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After this stroke of genius, Hines decides to add her own spin to Lohan’s deception by declaring that she’s engaged to the faux-father. (“I didn’t want people to think you were some sort of wayward skank,” she explains helpfully.) Labor Pains establishes Lohan as a semi-unrepentant party girl; after missing her sister’s parent-teacher conference to go to a bar with Hines, she answers her sibling’s back-sassing with “You’re 17. You should be out drinking and smoking.” That line would feel less creepy coming from anyone other than Lohan.

Like Hot Tub Time Machine, Labor Pains is a broad comedy that depicts contemporary life as a realm of infinite sadness and unrelenting despair. At work, Lohan is surrounded by dead-eyed automatons radiating bitterness and failure. She toils in a claustrophobic beige hellhole devoid of light, energy, and color, where the walls appear to be made of the finest Corinthian cardboard. She’s forced to resort to a ridiculous lie just to hold onto a job she hates with every fiber of her being.

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Lohan soon discovers what every expectant mother comes to realize: Life for pregnant women is incredibly easy, if not downright idyllic. Enemies turn into sycophants at the sight of a baby bump, and all the red lights in the world suddenly turn green. Will life as a fake pregnant woman make Lohan a better all-around human being? Will taking on the fake responsibility of caring for a new life lead her to embrace real responsibility for her career and future? Yes, Lohan is on a crash course with deep emotional growth, but first she has to endure slapstick complications like her asshole boyfriend inexplicably threatening her ruse during a pool party, and later popping her “baby” during an altercation with Parnell.

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Lohan hits the film’s sitcom beats with robotic proficiency, falling back on her default comic tics—a wide-eyed deer-in-headlights expression, nervous ranting to convey embarrassment, and girlishly excitable body language—but the film takes on a faintly tragic dimension. Lohan still looms large in our culture—as a train wreck and cautionary tale, if not as an actress—but the pictures have gotten small. Going from Mean Girls and A Prairie Home Companion to the low-budget, sweaty desperation of Labor Pains isn’t like going from the majors to the minors, it’s like going from pitching for the New York Yankees to riding the bench as a backup utility outfielder for a prison softball team.

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Back in 2006, however, Lohan was still considered capable of carrying a major studio motion picture, especially if the apex of the cinematic arts in question was Just My Luck, a frothy, frilly, pink cross between two of her previous hits, Freaky Friday and The Parent Trap. Only this time, Lohan wasn’t trading places with an identical twin or her mother; she was the world’s luckiest woman trading luck with the world’s unluckiest man in the world’s most gimmicky screenplay.

Just My Luck once again casts Lohan as a plucky city girl making a go of it in a glamorous industry. Lohan plays a career gal in a fairytale Manhattan of glistening boardrooms, kindly doormen, girl bonding, and romance waiting around every door. It’s a prepubescent girl’s fantasy of urban sophistication, a Sex And The City daydream of awesome clothes and dreamy strangers with bedroom eyes.

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Lohan is literally the luckiest girl in Manhattan. When she steps out of her apartment building, a thunderstorm instantly morphs into sunshine. When she needs a dress for a fancy party, a Dolce Gabbana frock in her size intended for Sarah Jessica Parker magically arrives at her front door. In her younger days, she was elected prom queen for a high school she didn’t even attend. Yet her boundless luck failed to catapult her to a professional status beyond secretary at a record label. If she were anything less than the human embodiment of luck, she’d be, what, a janitor? An unpaid intern? That’s a little like Jim Carrey using his godlike powers in Bruce Almighty to win back his job as a wacky newsman in Buffalo and give his girlfriend bigger tits. Many Hollywood screenwriters clearly have imaginations with decidedly concrete limits.

Future Starfleet commander Chris Pine co-stars as Lohan’s antithesis, a sad-sack would-be rock manager and bowling-alley employee whose handsomeness is cunningly concealed by geeky glasses and a wardrobe defined by homeless-man chic. He’s the male equivalent of the proverbial mousy secretary who just needs to take off her glasses and let her hair out of a tight bun to become a knockout. Just how unlucky is this modern-day Job? In the below clip, Pine gets run over by a jogger, is mistaken for a rapist, gets his pants dragged around his ankles, is kicked in the nuts, and finally handcuffed as the demo CD he’s shopping to a famous mogul is crushed beneath the wheels of the mogul’s car. In less than a minute! That is some efficient storytelling right there.

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Pine’s hapless striver manages McFly, a real-life rock mediocrity whose style he breathlessly dubs as “a fresh take on a retro sound,” like “early Beatles meets Blink 182.” (That line reminds me of the bit in Scharpling & Wurster’s first Mother 13 routine, where a cocky would-be future rock star brags that his band sound like a cross between The Who, Nirvana, The Clash, R.E.M., and Led Zeppelin. Then he plays a snippet of his latest single, the most punishingly generic grunge imaginable.)

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So it’s kismet that Lohan and Pine, the world’s luckiest and unluckiest human beings, meet one night during a masquerade ball thrown in honor of prickly mogul Faizon Love, and exchange a passionate kiss that changes their destinies. With that single saliva-swap, Lohan’s luck deserts her and Pine’s suddenly takes a dramatic turn for the better. Slapstick humiliation ensues, as do a disturbing number of gags involving Lohan getting punched in the face by an angry black lesbian. Just My Luck and Jersey Shore have taught us that there’s nothing funny about violence against women. Well, almost nothing.

In the hallowed, verisimilitude-rich tradition of The Jetsons, Just My Luck inhabits a black-and-white workplace world where every good idea is rewarded with an instant promotion and personal assistant, and the mildest blunder is punished with firing. (This is also true of Labor Pains.) So Lohan is promoted after her quick thinking impresses Love, and instantly fired the moment her luck turns sour. In a desperate bid to regain her luck, Lohan decides that she needs to re-kiss the mystery man from the masquerade ball. Since Pine was conveniently wearing a mask during said kiss, and was pretending to be a dancer, for reasons far too stupid to go into, this leads to numerous scenes where Lohan goes around playing tongue-hockey with strangers, including the winner in the clip below. Lohan is quite a Method actor: She was so committed to her role that even today, she can regularly be seen making out with strangers in real life.

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In its first half, Just My Luck functions as lifestyle porn for teen girls. It’s blatant wish-fulfillment as Lohan effortlessly scores hot, rich guys; gabs with her girls; and skates happily through a charmed life. The film’s second half is dedicated largely, if not exclusively, to Lohan’s life-and-death struggles with various inanimate objects, like an out-of-control washing machine. Oh, and her mounting insanity. In this clip, Lohan responds to her shifting fortunes the way anyone would: by ranting semi-coherently to a bunch of strangers in a restaurant. Gag in a goofy comedy, or nightmare descent into madness? You be the judge.

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Just My Luck is a sputtering, malfunctioning Rube Goldberg contraption of a movie, a gimmicky concoction duct-taped together with flailing slapstick and plugs for McFly that fall somewhere between product placement and viral marketing. The screenplay ostensibly plays to Lohan’s strengths. She looks healthy and fantastic—it’s a mystery why anyone with such gorgeous red hair would feel the need to go the bleached-blonde-skank route—and she’s afforded ample opportunity to stare open-mouthed and wide-eyed in horror as she contemplates her latest blunder.

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Just My Luck is wholly dependent on the charm and chemistry of its leads. Pine approaches the shenanigans with a light touch and a wink that suggests he’s all too cognizant of the film’s ridiculousness, but Lohan—who, let’s reiterate, was paid $7 million for her performance, substantially more than the film made during its all-important opening weekend—had too much professional and emotional baggage to be palatable in such fluff. It’s difficult to forget about Lohan’s tabloid infamy and focus on her acting when she releases music videos like 2005’s “Confessions Of A Broken Heart (Daughter To Father),” an almost unbearably intimate, sordidly confessional video about her tortured relationship with her father. It co-stars her younger sister Ali:

Audiences were far too intimately familiar with the tragedy of Lohan’s personal life to embrace her in a featherweight comedy. “It’s like I’m the anti-Midas. Everything I touch turns to crap,” Lohan’s Just My Luck character grouses. That dynamic seems to have carried over into her real life, and it shows no sign of turning around. The line more or less sums up her post-Mean Girls career. Or does it? Find out in the next installment of Lohan month here at My Year Of Flops, as I explore the dramatic side of the tabloid fixture’s oeuvre with a double Case File on I Know Who Killed Me and Chapter 27.

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Labor Pains
Failure, Fiasco, or Secret Success? Failure

Just My Luck:
Failure, Fiasco, or Secret Success? Failure