>>5391847Basically should stay with the Heisei Riser Series, so everything after Kuuga.
The movies used to be sort of an else world story, being separate from the TV shows, but since Decade or so it has been a mess of all Riders, Super Sentai, etc coming together, so I would not bother with them if you want to know the plot of the Riders they feature.
For movies, Kamen Rider ZO is a pretty good start, stays true to the theme of the original Kamen Rider and is a complete story. 555 (Faiz) movie is a self contained else world story so you can watch it with very little foreknowledge.
For the TV shows, I personally recommend Kuuga, Agito, 555, Kiva, W and Gaim. Those seem more true to "Kamen Rider-ness" to me, and have an overall plot, being less episodic structured than the newer ones.
I'm sure other people have completely different recommendations.