18. A definitive ranking of every Lindsay Lohan movie up to 2013 (apart from Liz & Dick)

I Know Who Killed Me isn't even nearly the worst one

Early on in the process of writing my book about women and fame in the noughties, I realised that I wasn’t going to fit my subject neatly into the confines of the decade. The same way historians talk about “the long nineteenth century”, I’ve settled on a “long noughties” — a period that begins, roughly, with “… Baby One More Time” (1998) and ends with “Blurred Lines” (2013). The reason for choosing that start point is, I hope, obvious: Britney is the definitive noughties star, and “… Baby” is the definitive Britney song as well as her debut. Apres the kiddult S&M, le deluge.

As for “Blurred Lines”, the backlash to that song is — in my recollection, anyway — the first significant moment a critical mass of feminist opinion made a dent in the cultural norms established in the noughties. It wasn’t, in retrospect, a very fair reckoning, not least because all of it landed on the hapless Robin Thicke and none of it on Pharrell Williams, who cowrote and produced the sex pest anthem as well as appearing in the abysmal last-shout-for-irony-porn-chic video.¹ (The year after “Blurred Lines”, Williams was being implausible trailed as a “poster boy for feminism”. Ask Kelis about that one.)

1998-2013 is also, by an amazing coincidence (and I genuinely didn’t know this before I started my research), the span of Lindsay Lohan’s career from her feature debut in The Parent Trap to the professional calamity of The Canyons — a film which generated very few ticket sales but did result in a damning set report in the NYT headlined “Here Is What Happens When You Cast Lindsay Lohan In Your Movie” (tl;dr, some incandescent Lindsay performances if you’re ever able to get her on set, which you probably won’t be, meaning you will definitely burn your budget on hanging around waiting for her). After The Canyons, she took a six year break from films.

So in honour of my incredible-critical-judgement-slash-extraordinary-good-luck, I’ve assembled a definitive ranking of all Lindsay’s movies up to 2013. There’s one I haven’t seen: the 2012 Lifetime biopic Liz & Dick, in which Lindsay plays Elizabeth Taylor, has proved impossible to get hold of.

I’d love to have been able to report that it’s a CV studded with hidden gems: it’s not. The easy way to read Lindsay’s career is as an act of self-sabotage, and that’s definitely part of what happened here. But it’s also a career governed by the normal disappointments of Hollywood.

Actors don’t have that much control over their professional trajectory. They can pick the projects (and Lindsay I think did pick smartly for the most part, even though what she had to pick from grew more and more constrained as her reputation got worse), but they can’t decide how those projects turn out. And almost none of Lindsay’s projects after 2004 turned out well. (This post is long so you might want to open in a new window.)

1. Mean Girls (2004)

Of course this is Lindsay’s best film. It’s also Tina Fey’s best film. It’s the best film of everyone involved in it, even the ones who subsequently went on to make other good films (and it’s Lindsay’s last good film). It’s the pinnacle of the high-school movie, bringing together the savvy of Clueless and the cruelty of Election to make something that is both absolutely without sentiment and totally life-affirming. I’ve got a tattoo in honour of it. Is Fey’s “don’t call each other sluts” monologue hypocritical in a film where half the lols come from deploying the word slut? A bit! I don’t care! You go, Glen Coco!

It’s also not really about high school. When the Plastics first show up, “too-gay-to-function” Damian explains them to Lindsay’s character Cady like this: “If North Shore had Us Weekly, the Plastics would be on the cover every week.” What is the Burn Book but a gossip blog made physical? Mean Girls is a riff on celebrity, including Lindsay’s. Her subsequent films will often try to engage her reputation to ironic effect, but after 2004, “tabloid Lindsay” will always fatally overpower “screen Lindsay”. Here, though, she’s dazzlingly funny and subtle enough to carry you with Cady even as Cady is losing the plot.

2. Freaky Friday (2003)

This is the one that convinced everyone that Lindsay really had the goods, but it’s also a showcase for Jamie Lee Curtis, who absolutely tears down the screen in this body-swap comedy. Mother and daughter switch psyches, pratfalls are had, lessons are learned, reconciliation is achieved and everything ends up in the right place in the end. It works because both stars have the craft to convincingly play each other’s characters. Joyously funny.

3. Life-Size (2000)

Have I lost my mind through prolonged Lindsay exposure? Maybe! But this — Lindsay’s second movie, and the last one where she looks like a button-nosed child — is delightful. Lindsay plays Casey, the daughter of a preoccupied widower. Tyra Banks is the doll Casey accidentally brings to life during an occult ritual intended to reanimate her mother (anyone with knowledge of the monkey’s paw will be glad it works out this way rather than as intended). Banks is surprisingly endearing, but Lindsay brings real range and depth. Unexpectedly moving.

4. The Parent Trap (1998)

It’s the original Lohan v Lohan, way before Michael and Dina got properly into it. Lindsay makes her feature debut in not one but two roles, as twins Hallie and Annie who are separated as babies by their clearly appalling parents (Dennis Quaid and Natasha Richardson) and then raised in ignorance of each other’s existence (APPALLING PARENTS) until they meet at summer camp and cook up a plan to reunite their appalling parents. It’s too long but keeps things brisk enough that you’ll only sometimes think about how badly Hallie and Annie need a social services intervention.

5. Confessions of a Teenage Drama Queen (2004)

Lindsay’s plays Lola (real name Mary “but I’ve always felt like a Lola”) — an NYC transplant to a New Jersey high school, intent on reinventing herself as “a legend”. The character doesn’t have the surprising depths Lindsay brought to Life-Size, The Parent Trap or Freaky Friday. But this is a charming bit of Disney froth, with early appearances from Megan Fox (dead-eyed hottie) and Alison Pill (adorable nerd). Bonus points for a fantasy sequence where Lola imagines herself as Marilyn: later, Lindsay would be insistently styled as Marilyn for photo shoots with increasingly grisly undertones (the message seemed to be: when will this gorgeous trainwreck finally crash for good?), but here it’s pretty sweet.

6. Get a Clue (2002)

Minor Disney comedy, with Lindsay playing a student turned freelance gumshoe poking into the mystery of a teacher’s disappearance. Of slight interest because Lindsay’s character’s sneaking maybe-kinda presages the sort of intrusion Lindsay would shortly receive from the media, but basically forgettable.

7. Herbie: Fully Loaded (2005)

Look, I just hate Herbie. I hate this Herbie and all Herbies. The idea of a sentient car is fundamentally very upsetting and I don’t know why anyone thinks this is fun. If you’re the kind of sociopath who doesn’t feel existentially disturbed by the whole premise, then Lindsay’s last Disney film is diverting enough, with a nice heel turn from Matt Dillon as the Nascar driver out to ruin Herbie’s freakish little dreams of victory. But this was a miss for both Lindsay and Disney. She was too old for kids film — her party girl reputation already established, and her boobs (as the blogs delighted in pointing out) too big for for the skintight jumpsuit she wore in the movie.

8. Labor Pains (2009)

And you thought The Parent Trap was contrived. Lindsay plays Thea, a young woman who fakes a pregnancy to avoid getting fired from her entry-level publishing job. Does this make sense given American labour rights? It absolutely does not, and the plot unravels badly well before the end. Very obviously post-Juno in style and tone, its biggest problem is that its main character is at best a psychopath and at worst in the grip of psychosis. Still, it’s impossible to feel totally ill-disposed to a film that includes Cheryl Hines (you’ll know her as “Larry David’s long-suffering wife”) and Chris Parnell (30 Rock’s Dr Spaceman).

9. I Know Who Killed Me (2007)

Lindsay got two Golden Raspberries for this film, in which she takes the dual role of nice-girl Aubrey and nasty-ho Dakota. At the time it was seen as a historic stinker in which Lindsay stank the worst — given Lindsay’s off-screen problems and the lack of a major hit since Mean Girls, it seemed to cement her fall. And look, yes, it’s very bad: part psychological thriller, part torture porn, a Hitchcock film given a pickax lobotomy. Lindsay appears as separated-at-birth twins again, and that really underlines the fact that by now she’d stopped playing characters and started being “Lindsay Lohan, professional hot mess” pretty much full time. At one point a psychiatrist writes the word “delusional” on a picture of Lindsay in exact imitation of one of Perez Hilton’s “doodles”. Incoherent and empty.

10. A Prairie Home Companion (2006)

I guess if I actually liked the NPR show this is based on, I might like this Robert Altman film. But I’ve always found Garrison Keillor’s whimsy a bit too contrived, and casting him as a version of himself feels like a major error: he slumps about the screen alongside a megawatt cast, sucking up charisma like a mardy potato. Lindsay is sweet as the angsty daughter of Meryl Streep, a country singer who’d like to see the family business continued, and our girl gets the showstopper when she performs “Frankie and Johnny” at the end with a winning mix of swagger and reticence that perfectly suits the character. Altman films tend to be either dazzling meditations on the superficial, or just superficial, and this one’s just superficial. He died a few months after release, leading to Lindsay’s unkindly mocked eulogy: “BE ADEQUITE.”

11. Bobby (2006)

As well as being in a real Altman in 2006, Lindsay showed up in this ersatz Altman from Emilio Estevez. Neither was a bad shout: who’d pass up being in a film by the guy who made The Player, and who’d miss the chance to share the billing here with William H Macy, Martin Sheen, Harry Belafonte, Sharon Stone, Anthony Hopkins and etc etc etc? (Estevez said Lindsay was “rabid” to get the role.) But this ensemble film, set in the hotel where Robert Kennedy was assassinated in the hours leading up to his death, falls flat. It’s just too obviously a sad liberal’s lament for a timeline that could have avoided George W Bush as president, and that leaves all the characters here to drown in the moral significance of the proceedings. Lindsay plays a young woman marrying a boy she hardly knows to save him from frontline service in Vietnam, a role that asks nothing of her except that she be doe-eyed and self-abnegating.

12. Just My Luck (2006)

Another one that makes sense in theory and sucks in practice. Lindsay is the girl about NYC with the charmed life; Chris Pine is the born loser (albeit a born hot loser). They cross paths, kiss, exchange luck and undergo multiple scrapes until they realise (but you realised this in the first ten minutes) they belong together. The high-concept romcom was a solid genre at this point (Nancy Meyer, who directed The Parent Trap, made a fair few of them) and a better version of this idea could have fixed Lindsay’s trajectory as an adult actor in the Meg Ryan zone. But the film doesn’t know who it’s for: its tone is pitched to a tween audience, but it’s got jokes about prostitution. Good one. Lindsay had her first DUI arrest less than a year after this came out, making the two scenes of her being thrown in the cells here unfortunately prescient.

13. The Canyons (2013)

Somehow, in a film that costarred actual porn star (and now accused-though-he-denies-it rapist) James Deen, Lindsay was still considered the stunt casting. Director Paul Schrader adored her performances, when he could get them out of her: this was supposed to be her comeback, and instead it was the end of her and Hollywood for six years. The script, by Bret Easton Ellis, is really just an excuse to get Deen to be naked and sadistic as much as possible, although Lindsay is also naked plenty of the time. The story is impossible to care about because the characters are deathly vectors of amorality: they’re always only going to do bad things, and the people they do them to are also bad. Meh. Reports from the set blamed Lindsay’s flakiness for problems with the finished product, but she’s still the best thing here.

14. Georgia Rule (2007)

Heartwarming intergenerational girl-power drama about, um, child abuse? Lindsay is up to the mark against Jane Fonda (the grandmother) and Felicity Huffman (the mother), playing a teenage tearaway sent to the northwest for correctional fostering. (“She was raised in California,” is how the Fonda character explains her granddaughter’s bad behaviour to the neighbours.) The twist is that Lindsay’s revolt is inspired by the fact she was sexually assaulted by her stepdad, Cary Elwes. (Or was she?) (Yes she was.) That’s a lot of weight for a saccharine small-town drama to carry, and it fails to carry it: all the trauma and betrayal is supposedly swept away with a bit of clean Idaho air.

15. Machete (2010)

The definition of a joke taken too far. Machete is the feature-length film of the trailer Robert Rodriguez knocked together for Grindhouse. Watching it is like feeling the noughties die around you: turns out you cannot live on self-awareness alone. Lindsay plays the slutty brat daughter of a crooked businessman who ends up in a sex tape (lol) before she pulls on a nun’s habit (irony lol) and goes out to take vengeance on someone for something, I don’t care and nothing matters.

16. InAPPropriate Comedy (2013)

It’s a bad-taste sketch compendium and it’s still somehow not the worst film Lindsay’s ever been in. She’s Marilyn again, doing the bit from The Seven Year Itch. The barely-a-joke is that when the paparazzi gather, she asks if she can shoot them next and then she does. With a gun. God I feel so dead inside. This was pitched to the media as “Lindsay’s revenge”, a line that is slightly undercut by the fact the sketch also features director Vince Offer sitting under the grill, looking at her pants. Yes, it’s an actual upskirting gag. Thank you, gods of theme. I still wish this film didn’t exist

17. Chapter 27 (2007)

Desperately bad Jared Leto vanity project, in which no one’s favourite actor plays Lennon assassin Mark Chapman. Cleverly, Leto avoided having to think about “character” or “motivation” by putting on stunt amounts of weight and a creaky little voice. (Chapter 27 is a reference to Chapman’s obsession with the 26-chapter-long Catcher in the Rye, and we get lots of romantic shots of rye fields to underline… something.) Lindsay just has to show up and be an ingenue, which she could do in her sleep and basically does. Appalling.

1. Obviously non-ironic porn chic has thrived since.