WEBVTT 00:00:00.000 --> 00:00:02.100 Welcome back to the Deep Dive. We grab all the 00:00:02.100 --> 00:00:04.940 source material, the articles, interviews, the 00:00:04.940 --> 00:00:06.839 backstory, and try to piece together a really 00:00:06.839 --> 00:00:09.419 clear picture for you on, well, often pretty 00:00:09.419 --> 00:00:11.400 fascinating topics. And today, yeah, we're looking 00:00:11.400 --> 00:00:14.199 at someone whose career took a turn that's honestly 00:00:14.199 --> 00:00:16.359 kind of mind -blowing. It really makes you rethink 00:00:16.359 --> 00:00:20.960 one of the most recognizable faces in cult movies. 00:00:21.160 --> 00:00:23.120 We're talking about Alexander Ross Winter. Right. 00:00:23.300 --> 00:00:25.839 And for pretty much everyone, the name instantly 00:00:25.839 --> 00:00:29.609 brings up Bill S. Preston, Esquire. You know, 00:00:29.649 --> 00:00:32.350 the excellent dude, time traveling, air guitar 00:00:32.350 --> 00:00:34.829 shredding, the whole Bill and Ted thing. That's 00:00:34.829 --> 00:00:37.609 the global image, absolutely. The 89, excellent 00:00:37.609 --> 00:00:40.469 adventure, then bogus journey in 91, and that 00:00:40.469 --> 00:00:42.530 great comeback with Face the Music just a few 00:00:42.530 --> 00:00:45.250 years ago in 2020. But here's the thing, and 00:00:45.250 --> 00:00:47.369 this is really the core of our deep dive today. 00:00:47.950 --> 00:00:49.929 If you only think of Alex Winter as, you know, 00:00:49.929 --> 00:00:52.689 that beloved actor, well, you're missing out 00:00:52.689 --> 00:00:55.399 on like two decades of... Really intense, critically 00:00:55.399 --> 00:00:58.060 praised and seriously engaged work. Yeah. As 00:00:58.060 --> 00:01:00.979 a documentarian, an activist. Exactly. So our 00:01:00.979 --> 00:01:03.280 mission really is to unpack how that happened. 00:01:03.659 --> 00:01:07.260 How does the star of an 80s teen comedy become 00:01:07.260 --> 00:01:12.159 this like. expert investigative filmmaker focusing 00:01:12.159 --> 00:01:15.379 on the dark web global finance big corporations 00:01:15.379 --> 00:01:17.480 big tech it's more than just switching jobs right 00:01:17.480 --> 00:01:19.959 it feels like a whole different purpose a total 00:01:19.959 --> 00:01:22.480 shift in focus and the timing now looking at 00:01:22.480 --> 00:01:25.299 it from 2025 is super interesting because he's 00:01:25.299 --> 00:01:27.859 somehow managing to do both things like full 00:01:27.859 --> 00:01:30.579 force totally like on one side he did that gonzo 00:01:30.579 --> 00:01:33.579 horror comedy destroy all neighbors in 2024 just 00:01:33.579 --> 00:01:35.799 completely out there and then on the other side 00:01:35.799 --> 00:01:38.640 this fall He's going back to where it all began 00:01:38.640 --> 00:01:40.640 for him, essentially. That's right. Back to Broadway. 00:01:40.640 --> 00:01:42.659 He's co -starring with Keanu Reeves again, which 00:01:42.659 --> 00:01:45.000 is amazing in itself. Wow. In a major revival 00:01:45.000 --> 00:01:47.939 of Samuel Beckett's Waiting for Godot, Jamie 00:01:47.939 --> 00:01:50.299 Lloyd is directing. Okay, so you've got gonzo 00:01:50.299 --> 00:01:52.659 comedy, serious documentaries about tech and 00:01:52.659 --> 00:01:56.349 finance, and then... philosophical stage drama. 00:01:56.549 --> 00:01:59.209 It's a stunning mix. It really shows how he's 00:01:59.209 --> 00:02:01.629 pulling off this completely unexpected career 00:02:01.629 --> 00:02:06.069 pivot with just relentless energy. So let's dig 00:02:06.069 --> 00:02:08.409 into how he got here. OK, so to really get the 00:02:08.409 --> 00:02:10.430 filmmaker and the activist side of Alex Winter. 00:02:10.840 --> 00:02:13.340 We got to rewind. We need to look at the foundation, 00:02:13.580 --> 00:02:15.580 the artistic world he grew up in, because he 00:02:15.580 --> 00:02:17.520 wasn't just like discovered walking down the 00:02:17.520 --> 00:02:19.500 street in Hollywood. No, definitely not. He was 00:02:19.500 --> 00:02:23.280 born in London, July 17, 1965. He actually holds 00:02:23.280 --> 00:02:26.240 dual British and American citizenship. But the 00:02:26.240 --> 00:02:28.379 really key thing, like you said, is his parents. 00:02:28.439 --> 00:02:30.900 They were professional dancers. Right. So that 00:02:30.900 --> 00:02:34.979 world was disciplined, artistic. Deeply. His 00:02:34.979 --> 00:02:37.819 mom, Greg Mayer, she was American, born in New 00:02:37.819 --> 00:02:40.460 York, and she trained with Martha Graham. Like 00:02:40.460 --> 00:02:42.699 the Martha Graham. Wow. The pioneer of modern 00:02:42.699 --> 00:02:45.699 dance. Exactly. And she founded her own modern 00:02:45.699 --> 00:02:49.259 dance company in London back in the mid 60s. 00:02:49.259 --> 00:02:51.979 And his dad, Ross Albert Winter, who's Australian, 00:02:52.180 --> 00:02:54.370 he actually danced with her troupe. So this is 00:02:54.370 --> 00:02:56.969 serious avant -garde performance in his DNA, 00:02:57.129 --> 00:02:59.349 basically. Pretty much. Then when Alex was about 00:02:59.349 --> 00:03:01.490 five, the family moved over to St. Louis, Missouri. 00:03:01.689 --> 00:03:03.689 His parents started another company there, the 00:03:03.689 --> 00:03:06.849 Mid -American Dance Company. So Alex, as a kid, 00:03:06.969 --> 00:03:09.409 he got formal dance training. He learned that 00:03:09.409 --> 00:03:11.650 discipline, the physical rigor you need for that 00:03:11.650 --> 00:03:13.729 kind of work. The kind you need for Broadway 00:03:13.729 --> 00:03:16.270 or, you know, professional dance. Right. And 00:03:16.270 --> 00:03:18.530 even though his parents split up in 73, that 00:03:18.530 --> 00:03:21.389 performance background stuck with him. In 1978, 00:03:21.750 --> 00:03:23.699 he moved with his mom to Montclair. New Jersey. 00:03:24.300 --> 00:03:27.560 And that move was basically the key that unlocked 00:03:27.560 --> 00:03:30.039 his first career break. The stage. The stage, 00:03:30.259 --> 00:03:32.919 yeah. That's the part people often miss. They 00:03:32.919 --> 00:03:35.139 think Lost Boys or Bill and Ted was the start. 00:03:35.219 --> 00:03:37.900 But no, he was a working actor commuting into 00:03:37.900 --> 00:03:40.620 New York City way before all that. He was doing 00:03:40.620 --> 00:03:43.240 Broadway, off -Broadway. Yeah, look at the record. 00:03:43.340 --> 00:03:44.960 He was in some pretty big shows, like he was 00:03:44.960 --> 00:03:47.539 a replacement in The King and I back in 77, 78. 00:03:48.120 --> 00:03:51.680 And he played John Darling. That's a key part 00:03:51.680 --> 00:03:54.479 in the Peter Pan revival in 79. Right. And by 00:03:54.479 --> 00:03:57.240 81, he's doing Simon Gray's close of play at 00:03:57.240 --> 00:03:59.539 the Manhattan Theater Club. That's serious theater. 00:03:59.639 --> 00:04:01.860 It shows he was comfortable with that world, 00:04:01.919 --> 00:04:05.620 with complex plays, ensemble work, which makes 00:04:05.620 --> 00:04:08.840 his return to Godot now in 2025 feel like a real 00:04:08.840 --> 00:04:10.960 full circle thing, not just some celebrity stunt 00:04:10.960 --> 00:04:13.240 casting. Absolutely. And there's another layer, 00:04:13.319 --> 00:04:16.639 too, culturally. His mom's Jewish, Ukrainian 00:04:16.639 --> 00:04:19.300 Jewish descent. The family wasn't super religious, 00:04:19.399 --> 00:04:21.860 but he did go to Jewish summer camp, apparently 00:04:21.860 --> 00:04:24.620 learned some Yiddish from his grandmother. So 00:04:24.620 --> 00:04:26.620 you have that mixed to the dual citizenship, 00:04:26.860 --> 00:04:29.240 the cultural background. Interesting. But even 00:04:29.240 --> 00:04:31.959 with that stage success, it seems like his head 00:04:31.959 --> 00:04:34.540 was already turning towards making things himself. 00:04:34.699 --> 00:04:38.959 Totally. In 1983, he gets into NYU's Tisch School 00:04:38.959 --> 00:04:41.910 of the Arts. That's a big sign right there. He 00:04:41.910 --> 00:04:43.769 wasn't just trying to act, he wanted to direct. 00:04:43.930 --> 00:04:45.750 And that's where he met Tom Stern. That's the 00:04:45.750 --> 00:04:48.850 guy. Crucial collaborator. They hit it off, started 00:04:48.850 --> 00:04:52.149 making 16mm short films together almost immediately. 00:04:52.829 --> 00:04:55.350 Classic film school story. Did he finish Dish? 00:04:55.709 --> 00:04:57.569 He actually didn't. Dropped out before senior 00:04:57.569 --> 00:04:59.209 year, which, you know, happens a lot with young 00:04:59.209 --> 00:05:00.970 directors who are just itching to get started. 00:05:01.029 --> 00:05:03.269 He moved out to Hollywood specifically to write 00:05:03.269 --> 00:05:05.170 and direct. But Hollywood being Hollywood, you 00:05:05.170 --> 00:05:07.850 got to pay the bills. Exactly. So while he's 00:05:07.850 --> 00:05:10.089 trying to get short films and music videos off 00:05:10.089 --> 00:05:12.990 the ground, he lands that role. The one people 00:05:12.990 --> 00:05:15.329 do remember from before Bill and Ted. Marco. 00:05:15.949 --> 00:05:19.129 And the Lost Boys. Marco the Vampire, yeah. 1987, 00:05:19.550 --> 00:05:22.470 Joel Schumacher film. Total classic now. And 00:05:22.470 --> 00:05:24.629 that role, that visibility, it was kind of the 00:05:24.629 --> 00:05:27.029 perfect setup. Raising his profile just in time 00:05:27.029 --> 00:05:28.889 for the part that would, well, change everything. 00:05:29.689 --> 00:05:32.889 So Bill and Ted blows up. Huge global success. 00:05:33.230 --> 00:05:35.870 That gives Alex Winter what every aspiring director 00:05:35.870 --> 00:05:40.310 needs. Fame, access, basically currency in Hollywood. 00:05:40.449 --> 00:05:42.829 Right. But what's really striking is how fast 00:05:42.829 --> 00:05:45.370 he refused to just stay Bill. He cashed in that 00:05:45.370 --> 00:05:47.389 currency, sure, but he used it to push his own 00:05:47.389 --> 00:05:50.230 vision, starting with sketch comedy. Right after 00:05:50.230 --> 00:05:53.350 Bogus Journey in 91, yeah. Him, Tom Stern, and 00:05:53.350 --> 00:05:55.250 another collaborator, Tim Burns, they launched 00:05:55.250 --> 00:05:58.149 the Idiot Box on MTV. Super fast -paced, really 00:05:58.149 --> 00:06:00.009 weird sketch show. Didn't last long, though, 00:06:00.009 --> 00:06:01.829 did it? Only six episodes. But it definitely 00:06:01.829 --> 00:06:03.810 showed off their unique kind of bizarre humor, 00:06:03.889 --> 00:06:06.529 and that little bit of cult buzz, plus the Bill 00:06:06.529 --> 00:06:08.870 and Ted heat, led straight to a studio deal. 00:06:09.050 --> 00:06:11.610 Okay, see, that's the smart play. Totally strategic. 00:06:11.930 --> 00:06:13.930 They leveraged that momentum into a pretty big 00:06:13.930 --> 00:06:15.800 deal. deal, like $12 million from 20th Century 00:06:15.800 --> 00:06:18.920 Fox. But what they gave Fox was definitely not 00:06:18.920 --> 00:06:21.240 Bill and Ted 3. No kidding. We're talking about 00:06:21.240 --> 00:06:24.399 Freaked, 1993, his first time directing a feature 00:06:24.399 --> 00:06:27.360 film. Co -directed with Stern, co -wrote it, 00:06:27.439 --> 00:06:30.420 and he starred as the main guy, Ricky Coogan. 00:06:31.720 --> 00:06:34.139 How would you even describe Freaked to someone 00:06:34.139 --> 00:06:36.620 who hasn't seen it compared to Excellent Adventure? 00:06:37.079 --> 00:06:40.540 It's like night and day, a quantum leap into 00:06:40.540 --> 00:06:44.759 weirdness. Freaked is this Totally surreal, satirical, 00:06:44.920 --> 00:06:48.519 body horror comedy. It's just packed with insane 00:06:48.519 --> 00:06:51.899 creature makeup, crazy practical effects, and 00:06:51.899 --> 00:06:54.819 it's savaging corporate culture, fame, media. 00:06:54.920 --> 00:06:57.339 It sounds completely nuts. It's completely nuts. 00:06:57.439 --> 00:07:00.259 It shows right away he had this audacious streak. 00:07:00.339 --> 00:07:02.680 Like, you gave us $12 million. Okay, we're going 00:07:02.680 --> 00:07:04.259 to make the weirdest possible thing with it, 00:07:04.300 --> 00:07:06.040 totally uncomplicated. It's basically the definition 00:07:06.040 --> 00:07:08.930 of an anti -studio film made by a studio. and 00:07:08.930 --> 00:07:11.029 didn't get good reviews yeah surprisingly like 00:07:11.029 --> 00:07:12.709 the new york times entertainment weekly they 00:07:12.709 --> 00:07:15.389 reviewed it well at the time but fox they clearly 00:07:15.389 --> 00:07:17.730 had zero idea what to do with it how do you market 00:07:17.730 --> 00:07:19.790 that level of stranger they just did pretty much 00:07:19.790 --> 00:07:22.370 buried it never got a wide release which is a 00:07:22.370 --> 00:07:24.350 shame but it did eventually find its audience 00:07:24.350 --> 00:07:27.149 became this huge cult favorite later on through 00:07:27.149 --> 00:07:30.209 video and stuff still having your first big movie 00:07:30.209 --> 00:07:33.759 basically shelved by the studio That must have 00:07:33.759 --> 00:07:36.040 stung. Seems like it. Because he took a break 00:07:36.040 --> 00:07:38.000 from feature directing after that. A pretty long 00:07:38.000 --> 00:07:39.639 one, actually. Didn't direct another feature 00:07:39.639 --> 00:07:42.720 until 99. Almost seven years. And when he came 00:07:42.720 --> 00:07:44.160 back, it was a completely different vibe again. 00:07:44.279 --> 00:07:47.139 Totally different. Fever. A psychological thriller. 00:07:47.420 --> 00:07:50.079 And this is where people outside the, you know, 00:07:50.120 --> 00:07:53.240 cult movie world started to really take notice 00:07:53.240 --> 00:07:55.759 of him as a serious filmmaker. It got some real 00:07:55.759 --> 00:07:58.579 recognition, didn't it? Huge validation. Fever 00:07:58.579 --> 00:08:00.620 got into the director's fortnight at Cannes. 00:08:00.620 --> 00:08:03.819 That's a major deal for independent art focused 00:08:03.819 --> 00:08:06.660 cinema. And the critics really responded. The 00:08:06.660 --> 00:08:09.439 New York Daily News called it a claustrophobic 00:08:09.439 --> 00:08:13.779 mind bender worthy of Roman Polanski. Wow. From 00:08:13.779 --> 00:08:16.379 Bill S. Preston to comparisons with Polanski. 00:08:16.420 --> 00:08:19.139 That's quite a leap. Right. But then almost immediately 00:08:19.139 --> 00:08:21.800 after that, in the mid 2000s, he pivots again, 00:08:21.959 --> 00:08:25.560 this time into kids TV blockbusters. It feels 00:08:25.560 --> 00:08:28.279 like whiplash just talking about it. Fever, then 00:08:28.279 --> 00:08:30.699 Ben 10. Is that just about the money, you think? 00:08:30.800 --> 00:08:32.820 Or did he genuinely want to try family stuff? 00:08:33.100 --> 00:08:36.179 It definitely shows his range. But yeah, very 00:08:36.179 --> 00:08:38.779 likely a smart move financially to keep his independence. 00:08:39.139 --> 00:08:40.679 You got to have some commercial hits if you want 00:08:40.679 --> 00:08:43.080 to fund the weirder passion projects down the 00:08:43.080 --> 00:08:46.419 line. And he jumped into adapting Ben 10, which 00:08:46.419 --> 00:08:49.139 was massive for Cartoon Network. And these weren't 00:08:49.139 --> 00:08:51.759 small things either. The first one, Ben 10, Race 00:08:51.759 --> 00:08:54.659 Against Time in 2007. Didn't that break records 00:08:54.659 --> 00:08:56.960 for the channel? Highest ratings in their history 00:08:56.960 --> 00:08:59.620 at that point. Yeah. Then he did the sequel, 00:08:59.840 --> 00:09:03.539 Ben 10. Alien Swarm in 2009. That pulled in like 00:09:03.539 --> 00:09:06.200 16 million viewers over its opening weekend. 00:09:06.360 --> 00:09:08.840 That's insane for cable TV. blockbuster numbers 00:09:08.840 --> 00:09:11.899 really so that whole period proved he wasn't 00:09:11.899 --> 00:09:14.539 just the freaked guy or the fever guy he was 00:09:14.539 --> 00:09:17.299 also a super competent bankable director who 00:09:17.299 --> 00:09:19.759 could handle big budgets effects huge audiences 00:09:19.759 --> 00:09:21.980 it's hard to imagine him getting the funding 00:09:21.980 --> 00:09:24.480 for his later really complex documentaries without 00:09:24.480 --> 00:09:26.659 showing he could deliver both niche art house 00:09:26.659 --> 00:09:30.200 stuff and massive mainstream hits okay so now 00:09:30.200 --> 00:09:33.759 we get to the era that arguably defines his career 00:09:33.759 --> 00:09:37.259 now the documentarian era And it wasn't like 00:09:37.259 --> 00:09:39.720 he just fell into it. It seems like a very deliberate 00:09:39.720 --> 00:09:42.559 shift towards serious investigative work, mostly 00:09:42.559 --> 00:09:46.980 focused on tech, privacy, media. These big power 00:09:46.980 --> 00:09:49.960 structures. Yeah, it seems rooted in a real genuine 00:09:49.960 --> 00:09:52.019 fascination with the Internet, not just the tech 00:09:52.019 --> 00:09:55.000 itself, but the culture it created. Winter said 00:09:55.000 --> 00:09:56.779 he was really struck by the community aspect 00:09:56.779 --> 00:09:59.259 early on, how tons of people could talk about 00:09:59.259 --> 00:10:02.799 anything and everything anonymously. He saw something 00:10:02.799 --> 00:10:05.200 huge starting and he wanted to document it. Which 00:10:05.200 --> 00:10:07.139 led straight to his first big documentary, right? 00:10:07.200 --> 00:10:10.509 Yeah. About Napster and file sharing. Exactly. 00:10:10.710 --> 00:10:12.490 And right away you see his critical thinking. 00:10:12.669 --> 00:10:14.730 With Downloaded, he wasn't just repeating the 00:10:14.730 --> 00:10:16.309 standard line about, you know, piracy killed 00:10:16.309 --> 00:10:17.950 the music industry. Right, the easy narrative. 00:10:18.110 --> 00:10:19.970 He was actually pushing back against that, criticizing 00:10:19.970 --> 00:10:24.389 media companies, news outlets for, like, exaggerating 00:10:24.389 --> 00:10:26.389 how many people use Napster only for illegal 00:10:26.389 --> 00:10:29.809 stuff. He wanted to show the revolutionary side 00:10:29.809 --> 00:10:32.629 of it, how it changed access to culture. He wasn't 00:10:32.629 --> 00:10:34.470 buying the simple story. He wanted the deeper, 00:10:34.549 --> 00:10:37.529 maybe more complicated truth. Precisely. And 00:10:37.529 --> 00:10:40.250 that drive for the technical, complex truth led 00:10:40.250 --> 00:10:42.470 him to what's probably his most well -known doc, 00:10:42.730 --> 00:10:45.870 Deep Web in 2015. Which won a ton of awards. 00:10:46.029 --> 00:10:48.649 Multi -award winning, yeah. Deep Web tackled 00:10:48.649 --> 00:10:51.789 some heady stuff. The Silk Road, online black 00:10:51.789 --> 00:10:54.779 market. Bitcoin, back when it was still pretty 00:10:54.779 --> 00:10:56.799 mysterious to most people, the whole idea of 00:10:56.799 --> 00:10:58.860 the dark web. It premiered at South by Southwest, 00:10:59.200 --> 00:11:00.980 right? Yeah. And did really well commercially. 00:11:01.379 --> 00:11:04.360 Huge for a doc. Opened as the number one documentary 00:11:04.360 --> 00:11:06.919 on iTunes, which tells you people were hungry 00:11:06.919 --> 00:11:08.840 for this kind of information. And the Silk Road 00:11:08.840 --> 00:11:11.720 story itself is fascinating. Focused a lot on 00:11:11.720 --> 00:11:14.059 Ross Ulbricht, the founder who got, what, life 00:11:14.059 --> 00:11:16.860 in prison. Yeah. Sentenced to life. Winters' 00:11:16.899 --> 00:11:18.700 film didn't just explain how the market worked. 00:11:18.820 --> 00:11:21.179 It dove into that whole high -profile legal fight, 00:11:21.299 --> 00:11:24.080 asking big questions about government power online, 00:11:24.360 --> 00:11:27.559 anonymity, digital freedom. Where are the lines? 00:11:27.820 --> 00:11:29.820 What's really interesting is seeing the connections 00:11:29.820 --> 00:11:32.659 he makes. If Napster was about anonymous information 00:11:32.659 --> 00:11:35.539 sharing, his next films kind of follow the trail 00:11:35.539 --> 00:11:38.120 of anonymity into money and power. That definitely 00:11:38.120 --> 00:11:40.519 seems to be the thread. It leads straight into 00:11:40.519 --> 00:11:43.059 global finance. He put out two documentaries. 00:11:43.720 --> 00:11:47.139 basically back to back in 2018 that hit on similar 00:11:47.139 --> 00:11:49.980 themes. Right. First was the Panama Papers, all 00:11:49.980 --> 00:11:52.279 about that massive leak of financial documents 00:11:52.279 --> 00:11:55.340 in 2016. Which exposed all those offshore shell 00:11:55.340 --> 00:11:58.799 companies. Exactly. These like secret tools used 00:11:58.799 --> 00:12:02.100 everywhere to hide money, dodge taxes, basically 00:12:02.100 --> 00:12:05.360 operate in the shadows on a massive scale. Winter 00:12:05.360 --> 00:12:07.580 used the documentary to show why this hidden 00:12:07.580 --> 00:12:09.620 world of finance actually matters to regular 00:12:09.620 --> 00:12:12.419 people, why that anonymity is a problem. And 00:12:12.419 --> 00:12:14.360 the second one. that year looked at the tech 00:12:14.360 --> 00:12:16.940 side again. Trust Machine, the story of blockchain. 00:12:17.740 --> 00:12:20.200 So looking at the technology behind Bitcoin and 00:12:20.200 --> 00:12:22.779 crypto, he explored the potential decentralization, 00:12:22.940 --> 00:12:25.240 transparency, all the promises, but also looked 00:12:25.240 --> 00:12:27.059 critically at how it was really playing out, 00:12:27.220 --> 00:12:29.519 connecting it back to the financial systems he 00:12:29.519 --> 00:12:31.600 looked at in Deep Web and Panama Papers. OK, 00:12:31.659 --> 00:12:34.190 so there's a clear line. Anonymous culture with 00:12:34.190 --> 00:12:36.590 Napster, anonymous transactions with Bitcoin 00:12:36.590 --> 00:12:39.009 and the dark web, anonymous wealth with the Panama 00:12:39.009 --> 00:12:42.090 Papers. He's using his camera to look into these 00:12:42.090 --> 00:12:44.690 hidden systems, these places where power operates 00:12:44.690 --> 00:12:46.909 unseen. It's a really consistent investigation. 00:12:47.450 --> 00:12:50.110 But he wasn't only focused on tech and finance, 00:12:50.289 --> 00:12:54.210 right? He also turned his lens onto culture and 00:12:54.210 --> 00:12:57.980 Hollywood itself. like showbiz kids in 2020 yeah 00:12:57.980 --> 00:13:00.500 that was a really powerful one looking at the 00:13:00.500 --> 00:13:03.620 reality of being a child actor the pressure the 00:13:03.620 --> 00:13:06.559 intensity sometimes the danger given his own 00:13:06.559 --> 00:13:08.620 background that felt very personal and then the 00:13:08.620 --> 00:13:11.860 huge one also in 2020 zappa oh yeah the frank 00:13:11.860 --> 00:13:14.320 zappa documentary that was a monumental project 00:13:14.320 --> 00:13:16.799 and it really speaks to the trust and credibility 00:13:16.799 --> 00:13:19.259 he'd built by then because he got full access 00:13:19.259 --> 00:13:21.860 to the zappa family trust archives which are 00:13:21.860 --> 00:13:25.860 famously Tightly controlled. How did he swing 00:13:25.860 --> 00:13:27.580 that? It wasn't just handed to him. It came from 00:13:27.580 --> 00:13:29.440 the fans. They crowdfunded it through Kickstarter. 00:13:29.779 --> 00:13:31.740 It actually became the highest funded documentary 00:13:31.740 --> 00:13:35.019 ever on Kickstarter, raised over $1 .12 million. 00:13:35.399 --> 00:13:38.460 Wow. That's incredible. People really wanted 00:13:38.460 --> 00:13:41.009 him to tell that story. Definitely. They trusted 00:13:41.009 --> 00:13:43.509 his vision as someone who could handle that legacy 00:13:43.509 --> 00:13:46.590 properly. And then his most recent big doc, the 00:13:46.590 --> 00:13:49.889 YouTube effect from 2023, brings it right back 00:13:49.889 --> 00:13:52.129 to the Internet's power structures. Looking at 00:13:52.129 --> 00:13:54.730 YouTube's massive influence. Yeah. Produced with 00:13:54.730 --> 00:13:57.830 Gail Ann Hurd. big name producer, premiered at 00:13:57.830 --> 00:14:01.190 Tribeca, had a sold out theatrical run. He's 00:14:01.190 --> 00:14:03.169 still examining that online community he was 00:14:03.169 --> 00:14:05.909 initially fascinated by, but now with a much 00:14:05.909 --> 00:14:08.629 more critical eye on its global impact politically 00:14:08.629 --> 00:14:11.899 and socially. So this intense focus on systems, 00:14:11.940 --> 00:14:14.919 on power, on hidden vulnerabilities, it takes 00:14:14.919 --> 00:14:16.779 on this whole other layer, a really personal 00:14:16.779 --> 00:14:18.860 weight, when you consider something Alex Winter 00:14:18.860 --> 00:14:21.399 revealed back in 2018. Yeah, this is where his 00:14:21.399 --> 00:14:23.600 own story really connects with the themes in 00:14:23.600 --> 00:14:25.580 his work, especially something like showbiz kids. 00:14:25.860 --> 00:14:28.620 In 2018, he spoke publicly about having suffered, 00:14:28.799 --> 00:14:31.539 in his words, intense and prolonged child sexual 00:14:31.539 --> 00:14:33.580 abuse. And this is when he was working as a young 00:14:33.580 --> 00:14:35.379 actor. While he was acting on Broadway, yeah. 00:14:35.899 --> 00:14:38.419 by an older man who is now deceased. That just 00:14:38.419 --> 00:14:41.379 adds such a painful context to everything, especially 00:14:41.379 --> 00:14:44.000 his interest in the experiences of child performers. 00:14:44.279 --> 00:14:47.820 Absolutely. It reframes so much. He talked very 00:14:47.820 --> 00:14:51.539 openly about the impact, the extreme PTSD for 00:14:51.539 --> 00:14:54.240 many, many years, how it just wreaked havoc on 00:14:54.240 --> 00:14:57.120 him. His decision to investigate those hidden 00:14:57.120 --> 00:14:59.340 dangers within the entertainment industry, particularly 00:14:59.340 --> 00:15:02.460 for kids, you can see it as this incredibly brave 00:15:02.460 --> 00:15:05.299 public way of processing that trauma. And there 00:15:05.299 --> 00:15:06.980 was that really interesting paradox he mentioned, 00:15:07.019 --> 00:15:09.139 too, about how he coped. That's fascinating. 00:15:09.240 --> 00:15:11.559 Right. He specifically said that starring in 00:15:11.559 --> 00:15:14.100 the Bill and Ted movies was therapeutic for him. 00:15:14.179 --> 00:15:16.799 Think about that. The trauma happened in the 00:15:16.799 --> 00:15:19.360 highly professional real world of Broadway. Right. 00:15:19.740 --> 00:15:22.340 Intense, serious theater. And the therapy, the 00:15:22.340 --> 00:15:25.080 escape, came from playing Bill S. Preston, this 00:15:25.080 --> 00:15:28.220 character who's just relentlessly positive, goofy, 00:15:28.399 --> 00:15:31.399 almost aggressively simple and safe. It's like 00:15:31.399 --> 00:15:33.799 the hyper optimism, the sheer absurdity of Bill 00:15:33.799 --> 00:15:37.419 was a refuge, a way to heal. That iconic role 00:15:37.419 --> 00:15:39.980 for him was deeply therapeutic. It's a really 00:15:39.980 --> 00:15:42.899 profound link between this huge pop culture figure 00:15:42.899 --> 00:15:45.960 and a very difficult personal history. And that 00:15:45.960 --> 00:15:48.779 platform he built through acting, he's now using 00:15:48.779 --> 00:15:51.620 it very directly for activism. Which brings us 00:15:51.620 --> 00:15:54.899 right up to 2025 and some pretty bold public 00:15:54.899 --> 00:15:57.559 stances. Yeah, taking on some very big names 00:15:57.559 --> 00:16:00.500 and issues. Like in February 2025, he was actively 00:16:00.500 --> 00:16:03.480 involved in promoting these national Tesla takedown 00:16:03.480 --> 00:16:06.179 protests. Outside Tesla showrooms, what was the 00:16:06.179 --> 00:16:08.779 specific issue there? It was framed as a direct 00:16:08.779 --> 00:16:11.340 response to Elon Musk's political activities. 00:16:11.340 --> 00:16:13.720 And also this group Musk was promoting called 00:16:13.720 --> 00:16:16.519 the Department of Government Efficiency, D -O 00:16:16.519 --> 00:16:21.029 -G -E. W -E, like Dogecoin. Exactly. That acronym 00:16:21.029 --> 00:16:23.210 felt like a deliberate nod to the crypto meme 00:16:23.210 --> 00:16:25.950 culture Musk loves. So the protest wasn't just 00:16:25.950 --> 00:16:28.850 about cars. It was about Musk's specific brand 00:16:28.850 --> 00:16:31.570 of political influence, his whole persona as 00:16:31.570 --> 00:16:34.029 this corporate figurehead. And Winder was careful 00:16:34.029 --> 00:16:35.889 about how he positioned himself in that, wasn't 00:16:35.889 --> 00:16:37.730 he? Very specific. He made a point of saying, 00:16:37.850 --> 00:16:40.190 look, I'm an avid electric vehicle owner myself. 00:16:40.389 --> 00:16:42.710 This is an anti -EV. It's not even anti -Tesla, 00:16:42.730 --> 00:16:45.070 the company. It's anti -Elon Musk. He called 00:16:45.070 --> 00:16:47.769 Musk a toxic figurehead. So the goal was to pressure 00:16:47.769 --> 00:16:50.340 Tesla to distance itself from Musk. That seemed 00:16:50.340 --> 00:16:52.940 to be the stated aim, yeah. Using his own platform, 00:16:53.159 --> 00:16:56.159 even his consumer choice as an EV owner, to critique 00:16:56.159 --> 00:16:58.519 the leader at the top. And that willingness to 00:16:58.519 --> 00:17:01.500 get involved in tricky political areas didn't 00:17:01.500 --> 00:17:04.940 stop there in 2025. No. Later in the year, in 00:17:04.940 --> 00:17:07.460 September, he signed on to an open pledge with 00:17:07.460 --> 00:17:09.859 a group called Film Workers for Palestine. Okay, 00:17:09.920 --> 00:17:12.240 what did that pledge entail? It committed the 00:17:12.240 --> 00:17:14.740 people who signed it to not working with Israeli 00:17:14.740 --> 00:17:17.599 film institutions that the pledge organizers 00:17:17.599 --> 00:17:21.680 believe are complicit in genocide and apartheid 00:17:21.680 --> 00:17:23.839 against the Palestinian people. That's a very 00:17:23.839 --> 00:17:25.539 strong statement, especially within the film 00:17:25.539 --> 00:17:27.740 industry. It's a really bold move. It shows he's 00:17:27.740 --> 00:17:30.220 willing to draw professional lines based on complex 00:17:30.220 --> 00:17:32.720 international conflicts. It really cements this 00:17:32.720 --> 00:17:35.759 identity he's built as an engaged activist, someone 00:17:35.759 --> 00:17:38.140 using his industry standing for political ends, 00:17:38.299 --> 00:17:41.160 a million miles away from the slacker dude. persona, 00:17:41.240 --> 00:17:43.799 really. It really is something, isn't it? To 00:17:43.799 --> 00:17:47.579 trace this path, the deep dives into tech and 00:17:47.579 --> 00:17:50.279 finance, the political protests, the personal 00:17:50.279 --> 00:17:52.940 revelations, and then realize, oh yeah, he's 00:17:52.940 --> 00:17:55.559 also still acting and directing commercial stuff 00:17:55.559 --> 00:17:58.900 too. Like he's woven all these seemingly separate 00:17:58.900 --> 00:18:01.880 threads together. Completely. And maybe the biggest 00:18:01.880 --> 00:18:04.559 symbol of that weaving together was Bill S. Preston 00:18:04.559 --> 00:18:06.900 coming back. After all those years of development 00:18:06.900 --> 00:18:10.299 hell, he and Keanu Reeves finally made Bill and 00:18:10.299 --> 00:18:13.140 Ted face the music in 2020. And the plot was 00:18:13.140 --> 00:18:16.319 almost about his own journey in a weird way. 00:18:16.380 --> 00:18:18.559 Kind of meta, yeah. The whole movie is about 00:18:18.559 --> 00:18:20.460 how Bill and Ted haven't written the song yet. 00:18:20.519 --> 00:18:22.259 The one that's supposed to unite the world. They're 00:18:22.259 --> 00:18:24.900 dealing with middle age, family, the pressure 00:18:24.900 --> 00:18:26.900 of that unfulfilled destiny. That was perfect. 00:18:27.019 --> 00:18:29.160 Here's the guy who spent the last decade analyzing 00:18:29.160 --> 00:18:32.119 the actual real world complex systems threatening 00:18:32.119 --> 00:18:36.150 us. You know, the dark web, shady finance. And 00:18:36.150 --> 00:18:38.490 he's playing a character still struggling to 00:18:38.490 --> 00:18:41.109 save the world with just a rock song. It acknowledges 00:18:41.109 --> 00:18:44.109 that saving the world is maybe a bit more complicated 00:18:44.109 --> 00:18:46.170 than just being excellent to each other. It fits 00:18:46.170 --> 00:18:48.549 his trajectory perfectly. And he's definitely 00:18:48.549 --> 00:18:51.380 keeping both feet planted in both worlds. Looking 00:18:51.380 --> 00:18:54.180 at his recent stuff, it's still that mix. 2024, 00:18:54.579 --> 00:18:56.539 he was in that totally bonkers movie, Destroy 00:18:56.539 --> 00:18:58.839 All Neighbors. Back to the gonzo horror comedy, 00:18:59.039 --> 00:19:00.880 playing two parts in that one, Vlad on a public 00:19:00.880 --> 00:19:02.819 defender, just embracing the weirdness again. 00:19:03.000 --> 00:19:05.339 And then for 2025, he's wearing all the hats 00:19:05.339 --> 00:19:08.240 again. Produced, directed, and starred in a feature 00:19:08.240 --> 00:19:11.500 film called Adulthood. See? He's constantly flexing 00:19:11.500 --> 00:19:13.579 all those muscles, directing, producing, performing. 00:19:14.410 --> 00:19:17.109 Sometimes all on the same project. He's not choosing 00:19:17.109 --> 00:19:19.309 one over the other. But the thing that really 00:19:19.309 --> 00:19:22.009 feels like it closes the loop, maybe, the thing 00:19:22.009 --> 00:19:24.150 that connects the experienced filmmaker and activist 00:19:24.150 --> 00:19:26.609 all the way back to that disciplined kid taking 00:19:26.609 --> 00:19:29.390 the train into Manhattan, it's the stage return. 00:19:29.670 --> 00:19:32.609 Absolutely. Returning to Broadway, fall 2025, 00:19:32.950 --> 00:19:36.130 with Keanu in Waiting for Godot. That's not just 00:19:36.130 --> 00:19:39.230 any play, it's Beckett. It's pure, stark, minimalist 00:19:39.230 --> 00:19:42.220 theater. A deep philosophical dive into waiting, 00:19:42.339 --> 00:19:45.160 existence, meaninglessness. Talk about whiplash 00:19:45.160 --> 00:19:47.380 again. From destroy all neighbors and criticizing 00:19:47.380 --> 00:19:50.589 Elon Musk to Beckett. It's more than just showing 00:19:50.589 --> 00:19:53.009 range, though. It feels like a deliberate statement, 00:19:53.210 --> 00:19:55.710 solidifying his seriousness, maybe, returning 00:19:55.710 --> 00:19:58.349 to that high art standard from his youth. But 00:19:58.349 --> 00:20:00.970 now, as this globally recognized figure known 00:20:00.970 --> 00:20:03.029 for something completely different. It's like 00:20:03.029 --> 00:20:05.329 the ultimate synthesis. Exactly. The disciplined 00:20:05.329 --> 00:20:08.609 performer, the determined filmmaker, the documentarian, 00:20:08.650 --> 00:20:11.289 the activist, all coming together to tackle one 00:20:11.289 --> 00:20:14.430 of the most profound texts about the human condition. 00:20:14.529 --> 00:20:18.259 It ties everything together beautifully. So wrapping 00:20:18.259 --> 00:20:22.339 up this deep dive on Alex Winter, it's just been 00:20:22.339 --> 00:20:24.240 this incredible arc, hasn't it, from that... 00:20:24.680 --> 00:20:27.299 Really rigorous start as a child actor through 00:20:27.299 --> 00:20:29.779 the absolute cultural explosion of Bill and Ted. 00:20:30.019 --> 00:20:32.200 And then strategically using that explosion, 00:20:32.359 --> 00:20:34.299 that fame, not just to stay famous, but to pivot, 00:20:34.359 --> 00:20:37.779 to become this serious, award -winning documentarian 00:20:37.779 --> 00:20:40.680 digging into really complex stuff. Yeah, using 00:20:40.680 --> 00:20:43.299 that platform now to really scrutinize these 00:20:43.299 --> 00:20:45.819 massive global forces, anonymous digital economies, 00:20:46.059 --> 00:20:48.339 hidden money, the power of platforms like YouTube, 00:20:48.539 --> 00:20:50.460 even the political moves of huge figures like 00:20:50.460 --> 00:20:53.640 Elon Musk. He turned being Bill S. Preston into... 00:20:53.960 --> 00:20:57.019 like a tool for serious investigation. It really 00:20:57.019 --> 00:20:59.359 messes with your assumptions. The guy forever 00:20:59.359 --> 00:21:02.180 known as the most excellent dude who literally 00:21:02.180 --> 00:21:06.019 fought evil robot versions of himself. He's now 00:21:06.019 --> 00:21:08.019 the one making films that critically examine 00:21:08.019 --> 00:21:10.640 the financial and political wiring of our entire 00:21:10.640 --> 00:21:12.880 world. It leaves you with a pretty interesting 00:21:12.880 --> 00:21:15.160 thought, doesn't it? What does this tell us about 00:21:15.160 --> 00:21:18.490 pop culture fame? Can it actually be transformed 00:21:18.490 --> 00:21:21.809 intentionally into a platform for real social 00:21:21.809 --> 00:21:23.990 and political critique? And maybe the bigger 00:21:23.990 --> 00:21:26.670 surprise, how often is it the people we might 00:21:26.670 --> 00:21:29.369 write off early on, the ones labeled slackers 00:21:29.369 --> 00:21:31.849 or goofballs because of a role they played, how 00:21:31.849 --> 00:21:33.470 often do they turn out to be the ones paying 00:21:33.470 --> 00:21:35.809 the closest, most critical attention to how the 00:21:35.809 --> 00:21:37.430 world actually works underneath the surface? 00:21:37.490 --> 00:21:38.430 Something to think about.