Annie Hall (1977) Bogart and Bergman can have Paris. The rest of us will take the Manhattan of Woody Allen and Diane Keaton in Annie Hall. Somewhere between Freud and Groucho Marx, neurotic paranoiac Alvy Singer finds love, and Allen creates a masterpiece of romantic chaos. With superb dialogue and innovative style, the Academy Award-winning film is a hilarious, painfully astute take on modern love, as well as a fascinating time capsule of New York in the 1970s.
When Harry Met Sally… (1989) In this grand homage to Allen, the witty and wonderful When Harry Met Sally…distills Annie Hall to produce 100 percent pure romantic comedy so successfully, it becomes the winning formula for the next decade. Rob Reiner and Nora Ephron kick Hall up a notch by — bam! — adding even more New York, even more swing soundtrack, and introducing so much nutty Meg, it creates an inexhaustible cute jones for Ryan, especially when paired with Ephron. The legendary faux-big-O scene still gives genuine laughs, and the chemistry between Billy Crystal and Ryan endures (even if their ’80s duds do not).
Four Weddings And A Funeral (1994) No one does stammering romantic better than Hugh Grant. In his breakout role as the shy Brit in pursuit of luscious American Andie MacDowell, he sets the nervous-blinking, brow-kneading standard to which all others now aspire. But his performance is just one reason Weddings (not to mention its descendants, Notting Hill and Bridget Jones’s Diary) has charmed viewers on both sides of the pond. Is there anything more swoony than a buttoned-up Brit reduced to quoting the Partridge Family in the name of love?
Sense And Sensibility (1995) Rare is the actor who can also pen a mean screenplay. But Emma Thompson’s (who also plays level-headed Elinor Dashwood) wonderfully droll, Oscar-winning adaptation of then It Girl Jane Austen’s novel slyly tweaked the stale social mores of Regency-era England and displayed a keen understanding of love’s timeless ability to turn rational folk into tongue-twisted fools.
A Room With A View (1986) Merchant ivory, the peddlers of period ”doily movies,” introduce us to a ravishing Helena Bonham Carter (joined by a sparkling Maggie Smith) in this comedy of genteel Brits navigating the game of love. As proper Lucy Honeychurch, Bonham Carter must make a rather obvious choice: Stay with her prissy fiance, Cecil (Daniel Day-Lewis), or run off with a dashing admirer (Julian Sands) she meets in Florence. Italy’s sun-dappled piazzas are a bonus, becoming the perfect metaphor for sensuous, unbridled passion.
7 Sid & Nancy (1986) Love isn’t always roses and chocolate. Sometimes it’s shared syringes and torn fishnets—ugly and tragic. Perhaps no recent love story is as ugly and tragic as that of Sex Pistol Sid Vicious (Gary Oldman) and girlfriend Nancy Spungen (Chloe Webb). Alex Cox’s depiction of the punk-rock junkies — whose relationship ended in murder and a drug overdose — proves that romance can blossom in different shapes, styles, and sounds.