The Making of the 'Entourage' Pilot, as Told by the Creator and Cast

In celebration of 15 years, the 'Entourage' creator and cast reveal the history of the pilot and how it came together.

Entourage Oral History
Complex Original

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Entourage Oral History

“Maybe you can have it all” was a tagline used to promote Entourage’s third season, but it may as well have been the series mission statement. Fifteen years ago today, HBO introduced us to Vincent Chase, and one of the most alluring, enduring and yes, mostly male-oriented wish-fulfillment sagas was born.

Entourage isn’t a comedy though it was often funny and at times hilarious, it’s a living daydream grounded in the reality of everyday celebrity life, where even the banal is casually glamorous. Through Vince and his three childhood friends shamelessly living off of everything his emergent movie-star status affords them, the series was one half-hour fantasia of testosterone-fueled material delights after another.

But of course, there was more to Vince’s friends than clout and there was more to Entourage than foreign cars, gorgeous women and A-list cameos. At its best, the series celebrated genuine, ride-or-die camaraderie and loyalty—season 1’s tagline was “His fame is their fortune” but the series often posited Vince’s life as only being enjoyable by his ability to share the wealth, a borderline co-dependent. It also plumbed the depths of the Hollywood industry machine, offering a glimpse behind the curtain so authentic early viewers wondered if it wasn’t scripted. Even amidst detractors who argued the show reveled in surface materialism and lazy arcs with no stakes, Entourage’s hold on the zeitgeist only grew as it continued. Jeremy Piven as Vince’s bulldog agent Ari Gold became a breakout and Emmy/Golden Globe mainstay, in an ensemble that already included singular oddities like Kevin Dillon's perennially struggling actor Johnny Drama or Jerry Ferrara's baby-faced master finesser Turtle. Under the stewardship of music supervisor Scott Vener, who came aboard in season 2, the show's soundtrack became a phenomenon unto itself, with A-list rappers even opting to premiere songs in an episode. In plotting Vince's career as the gang traversed upward mobility in the movie business, creator Doug Ellin inadvertently predicted several trend paths Hollywood would go down. Call it incidental, sure, but it also belies a deeper understanding of Tinseltown than the show is given credit for.

Eight seasons and a movie later, the show's merits are in constant debate but its legacy is unquestionable. In honor of the series premiere, which bowed on HBO Sunday July 18, 2004, Complex wrangled Ellin, ostensible series lead Kevin Connolly, Ferrara, Dillon, and veteran executive producer Larry Charles to reminisce on making the pilot that led to the job of a lifetime. Read on for an oral history reflecting on the early days of the series, how it grew into the ratings hit we know today, and their thoughts on why it resonated.

The Entourage:
Doug Ellin - creator, writer, executive producer
Kevin Dillon - Johnny Drama, Vince's older brother
Kevin Connolly - Eric "E" Murphy, Vince's best friend and manager
Jerry Ferrara - Vince's best friend and driver
Larry Charles - executive producer 2004-2009, writer 2004-2005

I. the early stages

Around 2001-02, Mark Wahlberg's manager Steven Levinson approaches his friend and screenwriter Doug Ellin with a TV concept.

Doug Ellin: Steve Levinson said, "We want to do a show about Mark and his friends." I was like, "That's the worst idea I've ever heard.” And he said, "You'll figure it out.” So, that's really where it started, but there wasn't much of an idea besides that. Then I sat [with it] and thought about how I could make it more of me and my friends, with Mark's career trajectory.

I can't even tell you how many drafts I wrote. And it wasn't going, it wasn't going. I probably wrote 25 drafts before they even agreed to the script, so that took well over a year from when we sold the pilot. When we sold the pilot, we thought we were running the town [laughs].


[In one of the first drafts], there were 12 characters. I'd never done TV, I'd never written a pilot script, I'd never written anything really for television. And I had 12 characters. There was a fucking chef. There was a security guard. [Those drafts are] so crazy, looking at them now. To think that I even contemplated introducing 12 people in a 30 minute script. Then I just started whittling down, whittling down, and ultimately, we ended up with the four plus Ari.

II. casting the pilot

With the characters and a script finally locked in, Ellin, Levinson and Wahlberg set about finding actors to bring the entourage to life.

Ellin: It was probably like a six-month process to cast these guys. I wanted guys that I grew up with and it was really hard to find that. We had amazing actors come in for these parts that have had enormously successful careers, but they just weren't The Guy. You know?

The second Adrian [Grenier] got in front of the camera...It felt like he was this movie star, he had this "Why don't I know who this guy is?" quality. It started out looking for someone so much closer to Mark than Adrian was [but] once we got Adrian, it was so clearly the right way to do it.

Jerry Ferrara: At the time I had just signed with Steve Levinson. Not that I had an inside track, but I knew about the project. I had a meeting with Doug, where we kind of talked about what the world of the show was going to be like. At one point the show was a little bit darker and edgier, and then Doug had gotten some notes from HBO to make it lighter and more fun, and I came in on that version.

Kevin Dillon: I remember when I first went in, I told [my agent] I don't know what I can do with this material because it's a four-character piece and my character [at the time] had one small line here, one small there. She's like, "You've got to go in, it's HBO." And I said, "Okay, well can I do some of the other guys lines?"

Ellin: There's no one on the planet Earth that could have been better than Kevin Dillon.

Larry Charles: Kevin Dillon playing Drama could not have been more brilliant casting. He brought that character to life, it was very distinctive. It was really fun to write for him.

Dillon: I got all the laughs that I needed and felt good about it.

Ellin: From the second he walked into the room, I looked at Steve and I said, "This guy's going to win an Emmy."

Ferrara: I don't even know if they still do it like this anymore, but I got invited to the network test, which is the final stage, the final boss to beat. What they pretty much do is they bring two or three choices for each role, and they sit everyone in the lobby. So you're looking around like, "Wow, there's the Vinces, there's the Es, there's the Turtles." You see everybody who's reading for which role—there was only one Johnny Drama. Kevin Dillon was the only person. It's almost like they were trying to lock the network in. "We're not even going to give you another option, that's how much we love Kevin Dillon as Johnny Drama."

Dillon: It's easy when you get really good dialogue that you knock it out of the park.

Ferrara: We were in that network lobby, waiting, everyone's all nervous, Dillon stands up and is like, "Who else here is reading for Johnny Drama?" Connolly was like, "Nobody, it's just you. We're pretty sure you fucking got it." And Dillon goes, "Oh, all right. I'm going to go run out and hit the head and smoke a cigarette." I'm like, "Oh man, this guy is the fucking best."

When you go for your reading, you're in a black box. It's basically a theater but you can't really make out faces. So I wasn't even sure if Mark was there or not, and sure enough he was. He comes out of the room, pulls me over, and he whispers, "I just wanted to come out here and tell you, you're kind of blowing it right now. It's not that you were bad, you just weren't doing all the stuff you were doing, that got you [this far]. You were like this energetic, funny, New York kid—[now] you’re playing it a little safe, and I think you're blowing it. Just be you. I don't give a fuck about what the script says. Just give us the essence you were giving us, and you'll be all right." So that almost was like a punch in the face. It woke me up in a way.

Ellin: When we put Jerry Ferrara and Kevin Dillon in a room...I don't want to give the wrong ages, but Jerry was 23 or something and Kevin was 36 to 38—and we were pretending they go to high school together. I used to have fucking nightmares about this. I told Jerry not to shave for weeks before we tested him at HBO.

Ferrara: I don't even think I really had any facial hair yet. We were trying on all these bigger jerseys that I had, and just doing anything to make me look older, because I think Doug, Lev and everybody were worried that they were just going to go with someone who looked older to match up with everyone else. Because Kevin Dillon was a shoo-in.

Dillon: I remember the first time I met Jerry it was like a second audition, this callback. And he was sitting there [with] a pack of cigarettes. I [mooched] one and we got to talking about which part of New York we’re from. So I got to know Jerry a little bit and I ran into Kevin Connolly at one of [the screen tests]. We just all hit it off right away. It's that that New York guy kind of attitude and we just bonded right away.

Ferrara: I obviously knew Kevin Dillon, his work. I loved PlatoonThe DoorsThe Blob. When we did our mix-and-match, the first moment that guy opened his mouth, was like, "Oh my God, this dude's fucking hilarious."

Entourage 15th Anniversary

Ellin: Eric was the hardest one to cast and the last one we found. Five weeks before the pilot, the only guys who were even close were 6'3. I needed this little feisty, fiery guy who's not scared of anything, and we couldn't find him. I had friends who knew Kevin and they were like, "Kevin Connolly's the guy.” Kevin Connolly, who fucking wasn't even acting anymore.

Kevin Connolly: I'm sure Doug told the "Well, Connolly was retired” story.

Ellin: I'm trying to get a fucking meeting with him. He won't even meet with me.

Connolly: Have you ever seen Alpha Dog? I was the original director of that movie. I wrote the script with Nick Cassavettes and he and I are out trying to make this movie and then Entourage comes along—listen, hindsight is 20/20, but at the time there was just the pilot. And I've done a bunch of pilots.

At the time Leonardo DiCaprio and Tobey Maguire were attached to produce—me and my buddies were going to go out and make a movie, it was going to be a big family affair, and I couldn't turn around and say to those guys, "Hey, I'm going to go do this pilot."

Ellin: I said, "Mark, I don't know who this fucking Kevin Connolly is, but we've got to get him. Everybody tells me he's the guy."

Connolly: I didn't know Doug. I knew Mark from back in the day, since he did The Basketball Diaries. Mark is a very, very, very charming guy. So I knew that once Mark got me across the table it was going to be tough to say no to him. So I walk into the Polo Lounge at the Beverly Hills Hotel and Wahlberg and David O. Russell, one of the biggest directors in the world, are sitting at the bar like a mafia sit down. David O. Russell turns to Wahlberg and goes, "This our guy?" And Wahlberg's like, "Yep."

O. Russell [turns to me]: "What's the problem?" I’m like  "There's no problem." Mark said, "Kevin, listen. All I'm asking you to do as a favor to me is to go in and talk to the guys. And if you decide not to do it, that's fine.”

Ellin: I had dinner with Kevin. And sitting with him, I'm like,  this is the guy 100%. Kevin says, "You've got to tell me if I audition for this that I'm getting it.” I'm not in charge! Fucking HBO's going to decide at the end of the day, but I'm like, "You're the guy. That's all I can tell you.”

Connolly: No, I said to him, "You know what, bro? Now there's just too much hype. Now if I don't get it, I'm going to be mad.” And now, of course, Doug's one of my best friends.

Ferrara: They paired me up with Kevin Connolly, Kevin Dillon, and another actor for Vince, because Adrian was not there at the test. He had sent in a tape. We just did a scene, and it just clicked. It just felt good, and people laughed at the right spots, and we looked around like, "Shit, this is it.”

Ellin: When we put Jerry and Kevin and Dillon in a room, it was like...from the minute we got them all together, they just fit. And while I do feel good about my dialog, sometimes just the whole five of them together would just be hilarious.

Ferrara: I pulled into a 7-11 parking lot in Studio City after...maybe I smoked a joint, I don't remember. I'm just waiting, and then I got the phone call from Doug Ellin. He's like, "Yeah, hey buddy, you got it. It's yours. You're Turtle. Congratulations. We start shooting in like a week." Click. And I just sat in the car, frozen.

III. shooting the pilot

Armed with a cast and final script, the pilot goes into production.

Dillon: The pilot was stressful.

Ferrara: Pilots, historically in TV, are usually the worst episode. Obviously, there are exceptions to the rule: The Sopranos, Breaking Bad. But [for the most part], the pilot episodes are always the one where you're still figuring it out, you really don't know who these characters are. And so it's always a little scary.

Ellin: [Initially] the pilot opened up at the premiere [of Vince’s new thriller, Head On] and the movie was so bad. And Turtle just wouldn't shut the fuck up about how awful the movie was until the point where Vince ultimately kicked him out of the limo in the middle of the street.

My negativity from my first 10 years in the business was shaped by how many bad things happen, and you're with your friends when the bad shit happens. But [then-HBO CEO] Chris [Albrecht] really steered me towards [fun], which was smart.

Connolly: At the end of the day, it's HBO and that's about as high end as you get, right? It's HBO, and Chris Albrecht is a genius, and the pieces are just there [for it to be great].

Dillon: The pilot was good, not great, But I knew just from the pilot what we had here.

Connolly: Jeremy [Piven] had his thing going but as far as the four guys were concerned, Kevin Dillon was our captain. Nobody worked harder on that show than Kevin Dillon. Kevin is a real pro and it was an honor.

Ellin: One of the executives was standing next to me while we filmed one day. Dillon has this line [to Vince], "You see any parts for me, bro?" And I know how I wrote it—to be funny. But Dillon delivered it, and you're devastated for this guy, this fucking older, loser brother, you feel so much for him. And the executive looks at me and goes, "You know, I might actually watch this show."

Dillon: I didn't think I did anything all that special, I just did it like a guy who really needs a job. But I remember Doug and Steve Levinson, came out like this is it, this is what this show is going to be all about. And I hadn't realized I did anything special.

Ellin: Chris just kept pushing: "These are good things." We want to see a movie star who's actually enjoying it, not the fucking jaded writer who's having trouble getting scripts made. So, we wanted a premiere to show that he's a star on the cusp of hitting that next level.

"[The pilot] just had everything: the movies, celebrity life, the cars, beautiful women, the fun and then the camaraderie." - Kevin Dillon

Connolly: Well truthfully, initially it hit a little close to home for obvious reasons, I think.

Dillon: [The pilot] just had everything: the movies, celebrity life, the cars, beautiful women, the fun and then the camaraderie.

Connolly: As much as it might've seemed like there were parallels, [the Posse and Entourage] were two different things. [Me, Leo, Tobey] were running around, we were all actors. People's careers just took off at different times and on different levels, but nobody ever worked for each other. We're all our own guys, you know? But you knew when things looked right or felt real, because you'd been to parties like [the Playboy Mansion] or to Sundance or whatever.

Ferrara: You shoot the last scene and you wrap and you're like, "Fuck, man. This might be it." You're saying goodbye and you don't know for how long. And so many times you're like, "We'll all keep in touch for sure." And it never really happens that way, or rarely does. And we just didn't know what lay ahead at all.

Dillon: The guys were all concerned: is it gonna get picked up? I said "Not only is it going to get picked up, this show's gonna be a huge hit." I just felt it. I've been in pilots that never saw daylight, and I thought they were pretty good. Connolly reminded me that I’d said “this show is  going to be huge. I just know it guys.” And I knew it because I've been in ones that weren't and I knew that this setup had a long way to go.

Ferrara: And when we got picked up, of course, it was like, "See, I told you. This show is funny, it's going to last." He just was very positive and almost seemed like he knew something. He was very calming to Connolly and I, for sure, because we were probably the more nervous guys. I'm like, "Is this going to last? Because this is a lot of fun."

IV. season 1

Two agonizing months later after wrapping the pilot, HBO officially orders the show to a full season.

Ferrara: It was another fast phone call. I didn't even know [Mark] had my phone number: "Jerry? Mark, we got picked up, buddy. We start shooting in four weeks. Get ready." Click.

Ellin: The day before I went into HBO to pitch the show, my agent sent me the show bible to The Wire like, "This is what you should have to be ready." I’m like, "Are you out of your fucking mind? I can't do this." I always came up with stuff as it happened. I was just like, "Let's just fucking get on the air." That process of coming up with plot to build on everything we set up in the pilot was torture. The first thing I did was call my friend from high school, Rob Weiss, we got Larry Charles.

Charles: [At that time] I’m doing Curb [Your Enthusiasm] and things are going to really well at HBO and my agent is Larry David's agent, Ari Emanuel at the time, and he’s also Mark Wahlberg's agent. Ari called me up and he said, "Mark has done a pilot and HBO is on the fence about picking it up. They want to reshoot some of the pilot and I think if you got involved, you would guarantee the show getting picked up. You know what the show needs."

I met with Mark, Steve Levinson, and Doug Ellin. We all hit it off—we all kind of knew each other without knowing each other. I'm from Brooklyn. They're from Long Island. Mark is from South Boston. We're all kids from these enclaves and we know the kind of behavior and sensibilities that went on there.

Ellin: I did not have a long term plan. We did the pilot for two years and then we got picked up. At that time, I have no idea what the show is. I have no idea what the next episode is. I don't know where the fuck this thing is going.

Charles: I loved the [pilot], but just like with Seinfeld, I could see that X-factor missing... the little level that could still be sought, to bring the show to that point. First of all, you didn't want it to be a show about these four very privileged kids who have it all in Hollywood. That's not relatable, but if the kids have depth, if they're three-dimensional young men with stories of their own, then they are relatable to anybody.

Ferrara: My big concern with the pilot was, there's so many inside Hollywood references. We know people in L.A. are probably going to love it. Probably New York, too. [But would] anybody in middle-America or non-coastal cities really give a shit about the inner workings of an actor's life? But it was through the pilot with some of those scenes, where I [realized] This show is just as much about friendship as it is Hollywood."

Charles: It's really about human nature. Entourage's own weird subculture of show business—this was the brilliance of Doug's writing in the first place, that he captured that every-dayness, that everyman-ness of the Hollywood experience. This was about friendship, and that level of friendship that you have if you grow up on Long Island, in Brooklyn, involves a lot of hard-edged mean-spirited at times kind of comedy. That is the way people communicate their love there. So, all of that was there. That had to be just brought out further. It had to be clear that these were distinctive characters that could exist anywhere. They happen to be in Hollywood.

Entourage 15th Anniversary

Ellin: Ari was so light in my earlier draft, which is also interesting because he was the only one I knew. I wrote in my first outline, "Jeremy Piven is playing Jeff Jacobs who was my agent at CAA," who's nothing like Ari, but I loved Piven from The Larry Sanders Shows and he had a vibe that made me think of my agent. I never met Ari Emmanuel until I pitched the pilot to HBO. And I loved that meeting, and I said to Levinson, "This guy’s is a fucking character. This is the gold right here."

Charles: [HBO] was not convinced about the viral quality of Ari. I remember very, very distinctly at the marketing meetings that the original poster didn't have Ari on it. We were like, "You're missing a good bet here. He could be a breakout character. He's an important counterweight to the four guys." To HBO's credit—I think Carolyn Strauss was in charge at that time and she's a very brilliant woman. Of all the shows that were born under her reign, are all pretty classic shows really. She relented and we put Ari into the poster and gave him the prominence in the show that he deserved. I think that was something that I really, really pushed that wound up also being a factor in the success of the show.

Ellin: The first season was legitimately staying up until 4 o'clock in the morning screaming at each other in a room going, "What the fuck are we doing here, arguing about everything?"

Charles: Rob Weiss, Steve, and Doug were cool guys and very, very tight close childhood friends. At least 10 years younger than me. But they were extremely volatile. They really had never done a TV show before. So, part of my role was to show them how to do this. Part of that was breaking up fights. They would be fighting and they would literally get into it, like physically.

Ellin: I would sit down and write 15, 20 pages and give it to Rob and co. and they'd tell me what they hated, what they liked. It was really very disorganized, thank God for HBO.

Charles: At the same time, that was the same intensity and passion that the show had.  When we reached those points in those conversations I would just often say, "You know what? Let me go into my office for 20 minutes. I'll write out a rough draft of the scene and then we'll talk about it." I loved writing those ensemble scenes when they're all going at it with each other. That's why I would say to them, when they were having an argument, "I'm going to go off and write the scene." Because I heard those voices in my head very clearly and I was able to almost channel that onto the paper very, very quickly and to show them that that's how the characters talk like how they argued. They didn't realize they were writing the show while they were arguing.

Ellin: The third [episode] script which I just thought was so good, we—I don't even want to say handed in to Chris, because Chris was this figure you never really talked to or met, he was the big boss that you didn't hear from. I got a call: "Chris hates it. This is not the show he bought. This is not the show he wants to make." It was 2AM, I'm with Rob going, "What are we doing? What the fuck are we doing with our lives?"

Charles: I think Doug saw that a certain point, it's not a committee. This is what Larry David taught me. You have to take responsibility. It's your show. You have to take responsibility and Doug started to understand that when you reach that impasse, and people are saying to you, "Do it this way. Do it that way. This is bad, that's bad," you have to trust your instincts and write your version of it because that's what you're going to have to stand behind. I think that might have been the most important lesson I could've imparted to them.

Ellin: Whatever was in the first draft that Chris didn't like, what followed was probably 72 hours of Rob Weiss and Levinson trying to get me off a couch out of a catatonic state. I don't remember exactly what [we] changed after that, but it was the Jimmy Kimmel episode, which became one of my favorites.

Dillon: Episode three ["Talk Show"] when we were at Jimmy Kimmel, that's when the show got really good.

Ferrara: For some reason, that episode is the one I remember the most vividly from the whole entire first season. That, to me, is where Entourage really became Entourage.

Charles: That was a very exciting turning point for the show. First of all, it wasn't just the cameos in that case. It was also something you could see on The Larry Sanders Show. Then pushing that live thing and pushing the backstory between Drama and Jimmy —it was blurring the lines and inserting these characters into the reality of Los Angeles. It was like glamorous and glitzy and real and gritty and dark, all at the same time. It really gave it a very unique flavor. After that, the cameos kind of flowed, rather than oh look who's here—It's more that kind of an accidental random thing that happens if you actually live in Los Angeles.

Ellin: Thank God for Adrian [who knew Ali Larter from co-starring in Drive Me Crazy], because [our first ever cameo] was supposed to be Gina Gershon and she didn't come. She said she didn't know she was supposed to play herself. And we were sitting on set [with nobody] like, "Are we actually making a professional show?"

Charles: I think that's something that at that time, was not as common a practice as it is now [playing yourself]. The other thing— a lot people just don't know themselves.

v. The queens kids' journey

After season 1, the show finds its creative footing and slowly but surely becomes a phenomenon.

Connolly: My life, quite literally, changed in one day. That show aired on Sunday night, and by Monday, I was going to get coffee, it just felt different. I could feel the heads turning.

Ferrara: Someone came up to me on Sunset Boulevard [where the billboard was]:  "Oh, dude, you're from that show, Encore. Dude, I love that show.” I'm like, "Yeah, you really fucking love it. You don't even know the name."

Dillon: The first season was kind of stressful. The second season was a little bit less stressful. After the third season we were on autopilot.

Connolly: It wasn't really until season three where we realized that we were going to go the distance.

Ellin: I used to have this debate with the script—which I now completely understand—of what's funny and what's fun. Two guys in a car with funny dialogue is funny, but two guys in a Ferrari with funny dialogue is also fun. The fun and nuttiness of being in paradise with too much time and too much money on their hands.

"The first season was kind of stressful. The second season was a little bit less stressful. After the third season we were on autopilot." - Kevin Dillon

Charles: The truth is that I think when the show was at its best, it was able to traverse those two worlds. The underlying darkness, that underbelly of Hollywood part of it. I think that was a very important part of the show. It gave the show an urgency. Failure, rejection was always kind of hovering over everybody. At the same time, that also fuels the comedy as well because it gives the comedy a natural, authentic edge, and spontaneity. They are on the edge. They're on the edge of disaster, flirting with disaster, and it kind of brings out a certain gallows humor. It's very dark, but it's also very funny and cathartic.

Connolly: It was an inside look at Hollywood that people outside of Hollywood were responding to.

Ellin: The amazing thing about  season one, which I took as a compliment, was the times people would ask me if it was scripted. A small fraction of people almost thought it was a fucking reality show. They used to ask me, "Do you write this or do they make it all up?" Meanwhile I obsessed over every single comma.

My goal was to be as absolutely realistic as possible. There was nothing that I wrote that I didn't feel like was real, that either happened to someone I knew or whatever. Satire to me was always almost seeming like [it would be] over the top. There was nothing I was trying to do to be over the top.

Charles: Nothing was contrived on that show. That was something that Doug and I were both very insistent about. The tone of the show had to be real. What made the show comedic at times was the real dialogue came out of these real characters who were funny people. Drama's a funny character. Ari's a funny character. Turtle's a funny character. There's a lot of good playing off each other, a lot of good conflicts, a lot of good pairing off of people. We were able to refresh all those [archetypes] in a way that people really hadn't seen before, amazingly enough.

Ellin: I wrote the show through Eric's eyes. He was the lead. It’s in the pilot, it's all through his eyes. It's his journey. It's his conflict, with Ari.

Ferrara: The reason why I always thought you see Connolly's name first in the credits, he really was the lead of the show. You saw the show through his eyes, at least in those first few years. He was the audience. He was the point of view. He was the last character who moved out to LA, he knew the least about Hollywood, or at least everyone thought he did, only to find out he had the best instincts.

Connolly: My particular role might've appeared to be that, to a certain extent, but it was a true ensemble. Doug would always tell me, I was "the moral compass." It’s tricky because it's not really comedically driven.

Ferrara: E was the straight man in a way. Connolly would always joke around when me and Dillon were doing some of our stuff. He's like, "You guys get to go have fun.” He was kind of a moral compass of the show.

Connolly: I'd go yapping for pages and pages of dialog, and Kevin Dillon walks in wearing a bathrobe and the crew was rolling around on the floor laughing. Kevin Dillon just walked in, he didn't even say anything.

Doug always had an open ear. If there was a storyline where you [had input or concerns] he always heard you, and not all show runners are like that. You can get yourself in hot water telling your showrunner "Hey man, I don't like this." Doug was always open to that, and maybe sometimes it put a lot of stress on him that he didn't really love. But Doug was really good at spreading the wealth, and giving everybody their moments, their time to shine.

Dillon: They wrote me so much great stuff. He was such a complex character, and I didn't overly protect him—I wouldn't say “my character wouldn't do that” [about an arc]. And I think because I let him be that guy, he just got more fun.

Ferrara: [Turtle] was the last one to evolve and develop into his own person. But I think when he did, it was impactful because he had the furthest way to go in terms of becoming his own man.

Connolly: If you look at Jerry Ferrara's character, just Jerry, and Turtle, what he's done. Jerry completely transformed himself. And, as for Turtle, it's ironic that the show ends, and Turtle has more money than anybody on the show. Turtle is the rich one, which is just hilarious.

Ferrara: I remember putting on Beats by Dre in an episode being like, "What are these?" A few years after that, I was at Equinox one day benching and someone came and spotted me. I look up and it's this jacked dude, I thought it was Ray Lewis. I get up and it's Dre. He's like, "Hey man, just wanted to say, big fan and also, you’re the first one to ever wear Beats on TV."

Connolly: It was always important to Doug that whatever phone we were on, people needed to see that and go, "Holy Shit! What phone is that?" Whatever cars we were driving, and everything. I've had people be like, "I want to talk to you about Vinny Chase's finances” breaking down how it's impossible [their lifestyle]. “According to my calculations, Vincent Chase is in debt in a big way.”

Entourage 15th Anniversary
vI. The Highlights

Eight seasons and one movie later, the show went from an uncertain pilot to yielding some of the best moments of the gang's lives.

Ferrara: That episode we did on the beach with Gary Busey, that was the first time we ventured out of LA. We were only in Malibu, but that really was the first time where we could get outside the West Hollywood, Beverly Hills area and do this episode that sort of all takes place in one location for the most part.

Dillon: I really like season two a lot. They were all great, but there was something about two and three. We were still so fresh and it just felt so good. My favorite episode is [season 3’s “Return of the King”] where [Drama] ended up at the Grand Canyon in the Lincoln and he's so down and out you think he's gonna drive off the cliff and he finds it out [his show]Five Towns got picked up. That was actually the first time I did a “Victory!” outside of the Comic-Con episode.

Ferrara: I also have a fond place in my heart for the Sundance episode in season two because that was the first time we left LA. Legitimately got on a plane to go shoot on location and that sort of became our thing. Every year, we'd always start off with a trip. One year it was New York, one year it was Mexico, one year it was the Cannes Film Festival.

Connolly: I love [the season 4 premiere] “Welcome to the Jungle.” It was a little bit different. We spent very little time on actual sets. And that episode encapsulated the whole [filmmaking process] And also Rhys [Coiro], Billy Walsh. I mean, he's actually one of the greatest characters in the history of television. He's probably my favorite character on Entourage.

Ellin: Being on a set with Martin Scorsese, having James Cameron send me a fucking letter about why Aquaman can't bomb, shooting at Yankee Stadium and bringing half of my high school with me as extras. Getting Bono to say happy birthday to one of my characters on my birthday at the STAPLES Center.

Connolly: They buy us five floor seats, right? And I go, "Wait a second, wait a second. So we're going to stand on the floor at the STAPLES Center. You guys are gonna shoot us with cameras. And then Bono is going to say ‘Happy birthday Johnny Drama.’ Impossible. It is not going to happen.” But lo and behold, all of a sudden, we're like, "Holy shit. He said it!" How he remembered to do that, and how they got him on board to do that, I don’t know. I mean, Bono's hardcore, man.

Ellin: There's been a lot of amazing, surreal experiences.

Connolly: The Cannes episode. I mean it's really pretty remarkable. And again, that's an HBO producorial victory, to get us out there on that carpet, with that press line that didn't know who we were but agreed to stay there and take pictures of us for 60 seconds. It was the Ocean's 13 premiere, and the guy said, “Look, when George Clooney leaves the red carpet, you guys got 60 seconds.” How crazy is that?

VII. But, Was the Entourage actually talented?

In  the season 4 finale, Vince endures his first huge L, which opened the flood gates on the merits of the whole group: Is Vince actually a good actor? Is E a good manager? What does Turtle do?

Ferrara: I always played Turtle as the most loyal, like he genuinely believed that Vincent Chase is and should be the biggest movie star in the world. It was ride or die. I genuinely believe Turtle thought Vince was the most talented and biggest movie star on the planet.

Ellin: When I saw [the fake Medellin trailer] I thought it was fucking genius. But people didn't like it, they thought it looked goofy. I was reading all over the internet that people thought Medellin [Vince and E's passion project] looked terrible. So, I was like, "Oh, we'll make it a bomb," because it was supposed to be this big hit.

Connolly: Do I think Vince is a great actor? [laughs] No. He's a good enough actor.

"I always played Turtle as the most loyal, like he genuinely believed that Vincent Chase is and should be the biggest movie star in the world. It was ride or die." - jerry ferrara

Ferrara: Do I think he's Christian Bale? Maybe not. But do I think he's a fantastic movie star, the kind of guy who walks in a room and makes you feel special, the kind of guy that girls want to hang out with and guys want to hang out with too.

Ellin: In my mind, Vince is a great actor. He's underappreciated in the same way Adrian is.

Connolly: Adrian, you know, he really had the hardest job. You're asking him to sell himself as the biggest movie star in the world. It's not an easy thing to do.

Ellin: I think Adrian's nonchalance—people view [what he did] as easy. Sometimes when things look so easy to people, they dismiss it. But like I said, there's no one on earth I would cast over Adrian.

Connolly: Eric Murphy is no Rick Yorn [Connolly’s real-life manager]. Their hearts are in the right place. Over time he would have become a good manager. He certainly got off to a rocky start, but hey, he got [Vince] into a Scorsese movie. That's a victory right there.

Dillon: Drama wouldn't have worked as much as he did if he wasn’t good. I mean he got a lot of work through Vince, there's no doubt about that. But he had a nice career. If you look at his resume, he had done so many jobs. And by the way, he won a Golden Globe, which I never won.

VIII. The Legacy

Fifteen years later, Ellin and the cast are unsure they'll ever have a better experience than Entourage.

Ferrara: I want to go back. I want to live it again. It was such a great time. Yes, it was hard. Everyone thinks it was just one big party. But it’ll probably be the greatest job I'll ever have, or at least because it was the first big job, it's like your first kid. Yes, you love all your children, but it was the first.

Connolly: You could go on to win 22 Oscars. Never, ever, ever will there ever be an acting job better than Entourage, it's impossible. You can do a certain quality of work, but in terms of the day-to-day, and the fun and the things that we got to do from a creative standpoint, it just hadn't been done.

Dillon: The last three seasons it was the best job in Hollywood. We would show up early, but go home early. We were shooting so many ones—shots where you don't cut. They just keep rolling the camera and we do it all on the walk. So you can bang out four pages in one shot. As an actor to see a big walk and talk with no cut, as they're walking across the screen you got extras and they're tricky because they're some big shots, but that became our hallmark shot really, the walk and talk. So the show actually developed its own look as well.

"Never, ever, ever will there ever be an acting job better than 'Entourage,' it's impossible." - Kevin connolly

Connolly: A lot of times towards the end of shows, people will phone it in. But on Entourage, we bowed right up until the very last episode. We wanted our finale to be good, we gave it all we had. And, the last day of shooting, we're in a hangar in Van Nuys. And anybody that had ever done it, I mean there was hundreds of people there, hundreds. And after a take, you would just see a wall of flashes go off.

Ellin: I could never have imagined we would go eight seasons and a movie. From HBO telling me, "Get ready to be trashed because we do high brow entertainment here," and the New York Times saying we're the best show on television, to eight years later where Revisionist History wants to go, "You know what? It wasn't good.”

I saw some moronic article ranking us the 69th best HBO show. I'm like, "Okay, we just [won] fucking Emmys, a Golden Globe every single year, but now because of the MeToo movement it's suddenly like it's so horrible that we can't discuss this.

Connolly: Listen, times change. We're in a new world and you know, it's different. I think people would have more of a problem with things that were said and done, but you could say that about anything really. It's not just Entourage. The narrative has changed. And that's fine.

Ellin: If the world's a kinder, nicer place that's always better, but the truth of the matter is these guys were good guys who looked out for each other and words were words, but actions were really the key to it.

Charles: I think the cultural moment cannot be minimized in that case. The sensibility—that show sort of celebrated male aggression on some level. That would be much more controversial today and not so easy to pull off. Even though they were great guys. They were sweet guys, they were still macho guys from the neighborhood. That would be more controversial today, most likely.

Dillon: [Some of the jokes and dialog in season 1] I don't know if that would fly nowadays. We kind got away from that after a while. The guys became better guys. Nicer guys. And not as chauvinistic.

Connolly: I think it's just human nature too, that sensibilities evolve.

Ellin: I always try to be grateful and thankful that I had the experience. And I try not to even look back at it, but when I do, I go, "Fuck, whatever I contributed to this, we had a good thing." It's been a bizarre ride, but I could not be happier with the show. I could not have tried harder, and we accomplished more than I could have ever imagined. And the amount of times on a Monday I was somewhere and hearing people talking about the show from the night before. That's all the satisfaction you could ever want. The world will ultimately decide where it's place will be.

Ferrara: It was a lot of hard work that pilot, but it also was a lot of fun and in between those takes—whenever you're watching a scene in the pilot and that scene ends, we were really getting to know each other. Now I look back 15 years later, those guys were all just at my wedding and they're the first people I sent pictures of my son who was born two months ago. The show was great. It did a lot for me and a lot for my family, but I also have great value of the friendships that those guys and I made that will last forever. And that's what the show was about.

IX. Season 9? Entourage 2?

With reboots and revivals commonplace now, could another return to the boys of Queens Blvd be in the cards?

Dillon: I really felt that we had legs. We could've easily kept going.

Connolly: I would've done a hundred seasons of Entourage, but there does come a time [especially] after eight years.  All good things come to an end, it was just time.

Ferrara: Even with the movie, we always wondered, did too much time pass? We ended so strongly with the show and we really did so much to these characters.

Dillon: I went to a party in Malibu on the 4th of July, Emmanuelle Chriqui and Kevin Connolly were there and we all took a picture together. I put it on my Instagram and I [captioned] the word reboot and people went nuts.

Connolly: It's hard to say because I just don't know what that [would] look like.

Ellin: I don't even think about it.

Dillon: I get that all the time everywhere: "You guys gotta start it up again." Any of those options would be nice.

Ferrara: I think either more time would pass or the big idea that I think is just, you do the reboot— but just not with us. You start present day now. Because so much has changed. Not that we're old men, but I'm about to turn 40. It's like, what, do we all have kids? Is that what it is? It's like Three Men and a Baby?

"I really felt that we had legs. We could've easily kept going." - kevin dillon

Ellin: Obviously, so many people are getting paid for things they did 20 years ago and I loved working with most of the people I worked with. So, I would never say never to anything.

Ferrara: If it came back, you'd do an all female cast or you change genres where it's Entourage, but it's not acting, it's sports and their entourage. Or music. I think you keep the brand, but you lose the actors. Great, I just talked myself out of a job. Way to go, Jerry. Maybe they'll be nice enough to give us all producing credits.

Connolly: I’d be shocked if I got that call. But who knows? Stranger things have happened.

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