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.
Jack Pooley
Contributor
Stay at home dad who spends as much time teaching his kids the merits of Martin Scorsese as possible (against the missus' wishes).
General video game, TV and film nut. Occasional sports fan. Full time loon.
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