Lindsay Lohan: A Twisted Comeback Strategy

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Lindsay Lohan in Underground Comedy 2010

After years of bad behavior, evaporating movie work, and a 14-day stint in jail for violating probation, Lindsay Lohan is mounting a comeback. Sort of. On Friday the former Disney child star returned to the big screen for the first time in three years, playing a drug-abusing, spoiled wild child who dons a nun's outfit and mows down bad guys in Robert Rodriguez's bloodfest Machete. She's also gracing the cover of the October issue of Vanity Fair, in which she's quoted as saying, "I want my career back."

Machete winks heavily at Lohan's past: between the promotional poster, featuring a habit-clad Lohan suggestively licking a massive pistol, and the outrageously self-referential subplots (we first meet Lohan's character being rescued, barely conscious, from a drug den), the filmmakers appear eager to tap into her tabloid-queen reputation.

But that's nothing compared to Lohan's other newly completed project: an appearance in Underground Comedy 2010 — a film proudly promoted as "the single most offensive movie you'll ever see" — written, directed, financed by and starring Vince "the ShamWow Guy" Shlomi.

Shlomi, who goes by Vince Offer in the movie, is better known to late-night-television viewers as the infomercial pitchman behind the super-absorbent ShamWow and the Slap Chop kitchen gadget. He has been trying to break into the movie business for a while on the strength of Underground Comedy — a collection of tasteless sketches he's been working on since 1996 that was released briefly to horrified mainstream reviews in 1999 (the New York Times referred to the film as "wretched").

Lohan's segment of the film — in which she acts out a celebrity-revenge fantasy, shooting up a gaggle of paparazzi while dressed like Marilyn Monroe — is tame compared with the movie's other sketches, which include scenes of an infant being shot in a drive-by and a necrophiliac sexing it up with rotting corpses. But its very existence is a sobering reminder about how far the star of Freaky Friday and Mean Girls has fallen. Shlomi acknowledges that he wouldn't have had a chance to get her at the height of her game. "Ten years ago she's doing Disney, and now she's in the most offensive movie ever made," he tells TIME.

Shlomi had Lohan on his wish list for an attention-generating appearance and got to make his pitch personally last May at the Cannes Film Festival, where she was photographed partying — and where she claimed her passport had been stolen, preventing her from attending a key Los Angeles court hearing.

The aspiring filmmaker and his co-producer Courtney Bingham first approached the starlet over blaring house music at a VIP nightclub. "We sent her the scripts and told her that it was gross-out comedy," says Shlomi. "She'd done Funny or Die, so she has a great sense of humor. That's in the same vein, but our movie is a little tougher." (Which may be putting it mildly.)

Neither side would disclose how much Lohan was paid for her appearance, although Shlomi maintains the actress was clearly interested in the payday. ("Money talks," says Bingham.) But once the details were squared away, the biggest source of concern for Lohan was whether her court-ordered SCRAM alcohol-monitoring ankle bracelet would be a problem on the shoot.

Shlomi, however, was thrilled. "It looked cool," he says of the device Lohan was ordered to wear immediately after her return from Cannes. It also would bring the scene that much more publicity. Lohan even helped work it into the script when she changed a scripted fat joke about Monroe.

"The original line was, 'Marilyn could never fit in a size 0 dress,' " says Shlomi. "But [Lohan] was like, 'No, I don't want to make fun of Marilyn. What if I say, 'Marilyn would never wear a SCRAM bracelet.' We were like, 'Yeah!' "

Lohan also agreed to the last-minute script addition that had her pulling out a pair of handguns and happily mowing down photographers at a faux film premiere. That, combined with the visible SCRAM bracelet on her left ankle, promised instant headlines when an unrated trailer for the film was posted on the Internet in July.

"On YouTube, there are nearly 850,000 views for that clip alone," says Shlomi. "That's more than Machete's trailer."

While Lohan's official spokespeople declined to comment, some members of her camp contend there's no such thing as bad publicity. "It's cool to do these underground parts," says Mike Heller, a family friend and the CEO of Talent Resources, who has brokered business deals with Lohan (but not for this movie). "It keeps her current."

"She's not desperate," he adds. "Many deals have come through this office, and she's turned them down."

The Underground Comedy filmmakers wanted even more Lohan screen time in the film (Shlomi says he had three cashier's checks totaling $350,000 ready for her if she shot an additional psychologist's-office skit) but were happy enough to get her at all. "We offered her a lot more money, but she only wanted to do the Marilyn character," Shlomi says.

Though the movie appears most likely headed for a straight-to-DVD release, Shlomi hopes to either find a distribution partner or shill it to theaters himself for a late-November release. "With ShamWow, I had to become my own distributor because no one wanted it," says the undaunted pitchman. "Out of necessity you become something you're not expecting. It was actually a blessing."

While Lohan is slated to work next on a biopic of porn star Linda Lovelace, Shlomi is counting on Underground Comedy 2010 being such a success that he may have a shot at working with her again. "I'm actually doing a romantic comedy," he says. "And I'd love to send Lindsay a script."