#2. City Lights (1931)
Directed by: Charlie Chaplin
Written by: Charlie Chaplin
Starring: Charlie Chaplin, Virginia Cherrill, Florence Lee, Harry Myers
The films of Charlie Chaplin have always had a profound emotional effect on me – they’re truly funny, often innovative, and always full of heart. His 1931 film City Lights is without a doubt one of the most emotionally satisfying experiences in movie history. The romantic comedy has been praised as being one of the greatest movies of all-time, and features one of the most iconic romantic moments ever in its final shot. City Lights sees The Little Tramp (Charlie Chaplin) meeting and quickly falling in love with the blind Flower Girl (Virginia Cherill). That same night, the Tramp thwarts the drunken suicide attempt of an Eccentric Millionaire (Harry Myers), and the two return to the Millionaire’s mansion and form something of a unique bond. The next day, the Tramp borrows money from the Millionaire to buy all the flowers from the Flower Girl. After learning that the Girl and her Grandmother (Florence Lee) will be evicted from their home because they cannot afford to pay rent, the Tramp takes it upon himself to earn money for the pair. He takes a job as a street sweeper, takes part in a fixed boxing match, and once again becomes involved with the Millionaire. City Lights is as romantic a film as has ever been made – featuring Chaplin’s Tramp performing the most selfless actions imaginable for people who don’t even know of his existence. It’s a deeply moving story, and Chaplin uses the Tramp’s selfless nature as a launching point for some truly hilarious slapstick gags, including the aforementioned boxing match – which goes horribly wrong – and the scene where he saves the life of the Millionaire. Chaplin takes full advantage of the silent film medium, even though most of the world had since moved on to talking pictures – the silent film was Chaplin’s wheelhouse and he makes it seems as relevant as ever. Chaplin’s performance as the Tramp is as always intensely physical and goofy, with the character never seeming to be able to get ahead – he is constantly the butt of the joke, despite being the pinnacle of all that is good. Not only is City Lights still incredibly funny after all these years, but it’s also deeply moving and sad in many moments. The situation that the blind Flower Girl and her Grandmother find themselves in often seems hopeless. Even when the Tramp is making headway in making money for the two, they have no idea of his actions – it isn’t until the very end of City Lights that the two parties make formal contact. Chaplin’s film is as always humanitarian and full of themes of romance, justice, and happiness – nobody had heart quite like Charlie Chaplin. The fact that City Lights makes me weep like a baby in its closing moments is testament to how much power the film holds – the entire journey feels so worth it in the end. Only a master like Chaplin could have you crying tears of laughter one moment, and tears of sadness the next. City Lights is another example on my list of a perfect romantic comedy – it might even be the ultimate date movie. If City Lights doesn’t make you feel something deep down inside, then I’m not totally convinced you’re human at all.
#3. Annie Hall (1977)
Directed by: Woody Allen
Written by: Woody Allen, Marshall Brickman
Starring: Woody Allen, Diane Keaton, Tony Roberts, Carol Kane
Woody Allen is a writer-director who I’ve always revered – his incredibly amount of output and passion for the arts is a great source of inspiration for me as a writer and film enthusiast. Even when his films are bad or mediocre, there’s passion and heart to them. His 1977 film Annie Hall is arguably the greatest film he’s ever made, featuring a great love story, hilarious Woody Allen dialogue, and terrific performances. Annie Hall stars Woody Allen as Alvy Singer, a neurotic comedian reflecting on his relationship with Annie Hall (Diane Keaton), which we find out has ended a year ago. Alvy chronicles his childhood in New York, where he obsessed over the meaning of his existence, and was punished for his early sexual curiosity. Through a series of flashbacks, Alvy and Annie meet after a doubles tennis game with friends, and the two awkwardly hit it off. Things progress wonderfully until Annie moves in with Alvy, which creates tension in the relationship. The two eventually break up, date other people, and reconcile shortly after when Annie needs Alvy’s help with killing a spider in the middle of the night. Soon after their reconciliation, the relationship once again falls apart, this time permanently – both characters are glad to have loved one another, even if it wasn’t always filled with good times. Annie Hall is one of the most beloved romantic comedies in Hollywood history – it even beat Star Wars for Best Picture at the 1978 Academy Awards. The screenplay by Woody Allen and Marshall Brickman is highly intelligent and often morbidly hilarious, playing on Woody Allen’s fascinations with death, existence, and the creative process. Even through the script’s intellectual and neurotic nature, Allen and Brickman manage to create one of the most genuine and heartfelt romantic stories ever told on film – one that doesn’t just focus on the best moments in a relationship. The use of flashbacks and non-linear storytelling allows for Allen and Brickman to explore the past of Alvy Singer, including the failed marriages and relationships that have shaped his views on romance. Both Woody Allen and Diane Keaton shine throughout Annie Hall, carrying dramatic and comedic weight like no other on-screen pairing could. Woody Allen’s Alvy Singer is his usual highly neurotic and obsessive, but still confident and arrogant, self, while Diane Keaton’s Annie Hall is adorably goofy, strong-willed, and highly intelligent. The two had such obvious on-screen chemistry in their many collaborations, undoubtedly aided by their brief real life romantic relationship. Annie Hall is Woody Allen at his absolute funniest as a writer and a performer, somehow managing to make both Ingmar Bergman and holocaust documentary The Sorrow and the Pity humorous. The writing and storytelling feels personal and genuine, and the film’s ending feels groundbreaking for the time – not giving the audience the “fairy tale”-esque ending they might be asking for. Annie Hall is Woody Allen’s greatest achievement as a writer and director, and may even be the film where he finally found his voice. It’s hilarious, romantic, heartbreaking, genuine, and smart – everything a Woody Allen movie should be.
#14. The Apartment (1960)
Directed by: Billy Wilder
Written by: Billy Wilder, I.A.L. Diamond
Starring: Jack Lemmon, Shirley MacLaine, Fred MacMurray, Jack Kruschen
Billy Wilder’s Best Picture winning The Apartment is the cynical old master of cinema at his most heartwarming and endearing. The film starring the charming Jack Lemmon in quite possibly his most enduring role and a young, hilarious Shirley MacLaine was one of the very first “classic” movies I ever saw, and one that immediately won my heart. The Apartment tells the story of C.C. Baxter (Jack Lemmon) a down-on-his-luck pushover who rents his apartment to his many bosses so that they can carry out affairs with younger women. Baxter does so in order to climb the often difficult to navigate corporate ladder, and his strategy pays off in spades. After falling in love with the workplace elevator girl Fran (Shirley MacLaine), Baxter begins to have a change of heart. When he finds out that Fran had previously been seduced by his boss Sheldrake (Fred MacMurray) and the two had carried out an affair, things become complicated for the love triangle. The Apartment is Billy Wilder and I.A.L. Diamond’s strongest writing work together, in my opinion. The story features much of Wilder’s inherent cynicism, mostly in C.C. Baxter’s view of the world, and in Fran’s dealings with Sheldrake – there’s a lot of hopelessness and bitterness to be found. Luckily, both Wilder and Diamond also show a deeply human side to their writing, something they would continue to improve on in future scripts. It seems that Diamond brought out the very best in Wilder, making him look past the negatives and create something with spirit and heart. The love story the two men have crafted in The Apartment is truly touching and multi-layered, making it easily one of the most effective romantic-comedies ever made in Hollywood. C.C. Baxter is one of my all-time favorite screen characters – there’s something I find so compelling about his depressive and cynical, but deeply romantic and well-natured attitude. Jack Lemmon’s performance as Baxter is incredible, picking up a well-deserved Best Actor nomination at that year’s Academy Awards. Shirley MacLaine’s turn as Fran is equally as complex, with the sweet young woman towing the line between naive and entirely self-aware. The blossoming romance between both Baxter and Fran is entirely believable, and incredibly sweet – there’s something in the air when the two characters interact, especially in the latter half of the film when they share more screen time. Fred MacMurray’s supporting role as Sheldrake is probably the most I’ve ever enjoyed seeing the actor on screen – he is perfectly charming and unlikable when contrasted with Jack Lemmon’s endearing C.C. Baxter. MacMurray was always best used as a supporting player, and Wilder once again uses him to great effect in The Apartment. The film would go on to win Best Picture, Best Director (Wilder), and Best Writing (I.A.L. Diamond and Wilder) at the 1961 Academy Awards, creating the structure and style of modern romantic comedy films, and paving the way for generations of rom-coms to come. The Apartment is sweet, intelligent, funny, and deeply moving in a way that Billy Wilder was never quite able to recapture – though his 1961 film One, Two, Three is a personal favorite of mine.