Steve Samuels knows all too well how the movie industry can punish deep-pocketed neophytes like him. The real estate devel­oper, who is backing two new projects this fall—one starring George Clooney and the other directed by Paul Haggis—first tried his hand at film financing three years ago, with the ill-fated Demi Moore drama Half Light.

The $15 million picture was troubled from the start. First, the $3 million promised by the Isle of Man, whose government helps fund movies shot there, fell through. The production then moved to north Wales, where gale-force winds and rain destroyed some sets. A key banker died in the Asian tsunami of 2004. And just when it seemed things couldn’t get worse, one of the project’s investors, the head of German film-financing company VIP, was investigated for embezzling and tax evasion. “Very Interested in Prison—that’s what they were,” says Samuels, 48, who lost about $1 million on the venture. Half Light never even made it to U.S. theaters.

Now Samuels has two chances to do better. In the Valley of Elah, a father-­son soldier story written and directed by Haggis—who won an Oscar for Crash—and starring Tommy Lee Jones and Charlize Theron, is set to be released on September 21. Two weeks later comes Michael Clayton, the tale of a prominent law firm’s in-house “fixer” (Clooney) faced with a maverick partner whose sudden moral crisis imperils a huge case. Both movies, each with a production budget in the mid-$20 million range, were bankrolled by Samuels, who won’t say what he’s worth. But ask him if he’s heard the joke about the quickest way to make a small fortune in Hollywood—start with a large one—and he’ll laugh ruefully. “I hear it and see it every day.”

Born into a Cleveland real estate family, Samuels made his bones in the urban core of Boston, where he started his own development firm, Samuels & Associates, in the mid-’80s. But after 20 years in real estate, he was curious to try something new. When an old friend who’d become an agent at Creative Artists Agency suggested he invest in the movie biz, Samuels bit.

Rarely, if ever, do private ­backers write checks for a project’s entire budget. They typically play the role of guarantor, fronting expenses while trying to recoup their capital by preselling foreign (and sometimes domestic) distribution rights. Samuels followed this model for both of his new movies. With Michael Clayton, for example, he’s on the hook for the entire budget but has already defrayed some costs by selling U.S. distribution rights to Warner Bros. for more than $8 million.

For filmmakers, backing by an individual investor rather than a studio can mean more creative control. Tony Gilroy, the screenwriter of The Bourne Identity and its sequels, intended for Michael Clayton to be his directorial debut. A few studios passed, reluctant to take a chance on a first-timer. But Samuels had no such qualms, granting Gilroy not justthe director’s chair but final cut—a perk usually reserved for established directors.

Another player in the Michael Clayton deal is C.A.A., which makes money from financiers as well as artist clients. Rick Hess, the friend who enticed Samuels into the Half Light venture (yes, they’re still friends), runs the agency’s film-finance group, which charges investors like Samuels a consulting fee for hooking them up with projects. Haggis and Gilroy are C.A.A. clients, as is Clooney, who agreed to cut his fee on Michael Clayton in exchange for a piece of the film. Clooney will share not only in profits from ticket sales but also in an unusually large piece of home-video revenue. And whenever Clooney is paid, C.A.A. gets its take.

Word is that Clooney’s performance and the script’s portrait of corporate culture are strong. So forget “Greed is good.” If you hear the guy in the next office yelling, “I’m Shiva, the god of death!”—a line uttered more than once in the film—you’ll have Samuels to thank.