What I Learned Making Entourage

Two decades ago, Doug Ellin had just rapidly fallen from being Hollywood’s new comedy golden boy to totally unemployable.

He had just released his second feature length movie, Kissing A Fool starring David Schwimmer, which was tipped to be an indie hit and catapult him into the top tier of Hollywood filmmakers.

But then the film was not well received by critics or filmgoers, and the movie offers that were piling up on his desk were all quickly withdrawn.

He was thinking about giving up on his dream job and going to law school — his parent’s preferred career path for him that he had already resisted once as a younger man  — when his manager told him about an idea another of his clients, Mark Wahlberg, had for a comedy series called Entourage.

Doug hated the idea, but decided to give it a crack. Eight seasons, a movie and sackfuls of awards later, he’s pretty pleased he did. And now he is sharing some of the secrets of the show, his success and hearing the stories of other creatives and entrepreneurs in his new audio venture, ‘Victory The Podcast’, alongside Entourage star Kevin Dillon. And he’s plotting his next TV hit too, an Entourage-style show in the world of soccer, inspired by the life of Arsenal and France legend Thierry Henry.

Here Doug tells Mr Feelgood about how he, like the characters in his HBO show, came to Los Angeles as a fish out of water and hustled his way to the top — and we glean the wisdom that can be learned from his journey.

And, like Entourage, it’s a story set in Hollywood but has lessons that could apply in any walk of life.

YOUR FIRST ‘BIG BREAK’ MIGHT NOT BE YOUR BIGGEST

“I graduated from Tulane University in New Orleans and and was supposed to go to law school. But I just woke up one day, and said, ‘I can’t do it.’

So I went to Hollywood with no job and not a single contact in the entertainment industry. I started doing amateur stand-up comedy nights around town and I got a temporary job in the mailroom of New Line Cinema. And I didn’t like that, but it was a good move.

Mike De Luca, who was the VP of New Line Cinema, came to one of my amateur stand-up nights and gave me $10,000 of his own pocket to make a short film. So I’d never been on a film set before, but I ended up making a film.

We sold that short film to Showtime, then I started getting meetings about directing movies, like big movies — but I didn’t even know what I was doing. So I decided to go to the American Film Institute for a year.

After that, I got an offer to do a small movie called Phat Beach, which I made for about $100,000 and ended up selling and playing around the world — even though it was not very good. And then I got a second independent movie called Kissing a Fool, with David Schwimmer and Jason Lee, and we ended up selling that to Universal Studios. Before that movie came out, I was kind of, for a second, the hot comedy guy in town. Everyone really liked it. I was getting all these big offers. I was supposed to do a remake of The Heartbreak Kid. And then the movie came out and didn’t make any money and, all of a sudden, I was really not employable.

So after a decade of working, buying a house, having kids, I felt like my career was over. And I was thinking about going to law school again.

Then a friend of mine told me I should try the TV business, which I’d never done anything in. I said, ‘ How do you get into that?’ He said write a spec script for a show I loved. So I wrote a Curb Your Enthusiasm spec script, which means I just wrote something that interested me. And my manager, who is Mark Wahlberg’s manager, liked that script and said, ‘We’re kicking around this idea about Mark and his friends.’ And that’s where that started.”

IF AT FIRST YOU DON’T LIKE AN IDEA, TURN IT INTO SOMETHING YOU DO

“I actually hated the idea for Entourage. And my manager just said, ‘You’ll figure it out.’ So I went and thought about it, and then spent about 18 to 24 months getting the script into a place where HBO finally said: ‘OK.’

The thing that didn’t work for me, which is why I think the show worked, is the idea of an ‘entourage’ is not really my thing. I think of entourages as being about people using each other for things. But the idea of friendship is my thing. The friends that I’ve come up with, and that ultimately these characters became based around, we’ve always stuck together and try to help each other out. So it was much more important to me that this is a family and that everybody had a real purpose. Even if it was Turtle being the driver.

One of my favorite things was when some of the reviews said that the idea was terrible, but the execution was great. I felt very good about that. Because very few films or television shows about Hollywood have been successful.”

EMBRACE THE POWER OF FRIENDSHIP

“For me, this show had to be about four best friends, with Hollywood as the backdrop, but they could really be anywhere.

I made them kind of from where I grew up, which is similar to Mark (Wahlberg). Working class neighborhoods, as opposed to how people think of movie stars as just rich, with everything handed to them. The truth is, these were kids who had nothing, and one of them is sharing his success with all of them, and hopefully they all bring something to the table.

Much of the show came out of my real life experiences with my friends. I’m still best friends with my friends from kindergarten. We literally have a WhatsApp group of like 14 people I’ve know since I was seven or eight years old.

And, like in the show, it’s important that you have those people who knew you then and know everything about you. My best friends are still from back home more than LA, and I’ve been here 30 years.”

IF SOMEONE DOESN’T LIKE YOUR WORK, TRY TO FIGURE OUT WHY… THEN MAKE THEM FEEL LIKE PART OF THE SOLUTION

“It was far from smooth sailing (with HBO). The first script that I handed in, which we felt really good about, they hated it.  And I said to my manager, ‘What don’t they like about it?’ And he said, ‘They don’t like any of it.’ So that wasn’t good.

Most of the comments that I got back were about tone and making it fun. And not about me as a Hollywood writer, who is going through a lot of s*** that people really don’t care about. So it was about finding ways to make it lighter, while I still wanted to have the heart.

As far as notes go, it’s definitely one of the most important skills you can have in this business. I’ve had producers and executives that have given amazing notes, and I’ve had some that give terrible notes. But the key is be able to understand what they’re saying and to be collaborative because the fact is, it’s not a painting, millions of dollars needs to be given to you by somebody else in order to make these things. So when you take ownership as if it’s all yours, you walk into problems.

Even from my days as a stand-up comic, I always looked at the person who wasn’t laughing and want to know why. And often a note will not be exactly what the problem is. But it’s your job to understand that something is troubling this person and figure out if it’s just, you know, that they’re not very smart, or if you’re doing something wrong. And then, if you’re smart, you figure out how to make them feel like they’re actually addressing something.”

YOU HAVE TO HUSTLE — EVEN IF IT DOESN’T COME NATURALLY TO YOU

“This business is very entrepreneurial, and you really have to self-motivate and self-start and a lot of us, including me, are inherently lazy people. But it’s the type of business that if you want to be lazy, you’re just going to evaporate.

There are so many people who are going to go out there and hand out their scripts, or get up and do stand-up. When I was starting, getting out there was not something I enjoyed doing. I love stand-up as far as like being on the stage, but not everything surrounding it, like waiting around, not getting paid, a lot of other comedians and the late nights. But I had to do it.

And the same with handing out all these flyers to get everyone from New Line Cinema to come see me do the stand-up so I could raise money to make my short film. And the same with making that short film. It’s hard to imagine now, but like Turtle in the show, I was walking around handing it out to people and agencies and doing all that stuff.

The world is very different now, because you can send a link or post it on your Instagram. But back then, you had to really go door-to-door essentially and you can’t stop, because somebody else is right behind you and they’re doing it.

I’m not a salesman. I don’t like asking people for anything. And that was definitely tricky for me, but it was definitely a lot easier to have a finished product. Even when you have a short film, it’s not easy. But when you hand 100 pages of paper to somebody and tell them how great your script is, it’s a bad sign. But I got over it and I got some good breaks, and I think everybody needs those in this business. But you have to be persistent.”

DON’T GET TOO CAUGHT UP IN CRITICISM… OR PRAISE

“When you do an independent movie and Universal buys it and says they’re releasing it on 2000 screens, you think your life is set. Then it test screens through the roof and the executives are telling you that you’re a genius and you’re getting all these offers.

But then the movie opens and Roger Ebert tells you to go to screenwriting class. The movie makes no money and all of a sudden people that were offering you a million dollars are now offering you nothing. They won’t even let you do it for free. You become this like pariah.

So it’s very important in this town to not take these things personally, because they are ridiculous.

When Entourage came out, I was completely prepared to be trashed. I’d been trashed on the two movies that I did. And all of a sudden it came out it’s called the best show on TV in The New York Times. And, you know, it all feels really good. But you can’t get too locked in that because then you get to the next phase and people start turning on the show a little bit, and and the movie didn’t get great reviews.

I’m not good at it. I literally hate critics. But I have to not love them when they say I’m good, and when they say I’m bad I take them as what they are.”

KEEP CREATING AND LEARNING

“Kevin Connolly (Eric Murphy in Entourage) started a podcast company and lots of people had told me I had a good voice for a radio show.

And from my stand up background, I’d wanted to do a talk show since I was a kid, but it’s something I didn’t know how to pursue and just never did. So this was an opportunity to give that a shot.

So I thought let’s give it a go. I said to Kevin, ‘I want to get good at this. I don’t want to call in all the favors, and try to bring people in and get an audience and not be good. I’m going to work on it and get good.’

But I also wanted to find a way that we could break through and Kevin came up with the idea to get Kevin Dillon (Johnny Drama in Entourage) involved, and we’ll talk about the show. And my thought was I want to talk about a lot more than the show, for it to be essentially like a radio show. So we’re doing both.

I’ve known Kevin (Dillon) for 20 years and he still surprises me and makes me laugh. I do sometimes try to find where the line is between him and Drama.

The podcast is about entrepreneurial spirit and it’s about the fact that we are three guys from New York who came to Hollywood knowing nobody, and we wanted to talk about those experiences as well as bringing in other people’s experience. We want it to be light, we want to be fun, but we also hear about people’s progressions and how they made it from the different walks of life and their ups and downs.”

AND KEEP LOOKING FOR THE NEXT HIT

“It’s a show set in the world of football (soccer). We’re actively trying to get that going right now.

Thierry Henry (the former Arsenal and France striker) was in the Entourage movie so I’ve known him a long time. And Darren Dein, who is his long-time manager, is a good friend of mine.

It’s the friendships, the family dynamic, all that stuff behind the scenes. It’s inspired by Thierry’s life, similar to how Entourage was inspired by Mark Wahlberg.

We’ve just finished the script and we’re hoping. The world is closed down, and my opening scene takes place at a full Wembley stadium. But we can do that with cardboard cutouts and CGI. Thierry will consult as well as his manager to help us to make it as authentic as possible.

A couple of good things are happening this week. I can’t mention them until they happen, like everything in Hollywood, but I’m hoping to get good news in the next few weeks.”