10 of my Favourite Romantic Comedies

Tootsie (Dir. Sidney Pollack, 1982)

When I went to New York in 2014, the first two places I wanted to visit were the bench (yes, a bench) that Jack Lemmon sits on in The Apartment, the second was the Russian Tea Rooms - just so I could go to the same booth that Dustin Hoffman and Sidney Pollack sit at in Tootsie. But my parents wouldn't let me actually step a foot inside the tea rooms until I did my infamous Tootsie impression. It's safe to say I have a soft spot for this film. 

Michael Dorsey (Dustin Hoffman) is a struggling New York actor, his long suffering agent George (Sidney Pollack) has more or less given up on him due to his client's reputation for being one of the most difficult actors to work with (Michael once refused to sit down on a commercial, the logic being that he was playing a Tomato - and if they can't move then how are they going to sit down?). Michael's fellow acting friend Sandy (Terri Garr) is rejected from a role on a daytime, hospital-based soap and Michael's desperation leads him to take it upon himself to dress up in drag and try for the part himself, which he gets. He must keep up the charade of his new persona (Dorothy Michaels) to millions of viewers and everyone on set, including the leading lady Julie (Jessica Lange), whom Michael has fallen in love with. What's more, he has to deal with the affections of co-star John (George Gaynes) and Julie's father Les (Charles Durning), who have both fallen in love with him as Dorothy.

It's not just a comedy about a person in drag. It's alot more than that. It actually has things to say about sexism and the unrealistic beauty expectations that women are faced with. Hoffman has said in interviews that the film gave him an idea of how much pressure is put on women to look perfect all the time and how those who aren't generically beautiful are erased. This is touched upon in the film itself, Dorothy's looks are commonly remarked upon with those on set saying that she might look a little more attractive if the camera's pulled back... to Cleveland. Because of this, Dorothy asserts her authority with impulsive, ad-libbed dialogue changes on set that makes her character in the show a much more stronger and independent individual than the role originally wrote her to be, which helps it to become a ratings smash. Michael ends up being the most successful that he's ever been in his entire career, and he learns to become a better man after being a woman ("I was a better man with you, as a woman... than I ever was with a woman, as a man. Know what I mean?").

A few years ago it was voted the best movie ever by a group of actors. Perhaps this is because as actors, they could relate to the struggle that Michael and his acting friends go through, for example being so poor that the commute back from the day job each day was a toss up between spending all your money on a cab or the cheaper option of getting mugged while walking home. The opening montage of Michael going to different auditions and getting humiliated at each one must be all too familiar for some people, and it's easy to see Pollack's agent character as a manifestation of the frustrations that he felt due to the disagreements that him and Hoffman had on set.

Tootsie is endlessly quotable not just with funny lines ("no-one wants to see two people living next to chemical waste, they can see that in New Jersey"), but also entire scenes of dialogue that emerge out of the absurdity of Michael's situation and the fact that he's struggling to juggle different persona's. He's in love with a woman whilst pretending to be a woman, he has one leering co-star serenading him outside his apartment, another that wants to marry him and a best friend who is wondering why a man named Les is taking him for a lovely night in front of the fire. Like the two leads in Some Like It Hot he's got himself into a situation that he's fallen far too deep in to ever escape from, which snowballs more and more as the film rolls on, and it's hilarious: 

George: Julie thinks your gay?
Michael: No, my friend Sandy
George: Well sleep with her then.
Michael: I slept with her once she still thinks I'm gay.
George: Oh, that's not good Michael.
Michael: If I didn't love Julie before you should have seen the look on her face when she thought I was a lesbian.
George: "Lesbian"? You just said gay.
Michael: No, no, no - Sandy thinks I'm gay, Julie thinks I'm a lesbian.
George: I thought Dorothy was supposed to be straight?
Michael: Dorothy IS straight. Tonight Les, the sweetest, nicest man in the world asked me to marry him.
George: A guy named Les wants YOU to marry him?
Michael: No, no, no - he wants to marry Dorothy.
George: Does he know she's a lesbian?
Michael: Dorothy's NOT a lesbian.
George: I know that, does HE know that?
Michael: Know WHAT?
George: That, er, I... I don't know.

Dustin Hoffman's performance in Tootsie may be my favourite one in this whole list, he didn't take home the Oscar for this one but to my mind it's the best performance of his career. As testament to how convincing he is as Dorothy, he once went up to Midnight Cowboy co-star John Voight in drag and said how much of a fan "she" was of his movies, and Voight didn't suspect a thing. Dorothy's funny southern accent, colourful wardrobe, her complete disregard to just act out one scene as its written in her script and her friendship with Julia makes her a memorable and lovable character to us and to the characters within the film. His performance could have so easily turned into an over-the-top farce but instead we sometimes forget that Dorothy is a person in drag at all, and when Julie says at the end that she "misses" Dorothy, we do too. 

If that's not enough, Tootsie also gives you advice on how to best to deal with sexist men... zap them in the 'badoobies' with an electric cattle prod.

Trouble in Paradise (Dir. Ernst Lubitsch, 1932)

What really is the "Lubitsch touch?" Billy Wilder said that if he knew the answer then he would patent it. Read quotes from fellow filmmakers and critics and no two definitions seem to be the same. Wilder said it was the following: 

"It was the elegant use of the Superjoke. You had a joke, and you felt satisfied, and then there was one more big joke on top of it. The joke you didn't expect"

In Ernst Lubitsch's Trouble in Paradise, this definition is summed up best during the dinner scene between Gaston (Herbert Marshal) and Lily (Kay Francis), when the two accuse each other of being thieves. Gaston returns a pin that he has pickpocketed off Lily, only to check the time and discover that she has stolen his watch off him. The film centers around these two thieves who fall in love and decide to use their skills to rob a rich woman named Mariette (Kay Francis). 

Upon its release, Trouble In Paradise was a the type of film, the likes of which wouldn't come along again for a long time. Being a pre-code picture it had concepts that simply would never find their way into films in the decade succeeding it. Here we have two thieves that get away with their crimes, that sleep together without getting married, with one contemplating having an affair. In terms of the film's style; it has certain aspects that would have forbade its showing after the code’s implementation, since it used methods such as shadows and ‘do not disturb’ signs to suggest sex. This was the type of occurrence that Leland A Poague defined as the Lubitsch Touch: 

"A style that is gracefully charming and fluid, with an ingenious ability to suggest more than it showed".

Like Wilder, Lubitsch knew that the audience could add up two and two themselves. To put this more explicitly, Scorsese once said that "Lubitsch could do more with a closed door than another director could do with an open fly". The love triangle that occurs within the film is hinted at even as early as the opening credits, as the three names are displayed in a triangle above an image of a bed. Despite all of this, his films maintain a sophistication that has all but disappeared from romantic comedies today. Ultimately at the heart of the picture is still a warm love story, and regardless of a suggestion of an affair between Gaston and Mariette, it's clear that Gaston and Lily are the ones that are destined to be with one another; their profession is what makes them fall in love in the first place and being thieves they don't trust anyone besides each other. Trouble in Paradise is quite simply delightful and now Christmas is around the corner I'll be settling down soon to watch one of Lubitsch's other masterpieces soon: The Shop Around the Corner.

                                                                           Peter Bogdanovich discusses "The Lubitsch Touch"

The Goodbye Girl (Dir. Herbert Ross, 1977)

"Thank you Neil Simon for making us laugh at falling in love...again"

Richard Dreyfuss became the youngest man ever to win the best actor Oscar in The Goodbye Girl, in it he plays Elliot, an eccentric Chicago actor who has arrived in New York only to discover that the apartment that he is renting is already lived in by the recently dumped dancer Paula (Masha Mason) and her precocious daughter Lucy (Quinn Cummings). Unbeknownst to Paula, her ex boyfriend (also an actor), sublet the apartment to Elliot before abandoning the two and travelling to Italy, naturally she is now sceptical of men - especially actors. Elliot agrees to let the two stay in the apartment and the three must attempt to live together as harmoniously as possible.

Written by Neil Simon, the man behind productions such as The Odd Couple and Prisoner of Second Avenue, two of my other favourites (I like Jack Lemmon okay), The Goodbye Girl is genuinely one of the most sweet, heartwarming and touching comedies I've seen. Like Oscar and Felix from The Odd Couple, we see characters with clashing personalities being forced to spend time together in the confinements of their apartment (Elliot is a health food nut that plays guitar when he can't sleep and can't stand Paula's laundry hanging around the apartment). Meanwhile, the plight of the main character's job loss in Prisoner of Second Avenue is echoed in Elliot's perpetual frustration with his part in the ill-fated Richard III production which is a role that he's banking on to ignite his career. The Goodbye Girl had quite a troubled pre-production history but was ultimately a harmonious experience for those on set; originally entitled Bogart Slept Here, it was tipped to be directed by Mike Nichols with Robert De Niro in the starring role. When this fell through and Dreyfuss tested alongside Mason, Simon did a rewrite ("the script didn't work but they did) to make it funnier and more romantic: "I tailor-made the parts to fit in their specific and unique gifts". 

"Goodbye Girl was a wonderful script. Wonderful. And as actors we never got tired of it. Never...It was funny and loving. And the actors and actresses - especially Marsha and Quinn - were perfect" - Richard Dreyfuss 

The play within the film is probably the most hilarious theatre scene in a movie, up there with Gene Wilder's Puttin' On the Ritz scene from Young Frankenstein. The director of Elliot's off-broadway show of Richard III wasn't all that impressed with the way that Laurence Oliver played the historical figure and is convinced that the king was in fact a "flaming homosexual", so on opening night Elliot must prance around the stage in heavy eyeliner and lavender period-era costume while trying and failing to maintain some sense of dignity. Funny scenes like this are balanced with other more melancholy moments; such as immediately after the play when Elliot is sat in his dressing room slowly realising that he's destroyed his career, or when Paula is mugged in the street and cries about how everything goes downhill for her whenever an actor walks into her life. By writing characters that are vulnerable and who each hit rock-bottom at one point in the film, Simon makes them feel more genuine, stopping the picture from becoming nothing more than an endless stream of funny gags. 

Like the title suggests, the boyfriends who have abandoned Paula in her life have left her with a reluctance to fall in love with another man because she's afraid that he'll walk out the door too. Because of this, Elliot realises that he has to prove he's different from all the rest, and that the way to Paula's heart is through her daughter:

The Apartment (Dir. Billy Wilder, 1960)

One of the best closing lines ever, with one of the most heartbreaking reveals ever, The Apartment is one of those movies that got me into movies. Inspired by David Lean's Brief Encounter, Billy Wilder  and screenwriting partner I.A.L Diamond crafted this story of a New York insurance worker Bud Baxter (Jack Lemmon), who rents his flat out to his executives to use for their adulterous flings. He climbs up the corporate ladder, but soon discovers that elevator operator Fran (Shirley MacLaine), whom he is in love with, is one of the women that his boss has been taking back to his apartment. 

The Apartment is probably the bleakest film on this list, especially when you compare it to Wilder's more upbeat previous film, Some Like it Hot. In fact Jack Lemmon didn't regard this as a comedy at all. The world of The Apartment is full of lonely souls that drudge through their working day, who become invisible to their bosses amongst the hundreds of other workers typing away. The smoke filled bars of New York are also full of people looking for company in the lonely holiday season that the film takes place in, and not once do we see Bud with any friends of family. But Wilder created two perfect comedies in a row (seriously I'm sure any director would kill to have these two films under their belt), that despite being very different in tone still carry his expertly witty dialogue. 

Unlike lots of other romantic comedies, especially more modern ones that are populated by perfect people with perfect looks and perfect morals, The Apartment is full of flawed characters. Jack Lemmon is the hero, but he knowingly encourages his co-workers to cheat on their wives with the promise of his apartment, all so he can get a promotion. In addition, his cowardice initially prevents him from standing upto Sheldrake (Fred MacMurray), the man he knows is sleeping with the woman that he loves and who has no intention of ever treating Fran the way that she deserves (he gives her a $100 dollar bill after realising that he's forgotten to get her a Christmas present, essentially turning her into a prostitute). Bud is largely only moved to change his ways after a talking to by his exasperated neighbour Dr Dreyfuss (Jack Kruschen), who believes that Bud is the biggest playboy in town since he sees (and hears!) a different woman each day in Bud's apartment. The doctor tells Jack Lemmon to grow up... and "be a mensch", which he finally has the courage to do at the end of the film, when he wants to save Fran from her depressed stupor:

Bud: You're not gonna bring anybody to my apartment.
Sheldrake: I'm not just bringing anybody. I'm bringing Miss Kubelik.
Bud: Especially not Miss Kubelik...
Sheldrake: What's gotten into you, Baxter? 
Bud: Just following doctor's orders. I've decided to become a mensch. You know what that means? A human being.

It's probably one of the best blends of comedy and drama. Moviewise, there has never been anything like The Apartment love-wise, laugh-wise and otherwise-wise!

Also, you'll never look at your spaghetti colander in the same way again.

Jack Lemmon on Billy Wilder 

Bringing up Baby (Dir. Howards Hawks, 1938)

I maintain that the scene in Bringing Up Baby where Susan's (Katherine Hepburn) dress rips and David (Cary Grant) tries to cover her up is one of the funniest moments in cinema. It demonstrates Cary Grant's talent for physical comedy, with the usually super-suave leading man now acting as the nerdy, bumbling character that we very rarely saw from him. It also comes to symbolise one of the main themes of the film, that although he can't stand this women because she does nothing but irritate and embarrass the poor man, he really can't be without her. Brilliantly, this moment was based on a real incident that happened to Cary Grant; whereby he somehow got the zip of his fly caught in the dress of a woman that was walking past him - forcing the two to walk behind each other in search of some help.

“Now it isn’t that I don’t like you, Susan, because, after all, in moments of quiet, I’m strangely drawn toward you, but – well, there haven’t been any quiet moments.”

Not a success upon release, Howard Hawks attributes this to the fact that the characters weren't necessarily realistic: "There were no normal people in it. Everyone you met was a screwball", so maybe there was no one to relate to, but the nonsensical aspects of the picture don't take anything away from the enjoyment of watching it, these days it's one of the most beloved films of the entire genre - Harold Lloyd once said that "it was the best constructed comedy" that he had ever seen. The fact that the film centres around the search for a 'Intercostal Clavical' bone for David's dinosaur reconstruction tells you everything, because such a bone doesn't even exist in the real world, it was chosen simply because it's a funny name and a perfect MacGuffin for a screwball comedy.  

Leigh Singer points out in his video essay on the rom-com, that the love interests in films of the screwball genre often contained male and female leads of equal narrative weight - that is to say, the female role was just as substantial as the male one. Free spirited Susan has a sharp wit but clumsy nature that causes all sorts of trouble for David, he's not all that comfortable in her presence because her own quirky personality challenges his own more introverted one - she does what she wants and her actions leads to the absurd situations that occur, such as: 

When Harry Met Sally (Dir. Rob Reiner, 1989)

Like you didn't know this one was coming. I don't think I've read a "best rom coms ever" list online without this one popping up. There's a reason for that. 

Director Rob Reiner, when asked why there was a decline in romantic comedies, said simply that "there is no Nora Ephron". Although she also directed You've Got Mail and Sleepless in Seattle, I think her most lasting credit will be as a writer on this classic comedy. Reiner said that she was witty, brilliant and had great observational powers about men and women and how they relate to each other.

Whilst on a car journey to New York, strangers Harry (Billy Crystal) and Sally (Meg Ryan) debate whether it's possible for a man and a woman to be friends with one another without them eventually sleeping together. Years later the two bump into each other again and again by chance, until they soon become great friends. They're complete opposites - Sally is a perky, happy and conscientious woman who's extremely fussy when it comes to ordering her food ("I'd like the pie heated and I don't want the ice cream on top, I want it on the side, and I'd like strawberry instead of vanilla if you have it, if not then no ice cream just whipped cream but only if it's real; if it's out of the can then nothing") whilst Harry is more laid back a morbid individual, the type that reads the last page of a new book first just incase he dies before getting to the end.

When Harry Met Sally not only demonstrates Ephron's gift for writing dialogue, but her affinity for New York, the city she was born in. From that scene in Katz Deli, to the arch in Washington Square, to the autumn walk that the two take in Central Park, it's one of the most quintessential movies set in the city, the locations of which are instantly recognisable. After the 9/11 attacks, Ephron edited together a fantastic New York movie montage that Woody Allen presented at the Academy Awards, it was a call to filmmakers everywhere to never stop making films in the city. 

“There are no chase scenes. No food fights. This is walks, apartments, phones, restaurants, movies.” - Rob Reiner

Thanks to people on the internet who have alot of time of their hands. We now know that, should you want the New Year's eve finale of the film to perfectly sync up with the New Year's eve countdown in real life - press play on your DVD player or Netflix at 10:30:28 p.m on December 31st. The only question is do you watch this or The Apartment, which also ends on the last day of the year? (Hint: Just watch both because they're wonderful). 

Singin' In The Rain (Dir. Gene Kelly & Stanley Donan, 1952)

“I've made a lot of films that were bigger hits and made a lot more money, but now they look dated. This one, out of all my pictures, has a chance to last.” - Gene Kelly

I think he was right about that last part, Singin' in the Rain is ageless. 

This movie about moviemaking stars Gene Kelly as Don; a silent film star in the late 1920s who is  caught up in the industry's transition to talkies. Gossip columns throughout the country maintain that him and his shallow co-star Lina (Jean Hagen) are a smitten couple, even though in reality Don can't stand her. Whilst escaping from his adoring fans one day, Don has a chance encounter with a chorus girl with a beautiful singing voice, Kathy (Debbie Reynolds) who with the help of Don's friend Cosmo (Donald O'Connor) helps Don in his pursuit of capitalising on the popularity of talking pictures. 

There's alot of fun to be had from watching the characters trying to get over the hurdles that come with the new technology on set. First off, Lina is seemingly tone deaf and can't string two harmonious notes together, which means that her screeching voice is cause for disaster on any new picture that she is working on. This satirisation of the talkies process is best summed up when Lina is trying to film a scene with dialogue on a picture called The Duelling Cavalier - after a microphone  concealed in a nearby bush fails to pick up her voice, the director decides to hide the microphone in her dress, only for it to pick up her heartbeat instead. 

I've already written about how films such as The Purple Rose of Cairo (Allen, 1985) capture perfectly, the joy that we as audience members have when sitting down to watch a film. Singin' in the Rain is the same. The iconic musical number where Kelly is overcome with joy at his new love Kathy that he dances around the streets jumping in puddles and swinging on the lampposts is just about one of the most joyful scenes that any moviegoer will ever witness. 

"The single most memorable dance number on film” - Peter Woolen
Groundhog Day (Dir. Harold Ramis, 1993)

Self-centred weatherman Phil (Bill Murray) is forced to re-live the same day over and over again in a film that The Guardian called "the perfect comedy". At first, Phil takes advantage of the fact that there are no consequences to his reckless actions, then after falling for his colleague Rita (Andie MacDowell) uses his situation to learn about her so he can pretend the two have everything in common, until finally he realises that the only way to break the chain is to become a better individual himself.

Gilbey points out that the longevity of Groundhog Day lies in the fact that screenwriter Danny Rubin  refused to implement any pop culture references pertaining to 90s culture. Unlike for example the reference-filled, horror spoof comedy style of the Scary Movie franchise that will in a few years time become "incomprehensible", Gilbey says that people in decades time will always find the underlying message in Groundhog Day profoundRubin was attracted to the idea of how a man who seemed incapable of change in his normal life would be effected by the prospect of an eternal day-cycle. Phil's journey from an obnoxious and bitter individual into someone who deserves the love of Rita takes time, even when the predicament of his situation really hits him, the temptation to do things for his own gain and enjoyment still prevails over anything else. When he finally does change his ways and get the girl, we rejoice because we've followed Phil in his journey as he learns to play pianosculpt ice and improve the lives of the townsfolk  around him.

"I did feel from the very beginning that I’d stumbled upon a story with all the makings of a classic, so simple and true that it could be retold many different ways by many different storytellers." - Danny Rubin

These days, "Groundhog Day" has become a phrase in itself, it has been adapted into a play and last year Sky movies showed the film on a loop (open that link - it's a genius article) on February 2nd - the date of the Groundhog Day holiday. 

Bridget Jones's Diary (Dir. Sharon Maguire, 2001)

Now I work in London I like to think of myself a bit like Bridget Jones. I have about the same public speaking skills as she does, my cooking abilities are a mirror image of hers and my relationship between two men called Ben & Jerry is probably the most meaningful I've had. That's what accounts for the popularity of this loose modern retelling of Pride and Prejudice - that lots of women can relate to Renée Zellwegger's thirty something spinster. 

It's the new year and after her mother unsuccessfully tries to set Bridget (Renée Zellwegger) up with stuck up lawyer Mark Darcy (Colin Firth), she realises that she has to take control of her life, lose some weight, cut down on the cigarettes and find herself a sensible boyfriend to go out with. Unfortunately the man she chooses to get into a relationship with is her sleazy boss Daniel (Hugh Grant, who again shows how much of a great comic actor he is). After a while, Mark is soon also competing for the affections of Bridget after realising that he likes her "just the way she is". Like Bringing Up Baby, The Shop Around the Corner, You've Got Mail and others, Bridget Jones has that familiar romance trope: that the two leads must absolutely despise each other before discovering that they are soulmates, and it's really lovely watching Mark and Bridget fall slowly in love with each other throughout the course of the film. 

Upon its release, people were dubious about the choice to cast an American in the lead role, but now it's difficult to imagine anyone other than Zellwegger in this part. Her accent is spot-on, and every single hilarious and embarrassing encounter she finds herself in makes us love her even more. She's not perfect, and that's why it's funny, as Ricky Gervais once said: “No one wants to see cool people doing brilliantly. I want to see the struggle. That's the fun bit.” We love her friends too, caricatures maybe but they spur her on in the story and even do their best to pretend that her blue soup is delicious - best mate Shazzer (Sally Phillips), who can't seem to go two sentences without swearing is basically an embodiment of all my friends from University. 

I do like the sequels, but neither of them could ever match the charm of the first. 

High Fidelity (Dir. Stephen Frears, 2000)

Shifting from the London setting of Nick Hornby's source material to Chicago, High Fidelity starts its story just as record store owner Rob (John Cusack), has been dumped by his girlfriend Laura (Iben Hjejle), this prompts him to look back on his top five breakups of all time and explore what went so wrong. 

We all know someone like Rob. Whether it's a person obsessed with music or whether it's something else like movies or books, he takes what he loves seriously, putting more time and energy into compiling his top ten song lists than anything practical (I can relate to this at this exact moment, I could be flat hunting right now), even going so far as to re-organise his LP's autobiographically. His co-workers in the record store meanwhile are also the types of people that you run into very often, rock snob Barry (Jack Black) looks down his nose at anyone who buys an album at the shop that isn't within his tastes, preferring to educate them on their terrible preferences then to just sell them the damn LP and make money for the shop.

Nick Hornby books always seem to make for good adaptations. I could have easily put Fever Pitch or About a Boy on this list too. Fever Pitch of course featuring a similar main character, a bit of a man-child who has an obsession (Arsenal football club) that the woman in his life can't seem to appreciate.    The two are rom-coms that can be appreciated by men who usually hate the genre, but they both avoid the trap of becoming cliche'd "lads" films, instead simply exploring how important the interests and passions of a person are in shaping their personality.