This Entertainment Lawyer to the Stars Shares His Best Negotiating Secret

Hilarious and mega-powerful entertainment lawyer Allen Grubman shares his greatest secrets that’ve worked for decades to close deals and secure the biggest clients in Hollywood.

WOULD YOU HIRE a lawyer who doesn’t have a desk in his office, admits he rarely reads and won’t accept a memo longer than a single page from his legal colleagues? Mariah Carey, Lady Gaga, Elton John, David Zaslav and Bob Iger all did.

Allen Grubman, 82, is the last of a breed of entertainment dealmakers who have represented both the talent and old-school industry tycoons. He grew up in a middle-class Jewish home in Crown Heights, Brooklyn, to immigrant parents who worked in the garment industry. Sunday dinner meant going out for Chinese food; during the week, it was frankfurters with sauerkraut and mustard at the corner deli. At 11, a stint on NBC’s Horn and Hardart variety show exposed him to the glamour of the city—the steakhouses NBC treated the cast to and the limousines they sent to pick him up on Saturday mornings. He knew he wanted more.

Long before he would go on to become the only practicing lawyer honored by the Rock & Roll Hall of Fame (Grubman was inducted in 2022 for negotiating agreements that allowed artists to maintain more creative control over their work), he attended Brooklyn Law School. Graduates were “encouraged to work for ambulance-chaser negligence firms,” he says, but Grubman took a different path, charming his way into a law firm after several others would not hire him.

In 1974, he founded his own firm specializing in entertainment law, a niche many highbrow Wall Street lawyers dismissed as frivolous at the time. At first he signed disco and funk groups such as KC and the Sunshine Band and Kool & the Gang. Within a decade, he’d landed Bruce Springsteen and Madonna as lifelong clients, followed by Robert De Niro, Rod Stewart, U2, J. Lo, Whitney Houston, the Weeknd and Ana de Armas.

Looking back, he attributes his success to his humble beginnings. “The greatest gift my parents gave me,” he says, “was the gift of giving me nothing. I knew I had to roll up my sleeves.”

Is success fun?

Fantastic. I was an unimpressive kid from Brooklyn. For me, it’s a wonderful thing.

How’d you become a mega-lawyer?

Common sense, street smarts, the ability to communicate with people and have people respect you and like you and want to work with you. You can’t be taught that in school.

How much of your time do you spend being a psychiatrist for your clients?

100%. Seriously.

Do you have a good bulls— detector?

Everybody is full of s—, it’s just a question of degree. They exaggerate, they lie. Nobody tells 100% of the truth 100% of the time. You pay compliments to people all the time.

Are you OK lying ever?

I never, ever lie to anybody. I’m incapable of lying.

Not even a white lie to avoid upsetting someone?

I’m so blunt and direct. My wife says it’s amazing that I haven’t been run over by a car.

Do you prepare your clients for the downside?

I am not as honest with artists as I am with executive clients. Artists’ egos are more fragile. To become a very successful artist, you have to always be questioning yourself. Is this material good? Is this movie script good? CEOs make decisions every day; any one decision is not as monumentally important as it is for an artist preparing for a new album or to perform in a movie.

Were your parents tough on you?

I came from a very middle-class, immigrant Jewish family in Brooklyn. My parents gave me a roof over my head. They fed me. They loved me. But I understood if I was going to make something of myself, I had to do it myself.

Were you cool in high school?

I was a normal, average guy with average friends. I wasn’t in the in-group, you know, the most popular kids. Steve Rubell, who started Studio 54 many years later, was in my high school. Everybody loved him.

You say you weren’t a great student. How come?

I always say I graduated in the top 100% of my class. My grades suffered because I always had to work after school. I worked for Barricini candy. I worked at a button factory as a stock boy. All kinds of jobs, anything to make a few dollars. It wasn’t about using my mind. I was using my legs. If I didn’t work, I didn’t have pocket money.

You figured out how to hustle. What do you think about rich kids who don’t have to be stock boys or girls?

Being born with wealth, to me, is a curse. This is why many of my wealthy friends have children who don’t have ambition, hunger or this burning desire to achieve. It’s all been handed to them.

I find most self-made leaders are propelled by a childhood they wanted to fix or escape from. What gives you the drive to keep working at 82?

I remembered how glamorous the entertainment business was when I was 11 and 12. On Saturday mornings, an NBC limousine would come to the house for my part on the Horn and Hardart show. I wanted more of that. In my neighborhood, the only time you ever saw a limousine was behind a hearse at a funeral.

When did you start to feel rich?

In 1987, I separated from my first wife and was looking for an apartment. The broker opens the door, and there’s a butler. And I said, “What’s this?” He tells me the apartment comes with a butler. I said, “We don’t have to go inside. I’m taking it.” What does the butler do? “Yes, sir, can I serve you your breakfast?” It was hysterical. I said to my friends, “You got to come here. You got to see this.” That was the first time this kid from Brooklyn sensed that my life was different than an ordinary person.

It’s impossible to predict a hit in film or music. How do musicians keep writing music, not knowing whether it will succeed?

Musicians have to get the door open and then be smart enough to walk through. For example, a big record company was doing a dance album for some unknown movie. They wanted the Bee Gees to do three or four tracks as a favor. It’s a bulls— album! I make a deal for their producers in five minutes, an advance of a few grand for each of the band members. The Bee Gees banged out the tracks in a studio, not really knowing what it was for. Well, the movie was Saturday Night Fever. As for Barry Gibb, I don’t know if he said to himself, “This is an opportunity,” or “I’m getting stuck with a favor.”

You must know a lot about pop music, having represented Lady Gaga, the Weeknd and Mariah Carey.

I’m not encyclopedic about anything. I never absorbed a lot of information.

Do you have files all over your desk, with so many clients and contracts?

My office is a living room. I don’t have a desk.

So everything is in your head?

When anybody’s doing a deal in the office and they’re going to need my help, no matter how complicated the deal is, it has to be on one page. If it’s more than a page, I give it back to them. In fact, when they bring me the memo, I say, “OK, I put it down. Tell me what the issues are.”

What advice do you give to your CEO executive clients, say, of a media company?

As soon as somebody becomes CEO of a media company, the clock is ticking. They always end up leaving. It’s just a question of when. Do the best you can do, take advantage of every opportunity, but eventually you will end up having to leave.

Why?

That’s the system. The head of a media company is always under pressure to create successful content. At some point in time, you go through a difficult period, and when that happens, they bring in fresh blood.

Are you a tough negotiator?

People tell me and will tell you that I’m the greatest negotiator ever in the entertainment business.

What makes for a good negotiation?

When you walk away from negotiation, both sides should feel the same way—happy, but also a little sad that they didn’t get everything they wanted. That’s a success. If you walk away delighted that you got everything, the guy who got screwed will be waiting for the opportunity to get you back. Getting everything you want is the beginning of the end of the relationship.

What’s more important, cojones or luck?

Luck. Most people are not alert enough to recognize the opportunity.

Tell me about a lucky client.

I represented two French record producers from Paris who came to America to make their fortune. They put together a group of four random guys with an idea in their heads. One producer asked if he could borrow the piano in my living room. The French guy just sat down and wrote “YMCA” and “In the Navy” over an afternoon. I sent the tracks to a record company, not thinking much of it. Two weeks later, a guy from the company calls me in a panic about the songs: “Did you send the tracks to anyone else?” I’d forgotten that I sent it to him. They went crazy; they released it and it became the Village People.

You say your EQ is higher than your IQ.

I have 50 lawyers who work for me. They all have very high IQs. They went to Harvard, they went to Yale, they went to NYU. And what do they do? They’re great lawyers. They know how to draft contracts. EQ is emotional intelligence. It is something you’re born with, and hopefully you’re able to refine it to an art form.

What’s the biggest turnoff in Hollywood?

When someone tries to convince you who they are, when I know they’re not. I grew up in the garment business. Every summer we would go to the Catskill Mountains for a week. Everybody was lying about pretending to own their whole company. It was so obvious. The entertainment industry, you can’t lie, even if you want to. Everybody knows who’s successful and everybody knows who’s not.

What do you think about rich people being cheap?

If being cheap means that you don’t understand how you should enjoy every pleasure in life, materially, that you’re capable of having—if you don’t experience that, you’re a fool.

What about being cheap with people who work for you?

To me that is an enormous character flaw. The best way to spend money inexpensively and get the most out of it is overtipping people. Because the people you tip often don’t make that much money. They appreciate it 10 times more than the extra money costs you.

Tell me about greed.

The person that’s giving always thinks they’re giving too much. The person that’s getting always thinks they’re getting too little. That is the essence of life.

Do you like to buy stuff? Do you like to buy cashmere sweaters, watches?

Clothes are the only thing I spend money on.

Why not watches?

[Looks at his phone] It’s now 11:02. What do you need a watch for?

What kind of car do you drive?

I’m a pretentious Jew. In New York, I have a car and driver, a Maybach, you know? I deserve it.

Are you going to retire?

No. I don’t think New York guys really retire. I have no interests. I don’t play golf, I don’t play tennis. What am I going to do?