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It has been mentioned before, but Billy is based on show creator Doug Ellin's high-school friend and Entourage writer: Rob Weiss. Excerpts from an August 7, 2007 interview in the New York Observer:

HOLLYWOOD—Rob Weiss, a writer and executive producer of the popular HBO series Entourage and the inspiration for its bombastic director character Billy Walsh, was sitting outside at the Bourgeois Pig, a dingy coffeehouse at the foot of Beachwood Canyon. He looked wary.

Mr. Weiss’ nervousness with the press dates back to his days as the badly behaved writer-director of Amongst Friends, a film about young, affluent, aspiring gangsters (“Goodfellas meets Metropolitan”) that was the darling of the 1993 Sundance Film Festival. The film put Mr. Weiss, then 26, in the full glare of the media spotlight (he was photographed by Annie Leibovitz and Bruce Weber), but his self-important, swaggering tough-guy persona didn’t always come across well in print.

In one profile published in now-defunct Premiere magazine, Mr. Weiss, a former club promoter and dropout of the New School’s film program, coyly suggested—or at least did not deny—that he may have killed someone. He told The Observer he was misquoted, though, he allowed, “I’ve had some interaction with some unsavory characters in my life.”

Mr. Weiss does not deny that he has—or had—a temper; he once shut down the set of Amongst Friends over a lost cellphone and admits to “massive, screaming” fights with Mira Sorvino, who starred in the film. Now such youthful antics are being immortalized on the small screen via the fictional “suit”-hating auteur of Queens Boulevard and Medellin.

“We came up with the idea of putting a director in, and I wanted it to be Rob Weiss,” said Doug Ellin, the show’s creator, who went to high school with Mr. Weiss in the Five Towns section of Long Island and described him as “an extremely funny, slightly crazy, good-looking nutjob.”

Mr. Ellin even asked Mr. Weiss if he’d play “Walsh,” but Mr. Weiss declined. Instead, the role went to the Vincent Gallo-esque Rhys Coiro, to whom Mr. Weiss bears little outward resemblance. “I’m more Johnny Drama,” Mr. Weiss said, referring to Kevin Dillon’s physically well-maintained character. “I’m into grooming and metrosexual kind of ****. I’m the guy with like 900 products.”

In recent months, Billy Walsh has emerged as a surprise standout among Entourage’s ensemble of scenery-chompers, so much so that while the plan was to write him into five or six episodes this season, he will end up in nine or 10. According to Mr. Ellin, the character was becoming so dominant that he has received notes from HBO executives, warning him to “be mindful” about not overshadowing the show’s core cast: the buddy-family quartet of Vince, Drama, Turtle and “E,” and agent d’horreur, Ari Gold.

Mr. Ellin stressed that his own experience as a novice director (credits include Phat Beach) also informed the Walsh character, along with reading about Directors Gone Wild in books such as Final Cut and The Devil’s Candy. “I’ve taken all the crazy stories I’ve ever heard about directors,” he said, sitting in his Beverly Hills office, his blue and gold LeBron James Nike sneakers (“I only wear Nikes”) propped up on a coffee table. The Entourage episode in which a documentary filmmaker visits the haywire set of Medellin in South America was “an homage to Hearts of Darkness”—the documentary chronicling Francis Ford Coppola’s breakdown while making Apocalypse Now.

Nonetheless, it is Mr. Weiss who lies at the heart of Billy Walsh. And it’s not the first time filmic homage has been paid. He appeared as himself in Barry Levinson’s movie Jimmy Hollywood and surfaces, less flatteringly, in John Pierson’s indie-world tell-all Spike, Mike, Slackers and ***** as, among other things, a “posturing director” and “Vanilla Weiss.” (Mr. Weiss had a falling out with Mr. Pierson in the aftermath of Amongst Friends, for which Mr. Pierson provided financial backing. “I have bad feelings about that guy,” he said of Mr. Pierson.)
 

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I find the basic concept of Walsh – understanding that Entourage is a comedy and delves into parody (if unintentionally, at times) – believable. Of course, he's way over the top but there's certainly a seed of truth to him.

That said, they should have written him out in the first episode of this season - Walsh should have had a heart attack and died. He overpowers too many scenes.

Besides, I want more Turtle and Drama stuff...
 

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I agree that Walsh is a far less interesting character than the producers seem to think he is. He should have been in about as many episodes as Vince's obnoxious high school buddy.
 

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Anyone else kind of ready for this season to be over? I was all excited when they had the two seasons so close to each other, but now I think it was a big mistake. I am just waiting for these last few episodes to be over.
 

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Weiss' temperament is infamous. I imagine you'd have to be like that to date Shannon Doherty.

The tone has leaked out into "Entourage" on a handful of occasions. It would take someone of that personality to hold a grudge against "nice guy Kevin Smith" for nearly a decade because of something pretty trivial.
 

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I don't mind Billy, although I agree his screen time is taking away from the main characters, and I prefer them to him.

I don't see how the Anna plotline can go on too long: it's rare that an actor playing themselves lasts any amount of time in Entourage. In fact, with what happened with the cell phone coverage etc. my suspicion is that plot is already on the downhill side.
 

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edc said:
Weiss' temperament is infamous. I imagine you'd have to be like that to date Shannon Doherty.

The tone has leaked out into "Entourage" on a handful of occasions. It would take someone of that personality to hold a grudge against "nice guy Kevin Smith" for nearly a decade because of something pretty trivial.
What does Kevin Smith have to do with it? I must have missed something.
 

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Sirius Black said:
What does Kevin Smith have to do with it? I must have missed something.
Vince got pissed at Ari for signing him to do Aquaman 2 and 3 when James Cameron was only signed to direct the first one. Vince and E got pissed when they found out that Michael Bay was directing A2, and they got even more pissed when Ari told them that Kevin Smith was writing the script.
 

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Sirius Black said:
What does Kevin Smith have to do with it? I must have missed something.
There have been a few jabs at Kevin Smith - who was upset that Rob Weiss would constantly harass Shannon Doherty while Doherty was shooting Mallrats - in Entourage.

Hopefully edc remembers the others, but the most famous dig was when the studio wanted to rush out Aquaman 2 (early season 3), they hired Kevin Smith to write the script. (I'm doing a horrible job of 'explaining' it, but it was foul)
 

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hanumang said:
There have been a few jabs at Kevin Smith - who was upset that Rob Weiss would constantly harass Shannon Doherty while Doherty was shooting Mallrats - in Entourage.
So Rob is also the inspiration for Anna's boyfriend.

hanumang said:
]Hopefully edc remembers the others, but the most famous dig was when the studio wanted to rush out Aquaman 2 (early season 3), they hired Kevin Smith to write the script. (I'm doing a horrible job of 'explaining' it, but it was foul)
Where did I hear this before :D
 

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hanumang said:
There have been a few jabs at Kevin Smith - who was upset that Rob Weiss would constantly harass Shannon Doherty while Doherty was shooting Mallrats - in Entourage.

Hopefully edc remembers the others, but the most famous dig was when the studio wanted to rush out Aquaman 2 (early season 3), they hired Kevin Smith to write the script. (I'm doing a horrible job of 'explaining' it, but it was foul)
==

In the Sundance episode, Ari yells at Harvey that "If it wasn't for me, you'd be stuck producing Kevin Smith Movies for the rest of your life!"

==
VINCE: Cameron's the only reason I signed on in the first place. Who's directing ["Aquaman 2"]?
ARI: Michael Bay.
ERIC: Jesus Christ.
VINCE: They're just rushing this thing out!
ARI: Vinnie, this is what studios do; the thing is a monster hit. They're just trying to take advantage of it, that's all.
VINCE: I haven't even seen a script.
ARI: They're working on it!
VINCE: Andrew Kevin Walker writing?
ARI: Kevin Smith.
ERIC: Oh boy.
VINCE: F... you, Ari! I want off this movie!
==

A quick Google search reveals Smith's "side":

http://www.joblo.com/index.php?id=12101

There is a dude who is on staff named Rob Weiss, who made this movie called Amongst Friends many years ago – back in 1993, I believe. And he worked with a friend of mine, John Pierson. And John wrote this book Spike, Mike, Slackers and *****. And in it I do these kind of pre-chapter chapter, where John and I have this conversation that’s kind of relevant to the chapter that follows.

John was one of the producers on Amongst Friends. His chapter about Rob Weiss was called “Amongst Jerks.” John has a very distinctive take on Rob Weiss, having worked with him on that movie. I had worked with Shannon Doherty on Mallrats. Shannon Doherty was dating Rob Weiss through most of the mid-nineties. There were times when – he didn’t come to set; we were shooting in Minnesota – and he was the kind of guy who would call up and be like, “I’m going clubbing.” And she was like, “Well no. You shouldn’t be going out. I’m not there.”

Shannon’s certainly no wilting flower or anything like that. But when it came to Rob she was really passive. She would have to get off the phone because we were doing a take, and he would get mad that she was getting off the phone and he would say, “Well, f... it then. I’m going clubbing and I’m gonna pick up a girl.” And she would get all f...n’ frazzled and start crying and s**t and it would hold up shooting. And I was like, “What a f...in’ horrible thing to do to somebody.” And this dude’s a director; he ought to know better. So in that chapter preceding “Amongst Jerks,” Pierson talks to me about his movie and what-not and what a bad experience he had working with him, so I talked about that in the book.

Now this book came out in 1995. 11 years later he’s still smarting from it? And I didn’t remember everything I said in the book. All I remember from what I said in the book was saying, because Pierson comes down on Amongst Friends pretty hard-core. I remember saying I thought it was watchable… After I watched the Season Two Entourage boxed set and that episode where they took a dig at me, I grabbed the book and thought, “What did I f...in’ say?” And then I read it and it was pretty bad. [laughs] So I guess after ten years, the dude who hasn’t f...in’ done anything in ten years…well, more than that. Twelve years. He finally got a job writing on Entourage and found an opportunity to take a shot. I get it; it doesn’t hurt me. It’s totally fine. But I understand I had it coming.
==
 

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I thought this was a pretty so-so episode, but it did lay the groundwork for a rift between Vince and E, which should make for a good story.
 

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phox_mulder said:
Anubys said:
this show needs nudity...more often
Fixed it for ya.

They did have some a couple episodes ago.

phox
They had a quick flash in Ep 1 of this season (Billy watching the Medellin dailies), and then a couple eps later Vince and E tracked down Billy in a strip club, but other than that, there's been nothing.

I think that if you're making a show that allows nudity (which clearly HBO does), you have a fan base that wants it (predominantly a young male demographic), and you have actresses willing to do it, there's no reason not to include it. Yet there have been a couple of eps recently where they had a perfect opportunity to include it and inexplicably chose not to (Vince hooking up with the British blonde, the girls stripping to get in the hot tub on the "pot" episode).
 
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