>>55753014Agreeing with
>>55753415, though I'll give some more detail.
All of Kanto and Orange Islands.
For Johto, following the watch guide, all the non-filler episodes or all non-filler up until EP143 (GS Ball abandoned) or EP146 (Wobbuffet joins Team Rocket), then skip to the league for closure.
Hoenn is only good for May's contest arc. Rest of AG starting from the league and encompassing the Battle Frontier is decent enough from what I remember.
Rehash burnout hit for me in Sinnoh, so I don't recommend any beyond AG, or Orange Islands if you want to be extra cynical.
The first 5 movies are recommended along with movies 8 and 21.
Most Specials I would recommend with varying reasons from not featuring Ash, doing something different, or just cute Pokémon doing cute things.
All anime listed in the watch guide's Other tab are recommended and have no continuity with the main commercial anime.
Dub is fine for most, but Sub is a must for any Special in the Chronicles series (Chronicles's dub is really bad.), Movie 5 (Backstory cut from dub, original dub release ruined the colors.), and maybe anything after TPCi took over the dub during the middle of the Battle Frontier.