Counting Down My Top 5 Romantic Comedy Movies

Ringing in Valentine’s Day by celebrating my favourite films about love

If you’ve been paying literally any attention at all to what I’ve written prior, you might notice that, despite not stereotypically being the target audience, I have a thing about romantic comedies.

To be more accurate, I have a thing about love in general.

Counting this piece and another about Hitch that I have in the pipeline, of the 20 pieces I’ve written over the past year, around 8 or 9 have been about love or romantic comedies (two have been about cuddly bear men). Whether it’s gushing about a rom-com I love (which you should watch), ranting about a romance I hate, or going into unnecessary amounts of detail using bell hooks to analyze an anime relationship, there really does seem to be a pattern emerging.

Instead of going into why this is and writing a long paragraph about the origins of my obsession with love and the implications this has for me as a Black man in Britain, I figure the more fun thing to do would be to count down the top 5 romantic comedies I’ve enjoyed over the years, with an extra bit dedicated to the likelihood of that couple staying together after the movie ends.

Just to make it easier on myself, I won’t be counting musicals or the MGM classics like Singin’ in the Rain and I will also only be talking about films, so if you want to see my favourite rom-com novels, click here; and if you want to read about my favourite rom-com series, click here.

Now, let’s get into it.

5. The Wedding Planner

Fun fact: If you’d asked me like 5 years ago, this probably would have been number one.

Of all of the romantic comedies on this list, this one is probably the first one I remember watching, and the one that I’ve re-watched the most. The 2001 film stars Jennifer Lopez (of In Living Colour fame) as Mary Fiori, a VERY ITALIAN wedding planner who struggles to find the time or the will to focus on her own love life; that is until she meets and falls for Steve Edison or Eddie or Steve (an unsettlingly chill Matthew McConaughey) who she learns is the groom in the mega-wedding that she must plan.

There are a lot of things that I love about this film, most of them come down to the fact that it’s just so messy and ridiculous while also being insanely sweet. Eddie/Steve and Mary have instant chemistry, and watching the two leads bicker and play off of each other is just as fun as watching them slowly realize that they can’t resist each other. You also get Justin Chambers doing the most bizarre Italian accent and gleefully contributing to the madness of it all.

I also really love the narrative concept of a wedding planner who falls for the groom of a wedding she’s planning, and a groom who’s trying to balance his own cold feet with his growing affection for her. It leads to some really great character moments and set pieces (stay away from me when I’m eating M&Ms because I will quote this movie), with my favourite being the scene in which Mary discovers that Eddie or Steve is the groom, forcing her to confront him while also tangoing with him (because rom-com).

If I had to pinpoint exactly why I have so much fondness for this film, it’d probably be what an easy and heartwarming watch it is, the beautiful score (Plan On Forever has been one of my favourite songs for years), the chemistry of the two leads, and the fact that it never stops being sweet, messy and entertaining. It’s just a really fun, gorgeous movie.

Favourite Lines:

Steve/Eddie: Why you only eating the brown ones?
Mary: Because someone once said they have less artificial colouring because chocolate’s already brown. And it kind of stayed with me.
Steve/Eddie: You kind of stayed with me.

Massimo: Love can’t always be perfect. Love is just love.

Mary: You saved… my shoe. I mean, my life.

Steve/Eddie: Why did Steve go to the movies with you? Well, first of all, Steve likes the movies. Steve had the night off. Steve said, ‘Hey, a movie sounds good,’ plus he got an invitation.
Mary: Why is Steve referring to himself in the third person?
Steve/Eddie: What are you talking about?

Do they make it?

Hell yes, those two will be watching movies in the park, wasting brown M&Ms until they’re old and grey.

4. Rye Lane

In case I haven’t said so before, you should watch this movie.

I’ve made no secret of how much I adore Raine Allen-Miller’s 2023 British rom-com Rye Lane. It’s honestly a testament to just how much I love this film that it’s the only “modern” romantic comedy on this list, and the only reason it’s this low down is due to the strength of the top 3.

Rye Lane follows Yas (Vivian Oparah) and Dom (David Jonsson), two twenty-something South Londoners who connect over the course of a day while both reeling from their respective break-ups.

What can I say about this film that I haven’t said already?

Rye Lane provides the perfect antidote for so much of the cynicism that permeates a lot of modern romance stories and discourse around love in general (especially on Black British social media). It’s a film that is totally unashamed to be a romantic comedy, complete with references to rom-com classics that help it to serve almost as a love letter to the genre itself.

Raine Allen-Miller and the crew ensure that every camera angle, lighting choice, and musical cue imbues this film with personality, dynamism, and offbeat humour. There are so many surreal visual gags and small touches I love like Dom recounting his break—up to Yas as she sits in an imaginary cinema and her still having her popcorn in the next scene, or Dom accidentally playing his break-up playlist at a cookout.

Ultimately this film feels like such a clear labour of love. Jonsson and Oparah have endless chemistry and bounce off of each other perfectly, with Dom’s soft-spoken demureness contrasting Yas’ larger-than-life brashness, and every character in this movie brings something hilarious and charming to the table. It’s so refreshing to see a funny, earnest British rom-com starring two Black leads and I really hope I get to see more.

Memorable Lines:

Dom: …even though it was low-res, I knew that d*ck.

Yas: If people on a boat wave at you, you have to wave back. It’s the law.
Jules: Tourism funds sex trafficking.

Dom: YOUR HANDS ARE YOUR TOOLS!

Dom: Yo wassup man? Cool kicks.
Random Guy: What? D*ckhead. Suck ya mum.
Dom: Yep.

Yas: …I came up with a simple ethos to help guide me through all aspects of my life. If you make the hummus, you should get the head.

Dom: You know you’re very…
Yas: Peng? Refreshingly disarming?
Dom: You ask a lot of questions.
Yas: I’m interested in people’s messes.
Dom: What makes you think I’ve got a mess?
Yas: Everyone has a mess.

Do they make it?

Dom and Yaz?? Yaz and Dom?? Of course, they make it! They got that quiet-guy-animated-girl dynamic that we love to see.

3. Sleepless In Seattle

Narrowly beating out my favourite rom-com of the modern era is this 1993 classic Meg Ryan & Tom Hanks joint. It’s funny, I might be one of the few people who isn’t particularly moved by seeing Hanks and Ryan perform together, despite knowing that they were basically romantic comedy royalty back in the day (I like You’ve Got Mail but man that movie is long); I think the two have decent chemistry but it’s never been something that I really got.

That being said, this movie goes hard.

Sleepless follows Sam Baldwin, a widower whose young and overly intrusive son calls into a radio show to try and find him a new wife to make him happy. Though skeptical at first, Sam gradually opens up to the emotionally exploitative radio therapist, and it’s this openness that causes women all over America to swoon, with one of those women being Ryan’s Annie Reed. Annie feels a connection to Ben’s voice and soon becomes infatuated with him, motivating her to break off her engagement (oh right, she’s engaged) and travel across America just to meet him.

Honestly, the fact that this film is so high up on my list has a lot to do with the concept, the dialogue, the music, Hanks’ performance, and the relationship between Sam and his son. It takes a really special script to sell me on the idea of a woman connecting and falling in love with someone based on so little, but this film somehow sows the seeds for Annie’s connection to Sam perfectly, and it all just feels so romantic, like their meeting was destined to be. Hanks’ monologues over the radio and his fun bickering with his son are the highlights of the movie for me, I’m a sucker for comedy mixed with Pathos.

I think what pushed it over the edge is just how beautiful the idea of connecting with someone based on almost nothing, and following that loving intuition is; coupled with dealing with grief and slowly learning to love again.

Memorable Lines:

Doctor Marcia Fieldstone: People who truly loved once are far more likely to love again. Sam, do you think there’s someone out there you could love as much as your wife?

Sam Baldwin: Well, Dr. Marcia Fieldstone, that’s hard to imagine.

Doctor Marcia Fieldstone: What are you going to do?

Sam Baldwin: Well, I’m gonna get out of bed every morning… breathe in and out all day long. Then, after a while I won’t have to remind myself to get out of bed every morning and breathe in and out… and, then after a while, I won’t have to think about how I had it great and perfect for a while.

Do they make it?

Mmm… nah. Nah I don’t see it. Sam has a lot of options he should explore and Annie is a lil much at times.

2. Notting Hill

Now as a large Black man approaching his 30s, I am not ashamed to admit when a movie makes me cry, and, to paraphrase my cousin, this movie got some thug tears out of me still (the end of The Wedding Planner got me too, weirdly enough).

Notting Hill is the story of Hugh Grant’s Will, a failing bookshop owner who is still able to afford in Notting Hill prior to the bulk of its gentrification (which happened thanks, in part, to this very movie). When the most famous actress in the world, Julia Roberts’ Anna Scott walks into his bookshop and is immediately charmed by his posh Britishness (and the fact that he looks like Hugh Grant), Will is forced to contend with the relentlessness of Anna’s fame and the fact that he’s in love with a woman that the entire world wants a piece of.

Fun fact: After rewatching this movie, I once ran a poll on my Instagram stories to see how many people believed they could make their celebrity crush fall in love with them and the vast majority of people responded with a resounding no (which is crazy coz everyone who chooses to follow me is hot).

There’s just so much to love about this movie, I would argue that Roberts and Grant are the rom-com GOATs of their time so having them on screen together is basically a cheat code. The music is beautiful (She by Elvis Costello is some fine white music), the supporting cast is all super British and hilarious (especially Will’s flatmate Spike), the plot is both insanely unrealistic but also very grounded at the same time, and it’s just a really romantic and optimistic movie about a very improbably love story.

What ultimately makes this film magic for me is the romance between Will and Anna, and the perfect blend of Richard Curtis’ writing and the chemistry and quirks that the actors add to flesh their characters out. Will and Anna come from two completely different worlds but it’s totally believable that they fall in love with each other, it’s beyond heartwarming to see Anna find comfort in the humble authenticity of Will’s simple life, while Will’s struggle to find his place in the invasiveness and fakery that comes with Anna’s life provides an effective sense of tension and pathos to the story (I also really like rom-coms where the guy is on the back foot, not sure why).

The highlight of the film for me comes when Will and Anna break into a private park and find a bench with a memorial plaque that tells a small portion of the long-lasting love between a faceless widower and his wife. It’s such a small and beautiful moment that just speaks volumes about the simple, but lasting and authentic love that Anna wants and it’s a scene I find myself revisiting a lot.

I also really like that after being brutally reminded by Anna of the difference between his and her worlds, Will rejects her after her iconic “I’m just a girl, standing in front of a boy…” monologue. It’s such a painfully human moment where we see him finally give up any sense of optimism and give in to the hurt she’s caused him, before ultimately coming to his senses and deciding to risk it all and pursue her, spurred on by his dumb friends. Roberts’ smile when she agrees to stay with him is burned into my brain and it’s just the perfect ending for the perfect movie.

Honestly, it’s crazy to me that there’s any debate as to what Julia Roberts’ best romantic comedy is.

Memorable lines

William: I live in Notting Hill. You live in Beverly Hills. Everyone in the world knows who you are, my mother has trouble remembering my name.
Anna Scott: I’m also just a girl, standing in front of a boy, asking him to love her.

Anna Scott: Can I stay for a while?
William: You can stay forever.

Anna Scott: “For June, who loved this garden, from Joseph, who always sat beside her.” Some people do spend their whole lives together.

Honey: William just turned down Anna Scott.
Spike: You daft prick.

P.R. Chief: Dominic… if you’d like to ask your question again?
Journalist: Yes. Anna, how long are you intending to stay here in Britain?
Anna Scott: [pause] Indefinitely.

William: Sorry about the “surreal but nice” comment.
Anna Scott: Don’t worry, I thought the whole apricot honey thing was the real low point.

William: The thing is, with you I’m in real danger. It seems like a perfect situation, apart from that foul temper of yours, but my relatively inexperienced heart would I fear not recover if I was, once again, cast aside as I would absolutely expect to be. There’s just too many pictures of you, too many films. You know, you’d go and I’d be… uh, well buggered basically.

Spike: There’s something wrong with this yogurt.
William: Ah, that’s not yogurt, that’s mayonnaise…
Spike: Ah, right-o then.
[continues to eat it]

William: It’s not really a classic anecdote, is it?
Martin: Not a classic, no.

Martin: Let’s go crazy. I’ll have an orange juice!

Do they make it work?

Yep, but she definitely cheats on him.

Honourable Mentions

Here are some picks that very narrowly missed out.

The Wedding Party

Brown Sugar

Bride & Prejudice

Think Like a Man

I Think I Love My Wife

Hitch

Bridget Jones’s Diary

Pretty Woman

The Best Man

And now for number 1…

1. How To Lose a Guy in 10 Days

If you know me at all, you’ll know that it couldn’t have been anything else.

This film is batsh*t insane, and I couldn’t possibly love it more than I already do.

Benjamin Barry (Matthew McConaughey) makes a bet that he can make any woman fall in love with him in 10 days, but what he doesn’t know is that the woman who’s been chosen for him to woo is Andie Anderson (Kate Hudson), a journalist who is “forced” to use her friend’s relationship troubles to form a list of 10 things women do that turn off men.

It’s impossible to nail all of the different reasons I have for loving this film. If I had to pinpoint one, however, it would be that it’s a love story between two pretty toxic people, and it somehow manages to get that toxicity juuuust right. It’s easy to underestimate just how finely balanced the central premise of this movie is, despite being so full of laughs and ridiculous characterization, the film actually shows a lot of restraint in making sure that Andie and Ben both have motivations and nefarious reasons to stick with the fake relationship. This movie simply doesn’t hold up as well if one of our leads feels too much like the victim, it would be so much harder to root for them as a couple, but the fact that they’re both pretty sh*tty people really sells the fact that they deserve each other.

The two leads play off of each other brilliantly, Hudson is able to instantly flip the switch between being ambitious, savvy, and witty and playing up every “crazy girlfriend” stereotype known to man, while McConaughey’s reactions, general bewilderment, and general hatred of the situations he’s put in complement every scene perfectly.

Andi makes Ben miss vital basketball games, accuses him of calling her fat in public, embarrasses him in front of his friends and colleagues, gets him punched in the face, contacts his mother behind his back, and even gives his d*ck the most emasculating name imaginable before claiming later that he can’t perform. She puts this man through hell and while I feel sorry for him, it never feels like the dynamic is drastically unequal because while he’s going through it, she’s slowly falling for him and this presents its own set of problems. There’s just something about watching two master manipulators tear each other's defenses down in the funniest way possible that really hits.

The film is immensely quotable and full of stand-out scenes like Ben and Andi’s first meeting where they speak only in one-word sentences; Andi ruining Ben’s poker night; McConaughey trying to keep a straight face while Kate Hudson and Kathryn Hahn just improvise at him; the trip to Staten Island where Ben (who is NOT from Texas) introduces Andi to his family; the huge public confrontation between the two where they realize each other’s deception and sing You’re So Vain and one another, and their final reconciliation. The film is just highlight after highlight, and it’s just immensely fun to see this mutual game of cat-and-mouse end with both parties accidentally developing real feelings for each other.

One thing I always recommend to anyone watching for the first time is to watch it with someone else and discuss at what point you would be forced to dump Andie, it’s so much fun. Feel free to comment with your answer or just share your personal favourite romantic comedies.

Memorable Lines

Andie: Our love fern! You let it die!
Ben: … No, honey, it’s just sleeping.

Ben: Alright listen, you can’t name my… my member Princess Sophia.
Andie: Yes, I can!
Ben: Listen, if you are gonna name m… my member, alright, you gotta name it something hyper-masculine, okay? Something like a Spike, a Butch, a Krull the Warrior King!

Thayer: Is she on something?
Ben: God I hope so.

Michelle Rubin: So, tell me, how long have you guys been seeing each other?
Andie: Seven days.
Michelle Rubin: Seven days. Interesting.
Ben: Is that too soon to be seeing a therapist?
Andie: Well, Ben, seven days isn’t like a lifetime, or anything…
Ben: It’s like a week.

Andie: It’s our love fern! Oh, Bennie-boo-boo, boo-boo.

Andie: Nobody likes a Mr. Sniffles.
Tony: Yeah, uh, I hate Mr. Sniffles.

Ben: Look, look, look, wait a minute. The one night we even thought about having sex, all right, she up and decides she’s going to nickname my…
Michelle Rubin: Penis?
Ben: Yeah. “Princess Sophia.” You want to talk about shooting a man’s horse? Whop! Come on!

Andie: My boyfriend thinks I’m fat! And I can’t eat in front of him! I can’t eat in front of you! I have to go to the bathroom.
Ben: Honey, I don’t think you’re fat! I don’t think she’s fat!

Andie: You’re beautiful. The game, the whole thing. It’s just… I wish I ate meat. Mary had a little lamb, little lamb… You have to take it away before I gag.

Sensitive Moviegoer: Now, I’m going to go back inside and finish watching “Sleepless in Seattle”. Nobody screw with me.

Ben: Jesus! Five seconds ago I’m gay. Now I’m a pathological flirt.
Andie: I sweat when I get nervous.
Ben: Which one is it, Andie?
Ben: Besides, why would I need to hit on another woman?
Ben: You’ve got more than enough personalities to keep me completely occupied.
Andie: That was hurtful.

Do they make it?

I firmly believe that Ben and Andie stay together, settle down, and raise up the next generation of supervillains.