Billy Walsh, C’est Moi

And what do people have to say about Rob Weiss?

Actor Louis Lombardi (24, The Sopranos), who got his first acting break in Amongst Friends (his wardrobe of XXL track suits was provided courtesy of Mr. Weiss’ dad’s closet) recounted the grandiose, hyperbolic—indeed, Billy Walshian—way Mr. Weiss would carry on while making Amongst Friends, which had a cast of unknowns and was shot on a budget of just under $1 million (part of which was raised through gambling buddies of Mr. Weiss’ dad, who ran a casino junket business).

“His famous line was: ‘It’s gonna be epic!’” Mr. Lombardi said on the phone. “‘It’s gonna be huge, it’s gonna be unbelievable! You don’t know how fucking big this is gonna be! We’re gonna go to Sundance, you know how fucking big Sundance is, Lombardi?’

He was a passionate person speaking in a crazy, exaggerated way,” Mr. Lombardi continued. “That’s why we loved Rob. He’s psychotic! He’s totally Billy Walsh.”

Amongst Friends never made much money—Mr. Weiss estimated he’s made about $35,000 from the film—but led to a three-picture deal at Universal; a bungalow adjacent to Ron Howard and Brian Grazer; Vogue photo shoots; “high-profile girls” such as Shannen Doherty, to whom Mr. Weiss was briefly engaged; and offers to direct films such as Good Will Hunting and American Psycho, which Mr. Weiss turned down because he wasn’t interested in projects that “didn’t come out of my head.”

Mr. Lombardi and other members of the L.I. crew followed Mr. Weiss out to L.A., moving into his West Hollywood apartment and assuming entourage-ish jobs, such as shuttling Mr. Weiss around to meetings with agents and producers. “Turtle is a little bit like me,” Mr. Lombardi said. “I would pick Rob up and drive him to meetings with, like, Oliver Stone. I’d be sitting in the meeting with him and Rob, and Oliver would say, ‘Go through my library of scripts! Any movie you want to make, I’ll make!’ Rob was like, ‘I don’t know what I want to do, I want to make a big movie.’ … He had a big ego, and he’d let people know.” Still, he said, “he is a loyal guy. He’s a good friend to have.”

Indeed, Mr. Lombardi and the actor Frank Medrano, another Amongst Friends alum, would often help themselves to Mr. Weiss’ expense account at Universal and run up $300 lunches at the studio commissary.

The gravy train was short-lived, however. Although Mr. Weiss wrote another script—Milk Bar, based on his experience as a club promoter—he never again directed a film, a fact he blames largely on his then-belief that nothing was good enough for his outsized talents.

“There are a million things from my past that were great opportunities and I didn’t step up,” Mr. Weiss said regretfully.

After spending his late 20’s living off rewrite jobs and TV scripts, Mr. Weiss found himself “fucking dead” at 30, at which point he made an effort to turn his life around (and mellow out). He started by enrolling in therapy.

“There were long stretches of sadness,” Mr. Weiss said. “You know, a lot of internal work.”

Professional salvation came in in late 2003, when he received a call from Mr. Ellin asking him to work on a pilot the latter man had written that had just been picked up by HBO. Mr. Weiss, still hanging on to his directing dream, at first said no, but capitulated when his agent reamed him out.

Now, he has his own production deal at the cable network (Milk Bar may yet see the light of day)—not to mention some perspective. “At the end of the day, I’m just a middle-class Jewish guy who writes for a living,” he said, and lit his cigar. “I mean, I’m a 40-year-old man now. I go ballistic now in my life probably because my blood sugar level’s low from not eating lunch. Billy Walsh is supposed to be the retro Rob Weiss, the guy who couldn’t be controlled, the rebel, the guy acting out of insecurity, fear—neurotic, passionate, volatile. I’m not that guy anymore.”