1. Cary Grant
“Bringing Up Baby” (1938) Which first of all costars Katherine Hepburn as a ditzy socialite (You really wish they made blue bloods like that these days. I’d far rather watch her than the Hiltons or Kardashians). She is awesome. He is awesome. And it contains this quote:
KH: "Well you look perfectly idiotic in those clothes!"
CG: "These aren't my clothes!"
KH: "Well, where are your clothes?"
CG: "I've lost my clothes!"
KH: "Well, why are you wearing these clothes?"
CG: "Because I just went GAY all of a sudden!" --as David Huxley in BRINGING UP BABY (1938).
(Funny because he’s wearing her satin fur trimmed dressing gown.)
2. Paul Newman
“The Sting” (1973) Because he’s very handsome in early twentieth century duds. Plus the music is great and it takes place mostly on a train. True fact: This is the first movie I remember being able to watch and follow the whole plot. I remember seeing it on television when I was about three. (The whole train thing was a very big draw for me even then.)
3. Johnny Depp
“Cry Baby” (1990) Because he looks best in rocker mode. Also: I love rock and roll and John Waters and I miss the days when Ricki Lake wasn’t a skinny yuppie.
4. Sean Connery
It’s hard for me to not get nostalgic about all his turns as THE cool old guy. In cameos such as Time Bandits (1981) or Robin Hood Prince of Thieves (1991) or in starring/co-starring roles like in The Name of the Rose (1986) or Indiana Jones and the Last Crusade (1989) Connery could always be counted on show up and be the King or at least the kingly guy, the really smart old guy who had just lived everything and kept on going. Sort of like the dude in the Dos Equis commercials. But it see why he had credibility as that kind of man, you have to see him as James Bond. So I have to say “Goldfinger” (1964) for this one because it is the coolest, hottest, grooviest of Connery’s turns as 007.
5. Peter Sellers
I love Peter Sellers. One of the great pillars of the swinging sixties. “The Party” (1968) is my favorite Sellers movie. It doesn’t so much have a plot as a series of beautifully crafted (largely improvised!) comedic scenes. Also like many or Peter Sellers’ films it has a gorgeous moderne set design and a wonderful score by Henry Mancini. I think I attended that party in some other life.