Pop Culture Recaps

The top 20 rom-coms of the past 20 years… we decide!


The top 20 rom-coms of the past 20 years… we decide!

2020 not only marks the turn of a new year… it marks 20 years into the new millennium! We’re going to give you a minute to sit with that.


To celebrate the new year, and our ongoing LOVE for all things romantic-comedy we got four of our Romance.com.au authors, Courtney, Hillary, Saskia and Eloise, to each pitch their top 5 rom-coms from the past 20 years. Suffice to say…not everyone agreed…


Courtney’s Picks

She’s The Man (2006)

Courtney: Probably Amanda Bynes’s greatest work. Honestly, I quote from this movie far more than I do from Mean Girls – and She’s The Man is funnier. Don’t @ me, Hillary.

Eloise: Do. You. Like. Cheese? AGREED it’s the Bynes’s best work. Also Channing Tatum’s abs. Also a Shakespeare reference. Oughties rom-com classic. 

Hillary: Don’t worry Courtney I like She’s The Man as well. It’s just that one is a cultural icon and the other involves a tampon up someone’s nose. 

Saskia: Amanda Bynes’s greatest work is definitely Easy A! But agree that this is funnier, although less quotable, than Mean Girls.


The Holiday (2006)

Courtney: Arguably both one of the greatest Christmas and romantic comedies of all time; there aren’t many boxes The Holiday doesn’t tick. Jude Law in glasses saying ‘you’re lovely’ is enough to keep me emotionally satisfied for at least a month, tbh.

Eloise: No. Ew. The only good parts of this movie are when Kate Winslet is hanging out with the old dude. Everything else… Meh.

Hillary: I’m with Eloise here. I’ve got better movies to watch!

Saskia: Y’all are wrong, this is a masterpiece. The second best Jack Black film (next to School of Rock, obvs).


No Reservations (2007)

Courtney: Look, I’ve never fantasised about Aaron Eckhart, but I think this movie is HUGELY underrated. Catherine Zeta-Jones is just the greatest as a talented, intimidating chef, and we have the whole ‘enemies-to-lovers’ trope at its finest here. Come for the epic rare steak scene, stay for the orphaned-child-finds-new-parents feels.

Eloise: Haven’t seen… would watch for these two oughties icons tho. Also baking = good sexy fodder for romance scenarios…

Hillary: I can watch one episode of Friends and get just as much rom-com out of that instead.

Saskia: Courtney made me watch the steak scene at lunch once and I am hooked – Catherine Zeta-Jones is fierce and I am here for it.

Fool’s Gold (2008)

Courtney: You saw them in How To Lose A Guy In 10 Days, but they’re BACK and it’s a Caribbean island treasure hunt with Donald Sutherland and buckets of sexual tension. If you’re not already intrigued, I don’t know how to help you.

Eloise: Eh? It’s ok. Nothing special tho. How to Lose a Guy is better. If WILDLY problematic in 2019.

Hillary: Abs. 

Saskia: I don’t know why but something about Matthew McConaughey just does it for me (maybe the abs @Hillary?). Haven’t seen this (although would recommend him in Failure To Launch), but I’m adding it to my holiday watchlist FOR SURE.


To All The Boys I’ve Loved Before (2018)

Courtney: General consensus: The Actual Cutest Movie Of All Time. It’s a pure, wholesome journey, and as addictive as sweet and salty popcorn. Fake dating is a huge trope, but it’s executed so well and Noah Centineo was born to play a teen heartthrob, so I’m not complaining…

Eloise: THIS MOVIE. So damn adorable. I cannot wait for the sequel in 2020. Best rom-com of 2019.

Hillary: It’s a very cute movie, with a protagonist that is true to herself. One of the breakout Netflix originals with a fresh take on the fake dating trope. I wish it was around when we were in high school!

Saskia: Controversial opinion, but this is one of those rare times when the film is better than the book. I loved this and I am pumped for the sequel. @Eloise, movie night at yours in 2020?


Eloise’s Picks

Bridget Jones’s Diary (2001)

Eloise: As a BookNerd TM I can acknowledge the cleverness of this totally iconic rom-com that remakes Jane Austen’s Pride & Prejudice. As a savant of the romantic-comedy genre I can see the wit of this script (barring problematic fat and slut shaming NOT COOL MOVIE). But honestly. THE MOST ICONIC ROM-COM EVER. If you haven’t seen it what are you doing here. Go. Watch. We’ll wait.

Hillary: I have never seen this movie and I never will. 🙂 

Saskia: I think it’s ok to say this because half my family are British, but their accents in this movie drive me nuts. Also I can’t get past the early 2000’s attempt at being funny. Any kind of shaming is not cool. 

Courtney: Lol @ Hillary’s complete disregard for this movie. I personally have never watched it in full, only bits when it’s on TV. I’m just not a fan of any of the cast, and ugh she’s just a bit pathetic, isn’t she? Even Kate Winslet in The Holiday is more likable than Bridget Jones. #awks



Enchanted (2007)

Eloise: I couldn’t do this list without at least ONE musical. And what better musical than this wild fairytale-esque rom-com about a cartoon princess who gets trapped in the real world? The concept is weird. The execution = almost flawless. It’s hilarious (see: James Marsden’s Prince Edward attacking a bus), has a simultaneously bomb-ass and terrifying villain in Susan Sarandon’s Queen Narissa, Amy Adams is ADORABLE and FEISTY as a heroine, and it’s just a super heartwarming movie all-round. And Julie Andrews narrates. Nuff said.

Hillary: Enchanted was an adorable take on the classic Disney formula. My favorite part of this movie was the song in the park, in which Robert asks everyone how they just know all the lyrics to her song. Very meta, and something I often think about in musicals. 

Saskia: Look for about five minutes I thought this was Ella Enchanted and I couldn’t figure out where Anne Hathaway was. Cute movie, but not memorable imo.

Courtney: Not being as musically inclined as others *cough Eloise cough*, I didn’t love this film. I LOVED the beginning animation, and wish that was how the movie stayed. Glorious animated hair and flowing dresses in a magical forest, heck yes!  McDreamy, heck NO. 


Love, Simon (2018)

Eloise: This movie is a ball of gooey marshmallow fluff. You’ll laugh, you’ll cry, you’ll laugh while crying. That moment when he thinks he’s been stood up by Blue?! My heart literally stalled. I can’t. This movie is TOO MUCH. Heart-eyes emoji in movie form.

Hillary: A revolutionary film that has proved to be timeless!   

Saskia: @Eloise ‘Heart-eyes emoji in movie form’ is the BEST description for Love, Simon. This was the film 2018 needed, not the one we deserved. Someone please make my day and tell me they’re making a Leah film next?

Courtney: SO PURE. I WANT MORE. I would watch 100 movies like this.

via GIPHY 

Down With Love (2003)

Eloise: Ok so this movie ticks ALL the boxes AND NO-ONE HAS SEEN IT. Devastating. It has Ewan McGregor. Renée Zellweger. F*cking Sarah Paulson#@$^%!!!! It is a raunchy salute to battle-of-the-sexes rom-coms of the 1960’s with a playful modern wink. It has A MUSICAL NUMBER. There’s a whole montage of scenes where Renée and Sarah just wear increasingly extravagant ballgowns. Pure brilliance.

Hillary: I adore actual 1960’s rom-coms more to be honest, but Ewan McGregor cannot do wrong.

Saskia: @Eloise you’re right, I haven’t seen it, but your enthusiastic use of symbols has me excited. Sarah Paulson is a goddess so now I know I need this in my life.

Courtney: Alright alright alright I’ll put it on my list. Ewan McGregor can do anything. He’s like the male Meryl Streep – eternally and unfailing incredible. 


The Big Sick (2017)

Eloise: Based on the real-life experiences of writers (and couple) Emily V. Gordon & Kumail Nanjiani this movie is a big mug of smooth hot chocolate. It’s sinking into a hot bath at the end of a day. It’s curling up under the blankets on a cold night. Warm, loveable, and with enough smarts to make you think this movie is just wonderful. Love.

Saskia: This movie makes me a big sick…with excitement (pardon the pun). It sounds adorably heartwarming and cosy – perfect for the upcoming Christmas season!

Courtney: Oooo I remember when I first saw this trailer, and I thought it looked thoroughly not for me. It DOES look heartwarming AF though. Maybe when I pass my Grinch phase I’ll give it a go. 

Hillary: This movie is adorable and perfect and tragic and I love it.


Hillary’s Picks 

A Cinderella Story (2004)

Hillary: A naughties dream between Hilary Duff and Chad Michael Murray pre-creepy cult leader in Riverdale. The best live-action iteration of Cinderella IMO, and nothing will surpass it.

Eloise: While it will never surpass the perfection of Cinderella live-action remake Ever After for me (fight me @Hillary) I agree this movie is a teen rom-com classic. Definitely deserving of a place on the list. Also, a fun reminder about how obsessed we all were with chat rooms. *cringe*

Saskia:  I agree, Ever After is a gem, but so is Hillary Duff. I’m torn. @Courtney, settle the debate?

Courtney: Never fear Sas, I am here to overrule all opinions. Ever After is great, but also kind of depressing at times? Also the prince looks like my creepy optometrist… THEREFORE A Cinderella Story wins, hands down. *shrug emoji*


John Tucker Must Die (2006)

Hillary: The petty b*tch in me loves the scene where John has to scale a hotel while only wearing a lazy red thong.

Eloise: It’s not a good movie. It’s not a politically correct movie. But DAMN if it isn’t fun to watch. Also Penn Badgley pre-Gossip Girl fame (infamy?)!

Saskia: Definitely infamy @Eloise, I’m still salty. But I digress – JTMD is for every girl who has ever been wronged, political correctness aside.

Courtney: I feel like I was such a pure, innocent teenager in 2006, that I never watched this movie. I sort of feel like I’m missing out though, if only for that horrendous noughties fashion. *gags* 


Sweet Home Alabama (2002)

Hillary: We never thought that Lynyrd Skynyrd would inspire a Reese Witherspoon romance but here we are!

Eloise: Eh. I love a Reese movie. But not this one.

Saskia: This movie taught me that when lightning strikes sand it makes glass, and that’s about it. 10/10 good doggo though.

Courtney: YES Sas, it’s educational AND romantic! I could watch this movie a hundred times over and not get sick of it. Perhaps Eloise would be more of a fan if there were at least one musical number…?


Where the Heart Is (2000)

Hillary: It’s important to exchange buckeye trees between friends, and to ask God for forgiveness for fornicating on the very table you’re praying upon. Hilarious, heart-warming, a little trashy. Excellent.

Eloise: This movie looks like a lot. 

Saskia: Idk what this film is, but now I know not to eat straight off anyone’s dining room table.

Courtney: Honestly I just love looking at Natalie Portman’s face. She’s like a cute little chipmunk in human form. :3

via Gfycat

Suddenly 30 (2004) 

Known as 13 Going On 30 in the US

Hillary: As a 27-year-old I dread beyond reason turning 30 so once every six months I re-watch this film to make me feel better. When I turn 30, you bet I will be wearing glitter, starting a Thriller dance-off and dating Mark Ruffalo.

Eloise: YAS this movie! So delightful to watch. You can bet I’ll be whispering ‘thirty, flirty and thriving’ to myself when midnight hits on my 30th birthday. 

Saskia: What 13 year old doesn’t dream of being 30 and finally having control of their life? Love this movie and the whole twist on the ‘second chances’ trope.

Courtney: I genuinely do not know anyone that was ever or likely will ever be ‘thirty, flirty and thriving’ (especially in this real estate climate). Thirty, desperate and thrift shopping, maybe?


Saskia’s Picks 

Love Actually (2003)

Saskia: OK, it is absolutely shameful that I only watched this for the first time last year at my boyfriend’s insistence, and I will accept the consequences of that shame because this film is the equivalent of a Christmas dinner. Varied, mostly mouth watering to look at (I’m looking at you Harry – cheating is not appealing) and slow cooked to perfection. Bon appetit!

Eloise: It is truly BOTH a classic Christmas movie and a classic rom-com. Is it perfect? No. Can I survive Christmas without watching Hugh Grant boogie through 10 Downing street, Colin Firth fluster his way through a proposal in Portuguese and Emma Thompson break down in tears listening to Joni Mitchell? Not at all. Also the ‘All I Want For Christmas’ scene at the school pageant is EVERYTHING. 

Courtney: Agree with Eloise! Is it perfect? No, but it delivers the feel good feels every time. Liam Neeson is a precious stepfather and Hugh Grant as Prime Minister of Britain is just hilariously unrealistic.

Hillary: Love Actually is a romantic classic. No other ensemble romance movie surpasses it. Character-driven films with interlacing plotlines are clever and they keep you on your toes. I, too, took a little while to watch this one but once I did it became a Christmas tradition! 


The Proposal (2009)

Saskia: As someone who also works in publishing, I can confidently say that if I was about to get deported and lose my job, I’d marry Ryan Reynolds too. You know, for the sake of the job and all.
Also Betty White and that adorable af dog are the true heroes of this film.

Eloise: In this house we stan Betty White. Also can I please request 1 x Ryan Reynolds as MY assistant? 

Courtney: Probably my favourite rom-com of all time. Ryan is just a god and his deadpan sarcasm makes me swoon Every. Single. Time. Also sorry Saskia, but that dog can get eaten by eagles cos that is NOT a real animal. It is a living plush toy. #sorrynotsorry

Hillary: Favorite dialog: ‘What am I allergic to?’ ‘Pine nuts. And the full spectrum of human emotion.’ God I love this movie. 


Valentine’s Day (2010)

Saskia: As both a discerning film watcher and a shameless Taylor Swift fan, I am compelled to tell you that this film has some very average acting and some of the absolute worst acting I have ever seen, and I am trash for it. That is all you need to know.

Eloise: This movie is America’s sad remake of Love Actually. I can’t. 

Courtney: Honestly I feel like this movie will never die, just because it’s so bad you can’t look away. Ashton Kutcher is just the biggest sweetheart, though the older I get, the more I relate to Jessica Biel’s ‘I Hate Valentine’s Day’ party….

Hillary: I’m with Eloise on this one. This was just a tragedy waiting to happen. I actually felt overwhelmed and bored at the same time while watching this film, however, it is Gen Y’s answer to Love Actually, and will probably somehow become a classic too. 


Easy A (2010)

Saskia: Emma Stone and this film are a gift to this world. I challenge you to watch it and not sing Pocketful of Sunshine in your next shower. Impossible. This is my favourite rom-com of EVER and I will hear no bad words about it.

Eloise: YES to this movie! It’s a riff on Nathaniel Hawthorne’s novel The Scarlet Letter, stars Emma FRICKING Stone, and has the most iconic teen-movie parents in Stanley Tucci and Patricia Clarkson. Also a random musical staging of Knock On Wood. Also it totally comes for the gross culture of slut-shaming against young women. YES TO EVERYTHING IN THIS MOVIE. 

Courtney: This movie was the first time I saw Emma on screen, and I fell in love immediately. She’s just the funny best friend that everyone wants, but ACTUALLY I think my favourite character is Stanley Tucci. Just so DAMN hilarious. 

Hillary: Remakes of classic literature are my favorite rom-com movies because I can focus more on the characters and less on the plot. I love how this film tackles real issues of slut-shaming and religion, while also being completely tongue and cheek. The use of circular plot is also incredibly clever, asking the audience to participate in the first minute of the film. it’s cute, and Aly Michalka will always be my crush!


Crazy, Stupid, Love (2011)

Saskia: Everything Steve Carell touches is gold, and this is no exception. I too would throw myself out of a moving car if my partner cheated on me (@boyfriend, take note). Ryan Gosling and Emma Stone are just YES, and Julianne Moore’s acting is a standout here.

Eloise: I’m not overwhelmed. I’m not underwhelmed. I’m just whelmed.  

Hillary: My favorite fight scene of all time.

Courtney: This movie is so great it makes me depressed. Ryan Gosling and Emma Stone’s relationship is just so cute and lovely – where can I get some of that????? What sort of bars do I need to hang out in???? 



Did you agree with our list? Did we miss out on your favourite? Let us know in the comments below.


By Courtney Lunn, Eloise Plant, Saskia Largent & Hillary Albertson

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