Who would have made the best Captain America (and Red Skull) over the years?
1990s-2000s: Brad Pitt
The world got to know Brad Pitt in "Thelma and Louise" (1991), "Legends of the Fall" (1994), and "Se7en" (1995), and in his own "Cap" film, the then-developing leading man could have kicked off the superhero film era by bringing the comics legend to life. Starting with "Blade" (1998), the late '90s were the coming out of the superhero film as a form of viable and bankable big screen entertainment. His future roles in "Troy" (2004) and "Inglorious Basterds" (2009) proved that Pitt has the action chops, while his likability factor and effortless sincerity would make him a ideal Steve Rogers for any era. Yes, Chris Evans is note perfect in the role, and fans are lucky to have him, but Brad Pitt's Cap could have kicked off an earlier, very different Marvel Studios dynamic with an A-lister jumpstarting the Marvel cycle of films. (And while 1990 did see the release of a "Captain America" film starring Matt Salinger, we'll stick with the fantasy version instead.)