Lindsay Lohan, Just My Luck

Twentieth Century Fox

Guys like Robert Downey Jr. and Charlie Sheen get second chances in Hollywood, but do any women? Can Lindsay Lohan?
—WomanInna, Chicago, via the A.B. inbox

Well there was Winona Ryder, who got to appear in Star Trek, even after a shoplifting trial that was supposed to kill her career. She played Spock's mom and wore a cool dress with a built-in shelf and everything. Does that count? No?

Look, I'm trying, here. The answer to your question is, yes, Lindsay's gender may work against her, but not so much as her apparent lack of friends:

If Lohan wants to pull a magnificent Downey-style comeback, she will have two hurdles. First, she'll have to prove, to at least one powerful producer, that she can still bring in audiences. (Twitchy financial types usually refer to this as being "bankable.")

Second, film financiers, including the all-powerful insurers, will have to trust Lohan enough to accept her as a financial risk. Insurability is key in this business; just ask Downey, who, during his darkest days, was pinned with the usually career-killing label of "uninsurable."

Let's look at the producer hurdle first. Notable Downey-style comebacks tend to involve some sort of powerful mogul-type ally. For example, when Downey made his first stab at a comeback, it was with the help of—serious irony alert!—producer-actor Mel Gibson.

After his long bout with substance abuse, Downey was only able to score film work thanks to Gibson, who paid Downey's insurance bond for the 2003 film The Singing Detective. Gibson's seal of approval then spurred another producer, Joel Silver, to follow suit and cast Downey in Gothika. (Silver withheld part of Downey's salary until filming wrapped, but that's standard in dealing with less-than-trustworthy talent.)

Why did Downey garner such trust?

Well, Gibson and Downey were friends. But Downey also had a serious reputation for star power that went back more than 15 years, including films like Chaplin, Air America, The Pick-Up Artist and Less Than Zero, and his memorable—if inconsistent—stint with Ally McBeal.

Like another perpetual comeback kid—Charlie Sheen—Downey had a reputation for logging solid performances and the cash that goes with it, over and over again. And producers like Silver surely knew that.

Does Lohan enjoy that kind of reputation? Well, she's too young.

Yes, Freaky Friday and Mean Girls established Lohan as a bona fide star, but aside from her film debut in Parent Trap, the roles she's had haven't exactly proven memorable. (Do not try to tell me that her Herbie movie counts.)

Right now, Lohan has one producer who believes in her enough to cast her as Linda Lovelace, but it's too soon to say whether a Joel Silver type will step in next and let her continue with her uphill struggle.

Now, that hurdle isn't really gender related. But the insurability part is—indirectly.

Douglas Turk, executive vice president of leading entertainment industry insurance broker Aon/Albert G. Ruben, tells me that Lohan's gender will have no direct bearing on whether she's worth her insurance premiums.

But there could be serious indirect fallout because of her femalehood: Entertainment media is infamous for turning far more scrutiny—especially negative scrutiny—on female stars. For years, we've seen every stumble coming out of camp Lindsay, including breathless updates from her parents.

In fact, we've clearly seen more coverage of Lohan than we ever saw about Downey, or Kiefer Sutherland, or even Sheen, and, yes, it's partially because Lohan is a woman. And that intense coverage may not translate into favorable conditions for Lohan's eventual bid for a comeback.

"I am amazed by the volume of news surrounding Lindsay," Turk tells me. "Other actors have had better control in terms of the messaging. And underwriters read the news just as much as you and I do."

So does that mean that Lohan may eventually suffer the deadly label of "uninsurable"? Actually, Turk tells me, there isn't really such a thing in Hollywood.

"I don't think anyone is uninsurable," he reveals. "Anything is insurable at the right price. This is really a matter of Lohan being a risk that producers want to take—whether the benefits outweigh the cost."

Is that the case? We'll know soon enough—once Lohan checks out of her stay at the gray bar hotel.

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