EXCLUSIVE: Dan Pritzker, son of Hyatt Hotels magnate Jay Pritzker and a fixture on the Forbes list of 400 Richest Americans, might not seem that different from all the high net worth individuals who’ve turned the film industry into their playground. Unlike Sidney Kimmel, James Robinson, Bill Pohlad, Thomas Tull or others who entered the game as producer/financiers, Pritzker took his plunge by getting behind the camera and spending nearly three years on two passion projects no studio would have made with a first-timer. Bolden! is his biopic of an obscure horn player Pritzker suspects invented jazz (he went insane and left behind no recordings, so it’s hard to verify). Louis is a 68-minute silent film–complete with title card dialogue–that turns the childhood of Louis Armstrong into an improvisational jazz riff, centered by a Chaplin-esque villainous turn by Jackie Earle Haley.

Pritzker, who began shooting both films in 2007, has released a trailer as part of an intriguing distribution strategy for Louis, the silent film that debuts in a series of concert halls with live musical accompaniment led by Wynton Marsalis. The tour starts August 25 in Chicago and includes a stop in Harlem’s Apollo Theater on August 30. As for Bolden!, some of the news is good, and some surreal. The good news: Anthony Mackie, a relative unknown when Pritzker cast him to play Buddy Bolden, is now a rising actor who last starred in the Oscar-winning The Hurt Locker. The surreal: Pritzker is still shooting. He dusted off the period sets that had been mothballed in Wilmington, and added a bunch of extra scenes. Pritzker finally wraps today before jumping into rehearsals with Marsalis, who’ll lead the 10-piece jazz ensemble that will replicate the soundtrack for Louis.

Ask Pritzker if he’s gone off the deep end, and he doesn’t take offense. Fortunately, he’s a musician by training and hangs with that crowd more than captains of industry. They are more tolerant of his  movie-making odyssey. “I don’t get people looking at me and saying, what the hell are you doing Pritzker, because I think I pitch a pretty good story that sounds compelling in the telling,” Pritzker told me. “Nobody has heard my pitch, looked at me and said, `are you’re out of your fucking mind? Even if I have that question in the back of my own head sometimes.”

Actually, Pritzker has gotten close to that reaction from Mackie. Said Pritzker: “Anthony is an extremely animated individual, who calls me from time to time and usually says, `You’ve been working on this for three years, what the fuck are you doing?’ It was difficult thing for him, coming back and dusting off his playbook, 2.5 years after creating that character. But fortunately, he looks like he hasn’t aged, and he came in and did a really fine job.”

Pritzker said after he shot and cut Bolden!, he had time most filmmakers don’t get to meditate on it. Pritzker came up with some bold new ideas he just had to insert. I watched an early cut of the silent film, along with some Bolden! scenes in early 2009. His DP is Vilmos Zsigmond and what I saw was quite stylish and thoughtful, though I haven’t seen enough silent films to really compare to an art form nobody has bothered with for 80 years. Back then, Pritzker admitted to me that his original $10 million budget had grown closer to $25 million. He won’t say how much that has escalated during time and reshoots.

“I probably committed the cardinal sin, because when you’re the writer and director and financier, you don’t have a good governor,” he told me. “I got a good tax break shooting in the Carolinas, and while it’s an expensive proposition, it hasn’t gotten entirely out of hand. If a studio tried to make a period jazz film for around $25 million, I doubt they could.”

Pritzker, who notes often how lucky he is to be in the financial position to see through an undertaking he’s dreamed of and planned since 1995, will soon get critical feedback on Louis. He expects to complete Bolden! by January and show it to distributors shortly after.

“Louis isn’t about getting a weekend at Landmark Theaters,” he said. “I’d like to get out on the road with it. I hope Wynton will do more dates, but we could do it with other musicians too,” Pritzker said. “On Bolden!, there I’ll be pleading for my Landmark Theaters weekend. With Anthony and Jackie Earle, maybe there will be some demand. I have no idea, I’ve never done this before and I’ll rely on professionals to figure that out.”

Here is the Louis trailer:

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