The Best Classic Movies Worth Rewatching (or Checking Out for the First Time)

There have been a lot of really good movies out lately—like, no one is tired of watching the 2019 Little Women yet. But there are also plenty amazing classic movies that deserve our attention…especially for those of us who haven’t seen them before. After all, a movie that happens to be black and white or made more than 20 years ago doesn’t have to be boring. Many of them have actually dictated the way people make and watch movies in the years since their release.

Looking for a classic movie to rewatch or want to finally cross off more of these classics from your To Watch list? Here are some of the very best ones to get you started.


Originally released in 1943, Casablanca is widely regarded as one of the best movies of all time. Starring Humphrey Bogart and Ingrid Bergman, this movie tells the story of Rick Blaine, who has to make the decision to help his former girlfriend escape Morocco.

The Wizard of Oz

It’s hard to imagine that anyone out there hasn’t seen The Wizard of Oz, but if that’s you, watch it ASAP—and if that’s not you, watch it again, because this is The Wizard of Oz we’re talking about, and watching Dorothy (Judy Garland) get lost in Oz truly never gets old.

Singin’ in the Rain

Fans of musicals will love this one if they haven’t seen it already. In Singin’ in the Rain, movies are making the transition from silent films to “talkies,” but that’s bad news for Lina Lamont, who doesn’t have a singing voice good enough for the movie. This one stars Gene Kelly, Debbie Reynolds, and Jean Hagen.

Gone With the Wind

Need a good, long romantic movie to pass the time? Gone With the Wind might be a winner. This story is about Scarlett O’Hara (Vivien Leigh) living in the South during the Civil War as Atlanta burns…and she ends up falling in love with Rhett Butler (Clark Gable) in the midst of all of it.

My Girl

Anyone who’s looking for a good cry, look no further than My Girl. Anna Chlumsky and a tiny Macaulay Culkin play best friends who spend every day together. Chlumsky’s Vaeda is trying to figure out life, her crush on her teacher, and why her dad is dating again. You will get emotional, but you will also love it.

Breakfast at Tiffany’s

Unfamiliar with Audrey Hepburn’s work? This is a very good place to start. In Breakfast at Tiffany’s, Hepburn plays Holly Golightly, a woman who wants to marry a rich man but whose plans don’t exactly go the way she hoped. Bonus: It’s currently streaming on Hulu.

The Way We Were

Here’s an absolute classic when it comes to rom-coms—and a bit of a tearjerker. Starring Barbra Streisand and Robert Redford, this movie tells the story of a couple who fell in love after meeting in college, but unfortunately, their love story didn’t end up leading to the happily ever after they thought they would.

The Breakfast Club

At this point, most of us have seen this John Hughes classic, but for anyone out there who hasn’t, now is definitely the time. In this movie, Molly Ringwald, Judd Nelson, Ally Sheedy, Anthony Michael Hall, and Emilio Estevez all end up in Saturday detention together, and chaos ensues.

Mary Poppins

If any Disney movie were going to make it to this list, it had to be Mary Poppins—where Julie Andrews plays a nanny who changes the life of the family she works for before disappearing just as mysteriously as she arrived. There’s music, there are animated penguins, there’s nothing not to love.

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