The essential rom com guide for Valentine’s viewing

By Lucy Fitzgerald

Lucy offers a mini dissertation on the romantic comedy, discussing its winning components and her top 15 picks, so you have some viewing variety for this 14th February. 

The romantic comedy is an institution in film that works primarily to elicit joy, and yet it is often plagued by senseless calumny. I routinely wonder: do people not want to be happy? Why deny yourself life’s sweetest nectar, that is, watching beautiful people fall in love? I believe it is necessary to make room for such bliss and luxuriate in it. In the taxonomy of film genres, those with distinct feminine overtones have always been undermined and sidelined by the pessimistic and emotionally stunted. I find myself having to regularly defend the rom com’s merit, its healing power, its function as a balming lullaby, as well as a real tool for evaluating one’s own emotional intelligence.

Now, I am a regular cinema-goer who enjoys all genres; I get something out of sobbing when watching an opioid drama, having anxiety attacks when watching thrillers, and being trapped in the distressing four walls of a play adaptation that depicts strained familial relationships. But sometimes I do not want to choose pain. Sometimes, I like to see women being adored, instead of violently assaulted. And that is hardly a stain on my intellect. Some (film bros) attest the rom com’s vapidity without even engaging with it (I have found with those who don’t align themselves with the genre, that they are curiously still a proponent of Woody Allen’s, whose canon is replete with romantic comedies, the only difference being that his films forcibly speak to and from a man’s consciousness, I digress) and dismiss it as superficial conventionality.

But such an insult is baseless on several accounts: from a production standpoint, it takes sharp writing and nuanced acting to convincingly translate cheer on screen. For work to appear “light”, a heavy amount of work must be put in; the same weighty emotional insight that steers a drama is required, yet disproportionate respect is attributed. Actors who reside in the rom com field are considered lesser for it, their work considered frivolous. Though the context of these films might be exaggerated and the thoughtful gestures from the straight men improbable in real life, by fully enveloping yourself in the fantasy you can extract nuggets of impassioned wisdom for your own reality. Above anything else, watching two characters, two people, who separately have a very strong sense of self, undergo an evolution because they were enlightened by another human is just so damn wholesome. Rom coms enhance our lives with their pervasive optimism, operating as the most consistent mood booster in a media landscape that gets off on melancholia. So, if you are a serial sad boy, I recommend trying to embrace a tonal shift.

An accomplished romantic comedy follows a comforting structure: future lovers have a meet-cute and court, some form of conflict forces them apart, and then they reunite, make-up and make-out. Like roman plays, they fluctuate between a few stock tropes, these include: a transformative Pygmalion arc; a career dilemma; enemies or friends turning into lovers; manic pixie dream girls rejuvenating a despondent man (although this is one is thankfully fading out); an opening it’s not me, it’s you breakup setting them on a new path; a cocky man needing to be taken down a few pegs; one party learning to soften their hardened exterior etc. However, outcries from the masses online conclude that the classic rom com has experienced a decline in the last decade or so. A necessary spark and excitement has been lost – we seem to be all out of what she’s having (although, TV series have thrown us a lifejacket in the form of High Fidelity (2020), Starstruck (2021-) and New Girl’s Zoey Deschanel and Jake Johnson as on-again, off-again kindred spirits Jess and Nick). Starved of allure in the male-romantic-lead-in-movie department, Twitter regularly fancast Dev Patel, Penn Badgley, Manny Jacinto and Aaron Taylor Johnson, suggesting that they could reshape the dried-out mould – Now That’s What I Call Restorative Justice.

Below I have compiled a subjective list of feel-good rom coms, with a few omissions that I wish to contextualise: first of all, Clueless (1995), Pretty Woman (1990) and When Harry Met Sally (1989) naturally transcend any ranking, as they are proudly stitched into the very fabric of timeless pop culture (Nora Ephron and Nancy Myers were sentries for the sanctity of the rom com for decades, with their essence diffusing into the cultural ether that informs the work of many creators today). Secondly, in trying to keep my list fairly modern, some of the form’s previous greats, namely Hugh Grant, are absent. Although, The Big Lacuna is in dearth of queer content, because, frankly, I am still awaiting the release of well written queer love that is depicted joyously. Equally, none of my picks centre older people, so I want to give a couple honourable mentions to Book Club (2018) and Something’s Gotta Give (2003), where Jack Nicholson plays a horned up OAP. Generally, I feel we have moved past the 80s nostalgia that was very zeitgeisty in the 2010s, so John Hughes’ Pretty In Pink (1986) and Sixteen Candles (1984) are also unaccounted for. Finally, the exclusion of The Proposal (2009) is only due to a presumed January rewatch by many, in honour of Betty White’s passing. RIP queen. 

So, this Valentines, whatever your relationship status, soak up some schmaltzy, acted-out affection and do so not just without guilt, but with resolute pleasure. And remember: the rom com can always be applied to the pizza/sex analogy, in that “even when its bad, it’s still pretty good”!

*Spoilers ahead*

  1. My Best Friend’s Wedding (1997)

“It’s actually a very romantic story. I first met Julian…in a mental institution!” maniacally recounts Rupert Everett, who brings ardour and elasticity to the typically static gay best friend character. This film is the Sirius of the rom com constellation. Running on pure envy and short-sighted selfishness, America’s adorable 90s sweetheart Julia Roberts navigates, or rather bulldozes, her way through a love triangle between herself, Dermot Mulhroney and Cameron Diaz. We still root for her despite her toxic leanings, in the hope she gains some perspective and self-respect (lol). Standout moment: the crushing rise and fall of emotional beats throughout the boat scene.

Available to watch on Amazon Prime Video.

  1. Brown Sugar (2002)

“You are the perfect verse over a tight beat” – all screenwriters may as well retire because never again will more intimate words be penned in cinema. In a relationship grounded in a mutual passion for hip-hop, we watch childhood best friends journey a bumpy road to the realisation that they are in fact soulmates. The lovely Sanaa Lathan is both a plucky and tender leading lady and, sustaining his leading man magnetism from How Stella Got Her Groove Back (1998) and The Best Man (1999), the virtuosity of Taye Diggs as an animated presence on-screen is a treat to watch, as he effortlessly oscillates between being an agent of playful hilarity and steaminess! Standout moments: the restaurant confrontation (“we’re gonna celebrate what? my divooorce!”) and an endearingly nervous Mos Def. 

Available to watch on Disney Plus.

  1. Palm Springs (2020)

Trapped in a groundhog day time loop, two strangers go from pettily locking horns to loving each other deeply. What could be looked at as an allegory for surviving pandemic lockdowns (or just monotonous life under capitalism), they choose to find meaning in the meaningless by committing to love and actively carving out purpose in the abyss. Plugging in his on-brand dippiness, Andy Samberg shines and delivers a previously unseen sensitive disposition. Cristin Milioti’s performance spins the wheel of heightened emotions, going from inflamed anger to determined delusion, from all-consuming guilt to serene acceptance. Standout moment: a demented JK Simmons out for blood.

Available to watch on Amazon Prime Video.

  1. 10 Things I Hate About You (1999)

With whip-smart writing and a stellar ensemble cast, there is much ado about this near-perfect The Taming of the Shrew adaptation. The “bet” plot sets Heath Ledger’s Patrick Verona on a path of venal persuasion that aims to break down Julia Stiles’ unwaveringly stubborn and independent Kat Stratford. The two cater to each other’s temperaments, with a common fire that makes for entertainingly acerbic and cutting exchanges. Between Ledger’s dulcet tones when singing Frankie Valli, his female gaze-complimenting single silver ring and chain and his lethal smirk (I want to set up camp in his dimple), his performance is bewitching. Standout moments: Kat’s iconic tearful poem; a moment of mutual understanding for the couple. See also: Alison Janney’s balancing act between guidance counsellor and author of erotica!

Available to watch on Disney Plus.                                                                                                                                                                                                                                                                                                                                                                                                                                                                  

  1. How To Lose A Guy In 10 Days (2003)

A journalist and advertising executive toy back and forth, using each other as a means to a professional end, until real feelings threaten to cloud their judgement. Between Kate Hudson’s knowing grin and Matthew McConaghey’s unparalleled capacity for simizing, their electric chemistry is positively nourishing to watch; together they appear like a pair of smitten golden retrievers. It is a tale of two proud people learning to let their guards down. Plus, a hysterical Kathryn Hahn brilliantly supports. Standout moments: Hudson being a vision in that silk yellow satin gown and a frantic chase across the Manhattan Bridge culminating in a heart-on-their-sleeves admission of love.

Available to watch on Netflix.

  1. To All The Boys I Loved Before (2018)

In the last few years Netflix have laid some bricks to bridge the gap in the market for quality mid-budget love fixes, and to decent effect – see Always Be My Maybe (2019), Someone Great (2019) and The Lovebirds (2020) – but this is undoubtedly their most sovereign effort; TATBILB is 99 minutes of pure radiance. In sweet protagonist teen Lara Jean, played by Lana Condor, we see the full humanity of the girl next door recognised and respect given to her twee sensibility, hyper-femininity and vulnerability. Lara learning to communicate her sometimes overpowering emotions is a bind that can resonate with an audience of any age. Her love interest is summer 2018’s hot boy du jour Noah Centineo, who hits just the right register as good bad boy Peter Kavinsky. Her gorgeous family unit is helmed by Girl Dad of The Decade Dr. Covey, played by John Corbett – aka rom com aristocracy from My Big Fat Greek Wedding (2002). TALBILB has a profound depth that stands in stark contrast to its age-mate The Kissing Booth. Standout moment: the back-pocket spin in the school canteen.

Available to watch on Netflix. 

  1. Sleeping With Other People (2015)

Alison Brie and Jason Sudekis give assured performances playing former lovers trying, and failing, to sustain a solely platonic relationship. Watching them negotiate self-imposed obstacles that block this goal is where the magic happens (reciprocal, intimate emotional support and candidness on matters of the sex organs). With a tight, snappy script and the best use of Bowie’s Modern Love since its pretentious placement in the black and white Frances Ha (2012) trailer, this is a guaranteed good time. Standout moment: Jason Mantzoukas, beautifully unhinged as always, screaming at his child’s football game “MY LOVE IS CONDITIONAL!”.

Available to watch on Amazon Prime video / Apple TV.

  1. Crazy Stupid Love (2011)

You are probably familiar with multiplot festive films designed to make you go, “oh there’s yer man!”, think Love Actually (2003) Valentine’s Day (2010) and New Year’s Day (2011). Well, this is a more focused and elevated execution of that, where intertwining lives converge in a masterful backyard surburban showdown, with tense comic landing that rivals “Hey Cass … how long have you been fucking Nate Jacobs?” Steve Carrell has a midlife crisis and tries to rediscover his manhood, Ryan Gosling leaves the bachelor life behind, a 13-year-old contends with unrequited love, and Kevin Bacon brings his well-adjusted, EE cool as a quiet homewrecker. Standout moment: Marisa Tomei going apeshit at middle school parent’s evening.

Available to watch on Amazon Prime video / Apple TV.

  1. Intolerable Cruelty (2003)

Quirky, offbeat Coen fun. George Clooney’s initially beguiling divorce lawyer Miles is offset by Catherine Zeta Jones’ scheming gold digger Marilyn who out-smarts each of her romantic conquests with black widow devastation. This movie is a delicious tennis match of deceit and one-upping betrayal that will make you want to take a Family Law 101 class before you ever even entertain the idea of marriage. Standout moments: a spontaneous Little White Chapel wedding featuring kilts and bagpipes. See also: a chaotic cameo from Billy Bob Thornton. 

Available to watch on Netflix.

  1. The J.Lo trifecta: Jennifer Lopez is at her best in a rom com – although her new release Marry Me seems to have the most appalling movie premise in the history of cinema. Anyway … 
  • Maid in Manhattan (2002)

Lopez plays a single mum and hotel maid who serendipitously meets and dates Voldemort during his Republican senator era (Ralph Fiennes plays a besotted NYC dynasty politician). Class dynamics are fairly interrogated and multiple scenes are gently drenched in the smoky honey of Norah Jones soundtracking. Standout moments: the late, great Natasha Redgrave being a perfectly irritating, glamorous, social climbing bitch.

Available to watch on Amazon Prime video.

  • The Wedding Planner (2001)

(The one where J.Lo curiously has mismatched Italian-American ethnicity.) Picture this: a dishy doctor saves you from being run over. You share a series of undeniable moments over the course of a day. Then he turns up with his ​​fiancée to your work. He is now your client and you are planning his wedding … what an anecdote for the groupchat, am I right ladies? With a warm hue exclusive to certain 2000s flicks, this film is a tonic. Standout moment: Matthew McConaghey and Lopez lazing in the topiary and statue-filled garden of a stately home.

Available to watch on Amazon Prime video.

  • Monster In Law (2005)

Don’t let the 18% Rotten Tomatoes rating stop you from enjoying it, for Jane Fonda imbues it with irresistible campiness! Relish in ridiculous friction between the groom’s mum and the bride to be. On reflection, this is a cautionary tale about the unnecessary stress mummy’s boys will inflict upon your life! Standout moments: whenever Wanda Sykes rolls her eyes.

Available to watch on Amazon Prime video.

11. Set It Up (2018)

A very believable connection blossoms between Zoey Dutch and Glen Powell, as they portray two overworked assistants playing matchmaker with their respective high powered, workaholic, and crucially pitiless, bosses, in the hope of achieving some work-life balance. This movie implores you to only accept authentic, meaningful love and to believe in yourself every now and then – overall, it is a cute ol’ time with a genre favourite trope: a last minute airport dash. Come for Lucy Liu in top tier milf mode, stay for Lucy Liu in top tier milf mode. Standout moment: the broken lift scene (I will say no more).

Available to watch on Netflix.

12.  Love, Rosie (2014)

Childhood besties Rosie and Alex are caught in a frustrating cycle of missed opportunities, in this right person, wrong-time narrative arc. We watch them try and handle life’s curveballs together and separately from the ages of 15 to 25, as plans and priorities change, with study abroad places being won and babies being born. We find a terrific on-screen pairing in Sam Clafflin and Lily Collins, and are gratified with a welcomingly saccharine ending. Standout moment: the lead “Posh Totty” from St Trinians (2009) having a mental breakdown (lol).

Available to watch on Amazon Prime Video.

13. Friends With Benefits (2011)

This flirty romp with a lot of heart outshines its same-premise, same-year-twin No Strings Attached. The film’s title gifts us a self-explanatory plot; two emotionally unavailable twenty-somethings casually hook up under the strict covenant that they will not fall for each other, but ultimately face difficulty dodging such emotional entanglement. Being glowy and curt, Mila Kunis is in her element. It is true that Justin Timberlake’s sins outweigh his good deeds, but this is actually one of the latter. Dare I say he comes across charming? He holds his own and strikes the right balance of cocky and confident. Standout moment: Woody Harrelson iconically denouncing heterosexuality with slam-dunk phrasing: “me likes cock, so I’m strictily dickly!”. 

Available to watch on Netflix.

14. She’s All That (1999)

Suffering a bruised ego, a high school golden boy agrees to a wager that he can transform the very nerdiest of pariahs into a prom queen. In spite of being not particularly noble and actually downright problematic in parts, this movie still has a warmth I cannot properly articulate (is it the inclusion of the  delightfully delicate Kiss Me by Sixpence None The Richer during a key scene, that plays like icing sugar being drizzled over a fluffy sponge, or just the doting gaze of all-time stud Freddie Prinze Jr.?). The film’s needless 2021 update He’s All That (Netflix’s entry into the redundant reboot industrial complex) was the figurative bilge water of the grand rom com ship and marked Addison Rae an actress non grata. Standout moment: Rachael Leigh Cook’s physical makeover being perceptively described as “new, not improved, but different”. 

Available to watch on Apple TV.

15. Chasing Liberty (2004)

Ladies, gentlemen and people of the jury, I advocate against this film’s impolitely assigned mediocrity, as another blasphemous Rotten Tomatoes score threatens to sabotage happiness, but do not let it uninvite you from this compelling adventure! The ever winsome Mandy Moore plays the POTUS’ daughter in pursuit of social liberation, joining a good-humoured Matthew Goode on a motorbike across Europe. Her poor-little-rich-girl naivety is challenged as she gets a taste of the real world, and of true romance. Standout moment: action and amore in a gondola ride along the Venetian canals.

Available to watch on Amazon Prime video / Apple TV.


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