50 Years of Romantic Comedies: The Best Rom-Com From Each Year
Peanut butter and jelly, garlic bread and pizza, milk and cookies — all are classic pairings that have stood the test of time.. Romantic comedies can be added to that list as well, as they blend the chemistry and emotion of romance with the humor of comedy to create a crowd-pleasing formulas that delight audiences for generations.
Here we take a journey over 50 years and select our favorites, one movie per year, that are worth checking out for the first time or revisiting. But be forewarned, you’re going to need to keep your box of tissues handy. Tears in many cases are expected, some because of the love stories and some because of the laughter, but all will be welcome after viewing these 50 films. Want to know where they are airing? Just click on the movie title.
1950s
Everett Collection
1950 – Father of the Bride Spencer Tracy, Joan Bennett and Elizabeth Taylor starred in this exaggerated look at the chaos and fun involved in planning a wedding, a film that later spawned a remake with Steve Martin and Kimberly Williams in 1991.
1951 – Father’s Little Dividend The stars of the 1950 hit Father of the Bride returned for this look at Stanley Banks (Spencer Tracy) becoming a grandfather and his daughter Kay (Elizabeth Taylor) a mother.
1952 – Singin’ in the Rain We all remember the singing and dancing in this classic movie musical, but Gene Kelly and Debbie Reynolds were an amazing combination for a romance film, and Donald O’Connor definitely helped the couple “Make ‘Em Laugh” throughout this whimsical trip. A personal favorite and totally rewatchable over and over again.
1953 – Roman Holiday Gregory Peck and Audrey Hepburn star in a story about a sheltered princess who falls in love with an American reporter. A classic for anyone dipping their toe into the ’50s.
1954 – Sabrina Humphrey Bogart and Audrey Hepburn star in the story of Sabrina Fairchild, the daughter of a chauffeur who returns home after studying in Paris and finds herself caught in a love triangle between two wealthy brothers.
1955 – Lady and the Tramp An animated film? Of course, it’s a classic story with a true romance between a pampered cocker and a jaunty mutt that only Disney could make.
1956 – High Society A musical remake of the Oscar-winning A Philadelphia Story, the cast makes this unmissable with Bing Crosby, Grace Kelly, Frank Sinatra and Louis Armstrong, along with the music of Cole Porter. Love strikes the high society.
1957 – The Pajama Game Lots of possibilities, but we need to look to Doris Day here in a film about negotiations for more than a 7.5-cent-an-hour raise. The film was based on the Broadway musical featuring choreography from Bob Fosse.
1958 – Gigi Leslie Caron and Maurice Chevalier star in his musical about a free-spirited girl who is being groomed by her family to become a wealthy man’s mistress, only to upend their plans when she falls in love with him.
1959 – Pillow Talk Doris Day is back, this time alongside Rock Hudson in the story of an uptight interior decorator and a carefree songwriter who go from enemies to lovers while sharing a telephone party line.
1960s
Everett Collection
1960 – The Apartment: Jack Lemmon, Shirley MacLaine, and Fred MacMurray are featured in this all-time classic where an insurance clerk tries to rise in his company by letting its executives use his apartment for trysts.
1961 – Breakfast at Tiffany’s Audrey Hepburn stars as Holly Golightly, a charming but eccentric New York socialite whose glamorous lifestyle is disrupted when she befriends a struggling writer.
1962 – That Touch of Mink He wants an affair; she is saving herself for marriage. This is the only film featuring Hollywood icons Doris Day and Cary Grant together, and was one of the last major films in each of their respective screen careers.
1963 – Charade The French Alps serve as the romantic backdrop for this Cary Grant and Audrey Hepburn starrer. With Hitchcock-like spoofs, a silly plotline, and the duo’s magnetic charm, this film is forever fun, fun, fun!
1964 – What a Way to Go! Widowed four times, Shirley MacLaine’s character recounts her four marriages. With Paul Newman, Robert Mitchum, Dean Martin, Gene Kelly and more.
1965 – Beach Blanket Bingo This was the fourth of the successful Frankie Avalon and Annette Funicello beach party movies — we have to find room for an entire genre within the genre of fun.
1966 – How to Steal a Million Audrey Hepburn and Peter O’Toole are delightful in this fleet-footed caper with loads of charm.
1967 – Barefoot in the Park Riding in a horse-drawn carriage en route to the Plaza Hotel in New York City is romantic enough, but Robert Redford and Jane Fonda ooze with chemistry and make this film vivacious and fun.
1968 – I Love You, Alice B. Toklas! Peter Sellers as an uptight lawyer who falls for a hippie is precious fun.
1969 – Hello, Dolly! Barbra Streisand and Walter Matthau star. Before match.com, there were matchmakers like Dolly Levi.
1970s
Everett Collection
1970 – The Cheyenne Social Club Produced and directed by Gene Kelly, this Western finds James Stewart as a Texan cowpoke who inherits a Cheyenne brothel run by Shirley Jones. Henry Fonda also saddles up as one of Stewart’s pals.
1971 – Harold and Maude Hal Ashby’s classic about the unlikely love affair between a morose young man (Bud Cort) and an octogenarian (Ruth Gordon) that has landed on several best comedy lists. This unconventional romance is a must-see.
1972 – The Heartbreak Kid Charles Grodin and Cybill Shepherd star in this war of the sexes comedy, and Jeannie Berlin and Eddie Albert received Supporting Actress and Actor Academy Award nominations.
1973 – A Touch of Class Glenda Jackson won the Academy Award for the story of a married American businessman and a British divorcée who begin a carefree holiday romance that unexpectedly turns into love.
1974 – The Lords of Flatbush Members of this social club, played by Sylvester Stallone and Perry King, have more interest in romance.
1975 – The Fortune Trying to win the affections of an heiress, Warren Beatty and Jack Nicholson star as two hustlers going toe-to-toe who will stop at nothing.
1976 – I Will… I Will… For Now This year didn’t see much in the genre, so Elliott Gould and Diane Keaton are going to have to do in this quirky love triangle.
1977 – The Goodbye Girl Richard Dreyfuss was (at the time) the youngest actor to win the Academy Award for Best Actor for his performance opposite Marsha Mason.
1978 – Heaven Can Wait Warren Beatty stars in this film as a quarterback mistakenly killed in an auto accident, which was nominated for nine Academy Awards and eventually won just one for Best Art Direction.
1979 – 10 Blake Edwards’ film that established Bo Derek was pure genius. Also starred Dudley Moore and Julie Andrews.
1980s
Universal Pictures/Everett Collection
1980 – Seems Like Old Times Chevy Chase and Goldie Hawn re-team after 1978’s Foul Play and spark the same chemistry.
1981 – Arthur Dudley Moore stars in this story of a man searching for everything — on the rocks, of course.
1982 – The Best Little Whorehouse in Texas Burt Reynolds and Dolly Parton sing and dance their way into your heart. Charles Durning earned a Best Supporting Actor Oscar nomination.
1983 – Risky Business Tom Cruise showed us how following your hormones and business smarts can sometimes pay off.
1984 – Sixteen Candles Molly Ringwald in that most special of all teen birthdays and crushes.
1985 – Better Off Dead…/The Sure Thing Love hurts indeed. Two John Cusack films for the price of one. Better Off Dead… is an all-timer in the comedy genre.
1986 – About Last Night Starring Rob Lowe and Demi Moore alongside Jim Belushi and Elizabeth Perkins, two single Chicago professionals who try to turn a one-night stand into a relationship.
1987 – Can’t Buy Me Love Patrick Dempsey rents the most popular girl in school to make him cool. Starring Amanda Peterson as Cindy Mancini, the object of his affection.
1988 – Bull Durham Minor league baseball player teams with a muse to help train a fledgling baseball star. Kevin Costner, Susan Sarandon and Tim Robbins star.
1989 – When Harry Met Sally… Can friends fall in love? “I’ll have what she’s having” — Meg Ryan made that line possible with her showing Billy Crystal that faking it was possible.
1990s
TriStar Pictures/courtesy Everett Collection
1990 – Pretty Woman Julia Roberts and Richard Gere in the ultimate fairy-tale love story as a corporate raider hires a vivacious street-smart escort for social events.
1991 – Career Opportunities Jennifer Connelly is the object of Frank Whaley‘s affection.
1992 – Boomerang Eddie Murphy is a player, but even players get played when Robin Givens is involved.
1993 – Sleepless in Seattle Meg Ryan with Tom Hanks in the story of love over the radio.
1994 – Four Weddings and a Funeral Hugh Grant is a committed bachelor, but Andie MacDowell just may change that.
1995 – While You Were Sleeping The romantic side of Sandra Bullock with Bill Pullman along in this one. She plays a lonely woman who pretends to be the fiancée of an injured man and is charmed by his family.
1996 – Jerry Maguire You had us at Tom Cruise and Renée Zellweger, but then you threw in surprise fun from Cuba Gooding Jr., Regina King and Kelly Preston, and you made it a real winner.
1997 – As Good as It Gets Love and romance just don’t age, as Jack Nicholson, Helen Hunt and Greg Kinnear prove in this one. Nicholson plays a curmudgeon who finds love and friendship on a road trip.
1998 – The Wedding Singer While the music is definitely top billing in this film, Drew Barrymore and Adam Sandler prove that sometimes the right people can get together.
1999 – Runaway Bride Julia Roberts seems to never really want to go down the aisle, but with Richard Gere as a reporter following her, the chemistry between the two is back.
Remind 
February 2021
1990s Rom-Coms
Pop some popcorn and cozy up to feel-good movies and TV shows from a generation ago.
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