5 Fun Movies with Retro 50’s Era Settings

Retro Dee writes about music, fashion and other trends of the 1950s on this site.  Check out her blog, Retro Dee’s Guide to the Best Era Ever here, and her column here every Wednesday.

Hi there folks! It’s Retro Dee with some more 50’s-themed fun coming your way.

Today we’re going to look at five movies set in the past, some of which are now classics themselves. These films were not only made to wow audiences when they first came out, but also made to stand the test of time and entertain future generations.

You can see these on Amazon Prime, stream them on Netflix or just pop in a good ole DVD. Even if you’ve seen them, there’s no time like the present to enjoy a great movie again.

So if you want some fun, retro-themed entertainment, look no further!

5 Fun Retro-Themed Flicks

1. Cry Baby

This 1990 comedy starring Johnny Depp takes place in the year 1954. It’s become somewhat of a cult classic. It’s about a guy nick-named “Cry Baby” because he can make the girls swoon by shedding a tear out of just one eye.

The plot is kind of silly, but it has some great upbeat songs in it such as “Sh-boom” by The Crew-Cuts. I’m not entirely convinced that the setting is true to 1954, but hey, it’s a fun movie so you just have to go with it.

Movie Poster for Cry Baby (1990)

2. The House With A Clock In Its Walls

This strange fantasy film takes place in 1955. It caught my eye when I was sitting in a hotel room evacuated from my home during the 2019 California wildfires. I noticed that in the scenes that took place outside of the house, everyone was dressed in 1950’s era clothing. For me, that alone was reason to check it out.

This movie starring Jack Black and Cate Blanchett is a newer one (2018), and it’s certainly odd, but it’s worth watching if you like retro settings. Or clocks, for that matter.

Movie Poster (2018)

3. The Sandlot

One of the biggest comedy classics of the 90’s, The Sandlot takes place in the year 1961… A tad past the 1950’s, technically, but still pretty much the same era.

This movie is kind of like a more lighthearted, upbeat version of Stand By Me, and it’s a great childhood film with a baseball theme. Quotes such as “You’re killin’ me, Smalls” and the classic Babe Ruth dream sequence make this a nostalgic favorite.

The Sandlot Movie Poster (1993)

4. Pleasantville

This late 90’s movie is a real mind-trip.  It’s about a brother and sister (David and Jennifer) who somehow end up trapped in a 1950’s TV show about a picture-perfect town called “Pleasantville”. Everything in Pleasantville is innocent and simple, and of course, black and white.

But once David and Jennifer start living as the show’s children, things begin to get more complicated. I think what Pleasantville is trying to show, is that human beings are complex. To adhere to simplicity in a black and white world is impossible. Overall, the world is colorful; filled with ups and downs.

This movie has a fantastic soundtrack which includes hits like: “Rave On” (Buddy Holly), “Be-Bop-A-Lula” (Gene Vincent), “Teddy Bear” (Elvis Presley), and “Dream Girl” (Robert and Johnny).

Pleasantville Movie Poster (1998)

5. Back To The Future

Then there’s what could possibly be the most famous movie set in the 1950’s: Back To The Future. This movie was released smack-dab in the middle of the 80’s, in the Fall of 1985. If you somehow managed to miss this film, starring Michael J. Fox and Christopher Lloyd, I highly suggest you check it out. And if you’ve seen it 100 times, I suggest you see it 101.

From the catch phrase “Hello? McFly?” to the Clock Tower, the Flux Capacitor and the DeLorean itself, Back To The Future is recognized as a true classic.

The most memorable part of the movie to me, is when a confused Marty first arrives in 1955. “Mr. Sandman” is playing in the background. Marty looks around, bewildered. Everyone is dressed in 1950’s period clothing. Then the Clock Tower chimes… a man tosses a newspaper into a wastebasket. Marty picks it up and the date reads: “November 5, 1955”… I still get chills just thinking about it!

Back To The Future Movie Poster (1985)

Bonus Movie: Toy Story 4

I just recently watched this movie and although it’s not set in the past, I was delightfully surprised to meet a new character who does, indeed, come from the 1950’s.

Gabby Gabby, a sweet but manipulative talking doll, introduces herself as being made in the late 1950’s. With her freckled face, flaming red ponytails and cute yellow polka-dot dress, Gabby Gabby is a great example of a doll from her time period.

But is the cute, retro Gabby Gabby going to help or hinder Woody and friends from returning to their beloved Bonnie? You’ll have to see Toy Story 4 to find out!

PS: Watch for the jukebox in the 50’s section of Second Chance Antiques store!

Gabby Gabby (front left) is a 1950’s doll in Toy Story 4


Thanks for reading, I hope you enjoyed this post. For more, please follow Retro Dee’s Guide to the Best Era ever here on WordPress. You can also follow Retro Dee on Twitter @RealRetroDee and Instagram @mariepascal82

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