:16.769 --> 00:18:18.369 whole picture. Let's start with the feminist 00:18:18.369 --> 00:18:21.349 critique. This goes way back. Way back. In 1970, 00:18:21.609 --> 00:18:24.410 Hefner wrote an internal memo attacking militant 00:18:24.410 --> 00:18:27.970 feminists. He saw them as enemies of his romantic 00:18:27.970 --> 00:18:30.609 boy -girl society. He felt they were trying to 00:18:30.609 --> 00:18:33.789 ruin the party. He truly believed that Playboy 00:18:33.789 --> 00:18:37.480 adored women. But the feminists argued the party 00:18:37.480 --> 00:18:39.799 was rigged. Rigged for whom? Rigged for him. 00:18:40.680 --> 00:18:43.180 Suzanne Moore, writing for The Guardian, was 00:18:43.180 --> 00:18:46.180 incredibly blunt. She reported that Hefner threatened 00:18:46.180 --> 00:18:49.099 to sue her because she called him a pimp. A pimp? 00:18:49.200 --> 00:18:52.359 That is a heavy label. A very heavy label. But 00:18:52.359 --> 00:18:54.420 her argument was that he was a man who bought 00:18:54.420 --> 00:18:58.099 and sold women to other men. She wrote, part 00:18:58.099 --> 00:19:00.599 of Hefner's business acumen was to make the selling 00:19:00.599 --> 00:19:03.329 of female flesh respectable and hip. Putting 00:19:03.329 --> 00:19:05.450 a tuxedo on it doesn't change what the transaction 00:19:05.450 --> 00:19:07.869 is. That was her point. Exactly. And Robin of 00:19:07.869 --> 00:19:10.250 Tarion from the L .A. Times made a similar argument. 00:19:10.490 --> 00:19:12.630 She said he convinced women that taking their 00:19:12.630 --> 00:19:15.829 clothes off was empowering. But really, it just 00:19:15.829 --> 00:19:18.490 mainstreamed the idea that women exist to please 00:19:18.490 --> 00:19:21.130 men. The commodification argument. It is. Did 00:19:21.130 --> 00:19:23.690 he liberate women or did he just package them 00:19:23.690 --> 00:19:25.849 more expensively? Did he give them a platform 00:19:25.849 --> 00:19:28.690 or just a pedestal to be looked at? Right. But 00:19:28.690 --> 00:19:31.029 after he died, the criticism went from theoretical 00:19:31.029 --> 00:19:33.880 to criminal. We have to talk about the Secrets 00:19:33.880 --> 00:19:36.079 of Playboy docuseries that came out in 2022. 00:19:36.539 --> 00:19:38.680 This was a bombshell. This wasn't just he was 00:19:38.680 --> 00:19:41.420 a chauvinist. These were allegations from former 00:19:41.420 --> 00:19:44.660 employees and partners about serious abuse. The 00:19:44.660 --> 00:19:47.559 scope was alarming. We heard claims of systematic 00:19:47.559 --> 00:19:50.799 sexual misconduct, manipulation, and the rampant 00:19:50.799 --> 00:19:54.490 use of qualiludes. The leg spreader drugs. As 00:19:54.490 --> 00:19:56.470 they were allegedly called inside the mansion, 00:19:56.809 --> 00:20:00.150 there were accusations of sextortion, blackmail, 00:20:00.269 --> 00:20:02.910 and even rape. And the response from the company, 00:20:03.049 --> 00:20:05.690 which wasn't run by the family anymore, was telling. 00:20:05.809 --> 00:20:09.250 Yes. The PLBY group, which is now publicly owned, 00:20:09.509 --> 00:20:11.930 completely distanced themselves. They released 00:20:11.930 --> 00:20:14.589 a statement saying, quote, Today's Playboy is 00:20:14.589 --> 00:20:17.430 not Hugh Hefner's Playboy. Wow. They validated 00:20:17.430 --> 00:20:20.269 the women's stories. That is a corporate entity 00:20:20.269 --> 00:20:22.829 essentially disavowing its own founder. They 00:20:22.829 --> 00:20:24.569 looked at the file and decided they couldn't 00:20:24.569 --> 00:20:26.410 defend it. And the women who live there, the 00:20:26.410 --> 00:20:28.170 ones we saw on the reality show, they started 00:20:28.170 --> 00:20:31.150 talking too. Holly Madison wrote a memoir. Holly 00:20:31.150 --> 00:20:33.690 described a culture of intense competition and 00:20:33.690 --> 00:20:36.289 body image issues. She called it exploitation 00:20:36.289 --> 00:20:39.630 for professional gain. It wasn't the happy sorority 00:20:39.630 --> 00:20:41.650 house we saw on TV. Not at all. She described 00:20:41.650 --> 00:20:43.930 being pitted against other women for Hefner's 00:20:43.930 --> 00:20:46.250 affection and resources. And Crystal Hefner, 00:20:46.390 --> 00:20:49.650 his widow, released a memoir just recently, in 00:20:49.650 --> 00:20:53.390 2024. She called the mansion a hostile environment 00:20:53.390 --> 00:20:56.670 and said she felt imprisoned. The word imprisoned 00:20:56.670 --> 00:21:00.109 is striking. It contrasts so sharply with the 00:21:00.109 --> 00:21:03.619 concept of liberty Hefner preached. He sold freedom 00:21:03.619 --> 00:21:05.779 to the men reading the magazine, but the women 00:21:05.779 --> 00:21:08.000 living in the center of the empire felt trapped. 00:21:08.799 --> 00:21:11.200 And it wasn't just the women inside who criticized 00:21:11.200 --> 00:21:13.980 him. We also have the religious critique, which 00:21:13.980 --> 00:21:16.819 circles back to his origins. Ed Stetzer wrote 00:21:16.819 --> 00:21:19.440 in Christianity Today about the immeasurable 00:21:19.440 --> 00:21:22.480 damage Hefner did to the value of women and marriage. 00:21:22.740 --> 00:21:24.680 There's a detail from Stetzer's piece that really 00:21:24.680 --> 00:21:26.980 stuck with me. He mentioned that when Hefner's 00:21:26.980 --> 00:21:29.490 daughter Christy, who ran the company, would 00:21:29.490 --> 00:21:31.890 visit the mansion. Yes. Hefner would have the 00:21:31.890 --> 00:21:34.569 place cleaned up. To hide the reality. Exactly. 00:21:34.650 --> 00:21:36.609 He'd hide the parties to keep the reality from 00:21:36.609 --> 00:21:39.930 his own daughter. That implies he knew on some 00:21:39.930 --> 00:21:41.670 level that what was happening wasn't something 00:21:41.670 --> 00:21:44.430 his daughter should see. It suggests a compartmentalization. 00:21:45.319 --> 00:21:47.980 He built a world that he claimed was a utopia, 00:21:48.079 --> 00:21:50.819 but he had to sanitize it for the people he respected 00:21:50.819 --> 00:21:54.460 in a professional or familial capacity. It implies 00:21:54.460 --> 00:21:57.160 a consciousness of guilt, or at least a recognition 00:21:57.160 --> 00:22:00.140 that his philosophy had limits when it came to 00:22:00.140 --> 00:22:02.299 his own family. So we have this massive life 00:22:02.299 --> 00:22:05.500 full of noise and controversy, but eventually 00:22:05.500 --> 00:22:09.799 the party has to end. September 27, 2017. Hugh 00:22:09.799 --> 00:22:12.829 Hefner dies at the mansion. He was 91. He died 00:22:12.829 --> 00:22:15.789 of cardiac arrest and respiratory failure, complicated 00:22:15.789 --> 00:22:18.529 by sepsis from an E. coli infection. It was the 00:22:18.529 --> 00:22:21.569 end of an era. But even his exit was orchestrated. 00:22:21.650 --> 00:22:23.869 The sale of the mansion is wild. He sold it a 00:22:23.869 --> 00:22:26.730 year before he died, right? In 2016, he sold 00:22:26.730 --> 00:22:29.490 it for $100 million to Darren Metropoulos, who 00:22:29.490 --> 00:22:31.369 lived next door. But the condition of the sale 00:22:31.369 --> 00:22:33.730 was unique. Hefner got to live there until he 00:22:33.730 --> 00:22:35.880 took his last breath. So he sold the property, 00:22:35.960 --> 00:22:38.140 but not the lifestyle. He sold the cage, but 00:22:38.140 --> 00:22:40.539 he kept the key until the end. He ensured his 00:22:40.539 --> 00:22:42.440 environment wouldn't change until he was gone. 00:22:42.619 --> 00:22:46.160 And then the final symbolic gesture, his burial. 00:22:46.400 --> 00:22:49.039 Westwood Village Memorial Park Cemetery. It's 00:22:49.039 --> 00:22:51.759 a small, celebrity -filled cemetery in L .A. 00:22:52.059 --> 00:22:54.619 But Hefner isn't just anywhere. He is in the 00:22:54.619 --> 00:22:57.339 crypt right next to Marilyn Monroe. The woman 00:22:57.339 --> 00:23:00.380 on the first cover. The woman he never met. He 00:23:00.380 --> 00:23:04.519 bought that crypt in 1992 for $75 ,000. He told 00:23:04.519 --> 00:23:07.160 the Los Angeles Times, spending eternity next 00:23:07.160 --> 00:23:09.579 to Marilyn is an opportunity too sweet to pass 00:23:09.579 --> 00:23:12.819 up. It feels possessive. It is the ultimate claim 00:23:12.819 --> 00:23:15.900 of ownership. In life, he used her image to build 00:23:15.900 --> 00:23:18.740 his empire. In death, he physically positioned 00:23:18.740 --> 00:23:21.700 himself beside her forever. Wow. It ties the 00:23:21.700 --> 00:23:24.000 whole story together, the admiration, the exploitation, 00:23:24.279 --> 00:23:26.519 the branding. He wanted to be written into her 00:23:26.519 --> 00:23:28.700 story permanently. So what does this all mean? 00:23:29.000 --> 00:23:31.500 We've looked at the $5 raise, the civil rights 00:23:31.500 --> 00:23:34.039 battles, the silk pajamas, the dark allocations. 00:23:34.099 --> 00:23:37.000 The company Playboy has moved on. His son Cooper 00:23:37.000 --> 00:23:39.000 was involved for a while, but now the brand is 00:23:39.000 --> 00:23:41.539 trying to be something else entirely. Synthesizing 00:23:41.539 --> 00:23:43.559 all of this is difficult because Hefner was a 00:23:43.559 --> 00:23:46.339 man of distinct compartments. He was a man who 00:23:46.339 --> 00:23:48.200 fought for First Amendment rights and desegregation, 00:23:48.480 --> 00:23:50.799 and he genuinely used his platform for good in 00:23:50.799 --> 00:23:53.420 those areas. You can't deny that. You can't. 00:23:53.519 --> 00:23:56.700 Yet he is simultaneously accused of misogyny, 00:23:56.740 --> 00:23:59.380 abuse. and mainstreaming the commodification 00:23:59.380 --> 00:24:01.930 of women. It's a dichotomy. You can't really 00:24:01.930 --> 00:24:04.430 erase the civil rights advocacy, but you also 00:24:04.430 --> 00:24:06.710 can't ignore the secrets of Playboy allegations. 00:24:07.289 --> 00:24:10.089 Precisely. The question isn't, was he good or 00:24:10.089 --> 00:24:13.890 bad? It's, how do we hold both truths? He helped 00:24:13.890 --> 00:24:16.769 break down the puritanical walls of the 1950s, 00:24:16.769 --> 00:24:19.150 but the house he built to replace them had its 00:24:19.150 --> 00:24:21.849 own locked doors and dark corners. That brings 00:24:21.849 --> 00:24:23.630 us to the big question for you, the listener. 00:24:23.829 --> 00:24:26.329 Can you separate the sexual revolution from the 00:24:26.329 --> 00:24:28.890 man who profited from it? Did we need a Hugh 00:24:28.890 --> 00:24:31.289 Hefner to get where we are today? Or was he just 00:24:31.289 --> 00:24:33.650 a guy who found a way to monetize our curiosity? 00:24:34.029 --> 00:24:37.009 It forces us to ask what liberation really looks 00:24:37.009 --> 00:24:39.910 like. Hefner claimed religion was a myth. He 00:24:39.910 --> 00:24:42.569 rejected the Methodist god of his mother. Vehemently. 00:24:42.569 --> 00:24:45.309 Yet look at his life. He dedicated every waking 00:24:45.309 --> 00:24:47.750 moment to creating his own mythology. He built 00:24:47.750 --> 00:24:50.130 his own heaven on earth, the mansion. Exactly. 00:24:50.130 --> 00:24:53.089 It was a heaven with strict rules, its own deities, 00:24:53.170 --> 00:24:56.009 the playmates, and a patriarch who refused to 00:24:56.009 --> 00:24:58.420 leave the party until the very end. And maybe 00:24:58.420 --> 00:25:01.660 that's the final provocative thought. Was the 00:25:01.660 --> 00:25:04.759 Playboy philosophy actually a liberation movement? 00:25:05.200 --> 00:25:07.779 Or was it just a very elaborate high -gloss cage? 00:25:08.140 --> 00:25:10.599 That is for the listener to decide. Thanks for 00:25:10.599 --> 00:25:12.200 diving deep with us. We'll see you on the next 00:25:12.200 --> 00:25:12.339 one.