The Top 50 modern movie romances for Valentine’s Day

WTOP's Jason Fraley salutes modern movie romances

Valentine’s Day is the perfect time to watch a romantic flick, but with so many options, how do you choose?

Hollywood’s Golden Age introduced classics like “Casablanca” (1942) and “West Side Story” (1961).

The Hollywood Renaissance gave us landmarks like “The Way We Were” (1973) and “Grease” (1978).

And the blockbuster ’80s delivered hits like “The Princess Bride” (1987) and “Dirty Dancing” (1987).

But what if you’re looking for something more recent?

Instead of ranking the best of all time like past years, what if we only considered the modern era?

To define “modern,” I chose the last 30 years from 1989-2019 (after all, 2020 just began).

So without further ado, break out the flowers and the chocolates.

Let the countdown begin!

50. Henry & Lucy – “50 First Dates” (2004) 

After charming us in “The Wedding Singer” (1998), Adam Sandler and Drew Barrymore reunited for this beloved rom-com about an amnesic woman who keeps forgetting her boyfriend.

49. Kat & Patrick – “10 Things I Hate About You” (1999)

Based on William Shakespeare’s play “The Taming of the Shrew,” few movie moments are as romantic as Heath Ledger singing “Can’t Take My Eyes Off You” to Julia Stiles bounding down the high school bleachers.

48. Frank & Rachel – “The Bodyguard” (1992)

Whitney Houston not only romanced Kevin Costner, she also belted Dolly Parton’s “I Will Always Love You” into arguably the best cover song ever.

47. Juliet & Mark – “Love Actually” (2003)

One of the most iconic romantic scenes of the 21st century is also kinda creepy, as Andrew Lincoln stands on Keira Knightley’s doorstep flipping cue cards to profess his love.

46. Hitch & Sara – “Hitch” (2005)

Will Smith plays a charming “date doctor” trying to set up a hopelessly dorky Kevin James, only to find it much harder to woo Eva Mendes’ jaded gossip columnist in the hectic dating culture of New York City.

45. Anna & William – “Notting Hill” (1999)

After penning the Oscar-nominated script for “Four Weddings and a Funeral” (1994), writer Richard Curtis reunited with Richard Grant, only this time with Julia Roberts for the first of several rom-coms together.

44. Lucy & Jack – “While You Were Sleeping” (1995)

No list of modern movie romances would be complete without Sandra Bullock, who earned a Golden Globe nomination romancing Bill Pullman, who famously made a toll-booth “token” proposal. Asked when she fell in love with him, she replied, “While you were sleeping.”

43. Stephen & Jane – “The Theory of Everything” (2014)

Eddie Redmayne won an Oscar for mastering the physicality of Stephen Hawking, but it was his bond with wife Jane (Felicity Jones) that endures.

42. Queen & Slim – “Queen & Slim” (2019)

One of the most criminally underrated movies of 2019 is this modern “Bonnie & Clyde,” as Daniel Kaluuya and Jodie Turner-Smith go on the lam after their Tinder date is interrupted by a racially-charged traffic stop.

41. Clarence & Alabama – “True Romance” (1993)

Christian Slater’s pop culture geek marries Patricia Arquette’s call girl in this romantic crime adventure directed by Tony Scott and written by Quentin Tarantino.

40. Hannah & Jacob – “Crazy, Stupid, Love” (2011)

Penned by “This Is Us” creator Dan Fogelman, this tale of interweaving love stories first introduced us to the romantic potential between Emma Stone and Ryan Gosling.

39. Chow & Chan – “In the Mood for Love” (2000)

After his breakthrough hit “Chungking Express” (1994), filmmaker Wong Kar-Wai delivered this edgy Palme d’Or nominee with some of the finest cinematography you’ll ever see.

38. Adonis & Bianca – “Creed” (2015)

Just as Rocky and Adrian were iconic Hollywood lovers in the 1970s, Michael B. Jordan and Tessa Thompson kept the fires burning as boxer Adonis Creed and singer Bianca in Ryan Coogler’s sequel, “Creed.”

37. Carol & Therese – “Carol” (2015)

Director Todd Haynes lushly paints this heartbreaking tale of Cate Blanchett and Rooney Mara’s forbidden romance in an unwelcoming 1950s Manhattan.

36. Zula & Winter – “Cold War” (2017)

After winning an Oscar for “Ida” (2013), Polish filmmaker Pawel Pawlikowski followed up with this stark romance about a singer and music director fleeing communism.

35. Elisa & Fish – “The Shape of Water” (2017)

It should have never beaten “Get Out” for Best Picture, but Guillermo del Toro’s sci-fi romance is a modern-day “Splash” (1984), with Sally Hawkins’ mute janitor falling for a top-secret fish man.

34. Robert & Francesca – “The Bridges of Madison County” (1995)

After a career of Man with No Name westerns and Dirty Harry cop dramas, Clint Eastwood showed his soft side, directing himself as a traveling photographer who falls for lonely housewife Meryl Streep.

33. Stevens & Miss Kenton – “Remains of the Day” (1993)

Director James Ivory (“A Room with a View”) saw romantic potential in Hannibal Lecter, casting Anthony Hopkins in his next role as a butler falling for Emma Thompson’s housekeeper in pre-war Great Britain.

32. Johnny & June – “Walk the Line” (2004) 

Fifteen years before his Oscar win for “Joker,” Joaquin Phoenix did his best Johnny Cash impression in this “ring of fire” romance with Reese Witherspoon’s Oscar-winning June Carter Cash.

31.  Kumail & Emily – “The Big Sick” (2017) 

Kumail Nanjiani and Zoe Kazan yanked the rom-com right out of a coma, as tragedy forces the protagonist to awkwardly bond with her parents (Holly Hunter and Ray Romano) in this indie gem.

30. Andy & Trish – “The 40-Year-Old Virgin” (2005)

Most folks remember its chest-waxing comedy with Paul Rudd and Seth Rogen, but the beating heart of Judd Apatow’s best film is the adorable romance between toy collector Steve Carell and single mom Catherine Keener.

29. Juno & Paulie – “Juno” (2007)

Diablo Cody won an Oscar for her daring screenplay about a teen pregnancy between Michael Cera and Ellen Page, who debates adoption with her parents (J.K. Simmons and Allison Janney) and potential foster parents (Jason Bateman and Jennifer Garner).

28. Richard & Mildred – “Loving” (2016)

Joel Edgerton and Ruth Negga shine in this true story of Richard and Mildred Loving, who wage a historic Supreme Court case for interracial marriage in 1960s Virginia. “You tell the judge I love my wife.”

27. Melvin & Carol – “As Good as it Gets” (1997)

James. L Brooks directed Jack Nicholson to his third career Oscar as a grouchy author who memorably tells Helen Hunt’s waitress: “You make me want to be a better man.”

26. Tom & Summer – “500 Days of Summer” (2009)

Joseph Gordon-Levitt and Zooey Deschanel defined the genre for millennials as a split screen showed “expectations vs. reality.”

25. Christian & Satine – “Moulin Rouge!” (2001)

Ewan McGregor was never more charming than when he wooed Nicole Kidman by singing pop-song medleys directed by the dazzling Baz Luhrmann after his post-modern take on “Romeo + Juliet.”

24. Anna & Kristoff – “Frozen” (2013)

After 76 years of Snow White, Cinderella and Sleeping Beauty needing a prince to save them, Disney finally flipped the script with an adorable romance between Anna and Kristoff that would culminate in “Frozen 2.”

23. Pat & Tiffany – “Silver Linings Playbook” (2012)

Bradley Cooper showed his dramatic potential across an Oscar-winning Jennifer Lawrence, bonding over anxiety medication in David O Russell’s football-themed precursor to “American Hustle” (2013).

22. Theodore & Samantha – “Her” (2013) 

Joaquin Phoenix’s loner fell for Scarlett Johansson’s computer operating system in Spike Jonze’s Oscar-winning sci-fi romance that predicted online dating. Don’t worry, Amy Adams was there to comfort him when he finally looked up from his screen.

21. Amelie & Nino – “Amelie” (2001)

Audrey Tautou’s Amelie grew from mischievous prankster to scavenger-hunt lover in this French masterpiece that saw her literally melt into a puddle of tears at her coffee shop.

20. Phil & Rita – “Groundhog Day” (1993) 

Heralded for its magical realism of a repeating day of Sonny & Cher deja vu, Harold Ramis’ masterpiece is at its core a romantic comedy as Bill Murray learns to love Andie MacDowell.

19. Ted & Mary – “There’s Something About Mary” (1998)

Ben Stiller loved Cameron Diaz since high school, when an unfortunate zipper incident caused a “bleeder” in this laugh-out-loud rom-com by the Farrelly brothers that gave hilarious new meaning to hair gel.

18. Aladdin & Jasmine – “Aladdin” (1992)

I dare you to find another movie moment — animated or not — that’s as wondrously romantic as Aladdin and Jasmine singing “A Whole New World” on a magic carpet ride over Agrabah.

17. Jesse & Celine – “Before Sunrise” (1995-2013)

Before his 12-year longitudinal masterpiece “Boyhood” (2014), Richard Linklater checked in with Ethan Hawke and Julie Delpy every nine years in “Before Sunrise,” “Before Sunset” and “Before Midnight.”

16. Mia & Sebastian – “La La Land” (2016)

Emma Stone won an Oscar romancing Ryan Gosling in some of the most magical musical scenes ever put to film, before the rug was yanked from them in the final act by Best Director winner Damien Chazelle.

15. Jack & Ally – “A Star is Born” (2018)

Just when you thought no one could top Judy Garland singing “The Man That Got Away” or Barbra Streisand singing “Evergreen,” Lady Gaga belted the Oscar-winning “Shallow” for Bradley Cooper’s tragic musician.

14. WALL-E & EVE – “WALL-E” (2008)

Parents and kids barely noticed that Pixar’s animated masterpiece is virtually silent because they were so invested in the adorable romance between WALL-E and EVE amid a dystopian trash heap.

13. Sam & Annie – “Sleepless in Seattle” (1993)

Nora Ephron’s remake of “An Affair to Remember” (1957) may just be the superior version, as Meg Ryan and Tom Hanks agree to meet atop the Empire State Building on Valentine’s Day.

12. Vivian & Edward – “Pretty Woman” (1990)

Its rags-to-riches hooker premise now seems dated, but the charming leads undeniably defined the genre, as Richard Gere snapped shut a necklace box while Julia Roberts reacted with her infectious laugh.

11. Lloyd & Diane – “Say Anything” (1989)

Writer/director Cameron Crowe turned John Cusack’s Lloyd Dobler into a rom-com icon hoisting a boom box over his head to blast Peter Gabriel’s “In Your Eyes” outside his lover’s bedroom window.

10. Noah & Allie – “The Notebook” (2004)

Nicholas Sparks’ signature adaptation launched the careers of Rachel McAdams and Ryan Gosling as the younger versions of Gena Rowlands and James Garner, who beautifully die holding hands.

9. Forrest & Jenny – “Forrest Gump” (1994)

It was one-sided for much of the movie, but after facing her “free bird” demons, Jenny returned to her roots to live with Forrest. As Robin Wright listened to Tom Hanks recount his journey, she lamented, “I wish I could have been there with you,” to which he replied, “You were.”

8. Sam & Molly – “Ghost” (1990)

After sculpting pottery to “Unchained Melody,” Patrick Swayze solved his own murder from the afterlife by contacting his grieving lover, Demi Moore, via Whoopi Goldberg’s Oscar-winning conduit. “Ditto.”

7. Joel & Clementine – “Eternal Sunshine of the Spotless Mind” (2004)

Screenwriter Charlie Kaufman reached his creative zenith in this Oscar-winning sci-fi script about two ex-lovers (Jim Carrey and Kate Winslet) who seek out a new technology to erase each other from their memories.

6. Chiron & Kevin – “Moonlight” (2016)

Director Barry Jenkins followed Chiron’s sexual orientation awakening over three phases of life, building to the most romantic diner scene ever put on film — and landing a deserving Best Picture upset.

5. Jack & Ennis – “Brokeback Mountain” (2005)

Ang Lee won a Best Director Oscar helming Jake Gyllenhaal and Heath Ledger as tragic cowboy lovers who don’t even notice the love letters in their tackle boxes left by wives Michelle Williams and Anne Hathaway. “I wish I knew how to quit you.”

4. Belle & Beast – “Beauty & The Beast” (1991)

Angela Lansbury sang the Oscar-winning title song — complete with a crane shot swooping down from a ballroom chandelier — in the only hand-drawn animated film ever nominated for Best Picture.

3. Jerry & Dorothy – “Jerry Maguire” (1996)

Not only did Cameron Crowe pen the hilarious line, “Show me the money,” he also gave us one of the best rom-com climaxes in history as Tom Cruise said, “You complete me,” only for Renée Zellweger to cut him off saying, “Shut up. Just shut up. You had me at hello.”

2. Jack & Rose – “Titanic” (1997)

Love it or hate it, there’s no denying Jack and Rose as two of the most iconic star-crossed lovers in Hollywood history, as James Cameron’s unsinkable blockbuster won a record 11 Oscars set to Celine Dion’s “My Heart Will Go On.”

1. Harry & Sally – “When Harry Met Sally” (1989)

Most famous for its orgasmic catchphrase, “I’ll have what she’s having,” Nora Ephron’s script shines most during the final New Year’s monologue as Billy Crystal tells Meg Ryan, “When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.” Truer words have never been spoken.

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