Sunset Boulevard (1950)

Sunset Boulevard is one of the well-known classics stemming from the well-known director’s career. Showcasing his blend of intelligent writing and stylistic direction, it is some of the strongest work in an already stellar filmography.

The strength of Sunset Boulevard is made even better by the performances of leads William Holden and (in a career role) Gloria Swanson. Both actors are able to mine the rich emotional depth of Joe Gillis and Norma Desmond, giving life to the fascinating script (penned by Wilder). Sunset Boulevard is one of the classics of American cinema, and if you haven’t seen it, make sure to add it to your list.

One, Two, Three (1961)

One, Two, Three is a deep cut in Billy Wilder’s extensive filmography. The film features an excellent cast, led by James Cagney, Pamela Tiffin and Horst Bucholz.

The film follows Berlin Coke a Cola executive C.R. MacNamara (Cagney) as his life thrown for a loop when he finds himself babysitting his boss’ handful daughter (Tiffin). Things proceed as normal until the young woman ends up married to a handsome young… Communist (Bucholz).

The film is a fun (very much of its era) comedy, featuring a dynamic performance from Cagney. The seasoned actor absolutely sells the role and thrives in what can only be described as a complicated role.

Some Like It Hot (1959)

Some Like it Hot is a classic and stands out in Billy Wilder’s long (and varied) filmography. The movie is iconic, not only as one of the greatest American comedies, but also for a fascinating performance from Marilyn Monroe.

The film follows two jazz musicians (Curtis and Lemmon) who are forced to flee prohibition era Chicago when they witness a mob hit. It seems the only way they can do this is by posing as women and getting a job with an all-girl band.

The film combines Wilder’s typically snappy writing with stellar performances by all involved. Monroe shines, Lemmon is at his best, and Joe E. Brown brings a fun likability go what would be a boring role in less colorful hands.

Witness for the Prosecution (1957)

Witness for the Prosecution is a little bit of a deeper cut as it relates to Billy Wilder. In fact, I only saw the film a few months ago myself.

Witness for the Prosecution is a smaller production for Wilder, feeling more like a television piece of the era than a feature film. However, this movie is sold on two things: an all-star cast and an awesome script. From Charles Laughton and Elsa Lanchester to Tyrone Power, the movie is packed to the rafters with star power (each amazingly on their game). Each bring their immense talent to the clever script, which keeps you watching riveted until the closing minutes.

Sabrina (1954)

To wrap up, a little venture into rom-com territory. Is Sabrina problematic? Sure. Do I care? Not really. The film follows the well told story of a chauffeur’s daughter Sabrina (Audrey Hepburn) who finds herself caught in a love triangle between two polar opposite, wealthy brothers (William Holden and Humphrey Bogart). Who will she choose?

The film is a cute romantic comedy, bolstered by delightful performances. Hepburn is at the beginning of her career, showing the charisma and star power which has made her a legend. Meanwhile,  Bogart and Holden are at their peak, absolutely selling their characters.