50. Sunset Boulevard 1950
Director: Billy Wilder
Starring: William Holden, Gloria Swanson
Synopsis: An aging silent film star attempts to re-create her glory days with the help of a struggling young screenwriter.
Review: Swanson is exquisitely creepy as the delusional and reclusive Norma Desmond who is convinced that her star will rise once more. Her life is as much a wreck as the dilapidated mansion she lives in, but she blinds herself to all of this and becomes a walking parody of fame and fortune. Like Joe Gillis (Holden), we are drawn in to her bizarre world, and though the dangers of remaining in her dreamscape are obvious, we find it impossible to leave through a paradoxical combination of pity and disgust. It's sharply written with many memorable lines, well-acted all around, and deals with interesting issues that Hollywood tends to avoid. Fun fact: Swanson was herself a silent film star who didn't quite make the transition to talkies.
49. The Matrix 1999
Directors: Andy Wachowski, Dana Wachowski
Starring: Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss
Synopsis: A hacker discovers the world in which we live is a computer program and embarks on an epic quest to save humanity.
Review: Although the sequels leave something to be desired, the original film is as good as it has been influential on the action movie genre and popular culture. Reeves may not be the premier actor of our generation, but that's more than made up for by incredibly intense action sequences coupled with graceful choreography, and smart writing dealing with heady concepts that up until this film, was almost entirely absent from action movies. In addition there's great special effects, interesting use of colour (you may notice this film has a distinctly 'green' feel to it), a cool cyberpunk theme, and badass characters (Morpheus and Agent Smith spring to mind). Fun fact: This movie was in part inspired by the Ghost in the Shell movie.
48. Do the Right Thing 1989
Director: Spike Lee
Starring: Spike Lee, Danny Aiello
Synopsis: Tempers flare in a New York City ghetto on the hottest day of the year.
Review: When it was first released, some commentators feared that this film would incite race riots, which of course never happened, because this movie isn't a call to arms, but an honest representation of and commentary on racial tensions after the civil rights movement. Figures such as Martin Luther King Jr. and Malcolm X still loom large, but their philosophies have been boiled down to Love and Hate. There may not be colored fountains anymore, but things are far from equal. Sal may have a pizzeria in a black neighbourhood, catering almost exclusively to black customers, but beneath the surface the seed of racism still grows. It begins as a comedy, but as the plot rolls forward towards the dramatic climax the tension heats up to a breaking point and you know somebody has to pay the price. There are no easy answers provided with this movie, and Spike Lee doesn't fall into the trap of portraying his black characters exclusively as victims, nor the whites as oppressors. It's an incredible and vitally important film that should not be missed. Fun fact: Barack Obama went to see this movie on his first date with his now wife, Michelle.
47. Annie Hall 1977
Director: Woody Allen
Starring: Woody Allen, Diane Keaton
Synopsis: A neurotic New Yorker falls for the captivating titular character.
Review: Most people call this a romantic comedy, but I call it Woody Allen being hilarious. Although Alvie's (Allen) relationship with Annie Hall (Keaton) forms the emotional core of the film and is quite a nice story, the parts that stick out the most are all the clever one liners and off the wall humour. Allen gets quite inventive with this film that features a brilliant cameo by Marshall McLuhan, a conversation with subtitles showing what characters truly mean by what they say, and a brief animated bit. It's a charming and unpredictable film with solid performances from Allen and Keaton. Fun fact: This movie was originally meant to be a murder mystery until the editor convinced Allen to cut out that aspect of the plot and focus on the romantic relationship.
46. The Battle of Algiers 1966
Director: Gillo Pontecorvo
Starring: Brahim Hadjadj, Jean Martin
Synopsis: A terrorist cell and the French army go head to head for control of the city.
Review: A harrowing film if there ever was one, Pontecorvo doesn't water-down his depiction of the brutal conflict, nor does he lend more credence to the cause of one side over the other. Rather, he presents the violence perpetrated by both sides and how it dehumanizes oppressors and oppressed alike. The Algerians bomb soda shops filled with joyful youths and mow down civilians in the street, while the French are relentless and systematic in their methods to quash the rebellion which includes torture. The film has an almost documentary feel to it and records all of these events with a dispassionate eye that further heightens the sense of tension and revulsion. It's a brutally honest depiction of history than rings with more truth than any historical documentary can achieve. Fun fact: Surprise, surprise, the film was banned in France.
45. Butch Cassidy and the Sundance Kid 1969
Director: George Roy Hill
Starring: Paul Newman, Robert Redford
Synopsis: The infamous outlaws of the Wild West try to make money while outrunning the law. Review: Newman and Redford comprise one of the silver screens greatest pairings in this fun-filled western adventure story. You start off thinking that it's going to be a good old fashioned shoot 'em-up western and it delivers, but also gives you what is essentially a buddy comedy. It's a strange mix, but it works perfectly thanks to Newman and Redford's chemistry. And it's got a great musical number and a kick-ass ending to boot. Fun fact: There is some evidence that suggests that the two outlaws killed in the historical Bolivian shoot-out weren't the titular duo at all and that they made it back to the States.
44. Pan's Labyrinth 2006
Director: Guillermo del Toro
Starring: Ivana Baquero, Sergi Lopez
Synopsis: A young girl gets lost in her own fantasy world in order to escape the sadism of her stepfather.
Review: If nothing else, then this movie is a triumph of imagination. From the basic premise to the fantastic creatures, everything about this film bursts with creativity, and great writing, stunning visuals, and terrific performances (especially that of the young Baquero) are all present to back up the vision. The movie owes a great deal of its success to the way it employs all of these elements to play with polarities, particularly that of reality and fantasy. The real world is one embroiled in war and violence, filled with brutality, but even within this world there is some heart and compassion. Ofelia's fantasy world at first appears to be wondrous and full of beauty, but it is not without it's horrors. By the end the borders between these world's become blurry and the ending leaves much to audience interpretation. It's a magnificent film that simultaneously sets up and breaks down barriers between the real and the unreal, and it looks real purdy. Fun fact: It takes five hours to get into the Pale Man costume (the guy with eyes in his hands).
43. The Sting 1973
Director: George Roy Hill
Starring: Paul Newman, Robert Redford
Synopsis: Two con men attempt to fleece a banker for all he's worth.
Review: I probably should have spaced this and Butch Cassidy and the Sundance Kid out a bit, but oh well. Once again Newman and Redford pair up with director George Roy Hill to deliver a rollicking good movie with so many twists and turns that will keep you on your toes right to the very end. You never really know who to trust or how much characters actually know, and this air of ambiguity is increased because you never know what the plan is exactly until the final moments of the film. After watching this, it's easy to see where contemporary movies and TV shows like Ocean's 11 took their inspiration. It's a good mix of tension, action, and comedy that make for one of my all time favourite crime films. Fun fact: Robert Redford never saw the movie until 2004.
42. Goodfellas 1990
Director: Martin Scorsese
Starring: Ray Liotta, Joe Pesci, Robert De Niro
Synopsis: A couple of gangsters try to earn themselves wealth and power in the mafia.
Review: One of the all-time great gangster flicks which at first glance seems to glorify a life of crime, but upon closer inspection is actually an ironic look at the absurdity of it all. Henry Hill (Liotta) begins by saying that he always wanted to be a gangster, despite his outside status and, as becomes more apparent as the film progresses, the fact that he is clearly not cut out for this line of work. For most of the film he's a nervous wreck and his friends aren't much better. Tommy (Pesci) is a sadistic bastard even by mafia standards who feels that the only way to prove his manhood is through senseless violence, a belief which he pays dearly for. Jimmy Conway (De Niro) who is idolized by Hill as a great gangster, is revealed later to be insanely paranoid. At the end, shit hits the fan for Hill and everything comes crashing down in an appropriately insane way. He gets out by ratting on his former colleagues and enters the witness protection program, but even then he still glorifies the life of a gangster in his head. Scorsese is a brilliant director who gets strong performances from his all-star cast and crafts a violent, and twisted funny film. Fun fact: The word "fuck" is used 296 times in the film, about half of which are spoken by Pesci.
41. Dirty Harry 1971
Director: Don Siegel
Starring: Clint Eastwood
Synopsis: A cop who refuses to play by the rules tries to hunt down a serial killer.
Review: This movie could have ended barely half an hour in after Harry (Eastwood) gives his famous "Are you feeling lucky?" speech, and it still would have made this list, but it goes on for another hour of heart-pumping, intense action with one of the most badass characters ever put on film. The whole point of this movie is to watch Eastwood run around San Francisco, stopping crime in his own fashion. His methods are at once laudable and reprehensible, and he elicits a rather strange sort of sympathy. He's brutal and condescending, but he does everything necessary to get the job done, despite admonishments from higher-ups who'd prefer a more peaceful approach. Harry's motto essentially boils down to "the ends justify the means" which is a point of view that isn't easy to get behind, but damn if Clint doesn't make it seem attractive. Fun fact: 7 characters die in this movie.