You can't go wrong with Kuuga. It's the season that restarted the franchise. The production enjoyed very few restrictions filming in way more locations than most seasons and incorporating loads of motorcycle action. There's a grit to this season that no other has, and it's easy to fall right in.
Best advice I can give you,
Read the description of each season (Kamen Rider is like an anthology series where every season is a completely new story) and or watch all the openings and just watch the one first that most intrigues you
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Read the description of each season (Kamen Rider is like an anthology series where every season is a completely new story) and or watch all the openings and just watch the one first that most intrigues you