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Taking everything into consideration, I'd say Piplup is the best starter in the games. Water/steel is a great combo, the appearance is great, the name is great, and picking it forces Dawn to run around with a different starter than her correct one, which is hysterical.
Now let's get into the other generations.
Gen 1: Bulbasaur. It matches up well against most gyms and is the cutest in its base form. It's sad how it's picked last for the kickball team, but when it comes to the kickass team, Bulbasaur is a first draft pick.
Gen 2: Cyndaquil. None of the starters are very good from what I remember, but I believe Cynnamon here has the best match ups against gyms. It also has the best looking final evolution. Chikorita is the cutest of the bunch, however, and has the saddest arch in the anime since it becomes too big to jump into Ash's arms after evolving.
Gen 3: Mudkip. Best gym match ups, only one type weakness altogether, and it's the supreme meme.
Gen 4: Piplup. See above.
Gen 5: Oshawatt, I guess? These starters are shitty looking and I never really cared for them all that much. Snivy and Porkypine have weird stats as well. Fast and defensive? Bulky but defenseless? Unique, sure, but pretty crummy. Samurott looks the best and has well rounded stats, so I choose it.
Gen 6: Delphox is the one I chose for my only playthrough of the game on the account of it looking the best as a baby. Its next two forms are disappointing, though I like the typing of fire/psychic. I wanted a cute fox, not a normal looking mage wearing a fox head. That being said, Greninja is objectively the best for battling due to its type changing ability and fucking stupid ass speed. It has no right being so close to Jolteon's stats, and it especially has no right to have an "Ash form" that surpasses Jolteon's stats. I can't stand it because of that, but it's realistically the best starter. No comments on gym match ups since I can't recall any of them.
Gen 7: Poppilo since its final evolution is the best. I didn't use the other two since I hated their designs (I replayed the game once and decided not to use a starter). Stats and trial match ups don't factor in here since the designs are so poor I'm willing to take the hit in both areas simply to avoid having an eyesore in front of me the entire game.
Conclusion: Grass types have it rough against gyms in most games. Post-gen 4 starters are trash.
EDIT: Generation vs. Generation
1 > 4 > 2 > 3 in regards to design. 5, 6, and 7 don't deserve to compare in this department.
6 > 4 > 3 > 1 in terms of use in battle. Other gens aren't particularly useful like these 'mons, Greninja, Empoleon, and Blazekickin' Chicken in paticular.
1 > 4 > 3 > 6 in all categories.
Now let's get into the other generations.
Gen 1: Bulbasaur. It matches up well against most gyms and is the cutest in its base form. It's sad how it's picked last for the kickball team, but when it comes to the kickass team, Bulbasaur is a first draft pick.
Gen 2: Cyndaquil. None of the starters are very good from what I remember, but I believe Cynnamon here has the best match ups against gyms. It also has the best looking final evolution. Chikorita is the cutest of the bunch, however, and has the saddest arch in the anime since it becomes too big to jump into Ash's arms after evolving.
Gen 3: Mudkip. Best gym match ups, only one type weakness altogether, and it's the supreme meme.
Gen 4: Piplup. See above.
Gen 5: Oshawatt, I guess? These starters are shitty looking and I never really cared for them all that much. Snivy and Porkypine have weird stats as well. Fast and defensive? Bulky but defenseless? Unique, sure, but pretty crummy. Samurott looks the best and has well rounded stats, so I choose it.
Gen 6: Delphox is the one I chose for my only playthrough of the game on the account of it looking the best as a baby. Its next two forms are disappointing, though I like the typing of fire/psychic. I wanted a cute fox, not a normal looking mage wearing a fox head. That being said, Greninja is objectively the best for battling due to its type changing ability and fucking stupid ass speed. It has no right being so close to Jolteon's stats, and it especially has no right to have an "Ash form" that surpasses Jolteon's stats. I can't stand it because of that, but it's realistically the best starter. No comments on gym match ups since I can't recall any of them.
Gen 7: Poppilo since its final evolution is the best. I didn't use the other two since I hated their designs (I replayed the game once and decided not to use a starter). Stats and trial match ups don't factor in here since the designs are so poor I'm willing to take the hit in both areas simply to avoid having an eyesore in front of me the entire game.
Conclusion: Grass types have it rough against gyms in most games. Post-gen 4 starters are trash.
EDIT: Generation vs. Generation
1 > 4 > 2 > 3 in regards to design. 5, 6, and 7 don't deserve to compare in this department.
6 > 4 > 3 > 1 in terms of use in battle. Other gens aren't particularly useful like these 'mons, Greninja, Empoleon, and Blazekickin' Chicken in paticular.
1 > 4 > 3 > 6 in all categories.