We All Know Lindsay Lohan’s Greatest Hits, But Her Chris Pine Rom-Com ‘Just My Luck’ Is An Underappreciated B-Side

“You never get a second chance to make a first impression.” The ad wizards who wrote that copy were certainly onto something when they created this memorable tagline, but Decider’s“Take Two” series was specifically formulated in a laboratory by the world’s foremost pop culture scientists to provide a second chance for movies that made a less than stellar first impression upon their original release.

The biggest asset of Just My Luck, a movie which sits at a 14% approval rating on Rotten Tomates, is its star, Lindsay Lohan. Ironically, its biggest problem at the time of its release, was also Lindsay Lohan.

It’s not a novel opinion to say that Lohan was – is – a good actress. Her work in The Parent Trap, Mean Girls, and especially Freaky Friday, is impressive; she deserved stardom. What she didn’t deserve was the media examining her dysfunctional family life and subsequent substance abuse issues with a high-powered lens, the results of which ended up halting her career for the better part of a decade. Just its luck, Just My Luck had the misfortune of arriving just as Lohan’s substance abuse and her reputation as a “party girl,” as so many media outlets described her, started to overshadow her professional work.

Just My Luck is a romantic comedy that co-starred Chris Pine — fresh off his breakthrough role in The Princess Diaries 2 — as a hapless, always down-on-his-luck aspiring band manager named Jake Hardin. (The band he repped was played by the actual British group McFly, whose success was a flash in the pan, at least stateside.) Lohan played Ashley Albright, a woman for whom good luck was always on her side: always one to find a lucky penny or win on a scratch ticket, she never had a bad day in her life. (The character feels very reminiscent of Drew on 30 Rock, Liz Lemon’s handsome doctor boyfriend played by Jon Hamm who didn’t realize he received preferential treatment in this world because he was good-looking.) When the two, who are both wearing masks at a masquerade ball Ashley is throwing as a PR event for a record company, meet and kiss, magical realism kicks in and their luck is swapped.

After the kiss, Ashley’s life starts to become a disaster: she loses her job, her apartment floods leaving her homeless, she goes to jail (twice), buses splash puddles into her — you get the picture. Meanwhile Jake’s life starts to go great: McFly snags a record deal and he and the band are given a cushy apartment to live in. The only way to reverse the luck, Ashley is told by a tarot reader played by Tovah Feldshuh, is to kiss the masked man again, so Ashley goes on a kissing spree across New York City (ahh, pre-Covid life!) to find him. (Ultimately, when they do find one another, he helps her find work, she helps him promote the band, and they realize they both have great luck because they made a love connection.)

Of course there’s nothing plausible about the premise here, but there’s nothing plausible about the fantasy elements of similar rom-coms of the early aughts like What Women Want, Just Like Heaven, and 13 Going On 30 either, but those all received warm, or at least not entirely scathing reviews (all have over 50% on Rotten Tomatoes). Why was this one panned so badly? I have to think the blame lies in who it was targeted to, coupled with Lohan’s controversial image at the time.

Just My Luck was Lohan’s first film where she represented herself as an adult, a career woman who lived independently from her parents. Therein lies the problem. The movie, which was given a PG-13 rating for some innocent innuendo, is not a film for adults, but it was supposed to be Lohan’s attempt at appealing to older audiences. It shouldn’t have even tried. Released only a year after Herbie: Fully Loaded, Just My Luck is a romantic comedy that’s perfectly safe for kids to watch, a gateway drug before you get to the harder stuff peddled by Nancy Meyers and Nora Ephron and Garry Marshall. In Entertainment Weekly, Owen Gleiberman called the film “teenybopper junk” and even the film’s more positive reviews implied that it’s a kids movie (Joel Siegel wrote that it was “a film moms can take their daughters to”). Its PG-13 rating not only limited its target audience, but allowed adults to falsely assume this was a movie for them.

But here’s the film’s second problem. Lohan, 19 at the time of the film’s release, had become a tabloid fixture. The fact that she was in gossip rags all the time had begun to “[distract] from the work that I do” she told Jay Leno during a Tonight Show appearance that year. Leno himself tried aggressively to get her to admit that her friends Paris Hilton and Nicole Richie were “out of control” in that same interview despite the fact that Lohan, to her credit, resisted labeling them as such. The early aughts was an era of judgey, shame-y tabloid coverage of this kind of “party girl,” and Lohan, Hilton and Richie led the pack. The trouble is that Lohan had more to lose because her acting career was flourishing, while the other two were only notable at that time for reality TV work and for being nepo babies. “It’s a crime for someone to go out to a club. I get in so much trouble, people lose respect,” she told Leno, and indeed, after a busy 2006 and 2007, the work dropped off and she didn’t headline a film with any significance between 2008 and 2013. You can’t help but assume Lohan’s fans were outgrowing her and dismissing her now that she was more of a punchline than an actor and the bad luck her character experienced in the film was projected onto her in real life.

Donald Petrie, who also directed How To Lose A Guy In 10 Days, Mystic Pizza, and Miss Congeniality, all of which have achieved some variation of cult status, also directed Just My Luck, and while the film’s not going to win any Oscars, it feels unfairly maligned. Lohan and Pine are charming and prove to be truly capable actors, their chemistry is great, and the supporting cast is early aughts perfection: Missi Pyle is perfectly cast as the evil boss, Faizon Love is a formidable but tender-hearted music executive, and Makenzie Vega is great as Katy, Jake’s neighbor that’s essentially a little sister figure. I can’t help but wonder if Just My Luck would be viewed differently now that Lohan isn’t a tabloid fixture anymore.

We all know Lindsay’s greatest hits, but Just My Luck is an underappreciated B-side that deserves a closer look.

Liz Kocan is a pop culture writer living in Massachusetts. Her biggest claim to fame is the time she won on the game show Chain Reaction.