Kirk Douglas was well into his 80s and in a delicate state of health. Filmmakers wanted to cast the screen legend in a new starring role, but behind the scenes, Hollywood's business types simmered with questions and doubts: Would the actor have the energy to endure the physical rigors of filming?

No one wished to be disrespectful or morbid, but would the octogenarian—who already had suffered a debilitating stroke—live to the end of production? If he did not, the entire project might have to be scrapped, and all money spent to that point could be lost.

The biggest question of all: Would he be insurable? That is a prerequisite for an actor to work in a movie.

"He was half-paralyzed. He had a lot of issues," says Brian Kingman, a longtime insurance broker for film productions. "But if you have enough time, talent and money, anything is possible to insure."

Insurance is the talk of Hollywood these days. Ever since the very public meltdown of Lindsay Lohan last month—and now, the private struggles of Owen Wilson—speculation is spiraling over whether these talented actors have derailed their careers by jeopardizing their insurability.

But the issue may be more lip service than actual practice. In fact, the entertainment industry can be just as creative when formulating insurance for its actors as it is when writing screenplays and producing films.

Kingman, a director at Aon/Albert G. Ruben, ended up stitching together a policy for Douglas by persuading several insurance companies to each assume a small share of the total risk that the ailing actor could become disabled or die during production.

The production company, in turn, agreed to pay an additional premium "in the seven figures," Kingman says. As a result, the 2003 movie It Runs in the Family, starring the cleft-chinned actor alongside his real-life relatives, got made.

It surely helped in the insurance negotiations that one of the film's producers was Douglas's son, Michael. But as history shows, when there is a will, there's usually a way—even for the most out-of-favor actors.

"It always goes to the issue of budget," says producer Mike Medavoy, co-founder of Orion Pictures and former chairman of TriStar, who has been involved in the making of more than 300 features films. "The question is: Do you want to take the risk, or not?"