1. Michael Travis in O Lucky Man! (Lindsay Anderson, 1973)
The adult Michael (follow up to schoolboy Michael from If...) is so innocent and lovable. In an honest attempt to climb the ladder of success, trusting, vulnerable, charming Michael takes on the job of traveling coffee salesman. Everywhere he goes, he ends up being surrounded by corrupt people who take advantage of him. He means so well! He eventually gets set up by evil businessmen and ends up in prison. When he is released from prison, society doesn't treat him very kindly. Noooo! Why does it have to be that way? Michael's optimistic nature ultimately prevails. What doesn't kill one indeed makes one stronger.
2. Alex DeLarge in A Clockwork Orange (Stanley Kubrick, 1971)
Alex is charming like Michael, except he's a morally bankrupt delinquent who regularly behaves in destructive ways. Extreme violence is all in a day's work for Alex. Michael Travis was the good man who remained good even after being treated unfairly time and time again; Alex is the flip side. He's the bad guy who remains bad even after undergoing extreme therapy meant to "cure" him of his deviance. Marion Whyte is so profound. Somehow, we see Alex as the epitome of cool. I think it helps that he feels an intense emotional attachment to the music of Ludwig Van Beethoven; it's the one thing he loves with a passion. Awww :)
3. Harry Flashman in Royal Flash (Richard Lester, 1975)
Guess what? Harry is a charmer, too!!! I'm a big fan of George MacDonald Fraser's Flashman book series, and Malcolm McDowell was the perfect choice for the role of Harry. Swashbuckler... coward... heartbreaker extraordinaire... he always comes out on top, undeservedly, by sheer luck! This movie provides fun and exciting first class escapist entertainment and Malcolm is a pleasure to watch. You will smile :)
4. H.G. Wells in Time After Time (Nicholas Meyer, 1979)
Malcolm's portrayal of H.G. Wells is sweet. H.G. is not the charming thing that my other four picks are. Wells is a shy, reserved, tweed suit kind of guy, but the ingrained coolness of McDowell cannot be suppressed so it all just works. He is funny in his naive way. He's the rational guy in this adventurous chase flick about serial killer Jack the Ripper. He's just this cute little curious serious guy with a slight sense of humour who travels to the future in his time machine in order to stop Jack's killing spree. Great story idea by a writer named Karl Alexander and interesting performance by Malcolm. Worth watching!
5. Reggie Wanker in Get Crazy (Allan Arkush, 1983)
I only saw this movie once, when it was first released on VHS. I rented it from a local video store. I hardly remember it, but in this film Malcolm portrays a flamboyant rock star, his name is Reggie Wanker, and he is charming to beat heck, so I'm picking it as my number 5 choice here. Lou Reed is in this film too, significantly increasing the coolness factor of this movie all the more!