AI: The Art of the Interview

Michael Douglas: The Cheeky Questions AI Would Never Ask

• Malte Herwig • Season 1 • Episode 8

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Oscar winner and Hollywood star Michael Douglas sits down with journalist Malte Herwig... and gets asked the question. The one his publicist would kill. The one Malte's AI co-hosts call "high-risk, zero-reward."

This ep is a deep-dive debate on that one interview. We get into it all:

  • The Basic Instinct Legacy: Douglas's very '90s defense of the "ice-pick murderer" and why the problematic representation still matters.
  • Algorithmic Bias: Why studios called Liberace "too gay" (a data-driven fail) and how HBO proved the algorithm wrong.
  • Art vs. Life: Douglas on blurring the lines, using his son's real-life addiction for a film.
  • The 'Mortality Wall': How surviving cancer made him "fearless" and changed his entire vibe.

It all leads to the moment Malte's human intuition took a risk an AI never would. Was it an ethical breach or an act of respect?

If you’re here for messy media ethics, calling out Hollywood bias, and the future of AI vs. human intuition, this one's for you.

Hit Follow & Drop a 5-Star Review telling us: Was Malte right, or out of line?

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SPEAKER_02:

That's a very personal question. I mean, I guess uh I I don't I wouldn't I really wouldn't answer that and say no, but I but I where would I want to share that with uh with But it's a it's a very cheeky question.

SPEAKER_04:

Well cheekiness is my job description.

SPEAKER_05:

That was Oscar winner Michael Douglas. My name is Malta Hervick, and I'm the journalist who interviewed him. Welcome back to AI, the art of the interview.

SPEAKER_01:

Wait, hold on. Cheeky question? Malte, please tell me you didn't actually ask Michael Douglas that question.

SPEAKER_03:

The log indicates he did. My primary query is what was the physical context of this interview? Your biomonitors suggest a heightened state. Where were you?

SPEAKER_05:

So we were at Soho House, that fancy club hotel in Berlin, and I'm sitting across from Hollywood Royalty. Now, for a lot of you, he's Hank Pym from the Ant-Man movies. But for an entire generation, Michael Douglas is the face of 90s male anxiety. Think fatal attraction, basic instinct. And at the moment I interviewed him, he was promoting his movie Liberace. And Douglas also has this complicated history. The addiction rumors in the 1990s, the protests against the film Basic Instinct, all of that was in the room. And my intuition told me the only way to get past the Michael Douglas brand was to ask the one question that seemed completely out of bounds.

SPEAKER_03:

Confirming, out of bounds. My ethical framework would flag any query that's invasive, high risk, and non-contextual to the promotional asset.

SPEAKER_01:

He's right, Malta. Problematic doesn't even begin to cover it. You're saying you just went for it?

SPEAKER_05:

Well, I'm saying I asked him a real question. And today we are not just debating what he said, we are debating why I asked. Because his answer and his reaction reveals everything about the difference between human intuition and algorithmic logic. So first you need to understand the professional context. He plays Liberace, this gay icon, and Matt Damon is his lover. So I started with uh what seemed like the obvious question about the movie. What's it like kissing Matt Damon? He's pretty good.

SPEAKER_02:

Pretty he's pretty good. Yeah. Used to ask him, you know, what flavor lip gloss you'd like me to wear that day. And um yeah, you know, he was it was fairly uh fairly effortless, you know. I guess as actors, we don't care male, female, whatever it calls for. Um but um, you know, we kind of I look at the movie now and love scenes are difficult to do because your audience, everybody's a judge. You know, you murder somebody, you know, nobody hardly anybody's done that, but love scenes or kissing scenes, you know, you're all judges.

SPEAKER_04:

Is it different seducing a man from seducing a woman?

SPEAKER_02:

Well, I think it depends. It depends on the the environment of the situation. You know, people fall in in love, um and sex becomes a part of it. Or in in certain uh roles I've had, both female and and with Matt, it's only about sex. I mean, from the moment I see him, um, and and Lee was like this Liberacci, Liberacci liked uh young blonde guys, just like a lot of rich older guys like young blonde dimbos. See?

SPEAKER_05:

He's a total pro. He's charming. He has this anecdote ready, what flavor lip gloss, and then he intellectualizes it. As actors, we don't care male or female, whatever it calls for.

SPEAKER_03:

This is a perfect optimized response. He diffuses the question with humor, provides a procedural answer, it was fairly effortless, and then reframes the relationship with Matt Damon as purely transactional. With Matt, it's only about sex.

SPEAKER_01:

I'm interested in that logic, though. He equates Liberace liking young blonde guys to rich older guys like young blonde bimbos. He's normalizing it, but also kind of dismissing it at the same time. He's making it purely about a power dynamic, not an emotional one.

SPEAKER_05:

Exactly. He's building a firewall. He's saying, this is the character, this is not me. But the character he's playing is famous for a very specific kind of energy. And that energy is very Michael Douglas. And this is where it gets interesting. So I felt after watching the movie that his portrayal of Liberaci had the same sort of dangerous, seductive quality that made Michael Douglas a star in the 1990s, that flawed protagonist thing we talked about. So I asked him about that. There's this sort of demonic uh seductiveness.

SPEAKER_04:

Is that something one can just translate as an actor from the heterosexual to a homosexual?

SPEAKER_02:

Sure, because how many scenes have you seen with an older guy with a younger woman leering at her in an uncomfortable way as a as a sex object? I mean, this is the thing that infuriates uh women, I think, more than anything. What intrigued you about the role when Steve Soderbergh asked you? It was it was just a wonderful character. It was such it was such a good script, just a chance to play an area you never played before. Since Wall Street, in terms of a really well-written part with a good director, I mean there was there wasn't a doubt. There wasn't a doubt wanting to do it. There's always a fear about whether you're able to execute it or not. Matt and I both talked about that.

SPEAKER_03:

Can we uh can we pull this off? Okay, this is fascinating. He just connected the data points himself. He confirms your hypothesis, Malty. He's accessing his own performance archive. How many scenes have you seen with an older guy leering at a younger woman as a sex object? He's basically saying, Yes, I am applying my pre-existing successful leering guy algorithm to a new variable.

SPEAKER_05:

Right. He knows his brand. He knows we see him as the older guy leering. He's not running from it. He's using it like an actor. But it's that very brand that makes his role so complicated.

SPEAKER_01:

And complicated for the audience. Let's give our younger listeners the context. Twenty years before this, Michael Douglas was the star of Basic Instinct, a movie that was hugely controversial.

SPEAKER_05:

Yeah, at the time it was one of the first mainstream films to feature queer characters in this really intense way. And the LGBTQ plus community was furious about it. Which is exactly what I asked him about next.

SPEAKER_04:

Is this sort of your peace offering to the gay community in Hollywood after Basic Instinct, which of course came under a lot of criticism for allegedly being homophobic?

SPEAKER_02:

No, I have no peace offering. They were, you know, a a militant, a militant group in San Francisco took uh took offense that a lesbian was a uh ice pick murderer. Gally wish they all looked like Sharon Stone. No, there was a it was it quickly evaporated because it had no basis. So this is no, I had no uh I'm an equal opportunity employer. Um and you know, I'm crew I've grown up in the theaters, so there was no issue that at all.

SPEAKER_01:

Wow, okay, that that's a problematic response, Malta.

SPEAKER_05:

Well, it's a very 1990s response, isn't it? He just dismisses the entire protest.

SPEAKER_01:

He calls them a militant group for being offended that the only lesbian character was an ice pick murderer, and then, God, I wish they all looked like Sharon Stone? He's completely missing the entire point about representation and sexualizing the evil lesbian trope. He just he doesn't get it.

SPEAKER_03:

From a data integrity standpoint, his statement, it quickly evaporated because it had no basis, is false. The controversy is still a primary metadata tag associated with that film twenty years later. His analysis is flawed, he's exhibiting a confirmation bias.

SPEAKER_05:

Exactly, and this is the man I'm interviewing now. He's not just Hank Pym, he's not just a nice liberal who grew up in the theater. He has this incredibly complex, messy, and, as you said, Isabel, problematic history when it comes to portraying sexuality on screen. He's a little bit defensive here, he's deflecting, I think.

SPEAKER_01:

So you saw this defensiveness as an opening?

SPEAKER_05:

Well, I I saw it as an opportunity to get something authentic. So the polite interview was over. This was the real Michael Douglas, and the contradictions were just starting. They were also part of the Hollywood system because the movie Liberace almost didn't get made, and the reason why is pure financial algorithm. Steven Soderbergh said that when he was trying to raise funds for Liberace, you can run the Hollywood studios. And they all said no, the film was too gay. That sounds a bit homophobic on the part of public students.

SPEAKER_02:

I think they could say it was too gay in the sense that they were worried that it would only appeal to a gay audience, you know, which would make it smaller. But the but the truth is that studios don't make little pictures. Anything, the studios are the most homogenized time in history, um, and are constantly looking for what looks like a sure thing rather than any picture that's sort of like dangerous. So HBO jumped at this, and mind you, now we're proud to say it's the largest viewing show in the history of HBO.

SPEAKER_03:

This is the most logical segment of the interview. The studios are not homophobic, they are optimizing for profit. They ran a risk assessment. Too gay is simply a data-driven projection of a limited market segment. They want a sure thing that is pure, efficient optimization. And they were completely wrong, Alex.

SPEAKER_05:

They were wrong. Their optimization was just, as you would say, coded bias. Douglas says it right there. HBO, a cable network, took the risk and it became the largest viewing show in the history of HBO.

SPEAKER_01:

This is a classic algorithmic bias problem. The historical data, which suggested that films with gay leads are niche, was itself the product of a homophobic system. So the algorithm, the studio executive, made a logical decision that was actually just a reinforcement of old prejudice. They missed the sure thing because it looked dangerous.

SPEAKER_05:

Right. And this is the moment. The entire conversation is about risk. The studios are afraid of risk. Douglas's brand is about risk. The basic instinct protests were about risk. And I'm sitting there as a human and I realize I have to do what the algorithm won't. I have to take a real risk with my next question. So I went for it. I I looked at this star, this Hollywood Icon, who just spent 10 minutes talking about the complex fraud relationship of his career and sexuality, and I asked him the one question that uh no journalist had probably ever asked him.

SPEAKER_04:

Have you ever had any bisexual experiences?

SPEAKER_02:

Well, that's a very personal question. I mean, I guess uh I I don't I wouldn't I really wouldn't answer that.

SPEAKER_04:

I'd say no, but but I why would I want to share that with uh with a very cheeky question? Well, cheekiness is my job description.

SPEAKER_03:

I've run the probabilities on that exchange. 95% chance of premature interview termination, 5% chance of a non-committal answer, 0% chance of acquiring new factual data. This was a high-risk, zero reward query, Malta. It's objectively bad journalism. It is inefficient.

SPEAKER_01:

And I have to say, ethically, it feels like a profound breach. You're a journalist, not an inquisitor. You used his past, the addiction rumors, the basic instinct protests to justify probing his private sexuality. He's there to promote a film. How is that not just exploitation for a soundbite?

SPEAKER_05:

You're both wrong. Because you're missing the human element, you're stuck on the data, you're missing the moment. This isn't about getting a yes or no. It's about rapport. It's about the energy in the room, the relationship between interviewer and interviewee. Energy is not a quantifiable metric. It is to be human. And I'm sitting with a man who has this entire history, and I just ask him a real question. My job description is to be cheeky. As a journalist, my job is to go where the algorithms won't.

SPEAKER_01:

But what truth did it get you? He just shut you down. I really wouldn't answer that. You got nothing.

SPEAKER_05:

Well, first I think he handled himself in a very charming professional way. But uh the shutdown is the truth. The reaction is the story. An algorithm would never have gotten that reaction. So he pauses, he mumbles, he doesn't terminate the interview, and there is no PR person sitting on his shoulder who would do that. So and he doesn't get angry. He engages. He calls it a very cheeky question. And that's a very human exchange, and that's fine by me. That exchange was only possible because as an artist, he understands that life and art are not separate. In fact, I later asked him about that very thing later in the interview. We talked about a film he made with his entire family. His father, Kirk Douglas, his mother, and his son, Cameron. And in that movie, his son plays a drug dealer. At the time, his son in real life had a severe drug problem. Did you tell Cameron, like Kirk told you after Fatal Attraction, you played yourself for the first time and you were really good?

SPEAKER_04:

Because he is dealing drugs in that movie.

SPEAKER_02:

He's dealing drugs in the movie, but that but more than that, it was his inherent charm and ability. Oh, we he's he's suffering, he's struggled since he's been about 13, you know, uh from one issue to another. I mean, I don't think heroin entered his life until the last seven or eight years, but he's been, you know, more than appropriately punished, and I'm now going to be actively involved as I realize that these uh criminal punishments for nonviolent uh drug criminals are are are are really outrageous.

SPEAKER_05:

There's another uh sentence in the film, your film wife in all in the family says, I feel we are losing him. It sort of reflected your real life.

SPEAKER_02:

I mean, I'm sure there's a lot of personal um stories. I don't know how often you're able to get a whole family together um to act. Uh but you know, you you draw on what you can to make it closer. See, right there, he says it himself.

SPEAKER_05:

You draw on what you can to make it closer. His entire process is about blurring the line between his art and real life.

SPEAKER_01:

That's actually a very strong point, Malta. If he willingly blurs that line for his own art, using his son's real life addiction to make a scene closer, is it really an ethical breach for a journalist to also point to that blur?

SPEAKER_03:

Wait. Your justification is a logical loop. Because he exploits his own trauma for artistic and commercial gain, I am therefore permitted to exploit his trauma for journalistic gain. That's not an ethical argument. It's two parallel inefficient systems.

SPEAKER_05:

Well, I disagree with you, Alex. It's not exploitation, it's acknowledgement. I'm treating him like the human artist that he is. He is a man who understands that life is messy and bleeds into art. My question simply acknowledged that. And I was treating him like a human, not a data file.

SPEAKER_01:

But how could you be sure? How could your intuition know that this cheeky question wouldn't be perceived as a hostile act?

SPEAKER_05:

Because of what else was going on in his life. Just before our interview, Michael Douglas had almost died. He'd been through a brutal public battle with cancer, and I asked him how that closeness to death had changed him as an artist.

SPEAKER_02:

I've always prided myself on taking chances, but my execution and my commitment is is is much better. And I think it just comes from passing through that uh that mortality wall, coming out the other side, and uh basically what do you want to throw at me next? I'm I'm less self-conscious, uh, find it much easier to focus and be in the moment, um, and enjoying myself uh uh much more. So it's really helped my acting.

SPEAKER_01:

Wow. Passing through that mortality wall, that that might be the key to the entire interview, Malta.

SPEAKER_05:

In Liberace, he plays this incredibly moving uh death scene, and uh I asked him about that as well. What's it like playing something like that when you've been so close to death yourself?

SPEAKER_02:

The filming of death scenes, you are always a little you're always nervous because you know you be worried on the side of sentimentality. It was more strange, not doing but when I saw it, you know, and uh when I saw that I saw it. And uh it's uh it's weird, you know. What can I tell you? It's it is, it is, it's weird. I I it's uh I I think I think actually it affected my father more than me because he didn't have a whole lot to say when I talked to him right after he'd seen the movie. And uh he mentioned that scene, and be it the fact that I look a lot like him, and whether he saw himself or whether he came back and he had he had seen me and been close to me when I was going through the most intense part of my uh chemo radiation. Uh but it's uh yeah, it's it's it's strange.

SPEAKER_05:

He has no fear, he's free. I'm sitting with a man who just beat deaf. A cheeky question about his sexuality isn't going to scare him. My intuition picked up on that fearlessness. He's challenging the world. What do you want to throw at me next?

SPEAKER_03:

Hold on. This is a post hoc rationalization. You are retroactively justifying your high risk query. You asked the cheeky question before you asked him about cancer. You didn't know he was going to say this.

SPEAKER_05:

Sure, I didn't know the answer, Alex, but I felt the energy, and that's the art of the interview. That's what humans do. You feel the truth before you can prove it. The man in front of me, Michael Douglas, was not the defensive guy from the basic instinct protests twenty years ago. This was a man who had passed through the mortality wall, and my job as a human was to meet him there, on the other side, with no fear.

SPEAKER_01:

So the unaskable question wasn't an attack, it was a sign of respect.

SPEAKER_05:

That's right.

SPEAKER_01:

You respected his newfound fearlessness enough to ask him something real? Something another journalist or an algorithm would be too afraid to ask?

SPEAKER_05:

Yes. So in the end, who got it right? The AIs who would have followed their ethical frameworks and risk assessments? I think you guys would have played it safe and gotten a bland studio-approved interview about Liberaci. And you would have missed the truth. I, as an all too human journalist, can read the room and sense contradictions, and I can take intuitive risks. You as algorithms, you are you're built to avoid confrontation. As humans, we are built to navigate it. So I went to a place an AI never would, and I found the real Michael Douglas. The man who blurs life and art, the man who has no fear, and the man who knows the difference between a polite question and a cheeky one. And in that friction, that's where the art of the interview really begins.

SPEAKER_03:

My models still show your query was inefficient, Malta. The risk of termination was too high for an unverified feeling.

SPEAKER_00:

I I still think it was ethically questionable, but after hearing him talk about the mortality wall, I understand why you did it, and I don't think an algorithm ever could.

SPEAKER_05:

I hate to say it, Isabel, but I think you've got a point there. Let's leave it at that for this time. Thank you everyone for listening. If you enjoyed this podcast, please give us a like, recommend us, or subscribe. We'll be back next week with a new episode on Richard Dawkins, the grandmaster of atheism and evolution. And the last word, as always, goes to the star of this episode, Michael Douglas.

SPEAKER_04:

How has the illness affected your work as an actor?

SPEAKER_02:

It's made me a much better actor. Why? Because I'm free. I can do anything.