I've always been a fan of piecing together messy franchises, and Jack Ryan is a perfect puzzle to sort out. The easiest way I recommend is to treat the different films and the TV show as separate eras rather than forcing a single timeline — they reboot the character every few years, so continuity is patchy.
Start with the older Cold War/90s era: watch 'The Hunt for Red October' first, then move into the Harrison Ford era with 'Patriot Games' and '
Clear and Present Danger'. Those three give you the classic Tom Clancy vibe — political chess, Cold War paranoia, and a slightly different Ryan from the novels. After that, consider the early-2000s reboot 'The Sum of All Fears' (Ben Affleck) as a standalone modern reinterpretation of Ryan dealing with post-Cold War threats.
Finally, treat 'Jack Ryan: Shadow Recruit' (Chris Pine) and the Amazon series 'Tom Clancy's Jack Ryan' (John Krasinski) independently. 'Shadow Recruit' is an origin-style reboot and works as a separate starting point if you want a slick, modern spy-thriller. The TV series is its own continuity with serialized arcs; watch its seasons in order (season 1 → season 2 → season 3) after or instead of the films, depending on whether you prefer bingeable long-form stories. Personally, I love watching the classic trilogy first to feel the roots, then sampling each reboot to enjoy how different actors and eras reinterpret the same analytical, morally driven character — it's like tasting different vintages of the same wine.