Romantic Movies to Fall in Love With All Over Again
(07/31/2020)
Romantic stories, especially funny ones, lift us up like Johnny Castle hoisting Baby into the air at the end of DIRTY DANCING. Whether you watch alone, with your partner, or as part of a virtual date night, these movies remind us of our best days, and offer the promise of more sweet nights to come in the future.
If you want to fall back into a relationship with your favorite films, here are seven romantic movies to fall in love with all over again.
My Best Friend’s Wedding (1997)
[Image Credit: TriStar Pictures]
We begin with a movie that features one of the queens of romantic comedy — Julia Roberts — and with a setup that shows how the rom-com can always do something different even when the basic formula is pretty consistent from movie to movie. MY BEST FRIEND'S WEDDING is nominally about the antics that food critic Jules, played by Roberts, gets up to in order to sabotage the wedding of the lifelong friend she realizes she's actually in love with. It's really about the platonic relationship between Jules and George (Ruper Everett), the gay friend who helps Jules pull off her scheme.
Tootsie (1982)
[Image Credit: Columbia Pictures]
An impossible-to-work-with New York actor dresses up as a woman to audition for a role and soon becomes the toast of the media set thanks to his fiery and very much off-script approach to the part. Dustin Hoffman plays both Michael Dorsey and his alter-ego, Dorothy Michaels, with just the right pitch of absurdity and vulnerability. The romantic comedy develops as Michael falls for co-star Julie (Jessica Lange) who doesn't know he's a man and is pursued by Julie's father (Charles Durning), who doesn't know he's a man. Director Sydney Pollack mines the script (which had input from uncredited giants like Barry Levinson and Elaine May) for insightful and very funny observations about the roles of men and women in the workplace and in relationships.
When Harry Met Sally (1989)
[Image Credit: Columbia Pictures]
Many movies have attempted to mimic the snappy patter and lively performances of the classic screwball comedies which are the bedrock of the romantic comedy — movies like BRINGING UP BABY, IT HAPPENED ONE NIGHT and THE AWFUL TRUTH. Rob Reiner's WHEN HARRY MET SALLY captures that lightning in a bottle, in such a way that it completely rewrote the whole idea of the genre. It's not a stretch to say that this story of two strangers who grow to love one another over the course of many years is one of the best, funniest and most "true" rom-com out there.
You’ve Got Mail (1998)
[Image Credit: Warner Bros. Pictures]
We often think of rom-coms in terms of grandiose and happy unions, but they are built on conflict. Meg Ryan and Tom Hanks star in YOU'VE GOT MAIL as rival booksellers — she a struggling independent and he the scion of a family which owns a mega-chain — who fall in love through anonymous online chat. Their journey towards a real-life romance is nothing short of enchanting. And if YOU'VE GOT MAIL is one of your go-to romcoms, make sure to check out the film it is based on. That would be 1940's THE SHOP AROUND THE CORNER, starring Margaret Sullavan, James Stewart and Frank Morgan, which is one of the most wonderful films of the classical Hollywood era.
Pretty in Pink (1986)
[Image Credit: Paramount Pictures]
With 20-something actors often playing high school students in movies, it's rare to see a movie that captures the tentative awkwardness of the teen years — but PRETTY IN PINK shows how it can be done. Molly Ringwald is more like perfect in pink as she plays Andie Walsh, who is caught in a triangle between the rich preppie Blaine (Andrew McCarthy) and quirky best friend Ducky, played by an iconic Jon Cryer. Their fumbling attempts to find romantic fulfillment lead to a genuinely tear-jerking climax that stands as one of the great '80s movie endings.
Clueless
[Image Credit: Paramount Pictures]
CLUELESS manages to be rooted deeply in the '90s, with deliberately exaggerated fashions and era-defining quotes, but it is also a timeless, all but perfect romantic comedy. Director Amy Heckerling made one of the great casting choices when she chose Alicia Silverstone to play Cher, a meddling matchmaker based loosely on Jane Austen's "Emma." Make that two choices, since she also picked the virtually unknown Paul Rudd to play the guy who finally catches Cher's eye.
Dirty Dancing (1987)
[Image Credit: Vestron Pictures]
We'll divert slightly from the comedy approach to swoon over this cross-the-tracks romance which subs in dancing for jokes. (It might, at least, fit into the Golden Globes "comedy or musical" category!) DIRTY DANCING pirouettes on the classic fantasy of finding summer love. With the emotionally rich performances from Jennifer Grey and Patrick Swayze — playing teen vacationer Baby and the slightly older dance teacher, Johnny — it's a giddy drama of infatuation with rich veins of weighty ideas buried in the love story.