Every Julia Roberts Rom-Com Love Interest, Ranked From Murderer To Prince Charming
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HONORABLE MENTION: Michael O'Neal (Dermot Mulroney) — My Best Friend's Wedding (1997)
Much to the dismay and ire of people reading this list, I'm sorry to say that I cut what might actually be Julia Roberts's best rom-com from this ranking. Anyone who has seen the film knows that Julia's Jules is secretly in love with her best friend Michael, and upon learning that he's getting married, attempts to undermine the wedding (not the last time she'll be doing that on this list). However, the film resolves with Jules realizing that Michael is actually well suited to marry his fiancé and that she should instead just hang out with her gay best friend (which honestly is probably better than marriage anyways). Because Jules and Micheal don't end up together (and weren't dating during the film anyways), it felt strange trying to slot him in here, so I gave him an honorable mention slot instead. Similarly, in Valentine's Day, it's revealed that Julia's valentine is actually her son, so that did not make the cut as well. Now, on to the real love interests.
13.Jerry Welbach (Brad Pitt) — The Mexican (2001)
There is no place but last to rank The Mexican's Jerry, because Julia's Sam spends the entire film trying not to get murdered because of his stupidity. Jerry, who is generally inept in every way, accidentally got a mob boss sent to jail and is now running errands for the crime syndicate to pay off his debt. Of course, Sam is taken hostage as collateral and is nearly murdered a dozen times over the course of the film. Jerry and Sam only reconnect in the film's final scenes were they bizarrely decide that they might as well stay together even though it sucks. Sam has significantly more chemistry with her gay handler Leroy (James Gandolfini), until he is murdered, and honestly, she should have pulled a My Best Friend's Wedding and just stuck with the gays.
12.Peter Brackett (Nick Nolte) — I Love Trouble (1994)
In the '90s, rom-coms loved to pair a young, hot feminist with an old, craggy misogynist and try to sell it off as cute, when in actuality, the guy is a perv, and the girl can do soooooooo much better. In this journalism-themed romance, Brackett meets Sabrina Peterson (Roberts) while investigating a train derailment for rival newspapers. In their first encounter, he says, "Where you from? Bitchville?" to her, but as the pair keep bumping into each other on the trail, the audience is told that she falls for him. It's a testament to Roberts that this is even slightly believable, as Brackett is an unlikeable womanizer who is pissed off because she won't sleep with him because he's semi-famous. While he does save her life once or twice while they're investigating genetically modified milk (I'm not joking), that's not enough to convince me he's a good guy. She should have found a gay in this film, too.
11.Ike Graham (Richard Gere) — Runaway Bride (1999)
While we're on the topic of skeezy journalists, let's talk about Ike, who on top of having questionable morals is also a crappy journalist. He's fired from his job when he reports false details about Maggie (Roberts), a woman who has jilted three men at the altar. While he's a smidge nicer than Brackett, he tracks down Maggie in her hometown, and after she asks him nicely to leave, continues to dog her around town, intrusively speaking to everyone she knows in hopes of getting a scoop that will earn him his job back. While he does eventually apologize for this behavior, he also kisses Maggie at her own wedding rehearsal, which is also in bad form. We're looking for guys who are supportive of a strong woman and not trying to beat one into submission. It doesn't really matter that he lets her cook her own eggs.
10.Eddie Thomas (John Cusack) — America's Sweethearts (2001)
I realize that all is fair in love and war, but making out with your girlfriend's sister, no matter how annoying the girlfriend and no matter how much you like the sister, seems like a bit of a no-go. In America's Sweethearts, Eddie is a part of an A-list Hollywood couple with Gwen (Catherine Zeta-Jones), but at some point, their relationship soured and he started to fall for Gwen's sister Kiki (Roberts). Eddie's not a bad guy per se, but he's pretty weak and gets dragged around by Gwen, his manager, and whatever whims strike him. There's also a very weird Julia Roberts-in-a-fat-suit plot that doesn't really impact the romance, but makes the whole thing feel a bit off. Eddie's not a horrible chauvinist, but he's coasting on pretty.
9.Edward Lewis (Richard Gere) — Pretty Woman (1990)
I know I'm going to get flack for rating Edward Lewis so far down since Pretty Woman is a more beloved (and much better) film than others higher on this list, but he starts out as a kinda horrible corporate overlord who makes money firing people. And yes, he changes over the course of the film, but that is not a good starting place. Plus, he can't drive a stick, and has to pay someone to be his date to work events because he can't get one on his own. The ethics of sex work are murky in the film, but I do think the power dynamics of him paying her to hang out with him sort of knock him down a smidge here as well. That being said, if someone wants to give me a shopping spree in exchange for being their date at work functions, I'm open to the prospect.
8.Joe Flynn (Tim Robbins) — Pret-a-Porter (1994)
Pret-a-Porter/Ready to Wear (as the film confusingly goes by either or both titles) is a large ensemble film set during fashion week. In a bit of rom-com chicanery, Joe and Anne (Roberts) are both journalists who end up in the same hotel room when Joe refuses to leave the room Anne booked. First, that's a bit rude, but aside from that, the pair basically just shack up in a hotel room for their scenes in the movie so there's not much to go on here. I'd say Joe is coming in just below the bad/good line of demarcation, so we're venturing into the more swoony leading men.
7.Larry Crowne (Tom Hanks) — Larry Crowne (2011)
Larry Crowne is a lovely, harmless enough man. He doesn't really have much in the way of excitement going on, and I'm baffled that someone like Mercedes (Roberts) would fall for him, but he doesn't really have many bad traits. He's a very sweet middle-aged man who goes back to college, becomes friends with one of his professors, and then, they slowly begin a romantic relationship that involves moped rides. Perhaps some of the earlier entries on this list had more razzle dazzle charm, but deep down, I believe they were worse human beings. Julia can do much better, but she could also certainly do worse.
6.Ray Koval (Clive Owen) — Duplicity (2009)
If I learned anything from watching Gossip Girl, it's that scheming together can produce very romantic results. In Duplicity, Ray, a MI6 Agent, and Claire (Roberts), a CIA operative, meet, fall in love, and attempt to bamboozle corporate overlords as shady consultants. Duplicity has more thriller energy than your standard rom-com, but Roberts and Owen have chemistry. And while they are both working under shaky ethical codes, they're at least on the same page with each other, which is a good sign. I'd gladly watch them try to rob another corporation if someone wants to work on Duplicity 2.
5.Felipe (Javier Bardem) — Eat Pray Love (2010)
Eat Pray Love is the worst movie on this list. It's so ripped out of the late aughts that it's painful. A rich white lady has enough money to take a whole year off and hangs out with poor people in India and Bali to help find herself. And the whole time she's on this expedition, it's because she needs to be single and spend time alone, AND YET she can't even go a whole year without falling into another relationship! But I digress. Felipe shows up in Bali and is generally very lovely and very sexy, and we can't blame him for interrupting her self-imposed sabbatical from romance. It is a bit suss that he's interested in Elizabeth, who is Julia's worst and most annoying character, but again, he seems very sweet and charming. If only Viola Davis had whipped more sense into her at the beginning of the film.
4.David Cotton (George Clooney) — Ticket to Paradise (2022)
Watching Ticket to Paradise, you just KNOW that Julia and George are good friends in real life. Their antics and banter and improvisation are so effortless, and their chemistry is off the charts. No couple on this list seems quite as realistic as Georgia (Roberts) and David (even if this film's premise is ridiculous). The divorced pair throw barb after barb at one another, but you can't help feel like they sort of enjoy the competition of it, and when they team up to end their daughter's engagement (another scheme!), they are just so in sync with one another. While a bit rude, David seems like a perfect equal to Georgia in wit, and as they slowly fall back in love, you're really rooting for it. Plus, never has there been two people who have had more fun playing a game of beer pong.
3.Danny Ocean (George Clooney) — Ocean's Eleven (2001) & Ocean's Twelve (2004)
If someone robs three casinos just to try and win you back, THAT is true love. Danny and Tess (Roberts) are basically on par with David and Georgia as both are divorced couples with great banter, but in the case of Ocean's Eleven, Danny is making a grand gesture to prove his undying love while also proving to Tess that her new boy toy doesn't value her enough. Their epic love story continues in Ocean's Twelve when Tess gets in on the con herself in one of the best meta film moments of all time. Tess was never supposed to be with Benedict anyways, she was too tall for him.
2.Charles Gordon Windsor Jr. (Adam Storke) — Mystic Pizza (1988)
Julia Roberts's first rom-com role, the one that put her on the map and proved to the world what an endlessly charismatic actor she is, sees her playing Daisy, a boy-crazy waitress at Mystic Pizza. While she comes from a lower-class family, she meets Charles playing pool one night, and the pair immediately hit it off. Charles may come from a family with a bit too much privilege, and sure, he's a bit air-headed at times, but you can tell he's completely and unequivocally smitten with Daisy from the jump. He's funny (the spare tire scene is great), he's attentive, and he handles her big personality with a patient calmness. When she dumps a giant vat of dead fish on his car due to a misunderstanding, he doesn't get mad, and when his family treats her poorly, he stands up for her. As far as teen boyfriends go, Charles is about as perfect as they come.
1.Will Thacker (Hugh Grant) — Notting Hill (1999)
Of all Julia's on-screen love interests, the best of the bunch is easily the British bookstore owner in Notting Hill, Will Thacker. A lovely average joe, he meets Hollywood starlet Anna Scott when she ventures into his bookstore one day, and despite being starstruck, he manages a semi-normal interaction. The pair then slowly fall in love as they wander the streets of London periodically over the coming years. Will is charming, incredibly witty, and very sensitive to Anna's needs. He has an eclectic group of friends that he loves dearly and who love him (something that speaks to his humanity), and he's even kind to his roommate, who might be the worst human being anyone has ever had to live with. While he could easily be out for Anna's fame and fortune, he actually is the one who nearly dumps her at the end of the film. It's very hard to keep up with Julia Roberts's charm (I'd argue that only George Clooney manages it on this list), and yet, somehow Hugh Grant manages to make himself the character you're rooting for in this film. He's just a boy, standing on our TV screens, asking us to love him. And we do.
