Pine played James Kirk for three “Trek” movies dubbed the Kelvin timeline films, and did a damn fine job with the role, but it’s still intriguing to imagine what Olyphant might have brought to it as well. The actor is super versatile, but he’s perhaps best known both for his swaggering charm in roles like that of “Justified” sharpshooter Raylan Givens, and his ability to play a man caught between a rock and a hard place, as he often did as Seth Bullock on “Deadwood.” Olyphant does smooth-talking as well as he does mulling moral dilemmas, and Captain Kirk has to do plenty of both, so it’s actually not difficult to imagine him in this role.
Still, it makes total sense that Abrams was going for a younger generation take on the classic series, with then 29-year-old Pine kicking off the saga with 2009’s origin story installment. Before Olyphant auditioned for Kirk, he actually had his eye on the role of ship doctor Leonard McCoy, AKA Bones. While Olyphant may have been a better fit age-wise for that role than the role of Captain Kirk (Karl Urban, who ended up cast as Bones, is only four years younger than him), he says the part was actually already filled when he expressed interest in it.