Sometime this year — his 20th as a producer — Arnon Milchan will make his 50th film. And while his name may not be as recognizable as Roger Corman or Oliver Stone, Milchan’s projects reflect the dominant identity he projects in Hollywood: That of the aggressive entrepreneur, a prized (by Warners) and respected (by every other studio) producer, a jetsetting dealmaker who barely lost out last year to Kirk Kerkorian for ownership of MGM/UA.

This being the Milchan the industry knows best, it is easy to overlook the revealing patterns and qualities in the actual movies he has made, first as an upstart independent producer in the ’80s, and now, as head of the growing New Regency empire in the ’90s.

And while Milchan may be thought of, as any producer would wish, in association with such hits as “Pretty Woman,” “A Time To Kill” and “Tin Cup,” and such franchises as the “Under Siege” and “Free Willy” movies, it is the remarkable list of risky, occasionally incendiary films that suggests that this sometimes-Monte Carlo resident is a high-stakes gambler as well.

Beyond the risky ventures, there is a clear desire for diversity in the Milchan output — from crime epics such as “Once Upon a Time in America,” “Q and A” and “Heat,” to biting social commentary within “Falling Down” and “Six Degrees of Separation,” to dramas with a sense of history like “Guilty by Suspicion,” “Sommersby” and “Heaven and Earth.”

Milchan’s Hollywood presence is increasingly notable for his skill at business diversification — with a TV production arm, a stake in Puma and other upcoming multi-media deals — yet little-acknowledged for his diversification of taste at choosing projects.

Writer-director Ron Shelton, who is one of the few filmmakers in Hollywood who can claim to actually regularly spend time on the ground with Milchan (who has backed his past two films, “Cobb” and “Tin Cup”), says that Milchan’s strength is precisely in not dwelling on a certain type of movie as a producer.

Milchan’s strategy, Shelton and others believe, is something other than that of the producer-as-star. “He’s doing what the studios used to do,” says Shelton. “He makes family movies, artistic ventures, franchises, light and heavy comedies, period and contemporary dramas, lots of different genres. The studios once did this, but now they’re into globally-aimed franchises with stars.”

Calling himself “a guy who has one step in the studio system and one step out, not really fitting into either the studio or independent filmmaker mold,” Shelton yearns for the old days of Orion Pictures, his first production home that filled the niche between low- and high-budget titles. “Nobody, except someone like Arnon, really fills that niche anymore. And even Arnon can’t really fit a niche like that, since he’ll go low- and high-budget as well. See, you can’t slot him, and you can’t slot me, which is one reason I guess why we’re together,” Shelton says.

Scanning the Milchan production list, a fascinating pattern emerges. The Israeli-born businessman’s entry into Hollywood was instantly marked by associations with some of the strongest signature filmmakers: First, in 1983, with Martin Scorsese on “The King of Comedy,” next, in 1984, with Sergio Leone on his large-scale finale, “Once Upon a Time in America”; then, in 1985, with Ridley Scott on “Legend” and Terry Gilliam on “Brazil.”

Notably, none of these were hits, some of them were marked with notorious production problems and/or conflicts with the studios, and all of them have attained cult status.

Despite this troublesome commercial track record, Milchan stuck with writer-directors up to and following his first blockbuster with 1990’s “Pretty Woman,” and the establishment of New Regency in 1991. There was the audience-dividing dark comedy, “The War of the Roses” (1989), followed by a succession of projects with writer-directors: Sidney Lumet (“Q and A”); Blake Edwards (“Switch”); Oliver Stone (“JFK,” “Heaven and Earth,” “Natural Born Killers”); producer-turned-helmer Irwin Winkler (“Guilty by Suspicion”); Craig Bolotin (“That Night”); Rowdy Herrington (“Striking Distance”); Michael Tolkin (“The New Age”); and Michael Mann (“Heat”).

And, just to make the mix all the more eccentric — if not always critically and commercially successful — Milchan has recently partnered with such veteran directors as Herbert Ross (“Boys on the Side”), Norman Jewison (“Bogus”) and Arthur Hiller (“Carpool”).

“It’s certainly an interesting list,” notes Newsweek film critic David Ansen. “You don’t get riskier in the commercial film business than a film like ‘Brazil,’ and even a supposedly commercial comedy like ‘War of the Roses’ has an extremely nasty edge. ‘Q and A’ is rather underrated, ‘The Client’ is probably the best of the Grisham movies, and the two Shelton movies he’s produced are quite ambitious.

“On one hand,” Ansen continues, “he has this clear line of hits, like ‘Pretty Woman’ and ‘Under Siege’ and ‘A Time To Kill,’ but on the other, you have to take your hat off to Milchan for employing difficult, unpredictable, but clearly talented, directors like Tolkin and Michael Cimino on ‘The Sunchaser.’ Both that and ‘The New Age’ bombed, but he stayed with them.”

Some creative relationships have proven too much to bear, such as with Stone, who parted with Milchan before the production of “Nixon.” (Stone biographers such as James Riordan have described the Milchan-Stone partnership as one of mutual admiration and insecurity, as if one might knife the other in the back at any moment.)

In another instance, however, Shelton thinks that Milchan’s intervention at a key moment saved his version of “Cobb” from a potentially disastrous “softening down” by Warners.

“We had one of those dreaded audience previews in Westwood — I never get good cards in those — and it got the kind of divided response that terrifies any studio. The Warners executives, Milchan and I went to a restaurant across the street, and I felt like I was at the Last Supper and there were Judases everywhere.

“Mind you, I hadn’t spoken to Milchan since we had shook hands on the deal to do the film. But before anyone said anything, Milchan stood up at the table and declared, ‘I want to say that I love this movie, that studios should be making more of these kinds of movies, and I will stand by Ron’s cut all the way.’ And he sat down. I know it made the difference in Warners’ support of the movie.”

Those who know Milchan say that this kind of support of writer-directors isn’t borne of some misty-eyed love of art, but of practicality, and that it reveals the heart of Milchan’s mindset.

“There’s no real deep secret behind his desire to work with writer-directors,” says Shelton. “It’s simple. He’s not comfortable with script development, the whole racket that sends zillions of dollars down the sewer. For Milchan, if he has the director who’s also the writer, he gets rid of the development problem.”

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