It’s usually pretty unpleasant when you run into your ex on the street or at the bookstore, or anywhere. You both shift your weight and ask questions you don’t care to hear the answers to and you’re so desperate to get away that you try and will yourself into passing out so the exchange can end. And so it’s pretty exceptional that Cameron Diaz and Justin Timberlake (who dated from 2003 to 2007) are on such good terms that they were capable of filming Bad Teacher together. I can’t think of any other instance where two people broke up after dating for a substantial amount of time and then decided they’d enjoy filming a movie together. It simply hasn’t happened. But that got me thinking about all the exes that I’d wish would just get over all their pettiness and come together again for the sake of my entertainment, just like Cameron and Justin did.
Susan Sarandon and Tim Robbins
Susan Sarandon and Tim Robbins were an item for 23 years but they never married. They met on the set of Bull Durham, where Sarandon played Annie Savoy, a baseball fan who habitually had affairs with minor-league players. Robbins played Ebby Calvin LaNoosh, the catcher to pitcher Crash Davis, played by Kevin Costner. After Annie very much perpetuated and enjoyed this almost two-hour game of tug of war, she ended up with Crash and left Ebby out on home plate by himself despite their obvious connection. However, since Sarandon chose Robbins over Costner in real life, it would be very tongue-in-cheek if the sequel had Annie realizing she made the wrong choice and ran back into the arms of Ebby, who had been waiting on his couch with her picture in his hand ever since she left. Even though Sarandon and Robbins have in fact slip up, they seem like good sports and even though there’s absolutely no need for a Durham sequel, they were so cute onscreen together that it almost necessitates another production.
Tom Cruise and Nicole Kidman
Tom and Nicole were in two movies together: Days of Thunder and Eyes Wide Shut. After getting married in 1990 and adopting two children, they divorced in 2001 and both eventually remarried (Cruise married Katie Holmes and Kidman married country singer Keith Urban). They’ve made it perfectly clear they don’t really speak anymore and probably go out of their ways to steer clear of each other in show business. But if for some reason they encountered a comedy that they both felt incredibly strongly about and neither one of them was willing to relinquish it to the other, they might consider doing it jointly if they were comfortable inviting the audience to laugh again about how dysfunctional their marriage must have been.
Jennifer Aniston and Brad Pitt
After marrying in July of 2000, Jennifer Aniston and Brad Pitt’s fall from grace and subsequent divorce in 2005 was extremely public and was reportedly the result of Brad falling in love with Angelina Jolie on the set of Mr. and Mrs. Smith. But it’s kind of understandable! The rumor was that Brad apparently wanted children but Jennifer did not want to abandon her career so quickly, and so he left her for someone whose desires coincided with his. Jennifer claims she and Brad still have a great relationship, but nobody really believes this because he’s too busy raising six children and traveling to take the time to call the set of an Adam Sandler movie to chat with her. She never passes up the opportunity to talk about how happy she is since her divorce though, and how its allowed her to do things like cut her hair and take up architecture and interior decorating as hobbies. But Brad has totally different priorities today then he did when he was married to her, and he probably finds her repulsive now. So in my mind, Jennifer wants to be in a movie with Brad more than Brad wants to be in a movie with Jennifer and the only way we’d see them on screen together is if Jennifer took enough care to find out where Brad was in the world, erected a movie set on some street he frequents, and have a cameraman film until until she had the opportunity to crash into Brad and act surprised at their meeting. But I’d still enjoy it!
Demi Moore and Bruce Willis
Even though Demi Moore and Bruce Willis ended their marriage of thirteen years in 2000, they’ve remained oddly close. Since their split they’ve walked red carpets together, invited each other to their weddings and are on surprisingly good terms. But not because they feel like they have to be for their three daughters – it just seems like they genuinely like one another and don’t hold any resentment over the dissolution of their marriage. In fact, they’re probably such big fans of each other and respect each other so much that they actually would do a movie together. They're both such stellar action heroes and in such great shape that whenever Ashton Kutcher is away filming a Nikon commercial, I bet they head down in the basement and comb over scripts for a Fun with Dick and Jane remake.
Alec Baldwin and Kim Basinger
There is no other ex-husband and ex-wife in Hollywood more contentious than Alec Baldwin and Kim Basinger. They met on the set of The Marrying Man and everything was fine and dandy then because they eventually married in 1993. They had a daughter, Ireland, in 1995 but by early 2001, they were looking to get divorced. Once their marriage was legally over, Baldwin began telling the media that Basinger was disobeying court orders by preventing him from talking to his daughter on the phone and from seeing her in person. Baldwin spent years criticizing Basinger’s psychologists and lawyers and faulted them for committing “parental alienation,” and even wrote a book called A Promise to Ourselves about how much money and time he spent fighting to stay in his daughter’s life. Basinger has never outwardly criticized Baldwin or responded to the claims that she wouldn’t let Ireland see her father, but since things seem to have finally quieted down between the two of them, we’re probably better off leaving them alone in their current bicoastal setup (even though their clearly tumultuous relationship would make for an excellent film essay on what the transformation from love to viciousness looks like).