There have been five Jack Ryan movies and one TV series and here's how to watch them in the correct sequence, kicking off with John McTiernan's "The Hunt for Red October" (1990).
Next is Phillip Noyce's "Patriot Games" (1992) followed by Phillip Noyce's "Clear and Present Danger" (1994) and then Phil Alden Robinson's "The Sum of All Fears" (2002).