Cruel Intentions (1999)
Ryan Phillippe and Reese Witherspoon
How do you make classic French literature sexy and appealing to the youths? Cast late ‘90s teen stars in your hip update of Dangerous Liaisons and play the story for disaffected youth laughs with bourgeois R-rated material. Roger Kumble’s Cruel Intentions brought together powerful, Aryan, blonde teen actors Reese Witherspoon and Ryan Phillippe as they trounced around in a New York romp full of teens and tawdry behavior. Oh, what a wicked game the kids weave when they learn to deceive. And do coke.
Phillippe and Witherspoon met on set, and, uh, the sexual tension is palpable by gum. They married soon after Cruel Intentions was released. The film itself became a cult hit over time, but was a commercial failure. Witherspoon and Phillipe’s marriage? Uh…
Relationship Status: Phillipe and Witherspoon split apart after nine years of marriage in 2008. Bummer. Witherspoon won an Oscar for Walk the Line in 2006 and married Jim Toth while Phillippe had a bit part in The Lincoln Lawyer … last we recall. Look, Reese Witherspoon’s just swell.
Eyes Wide Shut (1999)
Tom Cruise and Nicole Kidman
You might’ve heard some stories about this one over the years. (Like the one about Woody Allen being director Stanley Kubrick’s first choice for the Cruise role when he first started to piece together the project in the ‘70s. Can you even imagine?) Tom Cruise and Nicole Kidman’s real-life relationship was still humming along at the time, and the two ended up enacting no shortage of drama in Kubrick’s examination of a struggling couple’s attempts to seek the sexual validation that’s eluded their relationship. There’s all kinds of meta-text to read into that we’ll avoid here since it can’t really be discussed without devolving into the gossipy and the lurid, but Eyes is still a sharp, envelope-pushing investigation of the secrets even the most seemingly well-off couples keep from one another and the places they’ll go to find what they can’t at home.
Relationship Status: Welp. Kidman and Cruise would divorce shortly thereafter. She would refer to the whole proceeding as “awful,” and Cruise would move on to endless, pervasive rumors about the nature of his relationships. There’s some stuff involving a couch somewhere in there, too.
Will Smith and Jada Pinkett-Smith
What did Ali have to do with Will Smith and Jada Pinkett-Smith’s love life? Nothin’. How much onscreen chemistry did the real-life couple have? None. But hey, Will and Jada got to play lovey-dovey onscreen as Muhammad Ali and Sonji Roi. Roi was Ali’s first wife for two years in the ‘60s. It ended uninterestingly. So yeah, it’s not totally, like, an epic romance and stuff and totally deserves two minutes of screen time in a 165-minute biopic.
To be fair, Ali is remembered for Will Smith’s knockout leading performance as the legendary pugilist. The romance, the real-life love affair of Will and Jada, was more a secondary bit of lucky casting than it was about flaunting their love onscreen.
Relationship Status: The Smiths are still hitched, and their spawn are trying to take over Hollywood! Just look at Sony leak emails. The studio’s terrified that the Smith kids are running the studio. That’s the power of love, kids.
Jude Law and Sienna Miller
In Charles Shyer’s remake of the camp classic Michael Caine romance, Jude Law played a lecherous, loving Brit in New York that may have found the woman of his dreams in the attractive, young Sienna Miller. Right, we’re not here to talk about the art of Charles Shyer. Law left his wife of several years to run away with Miller after they met on the set of Alfie. The chemistry seems real onscreen, and the two were engaged in a big, splashy, public way around Christmas of 2004. Then the nanny. Law got busted for canoodling with his kids’ nanny while engaged to Miller, and despite a public apology (and sort of begging for forgiveness that perhaps he should have directed at Miller), the power couple split in 2006.
But wait, there’s more. They got back together in the fall of 2009. Aww, true love…
Relationship Status: Nevermind. They called it off in early 2011. Law and Miller never got hitched, despite several makeups and breakups. Law’s having a silver-foxed renaissance as a Brit character actor with a silky voice, and Miller’s getting cast in a million-and-one good movies, so the kids are alright.
The Break-Up (2006)
Jennifer Aniston and Vince Vaughn
Even the promotion of The Break-Up traded heavily on Jennifer Aniston and Vince Vaughn’s real-life relationship at the time. The dramedy (billed as a straight comedy, which was a mistake that turned off some audiences) about a couple mutually torpedoing their relationship while each attempting to keep their nicely appointed Chicago condo for themselves is less a wacky comedy of opposites than an examination of mutually assured destruction. It’s a surprisingly pointed piece of work, especially when considering the film’s bleak, later-changed original finale, in which months after the titular split, the two run into each other, each arm-in-arm with somebody bearing a striking resemblance to the other instead. The Break-Up is unwieldy, but also cuts to the heart of how most splits aren’t based on singular, cataclysmic events, but instead a series of small affronts that pile up over time and crush everything beneath them.
Relationship Status: While they came together making the film, ultimately both would move on, much like their protagonists.