As always when I compile one of these lists I expect this countdown of the top 50 best romantic comedies of all time to stir up some healthy controversy. Not only is there a wide gulf in what people find funny, but now you throw in the romantic part of the equation as well. What constitutes romance to one might seem completely cheesy to another. However, that is the fun part of making these lists. It is always interesting to see the perspectives of others that get left as comments. So if you disagree with anything on the list feel free to fire away, and let your opinion be known. That being said, on to the list. Here are my picks for the best romantic comedy movies ever made:
50 – Bull Durham – This one makes a great date movie. Baseball for the guys, romance for the women and plenty of humor for both. Kevin Costner’s baseball movies alone would constitute a successful career for many actors. Tim Robbins and Susan Sarandon are both stellar as usual.
49 – Sabrina – Okay, I won’t waste any time getting into the classics. For those expecting a list full of Hugh Grant, Drew Barrymore, Meg Ryan and Tom Hanks then prepare to be disappointed. Though those actors will make their fair share of appearances on the list the stars from days gone by deserve their due as well. Stars abound in this classic 1954 comedy about two brothers who fall in love with their family’s chaffeur’s daughter after she returns from Paris all grown up. Audrey Hepburn is classic as always in the lead role of Sabrina Fairchild and Humphrey Bogart and William Holden are just as good as Linus and David Larrabee, the two brothers suddenly vying for her attention.
48 – Knocked Up – Okay, so this isn’t your traditional romantic comedy, but I am going to try and include a little bit of everything on this list. Though this film starring Seth Rogen as Ben Stone, a pot-smoking slacker who impregnates Katherine Heigl’s Alison Scott during one fateful drunken night may be one of the raunchier selections on this list, it does have its tender moments too. Plenty of laughs with a sprinkling of romance thrown in nabs it a spot on the list.
47 – Shallow Hal – Again, not a movie that might immediately leap to mind when thinking of romantic films. Still this film about a man who changes his ways after a hex makes him see inner rather than outer beauty has plenty of charm. Jack Black is as funny as ever, and Gwyneth Paltrow shows she has a talent for comedic acting as well, pulling off her fat-suit scenes with impeccable comic timing.
46 – Juno – This movie about teenage pregnancy is just about impossible to shoehorn into any one genre, so romantic comedy is just as good as any other. Ellen Page earned an Oscar nomination for her fantastic work as main character Juno MacGuff, who must deal the consequences of a single impetuous act one afternoon. Michael Cera of Arrested Development and Superbad is excellent in a somewhat subdued role as the expectant father in this charming, quirky teenage romance.
45 – 50 First Dates – Well, it didn’t take long for Drew Barrymore to make an appearance on the list. She teams up again with funnyman Adam Sandler in this film about a man who finally thinks he’s found “the one” until he discovers that his soul mate suffers from short term memory loss. As a result he spends each day wooing her anew. The women will really love this one, and Sandler delivers enough goofy humor to keep the guys entertained.
44 – Roxanne – Steve Martin is known for his goofy brand of offbeat humor that made him such a popular star and guest host on Saturday Night Live. However, he dipped his toes into the romantic half of the equation in 1987’s Roxanne, a Hollywood retelling of the play Cyrano de Bergerac. As usual Martin’s physical comedy is hilarious as he tries to win the affections of Darryl Hannah’s Roxanne Kowalski.
43 – Music and Lyrics – After a small break Miss Barrymore’s name surfaces again on this list of great romantic comedies. This time she is paired opposite another actor who has made his fortune playing the lead role in date movies. Hugh Grant is brilliant as a struggling musician who once enjoyed international stardom as part of an 80s pop music super-duo. The music and the dancing really made this movie for me. If you grew up in the 80s you will love this one.
42 – Never Been Kissed – Okay, I didn’t do this on purpose I promise. I ranked them without paying attention to the lead female in each role. Yes, Drew Barrymore is back for the third time in this cute movie about a geeky journalist who returns to high school to research a story. It is hard to imagine the outrageously flirtatious Barrymore in a shy role, but she actually manages to pull it off quite believably.
41 – So I Married an Axe Murderer – Though Mike Myers is far more famous for his roles in movies like Wayne’s World and Austin Powers: International Man of Mystery in my opinion this is actually his best movie. Myers plays a man who becomes increasingly paranoid that his bride to be (Nancy Travis) is a serial killer. If you like Mike Myers and have somehow missed this one, definitely give the DVD a rent.
40 – Say Anything – John Cusack is one of my favorite actors, and one of the most underrated leading men in Hollywood in my opinion. This film was one of the best movies of the 80s in any genre and Cusack’s character Lloyd Dobbler and his ghetto blaster serenade are iconic representations of that goofy decade.
39 – About a Boy – Based on the novel by Nick Hornsby, this movie has a little bit of everything – drama, romance and of course, comedy. Hugh Grant gets a lesson on life and is helped to finally grow up with the help of a boy named Marcus. Though the story is mostly about Grant’s character Will and Marcus there is an ultimate love interest in the film and Grant finally finds happiness with Rachel Weisz in the end.
38 – Hitch – Though better known for making action comedies like Men in Black and Bad BoysWill Smith has shown amazing versatility throughout his career. From goofy TV comedy on Fresh Prince of Belair Smith has gone on to star in powerful dramas like Pursuit of Happyness and Seven Pounds. And in 2005’s Hitch he showed he could pull off the lead role in a romantic comedy as well, playing a cynical love doctor who ultimately breaks his own rules and falls in love with Eva Mendes.
37 – Sleepless in Seattle – You knew Tom Hanks and Meg Ryan had to show up somewhere on a list of the best romantic comedy movies. They set the screen on fire in this 1993 film about a widower whose 8 year old son goes on national radio to help his dad find a new wife (and a new mother for him). There are plenty of bumps along the way, but true love finally wins out in the end. Sappy in the extreme, but isn’t that the point of romantic comedies?
36 – Runaway Bride – I can’t believe I forgot to mention Julia Roberts on my list of actors most likely to appear in romantic comedies. Roberts stars alongside Richard Gere for a second time in 1999 movie about a woman with very cold feet, who has left a trail of broken hearts and devastated grooms at the altar. Not a lot for the guys in this one to be honest, but if you want to score brownie points it is a good one to rent for your wife or girlfriend.
35 – French Kiss – Though not as well known as films like Sleepless in Seattle and When Harry Met Sally this 1995 Meg Ryan film is a sleeper favorite, and it is one of the more underrated films on this list. Ryan is as cute as always, and Kevin Kline is superb as the silver-tongued thief Luc. If you are looking for a good date night movie try and nab this one at the video store.
34 – Love Actually – Speaking of underrated romantic comedies Love Actually certainly fits the bill. One of those movies without a central character the film actually follows the adventures of eight separate couples whose tales become interwoven during one hectic December. A far cry from the usual sappy tripe,Love Actually is a film that anyone, even those who hate romantic comedies, can enjoy.
33 – An Affair to Remember – Those a little longer in the tooth can breathe a sigh of relief as I give them a break from all the 80s and 90s cardboard cutout comedies. Starring Cary Grant and Deborah Kerr An Affair to Remember is a classic tale about the destiny of true love. Will they find their happiness in the end? Watch it and see.
32 – Something’s Gotta Give – Jack Nicholson is incapable of a bad performance and he once again delivers the goods opposite Diane Keaton in this 2003 movie about an aging playboy who finally falls for a woman who isn’t young enough to be his granddaughter. Ironically she is nursing him back to health after he has a heart attack while being intimate with her daughter.
31 – The Wedding Singer – Filmed in the 90s, but set in the 80s this film about a wedding singer who falls in love with the girl at whose wedding he is scheduled to perform is a true romantic classic – just ask my wife! Drew Barrymore and Adam Sandler show terrific chemistry and the laughs come non-stop from beginning to end, and there is even some tear-jerking sap at the end. One of the best romantic comedies of the 90s without question.
30 – What’s Up, Doc? – When it comes to screwball comedies few can keep pace with 1972’s What’s Up Doc?. There is plenty going on here, and the plot is too convoluted to sum up in a single paragraph, but suffice it to say that Barbra Streisand is hilarious as Juddy Maxwell, a hurricane of humanity who blows into Dr. Bannister’s life and sweeps him off his feet.
29 – You’ve Got Mail – You didn’t think you’d seen the last of these two had you? Tom Hanks and Meg Ryan again show off their perfect on-screen movie about a pair of complete opposites who have a romance online and a contentious friendship offline, unaware that both relationships are with each other.
28 – My Big Fat Greek Wedding – One of the most successful indie films of all time, this charming 2002 tale about a Greek woman who falls in love with an American man over the protestations of her family raked in hundreds of millions of dollars despite its modest budget. Written by and starring Nia Vardalos the story is an amusing look at love and family, and even the most jaded viewer will have to crack a smile at the father and his Windex bottle.
27 – As Good as It Gets – Jack Nicholson and Helen Hunt pulled off the rare double Oscar with this film, earning best actor and best actress wins for their work on this film. As strange a love story as you can imagine As Good as It Gets stars Nicholson as an obsessive compulsive writer without a filter between his brain and his mouth, who despite his many flaws manages to worm his way into the heart of Hunt’s Carol Connelly, a single mother and waitress who he tries to compliment, but continually manages to insult.
26 – Shakespeare in Love – Not all romantic comedies need to be set in contemporary settings, as director John Madden proved with his 7 Oscar-winning tale of 16th century love between Shakespeare and his muse for his latest play. Something about Romeo and Ethel the Pirate’s Daughter just didn’t ring true, but he managed to get it sorted in the end.
25 – While You Were Sleeping – This is a movie that every woman I know seems to have in her DVD collection and seems to be able to watch again and again without getting tired of it. Personally I was tired of it five minutes in. Different tastes for different genders at work here I guess. Still, I can’t deny that this bizarre love triangle between Sandra Bullock, Bill Pullman and Peter Gallagher is a hit with the ladies, and deserves its high spot on this list for that reason.
24 – The 40 Year Old Virgin – Much like Knocked Up this movie winds up on the raunchier side of the scale. However, there is a love story at the core, and no one can deny that Steve Carrell is absolutely hilarious in this movie. One of the funniest movies of the 2000s this movie belongs in anyone’s DVD collection (providing you can stand a little crude humor) because it is one you will definitely watch over and over again.
23 – High Fidelity – Another John Cusask flick makes the list. Though High Fidelity isn’t one of his more popular films among the mainstream movie crowd those who have discovered this gem count it among their favorite films in many cases. The movie is as much about the agony of breaking up as it is about love, as Cusack’s character, record store owner Rob Gordon knows only too well. In fact he narrates the film as a painful list of his top 5 break-ups of all time. Clever and original the movie is entertaining throughout with plenty of laughs thrown in for good measure. There is also a surprising amount of star power in this under-the-radar film including appearances by Lisa Bonet, Tim Robbins, Catherine Zeta-Jones, and Jack Black who is a crack-up in a supporting role.
22 – Jerry Maguire – Though probably just about everyone reading this list is completely sick of this movie and it’s vomit-inducing “You had me at hello.” Line there is no denying that at the time of its release this was hugely popular. The movie drove Tom Cruise to new heights of popularity and basically launched the careers of co-stars Renee Zellwegger and Cuba Gooding Jr., who won an Oscar for his turn in the movie.
21 – Groundhog Day – The inimitable Bill Murray does some of his best work on this film about a weatherman who winds up reliving the same day over and over again. Somehow, despite his bizarre circumstance he finally manages to win the love of his produce Rita, played by Andy McDowell. As quirky and original as it is, Groundhog Day certainly sets itself apart from most of the other films on this list.
20 – Pretty Woman – It seems appropriate that a Julia Roberts/Richard Gere movie should mark the entrance to the top 20 romantic comedies ever made. About a hugely successful businessman who falls in love with a prostitute the story is 90 percent romance and 10 percent comedy. Still there are enough laughs (barely) to keep the guys entertained while the women swoon over the romance.
19 – Breakfast at Tiffany’s – Back to the classics we go. Audrey Hepburn delivers another classic performance in this loose adaptation of Truman Capote’s novel about a young woman living a truly crazy life in Manhattan, where she divides her time as an escort and an information carrier for an incarcerated drug lord. Her occupations aren’t half as bizarre as her other relationships though. Hepburn’s Holly is a truly dizzying character that will leave you bemused, but by the time the end credits roll you’ll realize you enjoyed it immensely.
18 – Adam’s Rib – This time it is Katherine Hepburn starring in the lead role, opposite Spenser Tracy in this courtroom comedy about a pair of husband and wife lawyers who find themselves on the opposite side of a case. Not a traditional romantic comedy by any stretch of the word (the couple are already married) but I’ll take a little license with this one as it is one of my favorite films.
17 – Bringing Up Baby – The Hepburns are on a roll now. This time Katherine is starring opposite Cary Grant in this 1938 romantic comedy about a paleontologist, a millionaire heiress, a leopard cub named Baby and a dino-bone stealing terrier named George. Screwball comedy at its best, and one of the best movies of its era in any genre.
16 – The Princess Bride – I don’t believe there were any Hepburns in this film, so the streak is broken. Cary Elwes and Robin Wright-Penn star in this fairytale comedy about true love, and a man who defies death itself to obtain it. Mandy Patinkin, Billy Crystal, Andre the Giant and Wallace Shawn are all terrific in supporting roles in this adaptation of William Goldman’s novel of the same name.
15 – His Girl Friday – This one is almost like a reverse romantic comedy. Cary Grant stars as Walter Burns, a Chicago newspaper editor whose ex-wife is about to get remarried. He could take that particular blow, but he is more worried about losing her from his newspaper as she is his star reporter. As a result he tries every lowdown trick in his arsenal in order to derail the engagement. His Girl Friday is another gem from this classic era of screwball comedies.
14 – The Apartment – In a rare turn without wingman Walter Matthau, Jack Lemmon stars as a man so desperate to climb the corporate ladder that he loans out his apartment to company bigwigs for illicit trysts. However, things get complicated when he falls in love with the mistress of his boss. The film went on to win the Oscar for Best Picture, a very rare achievement for a comedy film.
13 – Wall-E – One of the best animated movies of all time is also arguably a romantic comedy at heart. Pixar continues to crank out one original story after another and Wall-E is no exception. Wall-E is the story of a trash-collecting robot who falls in love with Eve, a robot scout who visits his planet, ends up following her onto her ship, and gets in a series of misadventures that ultimately end in the salvation of mankind. Not just your average cartoon, as you can see. Wall-E is not only a touching story, but there is plenty of humor for kids and adults alike. Don’t dismiss it as just a kid’s movie. It has more depth than most romantic comedies by far.
12 – Moonstruck – There are few plot devices more popular in romantic comedies than the love triangle. Moonstruck puts its own twist on the genre as Cher gives an Oscar-winning performance as a widow who finds herself choosing between two brothers, one who represents safety, stability and comfort, and the other who represents excitement and adventure.
11 – Harold and Maude – Now this one definitely sets itself apart from the other movies on the list if only because of the age difference between this bizarre couple. Harold, 20 and Maude, 79 aren’t your average movie couple to be sure. He is moody and obsessed with death, and she has a passion for life unmatched by most. Intrigued? If you haven’t seen the film you will be surprised at how it all works out.
10 – Roman Holiday – Audrey Hepburn, not to be outdone by Katherine, squeaks into the top 10 romantic comedy movies with this 1953 film about a Princess who manages to shake loose from her entourage only to fall asleep on a park bench. It is here that Joe Bradley (Gregory Peck), a newspaper reporter discovers her, though is completely unaware of who she is. Things get complicated once he discovers the truth, and the comedy really starts to roll.
9 – City Lights – You’ll note the absence of Drew Barrymore and Tom Hanks as we get into the true all time classics on this list. City Lights is considered one of the best films of all time in any genre, and its star Charlie Chaplin is as big an icon as any in the history of movies. Chaplin delivers his usual entertaining brand of slapstick in this touching tale about a tramp who goes to absurb lengths to raise money for surgery to restore sight to a blind girl he meets on the street.
8 – Manhattan – Woody Allen and Diane Keaton team up in this Woody Allen creation about a man with a complicated love life to say the least. After his wife (Keaton) divorces him, he goes on to date a high school girl of just 17 years of age. However, dissatisfied with the relationship he sets his sights on the mistress of his best friend. As you can imagine complications ensue, and you can’t help but laugh at the plight that Allen’s character Isaac has gotten himself into.
7 – Four Weddings and a Funeral – Though we may have seen the last of Drew Barrymore on this list Hugh Grant manages to sneak in one more appearance on this list. This time he plays the part of Charles, a bachelor with a string of failedrelationships behind him. However that is all fated to change as he keeps running into an American woman named Carrie (Andy McDowell) at every wedding (and funeral) he attends.
6 – Some Like It Hot – Again we find Lemmon without Matthau in this classic comedy about a pair of musicians (Jack Lemmon and Tony Curtis) who witness a mob hit, and try to escape detection by dressing in drag and joining and all girls band. Marilyn Monroe also co-stars in the film widely considered to be one of the best ccomedy movies of all time.
5 – It Happened One Night – The 1930s seemed to be the era of screwball comedies, and It Happened One Night fits both the time period and the genre. Claudette Colbert stars as Ellie, a millionaire’s daughter who marries against her father’s wishes. Enraged, he has the marriage annulled and tries to take her back home against her will. She escapes, and accepts the aid of reporter Peter Warne (Clark Gable) who agrees to help her get back to the man she loves in exchange for a story. To further complicate matters (because complication is the key component in a screwball comedy) the two fall in love along the way.
4 – Eternal Sunshine of the Spotless Mind – This one might not be on the radar for most people when it comes to romantic comedies, but it is one of the truly touching and original movies to come out of Hollywood in the past decade. Jim Carrey stars in a role that is a departure from his early movies like Ace Ventura: Pet Detective and The Mask. In the film he plays Joel, a man whose recent break-up is made even more painful when he discovers his ex has had a procedure to erase all memory of him. He decides to return the favor, but as the procedure begins to take effect he decides he can’t part with the memory of her, no matter how painful it might be.
3 – When Harry Met Sally – This one is on just about everyone’s list of good romantic comedies and was a no-brainer for a high spot on my list as well. Meg Ryan is at her best, and Billy Crystal is even better opposite her than Tom Hanks. Crystal’s sarcasm throughout the film is hilarious and Ryan’s fake orgasm in the restaurant has gone on to become one of the most famous scenes inHollywood history. Ultimately the movie is about whether friendship between a man and a woman can withstand the pressure of sex, but it is the adventure along the way that is truly entertaining.
2 – The Philadelphia Story – It should be a surprise to no one seeing Katherine Hepburn one more time on this list. This time she has her hands full of suitors as she finds herself caught between her ex-husband, her fiancée, and a handsome reporter she finds herself attracted to. A love triangle is bad enough, but she has herself caught up in a love square. What is a girl to do?
1 – Annie Hall – Woody Allen’s semi-autobiographical story of life in New York with Diane Keaton narrowly scoops top spot on the list of the top 50 best romantic comedies of all time. This time Allen plays a comedian who falls in love with a singer named Annie Hall. The pair are completely neurotic when separated, and together they are exponentially worse. Eventually they break up, and much of the film focuses on Allen’s bizarre recreation of events as he tries to pinpoint what caused their love to fracture.