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I like to measure by taking these quizzes asking you to write all Pokémon of a given Generation, note that these are my own memories so they may not match with yours depending on what games you played, Pokémon media you consumed, and whatnot. I kind of rushed it and my references are mainly on the games and very little on the rest, so some of these might be weird:
>Gen 1
Sandslash line, Ninetales line, Slowbro line, Kingler line, Marowak line, Lickitung, Cloyster line, Seadra line
>Gen 2
Stantler, Smeargle, Granbull line, Lanturn line, Quagsire line (This one's really bad I should have remembered it), Politoed, Yanma, Gligar, Ursaring line, Wobbufet, Girafarig
>Gen 3
Breloom line, Azurill, Delcatty line, Aggron line (Once again shameful), Volbeat, Illumise, Roselia, Swalot line, Sharpedo line, Grumpig line, Whiscash line, Crawdaunt line, Absol, Wynaut, Luvdisc
>Gen 4
Pachirisu, Ambipom, Mamoswine, Chatot, Bonsly, Munchlax, Toxicroak line
I suggest people to take these quizzes because these are interesting
Could have done 5 too but i'm lazy, 6 and onward I really don't know well
