Honorable Mention
L.A. Confidential (1997), The Usual Suspects (1995), Kicking and Screaming (1995), Office Space (1999), Notting Hill (1999)
10. Heat (1995)
Don’t get me wrong, there were good heist films prior to Heat, but Heat really acted as a trailblazer for the 2000s and 2010s era of heist films like Inside Man, The Town, and Baby Driver. What’s great about Heat is that this is the first time since The Godfather Part II that Al Pacino and Robert De Niro worked together, but it’s the first time they actually share scenes with one another. And boy, that infamous diner scene is some of the best dialogue I’ve ever heard. “What the fuck is that? Barbecues and ballgames?” Outside of De Niro and Pacino being fantastic, the supporting cast of Tom Sizemore, Val Kilmer, Jon Voight, and Amy Brenneman is unreal. It’s the heist movie of all heist movies.
5/5 Stars
9. Glengarry Glen Ross (1992)
I can understand why some people could be turned off by Glengarry Glen Ross, but then again, I can’t understand how someone couldn’t love this film. The monologue alone where Al Pacino berates Kevin Spacey saying “You stupid fucking c**t. You, Williamson, I’m talking to you, shit head. You just cost me six thousand dollars. Six thousand dollars, and one Cadillac. That’s right. What are you going to do about it? What are you going to do about it, asshole? You are fucking shit. Where did you learn your trade, you stupid fucking c**t, you idiot? Who ever told you that you could work with men? Oh, I’m gonna have your job, shit head.” It’s hilarious, yet also mesmerizing when you see a wound up Al Pacino, and that’s on full display in this film.
On top of the obscene language that I happen to love in Glengarry Glen Ross, we are delivered an awesome Alec Baldwin performance. He’s in the film for only eight minutes, but proves to be a titular figure to the men at the core of it. Just dynamite all around.
5/5 Stars
8. Goodfellas (1990)
While I don’t think it is, many film lovers across the globe would proclaim Goodfellas as Martin Scorsese’s best film. Personally, I reserve that crown for The King of Comedy or The Wolf of Wall Street. Nevertheless, Goodfellas is a genius picture. It’s the emergence of Ray Liotta as a star as he delivers one of the finest acting performances I’ve ever seen. Watching his rise to the top of the New York mob scene to his decent into madness where he’s paranoid beyond belief felt biblical. Then around him, you had two veteran stars, and two of the best to ever do it with Robert De Niro and Joe Pesci. Goodfellas is the quintessential mob film and it came from the guy who’s mastered the genre.
5/5 Stars
7. American Beauty (1999)
I recently found a disheartening trend on Twitter X of people who HATE American Beauty. While I completely understand people loathing a problematic relationship between an adult and a teenage girl, there is a subtle genius to what Mendes does with American Beauty. Mendes makes you despise, yet sympathize with a character, played by Kevin Spacey, who has reprehensible morales. You see him preying on a teenage girl and think “what a creep“, but then you hear his wife bitching at him and you think “God, this guys life is hell.“
I really enjoyed the way that Mendes weaves this characters in with one another to go full circle for the plot. The camera kid who is obsessed with Spacey’s daughter becomes his drug dealer. But that kids dad, played by the extremely talented Chris Cooper, ends up coming out of the closet to Kevin Spacey by kissing him, and then ends up killing him. It’s tremendous writing and even better acting. The big question is, did it deserve to win Best Picture in 1999? Personally, I think it should have gone to Magnolia or The Insider, but what has the Academy gotten right? Next to nothing.
5/5 Stars
6. Fight Club (1999)
“You met me at a strange time in my life.” Cue the Pixies. Even though I’m a self-proclaimed Fincher sycophant, I didn’t see Fight Club for the first time until 2021. Yes, yes I’ll take the boos from the crowd. But after seeing it, I grew an even bigger admiration for my all-time favorite director. He’s the king of twists, whether it’s Se7en (which we’ll get to) or Gone Girl or The Game, Fincher constantly loves to leave the audience slack jawed. And I can assure you, nothing can prepare you for the twist in Fight Club.
While I could drone on and on about the twist of Fight Club, what gives the film its charm is the chemistry between Ed Norton and Brad Pitt. It feels like a real life friendship between two friends — one is a thrill seeking extrovert and the other is a depressed introvert. And that extrovert is pulling his introvert friend out of his shell. In the case of Fight Club though, it’s on a larger scale. My final note on Fight Club is that, much like American Psycho, it has gained traction in the past two years in all the wrong ways. Fight Club isn’t supposed to promote toxic masculinity. It serves as a satire on toxic masculinity. “Look at all these fake tough guys fighting each other because society is against them — RAH!”
5/5 Stars
5. American History X (1998)
All of these films on this list I’d say I’ve seen more than three times in my life. Some of them more than five times. But the one film I’ve only given two viewings to, that I absolutely love, is American History X. The extremely graphic nature of Ed Norton curb-stomping a man and Norton getting raped in prison doesn’t make it easy to watch. But aside from that, Tony Kaye makes a moving film that’s poignant about how people see other races. And it shows the way in which people can change and leave their bigoted behavior in the past. Ed Norton delivers, probably his best career performance here and it came in the midst of a massive run from him with Primal Fear, The People vs Larry Flynt, American History X, Rounders, Fight Club, and 25th Hour.
5/5 Stars
4. Magnolia (1999)
Right off the rip, every time I write about this film, I note that this is my favorite Tom Cruise performance because it takes him out of his element. He goes from being a heart throb in Jerry Maguire to a toxic male manipulator. It’s hilarious and mind boggling to witness happen and he’s pure lightning in a bottle with every word that comes out of his mouth in Magnolia. That coupled with a plot of intertwining lonely people hit me in the right spot because every character had a different story, but the crux of their being is loneliness. It’s sad in the ways that Boogie Nights and Hard Eight are, just a little more tame. Maybe that’s why I like it though is because it’s more tame. There’s not a hundred different wild things happening and it lets you focus on the characters more.
5/5 Stars
3. Reservoir Dogs (1992)
Some may argue me here, but I don’t consider Reservoir Dogs to be a heist film in the way traditional heist films are like Heat. I view it more as a gritty crime film. In addition to that, I also think this is Tarantino’s best film. Some would say Pulp Fiction — fair. Some would even say his later work like Inglorious Basterds and or Django Unchained are his best — also fair. But in my eyes, none possess the raw charm that Reservoir Dogs has. Hearing these buffoonish criminals break balls adds the charm, like when you hear Mr. Pink as “Why am I Mr. Pink?” and Joe Cabot snaps back quickly with “Because you’re a f****t, alright.” It’s funny, vulgar, and even gory to the point you look away when you watch Mr. Blonde sever a police officers ear.
5/5 Stars
2. The Shawshank Redemption (1994)
When people name the best films of all time, you’ll usually hear one of two answers — The Godfather (I or II) or The Shawshank Redemption. If you’d like to go off re-watchability, then it’s definitely The Shawshank Redemption. It seems like a joke, but any time it’s on television and I’m just surfing through the channels, my whole day gets derailed because I’m going to watch it all the way to the end. Whether it’s at the scene where Captain Hadley is holding Andy over the building or Warden Norton is planning the killing of Tommy, I’m in. I think this is probably Stephen King’s second best adaptation behind The Shining.
I love the on-screen chemistry between Morgan Freeman and Tim Robbins, and I can’t really think of anyone you’d cast in that role in that time frame to replace either. The Shawshank Redemption has many great performances and moments, but my favorite moment is the monologue Warden Norton gives towards Andy when he’s in solitary confinement. “Nothing stops. Nothing… or you will do the hardest time there is. No more protection from the guards. I’ll pull you out of that one-bunk Hilton and cast you down with the Sodomites. You’ll think you’ve been fucked by a train! And the library? Gone… sealed off, brick-by-brick. We’ll have us a little book barbecue in the yard. They’ll see the flames for miles. We’ll dance around it like wild Injuns! You understand me? Catching my drift?… Or am I being obtuse?” Goosebumps.
5/5 Stars
1. Se7en (1995)
You’re damn right Fincher is on this list twice. Three times would have been pushing it because I’m not sure I could even convince myself to make a case for The Game or Alien 3. But Se7en, I still will argue is Fincher’s best and is one of, if not the best film of the 1990s. You get a twist better than that of Fight Club and Usual Suspects along with great chemistry between two of the best actors ever, Brad Pitt and Morgan Freeman. It’s rare that a director’s best films comes at the start of his career, but it’s not his or hers peak. The start of their work is their best, but they continue to produce tremendous film after tremendous film.
I’ve written a lot about this film over the years and the long and the short of it is that I adore this movie. I have watched it over 50 times and in every watch, I find new things to love. Whether it’s recognizing that R. Lee Ermey is great in his limited screen time or that it’s genius that Fincher had John Doe as the photographer in the stairwell, it gets better and better.
5/5 Stars