Will Lindsay Lohan's West End debut in Speed the Plow be the turnaround moment of her career?

"I know what it is to be bad. I've been bad, I know what it is to be lost." These are the first lines Lindsay Lohan will speak, all things being well, when she makes her West End debut in David Mamet's play Speed-the-Plow tonight at the Playhouse Theatre in London.

The part she plays is Karen, a secretary to two Hollywood producers who turns out to be much smarter than she first appears. The hope of punters – and everyone involved in the play – is that she won't be "bad" at all; that the star will turn up, know her lines and maybe even pull off a fantastic performance. In short, they're hoping that this will be the big turnaround moment, the point at which Lohan puts her troubled past behind her and reboots her career by reminding everyone she's a talented actor.

Whether she'll pull it off or not still remains to be seen, but history shows it's not easy for Lohan to stay on the straight and narrow. From the ages of 19 to 26, Lohan was caught twice for drunk driving while in possession of cocaine and had six stints in rehab. She even served two weeks in jail after she breaching her parole. The turbulence in her personal life affected her film work and her most recent movie, erotic thriller The Canyons, which came out last year took a slamming from critics. During the publicity stint for the film, Lohan's director Paul Schrader publicly denounced her on Facebook because she failed to turn up to promote the film. "I hired her when no one else would," he wrote. "She fought to keep the role when I wanted to fire her for unreliability. She has no other films in the can... I can only surmise that Lindz had decided that Canyons is part of a reprobate past she must put behind her in order to move forward."

The 28-year-old has indeed managed to stay out of prison and rehab since that point and even Schrader's attitude toward her seems to have mellowed somewhat since then. When I contacted him via email he wrote back with just this to say: "I haven't seen Lindsay in about a year. She lives such a mercurial life I don't know if experience from the past predicates the future. All I can say is I wish her the best." The move from New York (where she moved to escape LA) to London and the choice to take on a West End play could also be seen as part of that decision to start afresh.

While Lohan's name should have pulling power at the box office, her reputation for unreliability could also cost the Playhouse theatre dearly. "People are very wary of stars who are notoriously unreliable, so to begin with I think the worry will be that she won't turn up," says Mark Shenton of The Stage. "Lindsay could well redeem herself but there's a lot of baggage attached to her image and so she's sort of doomed before she begins. But I'd like to give her the benefit of the doubt." Unusually for such a big name, the show hasn't sold out before the run begins; in fact when I checked there were still a handful of tickets available for opening night.

Lohan has grown up with cameras watching her. When she made her film debut in The Parent Trap, aged 11, she was already experienced, having been a model from the age of three and appearing as a regular in a US TV series, Another World, when she was just 10. When she took the starring role in Mean Girls in 2004, she was only 18 but had the confidence and charisma of someone much older. Last year she did a deal with talk show host Oprah Winfrey for her TV channel OWN, where she allowed cameras to follow her through every aspect of her life, charting her struggles with sobriety. But even though she's completely comfortable being filmed, the stage is an entirely different beast to master.

Lindsay Posner, the director of Speed-the-Plow, has coached many film stars through their first forays into theatreland. "Making a London debut for an American actor is an event at the best of times because it has premiere kudos in transatlantic eyes, so you find with actors they either put themselves totally in the director's hands because of that anxiety or they become completely neurotic and try to apply different methods... Lindsay is in that first group."

David Mamet's plays are not the easiest for a screen actor to adapt to. The words are layered with meaning, very rhythmic and precise. "It's almost like conducting music," says Posner, who's a Mamet expert, having directed more of the playwright's work than any other British theatre director. "I'm pleased to say Lindsay has taken to the process [of repetition] faster than any other debut actor that I've worked with. All the dimensions of vocal technique are coming naturally to her and she naturally has a very big voice." Posner has worked with several Hollywood actors and has found that one thing they all struggle with is the process of rehearsing the scenes.

"When I worked with Juliette Lewis [in Fool for Love], her problem was repetition," he says. "She said, 'What do you mean you want me to do it again? You think I'm some LA retard?' but of course that is just the way theatre is done and after a while she adjusted to that." Learning from his experience with Lewis, Posner met Lohan three times before taking her on, and talked her through what would be expected of her in terms of "drilling" the lines so that she'll have an idea of what to expect. He tells me he became increasingly confident over that time that she would be "perfect" for the part, not in spite of but because of her difficult history and her relationship with the Hollywood system. "She has sexual charisma, a feistiness and a complex vulnerability combined. It's a difficult part to play and she has had experiences, both very bad and very good... Karen is someone who has been burned very badly by the Hollywood system."

The role does, however, have a pedigree of being played by theatre novices. When Speed-the-Plow premiered in 1988, Madonna played Karen. It's ideal for a first-timer because although the part of Karen is critical to the story it isn't a huge role and she doesn't even appear on stage for most of Act One.

By all accounts Lohan is nervous about the role, but not so worried that she's locked herself in with nothing but Mamet's oeuvre for company. Last week she was spotted by the Mirror newspaper, reportedly appearing at a singles night at London's Cirque le Soir nightclub at 1.30am, then leaving at 2am. When I ask Posner about her punctuality, there's a pause. "It took a few days," he says. "I think that when someone is not used to the discipline and rigour of what a rehearsal involves it can be a difficult adjustment to make. It took her a few days to key in to that." But now, he says, she's doing amazingly well.

He is quick to reassure me, in fact, that Lohan is as perfect for the part as he hoped. Does she feel that she has a lot to prove? "Inevitably, she's nervous," he says, "She's never done this before. But what is surprising is she has an absolutely instinctive talent. Not like a drama school-trained actor, but a natural talent... I think we are making something quite special." After all that she's been through, it really does feel that this might be Lohan's chance at redemption.

'Speed-the-Plow' , Playhouse Theatre London WC2 (playhousetheatrelondon.com) to 29 November