100. The Pope of Greenwich Village, 1984
Director: Stuart Rosenberg
"They took my thumbs, Charlie!" Spoken from the hysterical Paulie, played brilliantly by Eric Roberts. The Pope of Greenwich Village is really a Mickey Rourke vehicle and it's one of my favorite Rourke films. Mickey was really at his prime here even though The Wrestler proved he can still give one hell of a performance. In the '80s though, Mickey Rourke was a hot commodity and watching Pope, he does have a screen presence that is very reminiscent of a young Marlon Brando or Robert Deniro. This is really a film to watch to see some great performances from actors who kinda lost their way. Eric Roberts is another one. I actually think he's amazingly demented in this movie, I'm surprised his career really went downhill not too long after this movie.
99. My Dinner with Andre, 1981
Director: Louis Malle
I can really get into a film like this. It's a very simple concept and a film that seemed to come out of nowhere as there's really nothing like it. It's just a movie with two people talking over dinner. Those two people would be Andre Gregory and Wallace Shawn. But within this conversation is a rather fascinating look at how these two people live, who they are, what they think, what makes them tick. It's a wonderful dissection of two people through conversation and it's a movie that shows that it doesn't take much to make a great film, an interesting conversation between two people will suffice.
98. Caddyshack, 1980
Director: Harold Ramis
Caddyshack is such a funny movie that it manages to hide the fact that it really is kind of a mess. Starring Chevy Chase, Bill Murray, and Rodney Dangerfield, all three of whom are at their sharpest and funniest including Bill Murray who is just a blast to watch on screen. Caddyshack is a classic.
97. Ferris Bueller's Day Off, 1986
Director: John Hughes
It's really kind of incredible how prolific John Hughes was in the 1980s. He just churned out memorable teen comedy after memorable teen comedy, year after year. Ferris Bueller's Day Off features Matthew Broderick at his most charismatic, also memorable on screen is Alan Ruck, and the always creepy-looking Jeffrey Jones. The comedy in this film is all character which is why this film holds up so well even today.
96. Princess Bride, 1987
Director: Rob Reiner
At a time when Rob Reiner could do no wrong, Princess Bride came out and made people laugh their asses off once more. Cary Elwes, Christopher Guest, Wallace Shawn, Andre the Giant... this fairytale comedy is just highly entertaining on all levels.
95. Risky Business, 1983
Director: Paul Brickman
This movie is really just a coming out party for Tom Cruise (no, not that kind of coming out party), but that's what is so great about it. There aren't many actors who arrived so loudly as Tom Cruise. Risky Business started out a string of very successful films for Tom Cruise and his A-list status continued up until around the mid-2000s. Even now people seem to have forgiven Tom Cruise because he's just so fun to watch on screen. Risky Business itself really has a plot that is just completely implausible and it's so very '80s, but it's still an important footnote in film history just for the arrival of Tom Cruise. And really, it's a very entertaining film despite the ridiculous plot.
94. Escape from New York, 1981
Director: John Carpenter
Apparently, in 1997, New York didn't get the memo. It was supposed to be a giant maximum security prison that Snake Plissken was supposed to badass his way out of. Escape from New York is an awesome action movie featuring a very cool Kirk Douglas and directed by John Carpenter, who like Rob Reiner, could do no wrong in the '80s.
93. The Untouchables, 1987
Director: Brian De Palma
What The Untouchables lacks in historical accuracy, it more than makes up for as a very entertaining period crime drama. An excellent cast featuring Kevin Costner playing Eliot Ness, Sean Connery as Jim Malone, and Robert Deniro as Al Capone. Now Deniro doesn't exactly play the greatest Al Capone in the world and the Capone makeup job wasn't all that great, but you can't help but love him in this movie playing the foil to good guy Kevin Costner. Also worth noting is the great script by David Mamet (whose film "House of Games" just barely missed the list). I would also be remiss if I didn't mention Brian De Palma as this is really the last film from his "classic era." He really hasn't been the same since "The Untouchables" even though he did make one more great movie after this (Carlito's Way).
92. The Killing Fields, 1984
Director: Roland Joffe
The Killing Fields is a great film that's marred by a few poor choices. The film's score is kind of distracting and it takes awhile for the movie to really get going. Conversely, Sam Waterston does a great job of carrying this film, Haing S. Ngor deservedly wins an Oscar for his role of Dith Pran (in what was sort of art imitating life for him) and then you have some good supporting roles from John Malkovich and Spalding Gray. And overall it's a powerful story about a journalist who stops at nothing to get to the bottom of the truth and a photographer who winds up getting trapped within the horrors of the war. Very strong, compelling stuff.
91. Airplane!, 1980
Airplane! is just an off-the-wall comedy that never lets up even after the credits have rolled. Airplane is ridiculously funny, it's absurdly funny. A joke in every scene. It's a movie that made people re-think just how far you could go, comedy-wise, in a movie. Airplane is one of my all-time favorite comedies and yet it's only 91 on this list simply because compared to other '80s films, it's pretty slight (as it should be). If you love the Zucker/Abramas trio, you'll also be disappointed in knowing I didn't include The Naked Gun which is another hilarious movie, but really is just more of the same from them. Back in the '80s, you could always rely on these to bring some highly energetic, no holds barred type comedies. They pioneered the spoof genre which has unfortunately been completely ruined over the years. Airplane is still a great fun to watch.