The best gateway Old Hollywood films

I have always loved watching Old Hollywood movies. This fascination started when I was little, watching classics like “The Wizard of Oz,” “The Sound of Music” and many others with my family, particularly my mom. As I got older, my film repertoire expanded as the two of us began watching more films spanning different decades and genres. 

Over time, I began to appreciate different aspects of them, from the cinematography to the music and, of course, the fashion. That being said, over the years I have noticed that people tend to avoid old films, thinking that they will be bored watching them, or they do not like the idea of watching films in black in white.

So, here is a list of films that are great gateways into the Old Hollywood genre. 

Romance Films 

“Pillow Talk” (1959) 

“Pillow Talk” is a romantic comedy starring Doris Day and Rock Hudson as neighbors who share a party line telephone, which is a phone service that connects multiple households to one phone line. Hudson and Day get to know each other through this line and, of course, end up falling for each other. It is a classic enemies-to-lovers film that would be great for people who like the ‘90s film “You’ve Got Mail.” The plot of this film is simple to follow, and the late ‘50s New York setting makes this film a fun watch for romance lovers. 

“Roman Holiday” (1953) 

While this film is in black and white, do not let that put you off this charming romance starring Audrey Hepburn in her debut role as Princess Ann, and Gregory Peck as Joe, a journalist looking to get an exclusive interview with the princess. The film follows Ann and Joe as they gallivant through Rome, falling in love in the process. This is one of my favorite Audrey Hepburn films, and is a must-watch for fans of romance, beautiful scenery and amazing fashion. 

Musical Films 

“Singin’ in the Rain” (1952) 

This musical comedy is a classic for a reason. Starring Gene Kelly, Debbie Reynolds and Donald O’Connor, this movie takes place during the roaring ‘20s and follows a film studio struggling to transition from silent films to “talking pictures.” This movie contains some iconic musical numbers and dance numbers like “Good Mornin’” and the namesake song “Singin’ in the Rain,” which makes this film perfect for those looking to get into old musical movies. 

“White Christmas” (1954) 

Yes, I realize this is a Christmas movie, but hear me out. This movie stars Bing Crosby and Danny Kaye as famous performers and producers who band together with two sisters, played by Vera-Ellen and Rosemary Clooney, to help save a Vermont inn. The musical numbers in the film are fun and feature an extremely talented cast. Plus, there are some great one-liners that make this movie a rewatch for me every Christmas. This movie also has some of my favorite costumes and outfits that were designed by Edith Head, who also designed the costumes in the previously mentioned “Roman Holiday.” So, even though it is not quite Christmas, I highly recommend giving this movie a try. 

Mystery/Thriller Films 

“Charade” (1963) 

Another Hepburn classic, this film has often been considered the best Hitchcock movie Hitchcock never made. It blends mystery, comedy and romance into a suspenseful, yet fun, mystery flick. Hepburn stars as a wealthy woman who finds herself in the middle of a murder plot after her husband is suddenly found dead while they are traveling abroad. The movie also stars Cary Grant as Hepburn’s love interest, playing a mysterious man with a secret identity, who aids Hepburn in solving her husband’s murder. This movie is perfect for those who enjoy a good whodunnit mystery with a sideplot of romance. 

“North by Northwest” (1959) 

Another Cary Grant classic, this time in an actual Alfred Hitchcock movie. Grant stars as an advertising executive, Roger Thornhill, who is mistaken for a government spy. He soon finds himself on a deadly cross-country journey as a ruthless spy tries to hunt him down. Considered to be one of Hitchcock’s best films, this movie is perfect for fans of spy thrillers and action-packed stories that constantly keep fans on the edge of their seat.

If you are someone looking to dip your toes into the Old Hollywood film world, these are just a few films I recommend to help get you started.

• #oldhollywood
• entertainment
• style