Rom-com superlatives I just made up

Most overrated, best chemistry, best kiss, & more!

My friend Liz (also on Substack!) texted me this recently and I was like yup I will do that immediately. Thanks for doing half the work for me. She’s not wrong about Jack Black.

What’s the most recent instant classic rom-com? Based on box office, it’s Anyone But You, but I find that movie a little soulless. At least we got some good tabloid fodder from it.

Fortunately, I can live the rest of my life satiated by rom-coms of the ‘90s and ‘00s. The golden age. I have favorites, I have hot takes, I have strong opinions.

For the sake of this post, I’m strictly talking about movies with elements of rom AND com. Not dramas like Eternal Sunshine of the Spotless Mind and not comedies like Bridesmaids. The Notebook is a straight-up romance with a heartbreaking dementia storyline. Love & Basketball isn’t very funny. Is Miss Congeniality a rom-com? The romance is secondary, IMO. Same for The Devil Wears Prada and Legally Blonde.

Pretty much all of Hollywood’s most successful rom-coms feature straight white leads. The most diversity we get is an age-gap relationship. There are a few exceptions like 2004’s Saving Face and the more recent Red, White & Royal Blue. Listen up, movie execs: I’ll watch anyone with charisma fall in love. Especially if they’re willing to do a sex scene. Bring back sex scenes!

Tell me what I missed and feel free to recommend some underrated rom-coms in the comments. No Hallmark movies please, I’m a snob.

Superlatives of the rom-com genre

Most Overrated

The Proposal!! I really don’t like this movie. It puts me in a bad mood. I’m not charmed by Ryan Reynolds, he’s too in love with himself. They’re always playing this back to back on E! as if once isn’t enough.

Most Underrated

I’ve already talked about It Could Happen to You, which is a fantastic NYC movie and stars a ‘90s woman I love and miss — Bridget Fonda. This one’s a little cheesy but in all the right ways. It deserves more love.

About Time is another everybody must watch. It’s the best post-2010 rom-com and more layered, beautiful, and bittersweet than others in the genre.

Most Accurately Rated

What else could it be: When Harry Met Sally…

It’s a perfect movie, despite a 41-year-old Billy Crystal briefly playing 22. The credit belongs to Rob Reiner and Nora Ephron’s screenplay, New York City, and the chemistry between Billy Crystal and Meg Ryan. I don’t remember the first time I saw it, it’s always been part of my life. If When Harry Met Sally… is one of your pop culture blindspots, fix that for your own wellbeing.

Another that deserves its reputation is Dilwale Dulhania Le Jayenge. If you haven’t seen it, it’s the ‘90s Bollywood romantic comedy. I’ve listened to its songs over and over. The second half skews drama but the first half is really fun. DDLJ is the longest-running film in Indian cinema history, spending over 25 years in theaters. Obama once quoted it! If you’re down for a 3-hour movie and you want to understand the Shah Rukh Khan hype, DDLJ is worth it. Fun fact: the director wanted Tom Cruise for the role.

Best Best Friend

No disrespect to best friend legend Judy Greer (from Livonia, Michigan!), but I gotta go with Rupert Everett in My Best Friend’s Wedding. The most charismatic anyone’s ever been on screen. He pulls off a ridiculous musical scene and orchestrates one of the best endings in film history (“but by god, there will be dancing”).

Best High School Rom-Com

You’re all shouting 10 Things I Hate About You (it’ll get its moment) but I’m averting my gaze because Drive Me Crazy is my pick here. It’s my Substack 🤷‍♀️.

Best Chemistry

So many choices. Gosling and Stone. Gere and Roberts. I’m awarding it to Tom Hanks and Meg Ryan in You’ve Got Mail. I love watching their disdain turn to tentative friendship turn to love. They’re both khaki-ed out of their minds in that movie.

Khaki attack.

Weakest Connection

I love Jerry Maguire. “You had me at hello” is the single best line in a rom-com. Renée delivers it perfectly. But the film’s real love story is between Tom Cruise and Cuba Gooding Jr. Or Tom and Jonathan Lipnicki. I don’t buy that it’s true love between Tom and Renée.

Also, SJP and Matthew McConaughey in Failure to Launch. They don’t make sense together. At one point, they go paintballing. SJP isn’t meant to paintball, she’s someone who goes to see the philharmonic. That movie is also weirdly about Zooey Deschanel trying to kill a bird.

Best Runner-Up Love Interest

I love when the jilted lover isn’t an asshole. It has to be Patrick Dempsey in Sweet Home Alabama, right? His mom brings a lot of baggage to the situation but he takes rejection in stride. If The Notebook were more of a com, I’d give this to James Marsden.

Best Dressed

Everything Renée Zellweger and Sarah Paulson wear in Down With Love, which also deserves a spot among most underrated rom-coms. It’s a highly stylized homage to Doris Day movies, but it’s got a naughty, clever sense of humor. Watch Down With Love! Same director as Bring It On.

Two Can Play That Game deserves more love for its perfect early ‘00s fashion of sequined tops, satin pants, leopard print, pastel pantsuits, and chain belts.

Best Aesthetic

Emma. starring Anya Taylor Joy! It’s visually delicious and lovely. You think you’ve seen enough Jane Austen adaptations, well you haven’t.

Rye Lane also really goes for it, with the super-saturated colors and fisheye lens.

Worst Dye Job

Matthew McConaughey in The Wedding Planner. Why would they do that to his hair? Not to mention he’s a doctor who thinks brown M&Ms contain less artificial dye than other M&Ms. The brown dye isn’t made of chocolate, bozo. Revoke that fictional man’s medical license.

Best Dye Job

Not only because I named my cat Edward Norton, but Edward Norton in Keeping the Faith. He looks like a natural blonde to me.

Best Makeover

My Big Fat Greek Wedding because she doesn’t do it for a man, she does it for herself. She takes computer classes and learns how to apply makeup because she wants to feel pretty and be brave. As a result, she meets a great guy who was nice to her before she got hot (Aidan from SATC!), learns a new skill, makes friends, and gets a better job.

Best Love Triangle

Bridget Jones’ attraction to blatant womanizer Daniel Cleaver isn’t annoying or off-putting because it’s Hugh Grant. You can’t blame her. Her other option is Colin Firth, a curmudgeon who likes her just the way she is and is apparently a great kisser. "Nice boys don’t kiss like that." “Oh yes they fucking do.” You can’t go wrong in this movie.

Guiltiest Pleasure

Summer Catch. Don’t look at me!! I miss Freddie Prinze Jr. movies. Why isn’t Head Over Heels available to stream?

Best Musical Number

A lot of people would choose “Bennie and the Jets” from 27 Dresses but I have to stay true to my love for My Best Friend's Wedding and say the scene in which Rupert Everett corrals an entire restaurant into singing “I Say a Little Prayer.”

I also have to acknowledge the insane existence of “You’re Too Big to Fit in Here” in whatever version of The Sweetest Thing they can’t play on cable.

Worst Grand Gesture

The iconic cue card scene in Love Actually. This guy’s in love with his best friend’s wife, that’s bad enough. But he knocks on their door with all these romantic notecards ("To me, you are perfect"), and luckily she answers but what was the plan if his best friend appeared instead?

Best Grand Gesture

Also Love Actually. It’s Colin Firth learning Portuguese for Aurelia! His grasp of the language was shaky but he tried. I did Duolingo for 8 months before a trip to Portugal and all I've retained is “abacaxi,” the word for pineapple.

Best Violence

Cher slapping Nicolas Cage in Moonstruck. “Snap out of it!”

Best Use of Food

• Razzles in 13 Going on 30 (I still buy these when I see them)

• Sanaa Lathan’s hot dog in Brown Sugar

• All the street food in Crazy Rich Asians

Most Underutilized by the Genre

Dev Patel, hello!!! We are literally begging for Dev Patel in a proper rom-com.

I enjoyed Maya Erskine in Plus One and wouldn’t mind seeing her in another. I’d watch Sharon Horgan in anything. Chloë Sevigny would be cool. Do we know if Solange has aspirations to act??

Best Small Boob Representation

This is something I’m always on the lookout for. It’s obviously Kate Hudson in How to Lose a Guy in 10 Days. Her yellow dress is still relevant, I’m sure there are 100 copies of it on Revolve right now.

Best Leading Woman

Julia Roberts of course. She also wins best hair and best smile. Runaway Bride and America’s Sweethearts are fine, but Pretty Woman (probably my most rewatched rom-com) and Notting Hill are a killer combo.

Best Leading Man

Ryan Gosling despite being in only one true rom-com. I’m obviously a basic millennial woman because he’s still the pinnacle of male hotness to me. He can play sexy, aloof, sensitive, funny, cool. He can do the Dirty Dancing lift! Can Timothée Chalamet?

Most Hallmark-Movie-Ass Job

In The Holiday, Cameron Diaz cuts movie trailers and in Notting Hill, Hugh Grant owns a travel bookstore. Both pretty niche. But in Must Love Dogs, John Cusack makes handcrafted wooden racing boats and that’s just about the quaintest profession I can think up.

Best Dance Scene

I’ve already admitted I’m charmed by Kevin James’ moves in Hitch. I also get a kick out of Ben Stiller’s salsa dancing in Along Came Polly.

But by far my favorite rom-com dance scene is She’s All That, when the entire senior class breaks into a highly choreographed (by Usher), professional-level dance-off to Fatboy Slim. I guess I missed the detail that they attend the country’s most selective performing arts school?

Best Needle Drop

“Kiss Me” by Sixpence None the Richer in She’s All That immediately comes to mind, but so many deserve a shout-out:

• “Dreams” by The Cranberries in You’ve Got Mail

• “It Must Have Been Love” by Roxette in Pretty Woman

• “Let the River Run” by Carly Simon in Working Girl

• “Here With Me” by Dido in Love Actually

• Low-key… "Brighter Than Sunshine" by Aqualung in A Lot Like Love

• “In Your Eyes” from Say Anything (out of respect 🙇)

NOT Natasha Bedingfield’s “Unwritten” in Anyone But You. They cheaply try to capitalize on our love of that song but the movie hasn’t earned it. Not.even.close. I see right through that shit.

Most Outsized Impact on the Culture

500 Days of Summer.

I’ll explain in stream of consciousness: Mainstream hipster indie The Smiths Zooey Deschanel as a movie star Manic Pixie Dream Girl Joseph Gordon-Levitt in headphones that song by The Temper Trap the Hall & Oates scene Tumblr the Expectations vs. Reality split screen the Bradbury Building vintage dresses and bangs and skinny ties and cardigans.

Most Unexpected Tearjerker

50 First Dates. This is a pretty dumb movie when any of the supporting cast is on screen. And I guess the idea of consent is muddled due to her traumatic short-term memory loss. I think that’s what makes me cry. I feel so bad for Drew’s character and think she deserves love and Adam is so dedicated to making it work.

For the record, I feel bad The Wedding Singer has received nothing, I really like it.

Worst Cameo

Tr*mp in Two Weeks Notice.

Best Cameo

Keanu Reeves in Always Be My Maybe.

Most Enjoyed by Straight Men

Forgetting Sarah Marshall. My sample size is like three men.

Best Shakespeare Adaptation

I’ll let 10 Things I Hate About You have this. I love all the Julia Stiles-Heath Ledger stuff but don’t care about Joseph Gordon-Levitt as much. What’s with JGL playing characters who make women feel bad about not being into him?

Best Republican

Ralph Fiennes in Maid in Manhattan. A rom-com today would simply never include a Republican character you’re meant to root for.

Best Democrat

Michael Douglas in The American President. Hottie!!

Worst Behaved

Bradley Cooper in He’s Just Not That Into You, that dog. He has sex with his wife in his office while his mistress — who he was about to have sex with — hides in the closet.

Rom-Com That Isn’t a Rom-Com

Sleepless in Seattle. It’s not a bad movie. It features many likable actors. But there’s not an actual romance. Meg Ryan, you’re a stalker, girl.

Worst Title

How Do You Know with Reese Witherspoon and Paul Rudd. It’s such a nothing movie. They couldn’t even commit to punctuation in the title! Every time I try to remember what it’s called, I think it’s something like “Here We Go” or “Someone You Know” or “Be There Soon.” Close enough.

Best Kiss

It has to be Never Been Kissed. I know the purported teacher-student dynamic is a little icky blah blah blah but she’s not actually a student and Michael Vartan is so hot. His little jog out to meet her at the pitcher's mound! He comes in so smooth, especially in front of a crowd of people. It’s a great kiss.

Add that scene’s “Don’t Worry Baby” to the best needle drop category.

Most Personally Upsetting to Me

Reese’s Sweet Home Alabama character (Felony Melanie) leaves her successful fashion design career in NYC 🗽 to get back with her ex in small-town Alabama and attend Civil War Confederacy reenactments. No :/

Best Performance By an Athlete

LeBron in Trainwreck is legitimately funny. “Do you know Cleveland's great for the whole family?”

Best Performance By a Musician

Nicki Minaj in The Other Woman! Sorry to NSYNC, thanks for your work in On The Line.

Most Inspired Casting

Philip Seymour Hoffman in Along Came Polly. One of his best roles in a legendary career and what a bizarre subplot.

Most Wasted Potential

Set It Up.

I love Glen Powell and Zoey Deutch individually and still think they did their best work in Everybody Wants Some!! That’s Linklater’s punctuation, not mine. But in Set It Up, they’re both making the choice to play their characters with zero sex appeal. I get that they’re overworked twenty-somethings but play into the fantasy, you know? Distractingly bad hair on Glen Powell, like unforgivable.

Most Beautiful Pairing

One: Mississippi Masala. Fine, it’s a dramedy, but Denzel looks as handsome as a man’s ever looked. Sarita Choudhury aka Seema from And Just Like That... is gorgeous. She deserves best hair too.

Two: Michelle Pfeiffer and George Clooney in One Fine Day. Faces for the ages.

Most Deranged Premise

While You Were Sleeping. Sandra Bullock, you liar freak!!

My consumption this week (beyond rom-coms)

• I binged Overcompensating on Prime. I’m not as in love with it as the entire internet is, but I enjoyed it. Did you recognize Frenchy from Grease?

• Saw Final Destination Bloodlines in theaters and had such fun. People were hooting and hollering. 🤘

• I won a ticket to see The Picture of Dorian Gray on Broadway starring Sarah Snook and it was mind-blowing. The most impressive theater performance I’ve seen. She’s such an athlete. Tony incoming.

• I can’t stop watching those TikToks of men calling their friends to tell them goodnight. So wholesome/funny to hear the friends’ puzzled reactions. I want Drew to do it!