8. Leonardo DiCaprio - Richmond Valentine (Kingsman: The Secret Service)
The Role: Richmond Valentine, a Richard Branson-esque philanthropist who grants free SIM cards and Internet access for everyone, but uses it for his own nefarious ends, while having a peculiar aversion to violence of any kind. What Happened: In mid-2013, DiCaprio was in talks to play Valentine, though it eventually didn't work out for undisclosed reasons, and Samuel L. Jackson eventually landed the role. Who Should've Got The Part: Jackson, for sure. Though there's an undeniable curiosity factor about how DiCaprio would've fared in the role (and whether the costume department would've still kitted him out in that ridiculous all-orange get-up), and he probably would've killed it, Jackson was so great as Valentine that it's tough to imagine anyone one-upping him, even someone as insanely talented as Leo.