Gen 1

The OG generation, the first 151, the guys that started it all. I like to think I have Gen 1 ingrained in my memory mainly because Game Freak/The Pokemon Company keeps shoving them (or at least, the more popular ones) in my face 30 years after their introduction. Simple shapes and pallets make up this batch, the best thing about Gen 1 is that there aren't any complicated designs (there's a reason why a lot of people point at these guys and laugh at their simplicity). We're still in that stage where a kid could draw any of these guys pretty easily and you could tell who they were from a glance- give or take a few single and third stage Mons.

A very nostalgic generation for me, there's a lot of Pokemon here who I adore more than the ones from the previous game. The designs are still very simple for people to draw quickly and easily; everything has a cutesy, baby-ish, vibe to it that you can see in the faces and body shapes of a lot of Mons (other than the Beast Trio, the box legendries, and a couple third stage guys) and we could have had more if they didn't cut out some stellar designs (RIP to my lost boy Kotora- at least he lives on in fan games and Pokemon-likes). We won't be getting into the more complicated guys for a while.

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Gen 3

The cool generation, or at least the series' attempts at having more of an edge to it than the babies that came from the previous set of games (according to an interview I read at least). There's still some silly lil guys and cuties, but this is where we start seeing Pokemon get more of a cool factor to balance it all out and appeal to an older crowd.

Gen 4

I'm just gonna come out and say this right now...

Gen 4 is my least favorite generation- or least, it was my least favorite. I know, I'm awful but this is my webbed site and I'll cry if I want to. Continuing from the last Gen there's a lot of Pokemon here with an edge to them- big emphasis on darker colors, cooler designs, and more complicated monsters to further distance themselves from the earlier games that we'll start to see a lot more of as the series goes on. Don't get me wrong there's still a few here that I like (I will die on my "Luxray is the best Electric type PERIOD" hill), but I also think these are the weakest designs in series. This is probably the area where we'll start to see my memory get less accurate than usual recreating these Mons.

Gen 5

Why yes, I am a rabid "Gen 5 is the best Gen" person and I'm not upset about it, because it's true. Labeled as the "Reboot Generation", Gen 5 was a breath of fresh air in the series that gave us nothing but brand new, never before seen, Pokemon in every corner of Unova. No old favorites allowed, you will be forced to use and learn about these new Pokemon and you will like it. A lot of my favorite Pokemon come from this generation and there are A LOT of strong designs here that all range from super cute to super cool.

I know he doesn't hold rocks, but he looks so cute with it

Gen 6

The first Generation in the series that switched to 3D (sadly, RIP pixel art my beloved) Gen 6...isn't a strong generation compared to the games that came before it (there are far less new Pokemon to work with here and we- again- lost that gorgeous pixel art). The colors are dull, the models are stiff, and the designs aren't as memorable- despite having some decent Mons running around. I did randomly find a guy on Youtube who is challenging himself to give the same kind of bounce/life to the 3D models that the old sprites once had and it's been cool to see how it all comes together. For my own challenge however, this is where the struggle truly begins.

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Gen 7

Remember when I said Gen 4 used to be my least favorite in the series? Well, Gen 7 took that title pretty easily while also giving me baby's first buyer's remorse. But this isn't about the game play, or how the pacing falls apart towards the end of the story, or all the questionable decisions that went into this set of games to appeal more to those damn kids and their cellphones, this is about how well I can draw some monster guys from memory. Much like the previous generation there are some designs here that I like- and we even get a new creative twist with the Regional Pokemon- but there are also a lot of weaker guys. At some point my efforts to fill in the gaps of my memory just start looking like creative liberty.

Gen 8

Man, I still remember when people were pissed with how Gen 8 looked when it first came out. And like, I can see how people would be mad. There was a lot of controversy that went into Gen 8 but oh, oh buddy, nobody had any idea what was waiting for them down the line. Same as it ever was- there's some good, there's some bad, some Pokemon designs are stronger than others. I would die for Appletun and Snom.

Gen 9

What may very well be the final nail in the coffin for me as a longtime fan of the series. Like, wow. Those graphics. And all the glitches and bugs. The pop-in. The way it chugs. Oh lord. Did they just run out of money to pay any of the programmers and devs after getting Toby Fox to compose a few tunes and having Ed fucking Sheeran tack on a song for the ending credits???

Like I said with Generation 7, this isn't about my personal feelings towards certain games and the decisions that went into making them or the obvious lack of quality that rightfully pissed a lot of people off, this is about how well I can draw things from memory. And if there's one good thing about Gen 9 it's that there are a lot of really neat designs that make up this generation. Even if there are just as many weak designs as there are strong ones, they're still some interesting things to look at. Clodsire, Dundunsparce, Tinkaton are just a few examples when it comes to shape language and passing the silhouette test. We even get another creative twist with introduction of Convergent Species and Paradox Mons.