Because I have been too nice for too long.

In rough chronological playthrough order...

1. What is up with the Bulbasaur family? The initial starting Pokemon aren't that bad, but Bulbasaur definitely gets the worst final form of the trio. Charmander becomes a dragon, Blastoise gets a couple of cannons, Venusaur gets a flower. And aesthetics aside, Venusaur doesn't learn as many useful moves as its counterparts. No wonder it never got on the cover of the game in the West.
2. As for Charizard, why is it not a Dragon? There is no abundance of Dragon Pokemon in G1, and no shortage of Flying Pokemon. A Fire/Dragon starter would have been cool.
3. Actually, speaking of Dragons, why are they even here? There is one family of Dragon Pokemon,, the Dratini line, and a single move, Dragon Rage, which does fixed damage. Unless having tons of types is really important, there is no reason to have the Dragon type at all.
4. Same with Ghosts. The single Ghost line in this game is part Poison and lacks the moves to make it useful against Psychic types, thus negating the entire point of the Ghost type. That's two redundant Types from the word go. GameFreak could have used that space to include more Pokemon in other under-represented types, like Fire, Electric, and Fighting.
5. Pokemon Yellow has the worst starter in the franchise. You are given a Pikachu that can not evolve in a time before items like the Light Ball could make up for it. Other than dealing with Zubats on Mt. Moon and Misty, it is obsolete as soon as you get a Mankey, Nidoran, or Butterfree. It is ineffective against 3 of the first 4 gyms and too weak afterwards. Worse, the damn thing will whine every time you put it in Bill's PC.
6. The first thing you do with your starter is cross Route 1. There, you get stuck in Viridian City until you complete a fetch quest. This is padding.
7. You only get the Pokedex after going across Route 1 the second time, and only get the Poke Ball tutorial after the third trek across the route. Until then, you can only fight or run from foes due to your lack of equipment and the Poke Mart not selling anything.
8. When the Poke Mart finally does open up, they don't sell Potions (except in Yellow). Why the **** would you sell Burn Heals and not Potions? You're just going to get new players to waste money on useless garbage they won't know is nearly useless until much later, when they actually can afford them.
9. Speaking of which, remember the Town Map? Don't get it. It doesn't do much of anything, and inventory space is very limited for some reason. Even your PC can't hold all the junk you will end up collecting.
10. Money is also a mess. First, you lose half your money every fight, and since there's nowhere to keep it like in Gen 2, there's little reason to ever spend money. Not to mention that since trainers never fight you again, there is basically a fixed amount of cash in the game until you can beat the Pokemon League. Said amount shrinks drastically if you are saving up to buy expensive items and get beaten in a fight.
11. Route 22 is a great place to capture party members, especially in Yellow, but putting the Rival here with a tough team early on is cruel. Two Pokemon at levels 9 and 8 are pretty tough if one happens to wander here early on, especially if they haven't caught any Pokemon yet and are just looking around. Plus, in Red/Blue, a rival with Charmander will have a huge advantage over your Bulbasaur and will not be weak against any Pokemon you can catch at this part of the game.
12. Route 2 is surprisingly dull. At least give us an item to find or a trainer to fight. Sure, the grass contains Bugs, but considering the nearby Bug-themed forest, that's not exactly exciting.
13. About 30% of wild Pokemon in Viridian Forest are literally incapable of attacking you. This probably convinced countless children that letting their Caterpie or Weedle evolve would make them useless. In a Pokemon game, that is a terrible lesson to teach.
14. Bug Catchers have largely disappeared from the series, and this game shows why few care. They obviously trained their Metapods and Kakunas to be stronger than the wild Pokemon, but still only use Harden? The game's first dungeon should not be so tedious.
15. Red and Blue both make one of the two Bugs rare, but not impossible to find. Interesting, but I should be running into Caterpie/Weedle more than 5% of the time. Yellow solved this problem by removing the Weedle and useful version of Pikachu.
16. Pewter City is a decent place, but the Science Museum is a nasty newbie trap. The fee is not too high, but considering the lack of tangible rewards and the scarcity of cash, it only serves to punish the curious player.
17. Brock's Rock-type Gym is pretty nice, giving the basic formula of being able to avoid gym trainers at the cost of XP and cash, but he obviously hired the wrong Jr Trainer. He uses a Diglett and a Sandshrew, neither of which have anything to do with the Rock-type.
18. Brock himself is a good fight, but there has to be a better TM for him to give than Bide. Even sticking to G1 Technical Machines, Rage would be a great fit.
19. On Route 3, literally 90% of the wild Pokemon you run into are Normal/Flying. Because lord knows that everywhere other than Viridian Forest so far hasn't included enough Normal/Flying Pokemon to catch.
20. Also, why are all of the trainers to the far west end of the Route? The first couple of leges have a whopping seven trainers to fight, and the remaining 80% of the route has one you can walk around.
21. I actually like paying for the Magikarp in the Pokemon Center, but this is a good oppurtunity to mention that Gyarados is not Water/Dragon. That would both make more sense and be cooler, so there's no excuse.
22. Mt Moon is a great dungeon to show everything Pokemon has to offer with its dungeons. It is a big maze loaded with items, trainers, and plot points. It's just a shame that 75% of the Wild Pokemon are Zubats.
23. For those of you more experienced with Zubat's recent incarnations, please remember a few things. First, there was no Crobat yet, so the long-term viability of this line is minimal. Second, Poison/Flying is one of the most boring combos to work with in Gen 1, due to the lack of Poison and Flying moves and abundance of the two types. Third, Zubat only ever learns six moves naturally, the first one of value, Bite, coming a few levels later than Mt Moon Zubat. Fourth, the Zubat family can't learn many moves via TM or HM, including anything appropriate for its Typing. For example, it can't use Fly. So 75% of the time, you're facing a Pokemon that you will likely have no desire to ever catch.
24. There are some interesting wild Pokemon in Mt Moon. Though pretty weak, Paras and Parasect can cause status ailments and have a unique typing for this gen. Clefairy is not that powerful, but can learn a lot of diverse TM moves. However, they show up so rarely, it's entirely possible one would not know that they show up in Mt Moon.
25. Why can you only take one of the fossils? It's not like getting here was a collaborative effort. The Super Nerd was going to take both a moment ago before proceeding to ambush a kid who had just taken on the mob. Not to mention that this will lead to far too many Twitch Plays Pokemon references than appropriate.
26. Remember all that treasure you wanted to get in Mt. Moon but weren't able to get to the first time around? Well, I hope you don't mind not being able to go back for hours, because this route goes one way only!
27. Go to the Pokemon Center in Cerulean City immediately. Your Rival can ambush you before you know you're leaving the city, with the most powerful team you've faced yet.
28. Even after you heal up, you are now basically trapped. You need to beat your rival to head north or elsewhere, can't go back to Mt Moon, and also have to beat Misty. If you didn't level up very much in Mt Moon or were foolish enough to start with Charmander, become acquainted with that small patch of grass to the west. You will spend ages here.
29. Also, since you can get Jynx here, I am legally and morally obligated to denounce Jynx.
30. Nugget Bridge is a cool concept, but one has to wonder about the state of this region's security when Team Rocket is able to employ a Bug Catcher. If Team Rocket can just hire any random Bug Catcher to stand around on a bridge all day, they've already won.
31. Bill, the Pokemaniac, gives a nice reward for helping him out, a ticket to a cruise ship. That's great. The problem is that he invites you to look at his computer's database of Pokemon. There are four of them. Some maniac he turned out to be...
32. That Rocket Grunt broke into a house, stole a valuable item, and literally made a hole in the back of the building to escape. The local police can't find who did it, despite his being exactly four steps from the exit he made. This is either a clever insight on how police incompetence allows organized crime to gain power or lazy writing.
33. Unless you make sure to keep a Pokemon with Cut in your party, this poor guy's house is now effectively the entrance to Route 5 for the rest of the game.
34. Without the breeding mechanics and ability to leave multiple Pokemon at the Day Care at once, it is an extremely inefficent way to level up Pokemon. Not to mention that it still charges as much as latter games despite the lack of benefits and scarcity of cash.
35. Meowth is a godsend for a troubled player. Pay Day is the one reliable source of income prior to the credits, even though it does take a while to accumulate much cash. I know that in-game economics is a recurring theme in this list, but Meowth helps solve that problem. So why is it only available in Blue version?
36. That Bug Catcher on Route 6 has two Weedles and a single Caterpie all at Level 16. This means that on no less than 30 different ocassions, he saw that his Pokemon was evolving and quickly told them not to go through with it. I'd compare this guy's intelligence to a brick's but even a brick doesn't press the B button that often.
37. I'm not one to turn down the fee Squirtle in Yellow, but this was the worst time possible to get it. First, like Bulbasaur and Charmander, it is at Level 10. It was a bit low for the other two, but Bulbasaur had a big type advantage against Misty and Leech Seed going for it, while Charmander is simply one of the relatively few Fire types available for much of the game. Squirtle is a pure Water type in a region packed with useful Water Pokemon. And you are about to go up against an Electric-type gym. With a level 28 Raichu. Thanks Game Freak!
38. Don't get cocky Red/Blue players. If you get curious, you'll learn about the mysterious Farfetch'd, which can be your by trrading a Spearow. Little do you know that Farfetch'd is one of the worst fighters in the game, with only Ditto being notably worse. It'll be fine at first, but once you realize that it never evolves, it only becomes useful as an HM-slave for cut and Fly. And like Squirtle, it is nearly useless against the Electric-type gym.
39. The SS Anne is great fun, but does have a certain design flaw. It sails away after you get Cut. Why? The ship is full of trainers to fight and cool items to find! You could lose out on Body Slam and Rest, not to mention a ton of XP and money from trainers. THis is like if you couldn't go back to Mt Moon as soon as you entered Cerulean City. Oh wait...
40. Your rival is supposed to be pretty good, right? So why did he barely get any tougher since the last fight? Your team has probably gone up at least five levels each since the last fight, and that's assuming you haven't messed around in Diglett's Cave or Route 11 yet. His have gone up two levels each. True, Abra evolved into something useful (in Red/Blue), but your team also has had time for evolutions. And in Yellow, he has no evolved Pokemon at all!
41. I like Surge's boss fight and trainers. They are a great way of showing the power of Electric Pokemon and the value of checking out that little cave to the east. The problem is the puzzle. Not only does it involve going around and mashing the A button, it is largely randomized. If Twitch Plays Pokemon could tackle a puzzle with more ease than many players, the puzzle is probably not well designed.
42. Route 11 is a nice side-route that serves as a training ground now and a way to travel more easily later. Plus, if Abra is not your cup of tea, the local Drowzee is a viable alternative for the team's Psychic. It is a bit generic, but if you are playing Red/Blue, there are no huge issues. If you are playing Yellow though, the wild Pokemon are annoying. ONCE AGAIN, about 75% of them are Pidgey, Rattata, or their respective evolved forms. Drowzee breaks things up, but the Spearows, Ekans, and Sandshrew of Red/Blue, which helped make this route feel at least a little bit different, are absent. Isn't the third version of a Pokemon game supposed to be the best one.
43. Diglett is one of the least imaginative Pokemon ever created. You draw a semi-circle, add a couple of eyes and a nose, and you're done. If it weren;t cute and useful, I'd have more to say, but please think about how overly simple this guy's design is. The slimes of Dragon Quest had more fine detail than this thing.
44. Dugtrio is three Digletts. It's literally in the name. Dug-TRIO. Somebody at some point thought that the best evolution for Diglett was having a trio of them all close together, and people went along with it. Say what you will about recent Pokemon like Trubbish, but at least they tried to express an iota of creativity.
45. Of the five Hidden Machines in Red/Blue/Yellow, three of them (Fly, Surf, and Strength), are at least decent moves in their own right. Cut is worse, but at least is an option for a few Grass Pokemon with limited movepools. Not only is Flash a glorified Sand Attack, it is never actually necessary. A few areas become harder without it, but one can beat the entire game without ever using it. And considering how the Aide who gives it holds it back unless you've gotten enough Pokemon, it sort of seems like Game Freak realized this.
46. Route 9 has a Bug Catcher with a pair of Beedrills at Level 19. Finally, a Bug Catcher who is smarter than a brick! Then a few minutes later, you meet one with a Caterpie and Weedle each at Level 20. It makes you wonder if Bug Catchers are deliberately sabotaging themselves in an elaborate scheme to deny you XP, and there was one rogue agent who went outside of the system to delver a halfway decent fight. Because the alternative is that somebody hasn't evovled their Caterpie or Weedle by Level 20. And that's depressing.
47. Voltorb can be caught in Red/Blue at this point. It is a Pokeball with eyes. That makes Diglett look ambitious.
48. Electrode is Voltorb upside-down. It doesn't even change shape really. It's just upside-down. And the eyes are less angry, so it looks less dangerous if anything.
49. Voltorb and Electrode do not learn any Electric attacks naturally. This includes both direct damage moves like Thunderbolt and status related moves llike Thunderwave. It gets a few Normal moves, two of which are suicide attacks, and Light Screen. Sure, you can use a TM, but that only gives it one useful move to work with. Swift comes naturally and is a good second choice, but suicide attacks are pretty poor outside of multiplayer, and Voltorb doesn't even learn that many moves via TM or HM, so what does it have going for it?
50. Oddly enough, Yellow version players get the more useful Magnemite instead of Voltorb, despite starting with Pikachu. It never learns anything exceptionally powerful, relying on Thundershock until you get it a TM for Thunderbolt of Thunder, but I appreciate the step in the right direction. That said, Magneton is from the same lazy school of design as Dugtrio, where drawing the same Pokemon multiple times equals an evolved form. That is stupid.
51. Although Rock Tunnel is better than some caves, half of the Pokemon here are still Zubats. What's funny is that this supposed "Rock" Tunnel doesn't actually have that many Rock type Pokemon. The mixture of Geodudes and Onix's (Onixes? Onixi?) only makes up 30% or 35% of wild encounters, depending on the version of the game and which floor one is on. I know there were only 151 Pokemon at this point, but they could have thrown in a Graveller or Rhyhorn every so often? The Old Amber could have been found in here also, which would have attached another Rock Pokemon to this area later in the game.
52. This big cave, which essentially locks off half of the game's world until after you explore and get through it, contains no items. There is no rare TM, no Nugget in a hidden corner, no Antidote in an obvious place. There is zilch.  If I'm going to be wandering around in the dark, bumping into something nice ocassionally would be nice. At least the GBA remakes threw in a couple of little things like a Revive and Escape Rope.
53. When you finally get through Rock Tunnel, there is a random chunk of Route 10 with a few trainers to potentially ambush you. Considering how the Pokemon Center is on the other side of the cave and the nearest Mart was a couple of routes before that, it is entirely possible to lose to a no-name trainer just outside of Lavender Town and have to do the Tunnel over again. Especially if you make the mistake of using the ledge to the left.
54. Lavender Town is appropriately creepy, but Pokemon Tower is a bit odd. And I'm not just referring to the generic name. Countless Pokemon have graves here. Are they buried? On each floor? If I'm on the third floor, can architectural failure lead to the corpses of dead Pokemon falling down on me from the fourth floor? And what about Pokemon that are large and/or heavy? Rock Tunnel is just to the north, and one of the two Snorlaxes in the game is a bit south, so this town in particular is going to have Pokemon that are a bit hard to pull a Telltale Heart for, especially on a large scale. And these can't simply be memorial stones; the word "grave" is used repeatedly. My best guess is that Pokemon are cremated and then the ashes are buried, but even that is problematic in some cases. Magnemite is going to leave behind bits of iron ore, not ash.

Lol this is hilarious. I love it because a lot of it is true and people are blinded by nostalgia when they say those were the best games. Yes, they started the entire series and changed the gaming industry, but when compaired to their successors, no, they actually really suck. Haha

The ghost thing was apparently an oversight? I'm not sure what they were thinking there tbh.

It could be argued that the first Pokemon game was the best of the series, relative to the time of its release. A similar line of thought is usually used when people call something like OTT the best Zelda, despite many of its 'innovations' now being fairly standard or outdated. It's likewise how i can call FF9 my all time favorite game.

I don't have much of an opinion for either side, but it's definitely a viable argument.

This. Although my favorite is gen 2. After that Pokémon became too forumalaic and stale. Pokémon was still fresh in the first two generations.

As someone who actually was dumb enough to get stuck there on their first time through, that stupid enclosed area on Route 25 with the TM inside. Idiotic, granted, but the fact it's even possible is ridiculous.

This should interesting... would like to see the other things to be added to the list

Generation 1 started the formula. Gen 2 perfected it.

Geodude has no legs. How it moves is a total mystery.

Gym leaders can leave for several months at a time with apparently no ramifications. Oh you want to challenge the elite four? Too bad, Giovanni's out cruising for chicks.

Every flying type is dualtyped for some reason.

Rhydon, who is doubly weak against water, can learn surf.

Amnesia effectively doubles your special attack and special defense. Broken.

Mom takes all of her parenting advice from the TV.

Flareon gets crazy high attack, and never learns a useful physical move.

A zubat can travel with a ten year old child 10 times its size on its back.

Hypno lures children away during the night. What does he do with them? That's better left unanswered. Seriously, every trainer should stop the gym BS right now, and put a stop to this Hypno epidemic once and for all.

I never heard of this.  How does that happen?