If

Stanley Kubricks's Lolita....starring Hayley Mills!

If that sounds far-fetched (or downright creepy) keep in mind that the Parent Trap moppet was actually considered for the role, before her father nixed it. So was Tuesday Weld (I'm sure Kim Morgan of Sunset Gun would've loved that casting choice.) As for Humbert, actors who were offered the part include Marlon Brando, Cary Grant and Errol Flynn, among others.

Historians have devoted a whole field to speculative history -- geopolitical brain-teasers like what would happen if Archduke Ferdinand had not been shot, or Hitler hadn't killed himself before the end of World War II -- so I hope you'll indulge me in a little speculative movie history. Keep in mind these are ALL real casting choices that were considered for these films:

WHAT IF...Jane Fonda or Shirley MacLaine had played Bonnie in Bonnie and Clyde? and Truffaut or Godard had directed?

...Robert Redford had played The Graduate? (He was thought to be more in tune with the WASPy character in the original book.)

...Marilyn Monroe had portrayed Holly Golightly in Breakfast at Tiffany's, in accordance with author Truman Capote's wishes?

...Winona Ryder had taken the role of Marla in Fight Club, which eventually went to Helena Bonham Carter, or Mary in The Godfather Part III (instead of being replaced by a wooden Sofia Coppola?*)

...the character of Sam in Casablanca had been a woman instead of a man (mind-blowing, I know, but that was the original idea) played by Ella Fitzgerald or Lena Horne?

...Grace Kelly hadn't married Prince Rainier and would have been free to star in Marnie, Giant, and Cat on a Hot Tin Roof?

...Kate Winslet had played Nola in Match Point? (In my opinion, Scarlett Johansson made the role. She is so much more the bombshell type than Kate. But Kate would have been better than Gwyneth in Shakespeare in Love, another part she tried out for.)

...Kirsten Dunst or Sarah Polley had incarnated the "Band-Aid", Penny Lane, in one of my all-time favorites, Almost Famous?

...Leonardo DiCaprio had stood in for Christian Bale in American Psycho and Mark Wahlberg in Boogie Nights?

...James Cameron had gone along with the studios' choice for the male lead in Titanic and picked -- wait for it -- Matthew McConaugnehy? (Macaulay Culkin was also considered. Considering that even 13 years later, he still looks 12**, I'm glad the director went with someone else)

...Even worse, Nicolas Cage had ruined, I mean acted in, the main role in Eternal Sunshine of the Spotless Mind?

*Don't get me wrong, I worship Sofia Coppola. Just not as an actress. Though she was pretty good in that Black Crowes video.

**This may be a case of severe pot-calling-the-kettle-black syndrome, as I'm a 25-year-old who looks 14 at best.