The Funniest Old Hollywood Comedies You Might Have Missed
Assorted Flavors features listicles and other movie-related goodies.
By Rebecca Bain
I have loved Old Hollywood for as long as I can remember, and my love for this age of cinema has only grown over the years.
Since starting the Instagram account @old.hollywood.swoon in the summer of 2020, many of the movies I’ve spotlighted have been classic comedies from that era. Here are some of my underrated favorites.
Bringing Up Baby (1938)
This movie is screwball comedy at its finest. This was the movie that made me fall in love with Old Hollywood. Cary Grant and Katharine Hepburn are a perfect comedic match and apparently production was delayed multiple times because they had uncontrollable laughing fits.
A Night at the Opera (1935)
The Marx Brothers are extremely underrated. You can pick any of their films and it will be nonstop laughter. One of my favorite scenes is in the stateroom on board the ship. For more Marx Brothers zaniness I would also recommend A Day at the Races and Duck Soup.
What’s Up, Doc? (1972)
This movie was made to pay homage to the screwball comedies of the silver screen era, specifically Bringing Up Baby. It is one of the funniest movies I’ve ever seen and that is all due to the director/writer Peter Bogdanovich and the entire cast including Barbra Streisand, Ryan O’Neal, and Madeline Kahn.
How to Succeed in Business Without Really Trying (1968)
A lot of people might know this one because it is a musical, but I don’t think everyone knows that it is incredibly hilarious. It is about a man who buys a book titled How to Succeed in Business and quickly works his way from a window cleaner to the president of the company. That description might sound a little boring, but trust me when I say it’s an amazing film.
We’re No Angels (1955)
This one is a Christmas-themed comedy starring Humphrey Bogart and Peter Ustinov. It’s about some escaped prisoners who plan to rob a store but end up doing good deeds for the shop owner and family. Now that’s Christmas spirit!
How to Steal a Million (1966)
Audrey Hepburn and Peter O’Toole have to steal some forged artwork so her family’s name won’t be tarnished, all while wearing fashionable clothes, driving around Paris, and falling in love. What’s not to love about that premise?
Rebecca Bain started the Instagram account @Old.Hollywood.Swoon after she fell deeply in love with the works of Gregory Peck, and she is so thankful for all the support she has received that has made her continue posting every day.