With this list I have chosen films from the ‘50s up until the ‘90s that best capture the decade from which they were made. Although I was tempted to choose some more contemporary films that expertly convey the aesthetic of past decades (a film like Boogie Nights , American Psycho , and Wet Hot American Summer  to name just a few), I stuck with actual decade appropriate films. The following are not only alive with the culture, filming style, and ambiance of each decade, but they also happen to be some of my favorite films of all time. Coincidence? Actually, yeah. It worked out pretty well.
5) The 1950s: Rebel Without a Cause (1955) dir. by Nicholas Ray
Rebel is a great representation of the ‘50s for a few reasons. Firstly, James Dean was ultimate icon for disillusioned outsiders and rebellious teens in the ‘50s (though to be fair, I think he always will be). Secondly, the style of clothing, hair, and cars are so telling of the decade, and were highly influential on teens at the time. Additionally, Rebel marks Hollywood’s efforts to get the ‘50s home T.V. owners back out to the movie theatres. Rebel uses a more drastic aspect ratio, 2.55 : 1, which is very widescreen, making it unwatchable on home television sets of the ‘50s. Aptly so, Nicholas Ray takes every opportunity to fully use the widescreen space in almost every shot. It’s a prime example of the 1950s, and a beautiful film that still holds up today.
4) The 1960s: The Graduate (1967) dir. by Mike Nichols (Tie: Easy Rider )
Where do I begin with this one? For starters, The Graduate is a perfect depiction of the counterculture of ‘60s youth. Ben (played by Dustin Hoffman) captures the aimlessness and differing set of attitudes from the prior generation. Not to mention Simon and Garfunkel’s soundtrack to end all soundtracks. I keep going back to watch this movie expecting it to finally seem dated. Maybe it will be in another 50 years, but for now it still captures the ‘60s aesthetic while remaining entirely relevant.
3) The 1970s: Taxi Driver (1976) dir. by Martin Scorsese
Whether it’s the crooning jazz music that trails throughout the film, the grainy depiction of the dirty, sleazy, but still vibrant streets of New York City, or the chilling portrait of a detached war veteran, Taxi Driver is the pinnacle of 1970s film. The atmosphere is able to be disgusting and immoral, while somehow also conveying the nostalgia of the decade. I feel bittersweet about its recent arrival on Netflix; I am happy more people from recent generations will hopefully see it, but I am disappointed it will be on a medium that is subject to utter lack of quality and distracted viewing. I was lucky enough to see a 35mm print screening of Taxi Driver in college, and it was a completely immersive experience that I wish more people could have.
2) The 1980s: Fast Times at Ridgemont High (1982) dir. by Amy Heckerling
This may have been the most difficult decade to choose just one film from, because of how many classic ‘80s teen movies there are. I know a few may be disappointed that The Breakfast Club (1985) or Say Anything (1989) didn’t make the list. Fast Times, however, is definitely a personal favorite and captures a more far-reaching ‘80s aesthetic. It doesn’t just focus on a small set of friends, but instead allows for interweaving plots and storylines from a wide array of differently aged kids in high school. The film absolutely seeps the ‘80s vibe, and is easily one of Sean Penn’s greatest performances.
1) The 1990s: Clueless (1995) dir. by Amy Heckerling
Love it or hate it, it’s pretty undeniable this culture-crazy film is almost over the top in how ‘90s it is. Clothing style is at an extreme, and the lingo borders on laughable. That being said, the film is completely self-aware, which is what ultimately saves it from being too ridiculous or dated. Don’t you wish you could go back to a time when Alicia Silverstone was a stone cold babe and not a weird mom who chews her baby’s food to feed him like a bird? Seriously.