Favorites From 1999: Movies That Don’t Go Out Of Style

Every so often, people ask me about my favorite movies. Before they know it, I’ve listed a hundred…or more. I just can’t narrow them down; it’s an impossible task. That question is a hard one, especially to a film fanatic like me. My friends recruit me for film trivia nights for a reason.

This article is really just a beginning to my favorite films of 1999, but everything starts somewhere. I haven’t seen every film from that year, but it’s on the bucket list. The article started after I watched Double Jeopardy for the first time in a long time, and, well, it spiraled into this list of must-see 1999 films—at least, in my humble opinion.


Sleepy Hollow

I discovered this film just a few weeks ago, in time for Halloween. It’s now one of my favorite Tim Burton/Johnny Depp films. Depp plays a flawless Ichabod Crane; I loved how the story was woven with him as the protagonist as he uncovered the deadly secrets of the town alongside the motivation for the murderer that left his victims headless.

Johnny Depp in Sleepy Hollow with a foggy field in the background

It was dark and just the right amount of creepy to make it a noteworthy Burton film. I liked his take on the classic tale by Washington Irving; watching the mystery unfold kept me invested in the film, and Christopher Walken was certainly the right actor to play the creepy headless horseman.

The Bone Collector

My absolute favorite element of this film is the mystery. The murders are connected to murders written in a novel. The murders themselves are quite brutal and gory at times; I couldn’t help but grieve for the victims, and it can certainly make someone wary of a taxi ride, especially if a monkey hangs in the mirror.

Denzel Washington and Angelina Jolie in The Bone Collector at a Christmas party

The other thing I loved about this film was how Angelina Jolie and Denzel Washington’s characters helped one another through their struggles, and how they connected over the case. They didn’t always get along, but they persevered to solve the case, and came to realize how much they needed one another. Washington’s character helped Jolie’s accept her past, including her father’s tragic death, and in turn, she helped him find new purpose and encouraged him to keep living life, regardless of his quadriplegic condition.

10 Things I Hate About You

The woes of high school are prominent in this film, as love stories fail to unfold without hitches along the way. Though initially paid to date Kat (Julia Stiles), Patrick (Heath Ledger) actually falls in love with her for real, and she reciprocates, but the two have a few obstacles to overcome before they can truly be together. Plus, that scene where Patrick wins Kat over with help from the marching band? Love it!

Patrick and Kat sitting side by side in a playground, on swings in 10 Things I Hate About You

Not only is the film about a bittersweet love story; it’s also about sisters, in a way. Kat and Bianca (Larisa Oleynik) are incredibly different, and Kat later reveals to her sister that she once dated the same jerk that is now after Bianca and succumbed to peer pressure; Kat wanted Bianca to learn from her mistakes. Growing up isn’t easy, but it’s simpler when you’ve got a guide.

Analyze This 

Any comedy starring Billy Crystal and Robert De Niro has to be an instant classic. De Niro settles into his role as mob boss Paul Vitti perfectly, and Crystal plays an excellent psychiatrist named Ben Sobel that reluctantly treats Paul, who suffers from panic attacks, among other things.

Ben counsels a distraught Paul in a living room in Analyze This, Ben wearing a suit

The two play off one another splendidly, the film never short on humor, but at the root of it, they become unlikely friends that help each other out. Ben reminds me of Richard Dreyfuss’s character from What About Bob? to a certain degree, given Ben is fed up with Paul on more than one occasion. It’s part of the comedy, though, and the storyline offered all kinds of opportunities for humor.

The Mummy 

I’ve been a Brendan Fraser fan ever since I saw George of the Jungle. He plays a marvelous hero in this film, alongside Evelyn (Rachel Weisz) and Jonathan (John Hannah). After Evie reads from The Book of the Dead, mistakenly believing no harm ever came from reading a book, disaster ensues when Imhotep is at it once again and Evie, Jonathan and Rick (Fraser) are left to stop him.

Evelyn and Rick staring into each other's eyes lovingly, with the sun setting behind them

It’s a good adventure movie with plenty of comedy mixed in. Rick and Beni’s (Kevin J. O’Connor) tendency to give each other a hard time is purely hysterical. Slapstick comedy is presented throughout the film, lightening up the darker elements in a perfect blend, and above all, the film is a classic, and my personal favorite of the Mummy movies.

Notting Hill

Honestly, isn’t this movie a common fantasy among audiences? A famous celebrity falling for a bookstore owner! It’s a sweet story that covers both the ups and downs of such a relationship, in the beautiful and picturesque Notting Hill neighborhood no less. Something about such a charming place enhances the romance, at least in my mind.

Hugh Grant and Julia Roberts, kissing passionately in Notting Hill

It’s realistic in a sense too, because it takes a while for the two to work things out and truly be together. It’s not a perfect love story, it takes time and effort on both ends of the relationship to make things work, and for all their trouble, they’re awarded a wonderful happy ending—and who doesn’t love one of those?

Double Jeopardy

Ashley Judd plays a seriously badass mom that defies her parole officer in favor of tracking down her son. She’s placed in jail for a murder she didn’t commit, and even after losing years of her life, and years of her son’s life, all she wants is her son back—and she was prepared to let her husband, who’d framed her for his murder, go.

Ashley Judd and her on-screen son in a field, Judd bending slightly to look him in the eyes in Double Jeopardy

Her husband did not choose wisely, to say the least. Judd’s character is an inspiration because she never gives up; she is not only a fighter, but a survivor. Her sole purpose is her son; nothing and no one can keep her from him once she’s released from prison. Tommy Lee Jones is her troubled but determined parole officer that tenaciously pursues her, but in a twist of events, ends up helping her. She kills her husband—this time for real—when he tries to kill her, in one neat double jeopardy, and she is ultimately reunited with her son.

Blast From The Past

I love corny romantic comedies, and this is certainly one of them. Adam (Brendan Fraser) was raised in a fallout shelter by his eccentric father and his mother, who hates the idea of being sealed underground but abides by her husband’s wishes. As a result of being raised in the fallout shelter, exposed to pop culture, societal niceties and the like of his parents’ generation, Adam was in for a surprise when he finally leaves home to get more supplies and is faced with the modern day of the ’90s.

Brendan Fraser and Alicia Silverstone in Blast from the Past, sitting on a couch together and drinking from wine glasses

Eve (Silverstone) comes to fall for Adam, naturally, as he hires her to help him gather supplies, and to help him find a nice wife from Pasadena. I love Adam’s character; he’s genuinely a nice guy with good manners and a kind heart. He’s not like many characters audiences were seeing in the ’90s, or even now in 2020. Characters that stand out, and have an unusual love story, are among my favorite kind of stories, and Blast from the Past certainly contains both.


If you haven’t seen the films on this list, they come highly recommended from me. Of course these aren’t the only 1999 films I love—Never Been Kissed, Runaway Bride, Girl, Interrupted, She’s All That, Office Space, Anywhere but Here, Tarzan, and The Iron Giant all deserve shout-outs too, but I’ve got to cut myself off somewhere.

The truth is, I’ll never be able to list just one favorite movie. That’s a good thing though, because it produces articles like this one. I don’t know what year I’ll cover next—it depends on whatever movie I watch next.

Written by Kacie Lillejord

Kacie is a freelance writer versed in various forms. She loves pop culture, screenwriting, novels, and poetry. She has previously written for The Daily Wildcat, Harness Magazine, Cultured Vultures, and Screen Rant, with 25YL being her newest writing venture.

Leave a Reply

Film Obsessive welcomes your comments. All submissions are moderated. Replies including personal attacks, spam, and other offensive remarks will not be published. Email addresses will not be visible on published comments.

Emilio Estevez and Harry Dean Stanton drive around a city in Repo Man

Repo Man and the Definition of the Cult Film

The punk band performs Fish Story in 1975

Fish Story: The Tiny Ripples That Save Humanity