1999 Best Picture Nominees Ranked

featuring gruesome depictions of war and diva queens

One of my goals for 2025 is to watch every Best Picture nominee of the Academy Awards a.k.a. the Oscars from the year I was born to the present and rank them in order of my personal enjoyment of each. This is part one of that project: the Best Picture nominees from the year I was born. I’ll start the list at the bottom and work my way up.

5. Elizabeth (1998) dir. Shekhar Kapur

⭐⭐💫

Declared illegitimate aged 3. Tried for treason aged 21. Crowned Queen aged 25. The story of the ascension to the throne and the early reign of Queen Elizabeth the First, the endless attempts by her council to marry her off, the Catholic hatred of her and her romance with Lord Robert Dudley.

This movie quite simply wasn't my cup of tea, but I can't deny just how well-written and well-acted it was. Cate Blanchett in particular stands out and proves that overly emotional scenes aren’t necessary to display excellent acting proficiency. The production design made the setting felt very lived in and while the costumes were magnificent in general, I found some of the wigs to be atrociously distracting.

4. La vita è bella / A Beautiful Life (1997) dir. Roberto Benigni

⭐⭐⭐💫

An unforgettable fable that proves love, family and imagination conquer all. A touching story of an Italian book seller of Jewish ancestry who lives in his own little fairy tale. His creative and happy life would come to an abrupt halt when his entire family is deported to a concentration camp during World War II. While locked up he tries to convince his son that the whole thing is just a game.

I first watched this film back in 2019 at the recommendation of a friend, and I liked it back then. “Like” is probably the wrong term to use here given the subject matter, but upon rewatch, I still appreciated the movie for what it was. It had some solid cinematography and production design, and the acting was okay, but the story, while heart-wrenching, doesn't quite land as strongly as I wanted it to because of how abrupt the ending was.

3. Saving Private Ryan (1998) dir. Steven Spielberg

⭐⭐⭐⭐

The mission is a man. As U.S. troops storm the beaches of Normandy, three brothers lie dead on the battlefield, with a fourth trapped behind enemy lines. Ranger captain John Miller and seven men are tasked with penetrating German-held territory and bringing the boy home.

This is a well-loved film and for good reason. The production and sound design are incredible, and the cinematography was excellent especially in the combat scenes. However, I found myself not fully liking the story because of how aggravating it was. I thought the quality of acting performances was also inconsistent for many of the cast members. The depiction of war here is sickeningly realistic, and while I understand that the point of the film is to show how terrible war is, I was left more upset than horrified. I think it was partly because I found the scenes bookending the film focusing more on the glory of patriotism rather than the tragedy it begets.

2. The Thin Red Line (1998) dir. Terrence Malick

⭐⭐⭐⭐

Every man fights his own war. The story of a group of men, an Army Rifle company called C-for-Charlie, who change, suffer, and ultimately make essential discoveries about themselves during the fierce World War II battle of Guadalcanal. It follows their journey, from the surprise of an unopposed landing, through the bloody and exhausting battles that follow, to the ultimate departure of those who survived.

This was my introduction to Terrence Malick’s filmography and what a solid entry point it was! Despite the subject matter, this was such a beautiful movie. The cinematography was consistently impressive all the way to the end, the score was incredibly moving, and the acting performances were of a caliber that we simply don’t see anymore. All of the actors disappear into their roles and their performances were so effective in building affinity with the film’s viewers, particularly through the portrayal of brotherhood among military comrades.

I did have mixed feelings about the depiction of war here. I recognized the attempts made to depict soldiers as casualties of war and how government leaders take away their humanity by reducing them to pawns in international conflicts. However, the portrayal of the Guadalcanal locals in this movie seemed to serve no purpose other than to be a foil to the chaos of the combat scenes, which felt a bit off-putting to me.

Overall, a brutal yet unique depiction of WWII that somehow maintains an air of introspection despite being a war film.

1. Shakespeare in Love (1998) dir. John Madden

⭐⭐⭐⭐

Love is the only inspiration. Young Shakespeare is forced to stage his latest comedy, “Romeo and Ethel, the Pirate’s Daughter,” before it’s even written. When a lovely noblewoman auditions for a role, they fall into forbidden love – and his play finds a new life (and title). As their relationship progresses, Shakespeare’s comedy soon transforms into tragedy.

When I finished watching this film and went to Letterboxd to log my review of the film, I was so surprised by the number of people who were so upset that this won Best Picture. And while I understand that on a technical level, it’s not as showy as its fellow nominees, I absolutely loved it. This was probably one of the corniest, cheesiest movies I have ever seen, but I simply didn't care. I was swept off my feet by the romance and every single cast member from the two leads to Judy "Diva" Dench acted their butts off. This movie is proof that true love exists and that theater kids do in fact get laid. Gorgeous costumes and set design as well.

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Which of these films have you seen and which ones do you like? Let me know!