“He’s one lucky motherfucker.” One of a litany of one-line descriptions of Jerry Weintraub, Julia Roberts’ seems especially concise. Not to mention designed to showcase a combination of her earthy charms and his cool kids’ club appeal.  With other testimonies from George Clooney, Bruce Willis, and Andy Garcia, the opening of His Way introduces what’s coming—a cheerful portrait of a guy who has everything.

Airing this month on HBO, Douglas McGrath’s documentary offers not only interviews with celebrities and Hollywood insiders, but also the expected footage of his projects (the Carpenters, John Denver, the Karate Kid) and impressive photo array. As “King Creole” plays beneath (“When the king starts to do it, / It’s as good as done”), Weintraub smiles broadly with Elvis, Sinatra, Cary Grant, John Belushi, and Stallone and the Governator together. Not to mention George Bush the Elder and George Wallace too. Yes, Weintraub has lots of friends. And yes, he knows how to use them.

More a celebration than an assessment, the movie begins with Weintraub’s considerable reputation as a showman. Brad Pitt decrees, “He’s Ringling Bros., he’s Barnum and Bailey,” and Jimmy Caan calls him “Houdini.” As these talking heads appear in nice hotel rooms or set against self-consciously cheesy L.A. backdrops—blown-up photos of Van de Kamp’s

He’s a terrific storyteller too, and the movie lets him have at it. If his memories aren’t wholly accurate, it hardly matters. He’s selling something here, the story of Jerry Weintraub. 

Just so, Weintraub says, he took to heart his dad’s first lesson in economics, namely, that the red jacket he wanted as a boy who adored James Dean could indeed be his if… Weintraub recalls his father saying, “You go out, you get a job, you earn the $11, you give it to the man and get the jacket. That’s the way it works.” From then on, maybe, Weintraub was convinced that he would have whatever he wanted, as long as he put in the effort. Caan adds that he got his street smarts in the Bronx: “Jerry had the good fortune of surviving a neighborhood,” like Caan himself. And that helped him to know early on, “Who’s your friend.”

Of course, such knowledge depends on its underside, recognizing opponents and rivals, and knowing how to intimidate. “He’s the toughest guy in any industry,” enthuses CAA’s Bryan Lourd, even if “Sometimes, he doesn’t have a governor in his brain.” The mix of effects inspires Ellen Barkin ‘s description: “He’s tough as nails but he has, like, a mushy marshmallow center.” All this love is justified, the film allows, because, no matter what you think of Weintraub’s tactics or motives, he gets jobs done, from the Four Seasons and Neil Diamond to Nashville and Diner. And, of course, the films that brought him into contact with Clooney and company (including this documentary’s executive producer, Steven Soderbergh), the Ocean’s remakes. Everyone involved in these has good things to say, including Ralph Macchio, who notes that once an unwilling Weintraub was convinced that Pat Morita could do the part, he was “smart enough to let this go through.”

The happy family vibe is elaborated in references to Weintraub’s actual family. Following a brief mention of a first, unnamed wife (“I was not a good husband, I was not a good person for her”), Weintraub and Jane Morgan describe their first meeting, when her husband at the time recommended him as a new manager (here Bush remembers her from Kennebunkport, a whole new dimension of namedropping). “He came in my dressing room and I thought, ‘This guy is really unusual,’” says Morgan. “Something about the look in his eye, maybe a little crazy, but it was interesting, very interesting. And I like interesting and crazy. He became my manager.”

And, after they both got divorces, he became her husband too. “She believed in me and she helped me and she made me feel good,” says Weintraub. “I hadn’t experienced what she had, she had traveled.” As they worked together on expanding his horizons, “I was her manager, but she was my manager.” More recently, that is, 20 years ago, Weintraub started living with Susie Ekins, erstwhile PA. The film holds out this information until late, so if you don’t know coming in, it seems something like a climactic flourish. But according to his associates, the relationship among the three parties makes sense for them. While the jokes and asides could be too cute (Roberts lilts, “Come and knock on our door!”), Lourd points out, “They’re two remarkable women, to: a) put up with him, but, b) have the sort of confidence to live uniquely as they do.” 

For a moment, the documentary tips toward seriousness, in the vaguest, most upbeat way. Ekins says, “All I can say is, we fell in love.” Morgan says, “I think I had a different view of how people should handle their marital relations than a lot of Americans do, who haven’t experienced what I went through those years I lived in Europe.” One of Morgan and Weintraub’s daughters adds, “Somehow, my dad worked it out and that’s the way it was and however he does it, like everything he does, it just kind of worked out.” However he does it.