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HawkeTalk: 3 Lessons From Navigating Hollywood With Doug Ellin, Creator Of HBO’s Entourage


Listen in as Hawke Media CEO, Erik Huberman goes toe-to-toe with some of the most influential people in the world. Get the unadulterated stories of failures, successes, and everything in between from world-famous athletes, entrepreneurs, authors, and influencers from their point of view.

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With zero aspirations of ever joining the entertainment industry, Doug Ellin found himself (almost literally) thrust into the spotlight as a young man. Having discovered his passion, he put it all on the line for a career he believed in.

Here are three takeaways that shaped his perspective and life:

1. On the moment that lit him on fire

Doug: In college one of my friends signed me up for an amateur stand-up night at the local bar.

Erik: Was it a prank or did they actually think you should be doing this?

Doug: Well I think both. I think they thought I was funny, but I also think they thought I thought I was funny.

Because when we used to see stand-up comedians I was very critical, movies of myself as well, so I get the other critics. But if I see stand-up, sometimes I can’t stand this person. So they signed me up and I did it and I…I just got the bug and I told my parents I’m not going to law school.

I moved to LA the day I graduated Tulane University and started doing stand-up and got a job in the mailroom at New Line Cinema.

2. On the flop that defined him

Doug: I ultimately made a second independent movie called Kissing A Fool with David Schwimmer and Jason Lee and Bonnie Hunt and Milly Avital. We sold that to Universal Studios and it was released on 2200 screens so I had made two independent movies…

Erik: How old were you at that point? I’m curious.

Doug: Uh, kissing a fool came out in ‘96, so I guess I’m like…um, my brain doesn’t work for numbers anymore, maybe 28-29.

Erik: That’s quick! Out of college and a few motion pictures, that’s great!

Doug: Yep! And then Kissing A Fool came out, and you know I talk about this a lot because it had so much influence on Entourage, but kissing a fool was this independent movie that was made for about a million dollars and released worldwide.

Before that movie was released I was offered…you can’t imagine how many things I was offered and turned down. 

Then the movie came out and there was nobody who said it was an independent movie. It was released like it was a giant studio movie and I think we opened up against The Wedding Singer and whatever else.

We made $2.3 million. The movie cost a million dollars to make.

Yeah, nobody cared. They thought it cost 30 million, it was like on the cover of Variety as

the reason for the downfall of the Universal marketing staff. I mean, really bizarre stuff that I ultimately used in Entourage because whether it was–I’m proud of the movie–good, great, or not, it was an incredible, amazing achievement for all of us that were involved to take a movie, make it independently, and get it released on that type of scale.

But that being said, when it came out, I’m not joking, I was literally unemployable. Everything evaporated. I could not get a job at anything.

1. On his “stupid” comeback

Doug: I was looking at taking the LSATs and going back to law school after after making two movies and making enough money to live a life out here. 

Someone convinced me to get into TV. I wrote a Curb Your Enthusiasm spec script, which means I just sat in my house by myself and wrote my favorite show’s script. Which, it’s crazy, Curb is still on and that was the script I wrote.

But anyway, I gave it to my manager who represented Mark Wahlberg and was my friend from college and he said, “god we had this idea called entourage and, you know, you should write it.”

I was like, “Oh, you didn’t think of me till i gave you this script, you’ve known me for the last 15 years.”

But anyway, that’s how it happens. You need to be in front of the right people at the right time. Anyway, I didn’t actually like the idea for the show, I thought it sounded kind of stupid and he said to me, “go home and figure it out.”

That’s where it all started.

Special thanks to our friends at HawkeMedia for their insights on this topic.
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