Hey gents, don’t give up on the romantic comedy genre just yet. I can help. My wife loves romantic comedies, and I usually watch them with her. After a few waterboarding sessions, I would probably confess that I like rom-coms almost as much as she does. So in the course of thirty something years together, I have formed my opinions on the subject. First off, rom-com is a genre fraught with danger: many are mere chick flicks with plenty of soapy romance and a dash of lame humor, some feature annoying characters who talk too much, and finally some screen couples fail to strike a tiny spark of screen chemistry. However, once in blue moon, a romantic comedy comes along that is a pleasure to watch. The best ones deliver plenty of good laughs, and you find yourself genuinely rooting for the couple to get together which is the raison d'etre of the film in the first place. So gentlemen, listed below are my favorite romantic comedies, beginning in the 60’s and including at least one film per decade up to the present. Enjoy!
1. How to Steal a Million 1968
This movie has a lot of things going for it. The two outstanding leads, Audrey Hepburn and Peter O'Toole, both at the very pinnacle of their careers, make the best movie couple of the decade. The plot hardly matters as they fumble and bumble through some criminal hijinks. And Peter O'Toole, so famous for starring in serious dramas, seems to be thoroughly enjoying himself in this lighthearted caper film. As he drives through Paris in a convertible E-type Jaguar, with Audrey beside him, could you capture a better moment on the big screen?
2. They Might Be Giants 1971
This is an underrated rom-com film with a high quirky factor that is very entertaining with also some surprisingly touching scenes. The cast is excellent; even the minor characters are well done. The central performance by George C. Scott is outstanding. He has a genius for comedy, and perfectly portrays Justin Playfair, a respected judge who suffered a mental breakdown and thinks he is Sherlock Holmes. Justin, in his own fantasy world, brings Sherlock Holmes alive better than the troupe of “serious” actors I have seen before or since. Justin’s sympathetic doctor, Mildred Watson (Joanne Woodward), understands that Justin is a few clowns short of a full circus, and she tries her best to help him. Together Holmes and Watson go bravely in search of arch-enemy Moriarty, and in their own sweet, goofy way find true love.
A note about the title: It is derived from the Cervantes' novel "Don Quixote." Quixote tilted at windmills because he was sure they were giants. In this movie, Justin states that Quixote was crazy to think that windmills are giants. But to wonder if "they might be giants" - that's an entirely different matter.
3. “10” 1979
This movie was hot stuff when it came out in 1979: I am referring to both the movie, and actress, Bo Derek in her movie debut. Dudley Moore was already a box-office star, but nobody had heard of Derek before this movie. She became an overnight sensation, posed for Playboy magazine and so on. She didn't need too many lines in the film to make an impact; she simply walked down the beach in her bathing suit. The camera loved Bo, and the number "10" suddenly had new meaning in the parlance of pop culture. A mid-life crisis and a trophy wife are nothing new, yet the film guides us to ponder these themes without getting too serious. This is a career best role for Dudley... he's able to come across as a sympathetic, yet funny person. This film is also the solitary, 100% good movie in Bo Derek’s career (she was in a string of legendary film disasters following this flick). An outstanding supporting cast gives this movie solid depth with never a dull scene. A time capsule of the 70’s, and an artistic success. One for the personal DVD collection.
4. Something Wild 1986
Lulu (Melanie Griffith) has a certain clueless '80s charm at work here as she kidnaps yuppie Charlie (Jeff Daniels), and embarks on a crazy, sex filled road trip. Charlie agrees to pose as her date at her high school reunion. But then at the reunion party, it comes – wait for it! – a tone shift that may leave some viewers standing flatfooted looking in the wrong direction. A film shifting atmosphere from light comedy to twisted menace is quite rare, and keeps the audience guessing until the final scene. It's not often you get a movie that blends genres so seamlessly. An underrated flick.
5. Blame it on Rio 1993
A fun movie with plenty of humor, a taboo romance, beautiful scenery, and a surprise ending. What more do you want? Michael Caine does a wonderful job with an out of character comedy performance. His deadpan reaction and dry delivery is perfect for this lighthearted comedy. Michelle Johnson does an amazing job with a complex role. She adds energy and believability to the offbeat plot. She made this movie when she was only 18 years old, yet displayed more talent and poise than most of the more mature actresses we see today. Why this beautiful actress hasn't become a big star is puzzling.
6. Groundhog Day 1993
Here’s a much beloved film from the Captain Obvious List. Most of what can be said about this Harold Ramis romantic-comedy-fantasy has already been said a million times, and I won't repeat it. I will add, however, one generally unknown point; this film project resulted in a lasting rift between Ramis and Bill Murray. Too bad, there seemed to be plenty of glory to satisfy both of their egos. Guess not.
Other Rom-Com movies from Captain Obvious list: Anne Hall, Goodbye Girl and As Good As It Gets. These three film were swooned over by the TV critics and won glittery awards.
7. Dave 1993
Due to a combination of bizarre circumstances, Dave, a regular guy and small businessman, steps up to substitute for the President of America. He is indifferent to politics and his only qualification is a striking resemblance to the elected President; however, Dave takes to the task like a duck to water. He tackles the job with grit and common sense. With Dave’s leadership, the federal government actually starts to solve some long shirked dilemmas. The First Lady (Sigourney Weaver) falls for him along the way. So the deeper emotional core of this movie is the belief by all true-blue, backbone Americans that career politicians are easily replaceable and actually damage our republic with their incompetence. This underrated, lighthearted movie is deliciously subversive and makes a good rental. Dave is well played by Kevin Kline in his career best performance.
8. High Fidelity 2000
From the first frame, the movie dwells on a romantic breakup. That’s the old rom-com formula, right? Wait a minute, Rob (John Cusack) has a top-five list for everything, including his romantic breakups. If this plot sounds too heavy, don’t worry, it is not because much the of screen time is spent at Championship Vinyl, a record store owned by Rob. The best and funniest scenes in the movie are when we are inside Championship Vinyl seeing the staff (Rob, Dick and Barry) interact with each other and the customers. There is never a dull moment in Championship Vinyl; the guys argue with customers about music trivia, insult musical tastes and artists, or flirt with the girls, and battle shoplifters. Rarely does the cash register ring up a sale, but it is comedy gold every day the store is open for business. About the romance? I suggest you see the movie, learn some music trivia, and find out if they get back together. I love this movie. Oscars for everybody!
9. How to Kill Your Neighbor’s Dog 2000
Overall a smart script, crackerjack dialogue, and good acting by an impressive cast. Ken Branagh nails the part of Peter McGowan, a middle aged man battling writers block together with challenges of family and marriage. The love chemistry with his wife, Robin Wright-Penn, is as good as it gets in the movies, and the support characters were played to perfection – so believable and real, without a false note. The movie deals with several adult themes by using humor to soften the message, so it never drags or bores. The movie has plenty of funny scenes; the clash with the TV talk show hostess, the costume party, all the rehearsal scenes, and the fist fight in the bathroom – all these scenes are comedy masterpieces. About the dog – well, just watch the movie.
10. Cashback 2006
Ben Willis works the graveyard shift at a grocery store where his wacky coworkers decide to help him get some romance back in his life. Let the fun begin! This is an offbeat UK independent movie with an unknown cast of young, talented actors. Ignore the negative reviews about female nudity in this film because it is portrayed artistically. Ben is a struggling artist who has a passion for painting nudes. It is part of his life and his education. This film is very entertaining and not at all predictable. It is just the sort of fun movie the romantic comedy genre could use more often.
11. Eternal Sunshine of the Spotless Mind 2004
A clever futuristic device in a movie instantly catches my attention. I am hooked. So here we have a business that can erase the bad memories of a troubled relationship, enabling the patient to start over with a clean slate. Sounds terrific, right? Wait a minute. As we can easily suspect, altering the human brain and removing cupids love arrows will create unexpected consequences. No spoilers. Underrated actor Jim Carrey and Kate Winslet, as eccentric girlfriend Clementine, are fun to watch in the lead romantic roles. Arguably career best performances for the both of them.
12. Stranger than Fiction 2006
The charm of this feel-good movie is in the fresh concept and perfect casting. Harold Crick, an IRS field agent, finds he has no control over his life which leads him to really appreciate his life. Although the premise is 100% fantasy, the concept is intriguing and compelling. Very good ensemble cast: Will Ferrell plays it low-key and believable, Dustin Hoffman and Emma Thompson are unusual in a funny sort of way, and Maggie Gyllenhaal, as the anti-establishment baker being audited by Crick, is a delight watch in her career best performance. Pure movie entertainment with excellent performance by all the actors.
13. Blended 2014
This flick was a pleasant surprise; I laughed nearly the whole movie. Adam Sandler and Drew Barrymore make an entertaining movie odd couple, and Sandler is effective as a tenderhearted father of three girls. The film’s emotional impact is due largely to him. A funny supporting cast; especially Kevin Nealon and the staff at the African resort in Sun City. The boy-girl relationship gets off to a rough start, but of course we know how the story will end up. That’s the Hollywood law of the Happy Endings that we expect from the feel good flicks.
Written by Ben Clark. Copyright 2016-2021. All rights reserved.