One of the most pivotal moments in Rifkin’s career was meeting Bruce Willis, though he gives credit to his colleagues for the discovery:

“I have to give credit to the people that found Bruce. Gene Parseghian back in New York had seen him in True West. Cis Corman told Gene to go to the theater and see him. And then there was a show they were casting called Moonlighting.”

When Willis finally came to Rifkin’s office, the agent was immediately struck by his confidence:

“When he came into my office, he had a torn t-shirt, ripped jeans, and he pretended he was worth a billion dollars. He never doubted the fact. And he gave me the smirk. I knew the light in his eyes, and we became agent, and it was a journey.”

The casting of Willis in Moonlighting wasn’t straightforward. He had already been rejected twice and borrowed money from Sherry Rivera, Geraldo Rivera’s ex-wife, to fly to Los Angeles for another audition. Rifkin notes that Willis wasn’t the typical leading man: “He was not a typical leading man. Not at all. He had that brilliant quality of being self-effacing. And he was sexy. He had a swag.”

Perhaps Rifkin’s most famous negotiation was securing Bruce Willis’s casting in Die Hard for an unprecedented $5 million. The deal came at a crucial time when major stars had passed on the project:

“With arrogance. Hubris. Because the first round they went to every famous actor. Nobody wanted to do it. Die Hard was a battery at Sears, that’s what that was. And we had come off of a movie that, I won’t tell you the title, and nobody went. And the worldwide gross was $3 million.”

Rifkin’s strategy was bold and calculated:

“I said upfront, there’s only two things that could possibly happen here. We either succeed or we fail. So you have to pay him enough money to justify either. Either you become a hero, or no one could deny the fact that how could you turn that down. And the number was what it became, what was it? Five.”

The deal created shockwaves throughout Hollywood:

“Press, I was banned from Warner Brothers. Everybody’s salaries went sky high. Mel Gibson wanted 5 million. Michael Douglas said, how could you pay me two and a half and he’s a nobody, and you pay him five. I got hammered. Every studio said, Rifkin, what did you do? A $5 million deal to somebody who just did one movie that failed and did $3.2 million?”

Another testament to Rifkin’s negotiation prowess came with Edgar Bronfman and Seagram’s wine cooler campaign. When Bronfman initially balked at the price, Rifkin was willing to walk away:

“Edgar makes a proposal and he’s telling me what he wants. He wants the swag that Bruce has. Back in the day, there was the Marlboro guy, and now Bruce was the guy. So I gave Edgar a price, and he said, that’s way too much money. And I said, I don’t know how to fix it. If you’re not willing to pay, you wanna be one. And he said, okay, we’re done.”

A year later, Bronfman returned, having been unable to find the right spokesperson:

“Edgar comes back a year later and said, you know, I’ve seen 3000 men and I can’t find the guy that I want. So I’m back. He said, so I’m willing to pay you. I said, Edgar, it’s a year later. The inflation and all.”

The campaign was a massive success: “He paid a lot of money to get Bruce. And you know what? Within six months, he was number one.”

After 35 years as an agent, Rifkin made the decision to leave the business and partner with Bruce Willis as a producer. This transition coincided with a profound spiritual transformation:

“I told Bruce that I was leaving, and Bruce said, well, what are you gonna do? And I said, well, I’m not totally sure, but I wanna see what the other side’s like, I want to know the people who make the decisions on that side. I wanna see what that’s like. And he said, let’s do it together. I said, cool.”

The spiritual journey began through his trainer, who introduced him to a Native American spiritual guide:

“This experience with the spiritual guide. I had a trainer who would come and see me twice a week. And each time I saw him, I’ve never seen eyes so white and clear. And I said to Kevin, I said, what is it that you do that when you come, you know, six o’clock in the morning, you look…and he told me about this gentleman. He told me about the sweats.”

This 15-year relationship with his spiritual guide, Richard, deeply influenced Rifkin’s approach to life and business:

“I connected with Richard. And for 15 years, he took me on a journey. And Cheyenne, the whole dragonfly thing just came to me when I started reading about the different tribes and it fit.”

The relationship between Rifkin and Willis transcended typical agent-client dynamics, becoming a brotherhood that has endured through Willis’s health challenges:

“We could finish each other’s sentences. Yeah. And we wore the same size sweaters. So metaphor, I mean. Yeah. We lived together. I mean, there’s no doubt.”

Rifkin speaks candidly about Willis’s complexity as a person and star:

“Bruce was, when fame hit, I don’t know that he knew how to behave yet. And there were moments where it was inappropriate and there were moments that were amazing. But I feel as though he was a great father. And he loved to laugh. He loved to make people laugh.”

The cultural impact of Willis as John McClane became clear to Rifkin during an unexpected moment after 9/11:

“We were trapped and we went for a walk in Central Park and to understand the gravity of Bruce’s persona, we are walking, and Bruce has got his hat on his glasses. Nobody knows who he is. And we listen to somebody say, where is John McClane when you need him? Man. That was like, what? That’s insane. That’s cultural impact.”

Today, Rifkin continues his friendship with Willis despite the actor’s health challenges:

“There was a time where we were not, and it wasn’t an acrimonious time. It was everybody needed to move on for a while. I got the phone call from Stephen Eads, and I knew a little bit about what was happening, but I was not involved. And Stephen called and said that he’d like to see you, and are you open to that? And I said, absolutely.”

Their Friday lunch tradition continues: “So ultimately there was a small group of us and Fridays we would have lunch, and we had great moments. And there’s moments when he smiles and you almost know that he remembers that moment that we’re laughing at or whatever.”

Rifkin is now working on a documentary about Willis with his new company, Incite, alongside partners Jenner Furst and Justin Lee:

“Stephen and I both went to Emma at some point and said, we’re probably the only two people that know everything, between my vault and Stephen’s vault of memories. We’re the only people that could tell that story and tell it with love, tell it with authenticity. And give him the dignity of who he was.”

Reflecting on his decades in Hollywood, Rifkin shares the wisdom he’s gained:

“You have a choice. You can live in abundancy or you can live in scarcity. That’s my world. And it’s not about the car you drive, it’s really about what you feel. That’s what I would share to anybody as a 30-year-old.”

His management philosophy, which served him throughout his career, remains simple but powerful:

“Do not bring me problems. Bring me solutions. When we do solutions, we solve. You bring me a problem. I don’t need you. I can make problems on my own.”

Don’t miss the full conversation on Don’t Kill the Messenger to hear more about Arnold Rifkin’s Hollywood journey, his transformative deals, and his enduring friendship with Bruce Willis.

Don’t Kill the Messenger, hosted by movie and entertainment research expert Kevin Goetz, brings his book Audienceology to life. This bi-monthly podcast takes a peek behind the filmmaking curtain as Kevin talks with famous filmmakers, studio executives, stars, and other creatives about movies, filmmaking, audience test screenings, and much more.