Based on 50 career movies, I thought that the next logical list would be to rank his love interests. These would be females in which he is married to, was married to, or has a physical encounter, such as a kiss. Note that he has acted with some amazing females such as Demi Moore and Julianne Hough, but they were simply leading ladies and not his specific love interest.
As always, the best part about my list, is that it is my list. That is because each person has their own movie watching history, and while you may appreciate what I have assembled, you will likely disagree somewhere along the way. The uniqueness of each person in this world is one of the many things that fascinates me. It's what makes lists of this nature, so much fun.
19. Mia Sara, 1985 - Legend
17. Penelope Cruz, 2001 - Vanilla Sky
16. Olga Kurylenko, 2013 - Oblivion
15. Thandie Newton, 2000 - Mission: Impossible II
14. Malin Akerman, 2012 - Rock of Ages
13. Lea Thompson, 1983 - All the Right Moves
12. Elizabeth Shue, 1988 - Cocktail
11. Emily Blunt, 2014 - Edge of Tomorrow
10. Michelle Monaghan, 2018 - Mission: Impossible Fallout
9. Rebecca Demornay, 1983 - Risky Business
8. Rosamund Pike, 2012 - Jack Reacher
7. Nicole Kidman, 1990 - Days of Thunder
6. Kathryn Morris, 2002 - Minority Report
5. Sarah Wright, 2017 - American Made
4. Jeanne Tripplehorn, 1993 - The Firm
3. Renee Zellweger, 1996 - Jerry Maguire
2. Rebecca Ferguson, 2015 - Mission: Impossible – Rogue Nation
1. Kelly McGillis, 1986 - Top Gun