6. Swingers (1996) g124
Swingers introduced the world to Jon Favreau and Vince Vaughn, two out-of-work actors navigating heartbreak, rejection, and dive bar etiquette in mid-’90s LA. Some would argue it might still be the best work either has ever done, and yet because of poor latter career choices, Swingers is frequently forgotten about.
It’s easy to forget how fresh and funny this film was when it landed, bringing an alternative energy to pop culture that had been somewhat redefined by people like Quentin Tarantino.
But beneath the surface swagger is something surprisingly heartfelt, a film about loneliness, friendship, and trying to find your footing when you feel utterly lost. This genuine feeling is something that is frequently absent from much of Vaughn’s comedic work since and remains one of the all-time great ‘break-up’ films, ironically unlike The Break-Up (2006), which also starred Vaughn.
7. Cop Land (1997)
Sylvester Stallone gives one of his career best performances in Cop Land, a brooding neo-noir about corruption and compromise in a small New Jersey town populated by New York cops. Written and directed by James Mangold, it features a powerhouse ing cast including Harvey Keitel, Ray Liotta, and Robert De Niro.
Stallone, very much playing against type, is brilliant as Freddy Heflin, a half-deaf sheriff overlooked and underestimated by everyone, until he finally reaches his limit. Cop Land’s slow-burn pacing brings the best out of Stallone, and for those who simply pigeonhole him as Rocky or Rambo, Cop Land proves that he’s a much more versatile actor than people give him credit for.
The same could be said for the film itself; although many regard Cop Land as a decent piece of work, it deserves to be in the conversation as one of the best films of the nineties.
8. Pleasantville (1998)
Gary Ross’s high-concept fantasy comedy didn’t exactly flop, but it remains one of the most quietly profound films of the decade. A pre-Spiderman Tobey Maguire and Reese Witherspoon are teenagers who get sucked into a 1950s sitcom, only to start colourising the black-and-white world with modern ideas of rebellion, sex, and change.
What starts as a clever gimmick becomes a beautiful musing on progress, repression, and the chaos of human emotion. The visuals are still gorgeous today, the performances subtle (Witherspoon is superb) and the message surprisingly radical.
Pleasantville feels more relevant than ever, and its third act is genuinely moving. It would be very interesting to see what a remake would look like today.
9. Bulworth (1998)
Warren Beatty’s Bulworth is one of the strangest, most audacious political satires of the ’90s, a film where a suicidal senator hires a hitman to kill him and then starts rapping truth bombs on the campaign trail while waiting for death. It shouldn’t work. But somehow, it absolutely does.
Beatty is fearless, mixing absurdist comedy, scathing social satire, and a bizarrely sincere message about race, money, and media. It’s an unhinged film that feels way ahead of its time, especially in a world where political theatre has only grown more ridiculous and the public are frequently forced to accept absurdism as reality.
There are shades of another Beatty film that was also ahead of the curve; 1976’s Network, a film in which Peter Beale’s news anchor announces he’s going to shoot himself live on air. Bulworth is in the same bizarre ballpark, and although it gets nowhere near the acclaim that Network did, it’s more than worth hunting it down.
10. Election (1999)
Alexander Payne’s Election is one of the sharpest, funniest, and most savage comedies of the decade. Matthew Broderick plays a high school teacher at war with overachieving student Tracy Flick (Reese Witherspoon), and the stakes feel like life and death, even if it’s just a student council election.
Based on Tom Perrotta’s novel of the same name, the film landed Payne and Jim Taylor an Oscar nomination for best adapted screenplay, and the script absolutely warrants it, it’s sharp, funny, and toes the line of comedy and drama superbly.
Election potentially gets a career best performance from Matthew Broderick, the film’s voice-overs allow you to get into the mindset of its two leads, and Broderick sells the character terrifically. Reese Witherspoon is almost always wonderful, and her performance in Election is no different; it’s an effective two hander between her and Broderick.
Payne paints a scathing portrait of American ambition in miniature, one that’s only become more prescient with time. There’s not a wasted moment here. It’s wickedly good.