My 25 Favorite Love Story Movies

…and they lived happily ever after.

First of all, there is only one great love story – The Princess Bride eclipses all others in every way. Don’t @ me. I will cut a bitch.

Therefore, this list represents 25 OTHER great love stories that I find irresistible. Maybe it’s the writing, maybe it’s the chemistry, maybe it’s the soundtrack, maybe it’s Brad Pitt (OK, if he’s in it, it’s because it’s Brad Pitt).

This is a rolling list that I even debate with myself – I add, I subtract, I add some more. Also, I can’t rank them in a specific order, because that’s just too organized, so I chose categories and listed them chronologically, to the best of my ability (ie – I’m not taking the time to look up all the release dates, just ball-parking it).

Caveat: This whole thing started because a 20-something babysitter gave me a blank look when I mentioned “Reality Bites” and I realized I needed to work WITH Millennials and GenZ to ensure all of the quirky pop culture that defines my generation doesn’t get lost due to my GenX apathy – which means I don’t even *love* all of these, either – but they all felt essential for future generations and eventual quiz show knowledge.


“Shrieking Eels. Torture. Swordfights. The Pit of Despair. The Cliffs of Insanity. Dating sure was tough Once Upon a Time.”

The best book. The best movie. The best movie poster tagline. The best chemistry. The best cast. Just. The. Best. (why aren’t you watching it right now?!)


Officer and a Gentleman (Richard Gere & Debra Winger)

Bull Durham (Kevin Costner & Susan Sarandon)

Ghost (Patrick Swayze & Demi Moore)

Titanic (Leonardo DiCaprio & Kate Winslet)

Meet Joe Black (Brad Pitt & Claire Forlani)

Silver Linings Playbook (Bradley Cooper & Jennifer Lawrence)


West Side Story (Natalie Wood & Richard Beymer)

Grease (John Travolta & Olivia Newton-John)

Dirty Dancing (Patrick Swayze & Jennifer Grey)

Beauty and the Beast (yes, the animated Disney version)

Strictly Ballroom (Paul Mercurio & Tara Morice – Australian actors)


Sixteen Candles (Molly Ringwald & Michael Schoeffling)

Say Anything (John Cusack & Ione Skye)

Can’t Buy Me Love (Patrick Dempsey & Amanda Peterson)

Reality Bites (Ethan Hawke & Winona Ryder)


When Harry Met Sally (Billy Crystal & Meg Ryan)

Sleepless in Seattle (Tom Hanks & Meg Ryan)

Pretty Woman (Richard Gere & Julia Roberts)

Four Weddings and a Funeral (Hugh Grant & Andie McDowell)

Moonstruck (Cher & Nicholas Cage)


The African Queen (Humphrey Bogart & Katharine Hepburn)

Breakfast at Tiffany’s (Audrey Hepburn & George Peppard)

Casablanca (Humphrey Bogart & Ingrid Bergman)

Gone with the Wind (Clark Gable & Vivien Leigh)

White Christmas (Bing Crosby & Rosemary Clooney; Danny Kaye & Vera-Ellen)