Last updated on December 27th, 2021 at 11:02 pm
The 2021 Oscars are in the books. If you follow us on Instagram (and you should!) you may have seen my stories about how the Oscars were such a part of a ritual I spent with my mom. I even wrote about in the blog post about our Academy Awards traditions. But how did it all get started? What are the favorite classic movies that I watched with my mom growing up and what are my personal favorites?
For this list, I didn’t want to include the obvious choices, like “The Wizard of Oz”. We all know what a wonderful movie that is and will be for generations to come. Instead, I wanted to list movies that you may have heard of but not taken the time to watch or have never heard of at all!
Some of these are the favorite classic movies that I watched for the first time with my mom. Some are where I discovered my first movie star crushes (Hello Kurt Russell!). But all of them are special to me in some way and my hope is that they can become special to you, too. I’d love to find out that you decided to watch these with your niece, daughter, granddaughter, etc., and started a tradition of your own. Bring on the popcorn!
Each movie title listed below is a link to its IMDB page where you can read a plot synopsis, see the cast and watch the trailer!
My First Movie Memories
The Jungle Book (1967)
This is the first movie that I recall going to an actual theater. To this day I can remember how excited I was. I even had The Jungle Book board game that I played over and over again after the movie. I still remember the lyrics to “The Bare Necessities”: “Look for the bare necessities, the simple bare necessities, forget about your worries and your strife!”
The Computer Wore Tennis Shoes (1969)
If you’re part of my generation, then you might remember that Kurt Russell did several Disney movies in the 1970’s, including “The Barefoot Executive” and “Now You See Him, Now You Don’t”. These aren’t Oscar movies, but they were cool to a pre-teen girl at the time! And I thought Kurt Russell was sooo cute!
The World’s Greatest Athlete (1973)
Another crush. Jan Michael-Vincent was every young girl’s dream in this “Tarzan” like Disney story. It’s more silly humor, but I was just a kid, so it was funny to me at the time!
Chitty Chitty Bang Bang (1968)
I loved this movie and the soundtrack was one of the first records (yes, on vinyl) that I remember getting as a gift. I can still remember every word to the “Doll on a Music Box”. It was my favorite scene in the movie. Highly recommend this to watch with kids!
Movies My Mom Introduced Me To (That Are Now Among My Favorites)
I’ll Cry Tomorrow (1955) and I Want To Live (1958)
My mom loved the actress Susan Hayward, but she may not be familiar to you. I remember watching both of these with her a long time ago and years ago and I bought her the DVD’s so she could watch them again. “I Want To Live” was nominated for six Academy Awards, with Susan Hayward winning “Best Actress” for her portrayal of real-life death row inmate Barbara Graham.
An Affair to Remember (1957)
If you’ve seen “Sleepless in Seattle”, then you’re probably already familiar with this great movie. In my opinion, it’s one of the most romantic movies of all time. I had watched it long before it regained popularity. I still cry at the phrase “I was looking up”. If you’ve seen the movie, you know exactly why.
Miracle on 34th Street (1947)
When the remake of this movie came out in 1994, my mom refused to watch it (and never did). She could not believe that anything could be better than the original. She talked about this movie every year at Christmas, it was her favorite Christmas movie. It is still a classic today. I believe, do you?
National Velvet (1944)
One of Elizabeth Taylor’s early movies and a true classic, based on the book published in 1935. Elizabeth Taylor was only 12 at the time and as you know, would go on to be a two-time Academy Award winner for Best Actress and an all-round film legend.
All About Eve (1950)
If you haven’t seen this movie, don’t wait much longer. There’s a reason it won Best Picture at the 1951 Academy Awards. “A seemingly timid but secretly ruthless ingenue insinuates herself into the lives of an aging Broadway star and her circle of theater friends.” – IMDB. It’s fantastic.
Charade (1963)
Cary Grant and Audrey Hepburn are my two most favorite classic actors, so when you pair them in a movie, it doesn’t get much better than that. A classic tale of intrigue and romance, perfectly “Hollywood”. The 2002 movie “The Truth About Charlie” is actually a remake, but I’d go for the original.
Singin’ in the Rain (1952)
Is there anyone that doesn’t know and love this movie? Even though it’s not obscure at all, I had to add it. I can vividly remember how much I loved it the first time I watched it. And to this day, I will watch Gene Kelly’s famous “singin’ in the rain” scene on YouTube from time to time. It never gets old.
My Own Favorite Classics
It Happened One Night (1934)
When I first watched this movie, it was one of the oldest movies I had ever seen. It has that “old Hollywood feel” to it, especially being in black and white. Starring two old Hollywood legends, Clark Gable (before “Gone with the Wind”) and Claudette Colbert, the film won five Oscars including Best Picture, Best Actor and Best Actress.
North by Northwest (1959)
One of Alfred Hitchcock’s best and starring my fave, Cary Grant. You’ll be on the edge of your seat from start to finish. Make the popcorn and sit back and enjoy!
Sabrina (1954)
You might be familiar with this title because of the 1995 remake with Harrison Ford. The remake is good, but the original (like in most things) is much better. Audrey Hepburn, Humphrey Bogart and William Holden – all Hollywood legends. An early version of a contemporary rom-com, directed by the legendary Billy Wilder!
My Two Modern Favorite Classic Movies
When Harry Met Sally… (1989)
For everyone who knows me, they know that of all the movies out there, this is my all-time favorite. Any movie list I create, no matter the topic or genre, this has to be included. “When you realize you want to spend the rest of your life with someone, you want the rest of your life to start as soon as possible”. Gets me every time.
The Intern (2015)
And finally, one of my newest favorites. You might be surprised to find this little movie on this list. But, it reminds me so much of what “The Harper Girls” is all about. If you’ve seen the movie, then you know that it’s all about what the past can bring to the present and vice versa. As the poster says, “Experience Never Gets Old”. We couldn’t agree more.
What are some of your favorite classic movies? Are they the same as mine? Let me know in the comments below.
