Audrey Hepburn and Older Men
She was frequently cast with older leading men and a lot of people have thought she was best with them (the famous film critic David Thompson said she made men her own age seem "clumsy") but to me that's not the case. I think she nearly always blossomed on the rare occasion she got to act with a star closer to her own age. Look at her with Peppard in Breakfast at Tiffany's, Holden in Sabrina, Peter O'Toole in How to Steal a Million, and Albert Finney in Two for the Road. Even Gregory Peck in Roman Holiday was comparitively close to her age.
Conversely, movies where the chemistry doesn't work were generally with much older men, namely Bogart and Cooper. She and Fred Astaire were funny together in Funny Face, but I didn't really buy any romantic chemistry/sexual tension. Same situation with Rex Harrison in My Fair Lady, and on top of that Henry Higgins was most likely implied to be gay. It did work out with Cary Grant in Charade, though.
It's really a pity she didn't get to work with some of the younger male stars of her generation. Montgomery Clift was almost the male version of her and certainly would not have seemed "clumsy". There could have been an opposites attract type thing with Marlon Brando. I could see her in a movie in the mid-late 50's where Richard Burton plays an angry young man who breaks her heart. The roles practically write themselves.
Any thoughts?