Jack Ryan - Watch Order: Release Order
The Jack Ryan film series spans over two decades and features multiple actors portraying the titular CIA analyst across different timelines and reboots. The core of the franchise consists of three connected films from the 1990s that follow Jack Ryan's evolution from analyst to field operative during the final years of the Cold War.
It's important to note that The Sum of All Fears (2002) and Jack Ryan: Shadow Recruit (2014) are both standalone reboots with different actors, modern settings, and no narrative connection to the original trilogy. The first three films maintain continuity through recurring characters like Admiral Greer, despite the recasting of Ryan himself from Alec Baldwin to Harrison Ford.

The Hunt for Red October
A new technologically-superior Soviet nuclear sub, the Red October, is heading for the U.S. coast under the command of Captain Marko Ramius. The American government thinks Ramius is planning to attack. Lone CIA analyst Jack Ryan has a different idea: he thinks Ramius is planning to defect, but he has only a few hours to find him and prove it - because the entire Russian naval and air commands are trying to find Ramius, too. The hunt is on!

Clear and Present Danger
Agent Jack Ryan becomes acting Deputy Director of Intelligence for the CIA when Admiral Greer is diagnosed with cancer. When an American businessman, and friend of the president, is murdered on his yacht, Ryan starts discovering links between the man and drug dealers. As former CIA agent John Clark is sent to Colombia to kill drug cartel kingpins in retaliation, Ryan must fight through multiple cover-ups to figure out what happened and who's responsible.

The Sum of All Fears
When the president of Russia suddenly dies, a man whose politics are virtually unknown succeeds him. The change in political leaders sparks paranoia among American CIA officials, so CIA director Bill Cabot recruits a young analyst to supply insight and advice on the situation. Then the unthinkable happens: a nuclear bomb explodes in a U.S. city, and America is quick to blame the Russians.
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