Marge & Bart: I love both characters, but I think they're both distant 3rd and 4ths to Homer & Lisa for me. Marge came into her own as more and more seasons passed in the show, but she kinda starts out as a non-entity/frazzled and abused wife and I was only really big into the Simpsons for the first 6 or 7 seasons. (If I'm wrong on this, I will freely admit it's been decades since I've seen old Simpsons, but that's what my out-of-focus memories of her tell me.) Still, she's great. I mained her on the arcade game. Bart is fun, but also a dick and I found myself empathizing way more with his sister than him. The episodes that centered around him were never as great as the episodes that centered around Homer. But I definitely spent a lot of time in my youth telling people to not have cows.
The Brain: Fantastic character. Definitely follows many past archetypes, but was probably the best skit in Animaniacs.
Mojo Jojo: PPG was part of that first wave of anime-likes that took the late 90s by storm. I'm not a big fan of his faux Asian accent (it's kinda racist) but he's a funny monkey and funny monkeys are the best. Also, PPG is a great show. I hope at least one of the girls make it on the list.
Dr Orpheus: Definitely my favorite Venture Bros character, which says a lot when that show is just overflowing with incredible characters. He's definitely a Dr Strange/Dr Fate knockoff, but he's got so much texture and nuance of his own that he's solid gold.
Spike Spiegel: Not the Cowboy Bebop character I voted for, but a great character nonetheless. I would have put him on my list, but it felt redundant having both him and...
Lupin III: ...on my list at the same time. Fun fact: Lupin III was the highest ranking male character on my list. What I typed out to Johnny was:
He's like a mildly less problematic Japanese James Bond who is more on the side of being a loveable goofball than cancerous mass of toxic masculinity. He's a horndog, but it's almost always just performative and he's a gentleman when it matters. He fashions himself a master thief and criminal, yet he somehow manages to end up serving the public good instead on every adventure he goes on. He has an incredible rapport with his partners, and his escapades are essentially the blueprint for countless imitators throughout the years. He's got a mean, viscous streak that belies a dark and hidden past, and he won't abide by villains who harm innocents or his friends and will occasionally go on the warpath. But he's mostly characterized as oldened and wizened from his past in most of the franchise. He's immensely fun if you can look past his occasional horniness - which admittedly isn't great. Also Green Jacket Gang 4 Lyfe.
Starscream: Best transformer there is, hands down. (Dinobot is a close second tho.) He's so
out there in ways that villains just aren't allowed to be anymore. And he turns into a fighter jet which is the most badass vehicle any of the G1 transformers turn into. I think it says something that out of all the G1 Transformers, that besides Optimus, only Starscream's voice stands out clearly in my mind after like 30 years.
Zorak: Adult Swim peaked with Space Ghost, and Zorak was a big part of that.
Freakazoid: Probably my personal favorite of that whole era of WB cartoons. It's just kind of amazing and prescient to me that Freakazoid's entire backstory is that he was a dude who got sucked into the internet, and when he came out he was insane.
Zuko: I love Zuko. He's a great villain with a great face-turn. And he's voiced by Dante Basco! Which I think gave me an instant affinity to him. It's nice when Asian characters get to be played by Asian voice actors in American cartoons.
Astroboy: I probably should have put him on my list, but I don't have a lot of personal affinity for the guy. Still absolutely legendary and easily a top 5 most important cartoon character who will get mentioned in this whole thread.
Korone: I only dabble in vTubers, watching stray highlight videos that friends recommend. But Korone manages to be the most recommended vTuber I watch by a country mile. I don't think that's a coincidence.
Sadness: A good character with an important message to kids but oh boy does this character hit a little too close to home haha
Bagheera: Personal favorite Jungle Book character and it's not close. A very good kitty.
Winnie the Pooh: Prolly would have made my list had my list been more inclusive. Winnie the Pooh was a big part of my childhood, and Pooh was my favorite character. He's just so incredibly wholesome, and a very empathetic and emotionally intelligent character. And he's just fun. I love him dearly.
Master Shake: A total fucking asshole, and I wouldn't have him any other way. I am probably going to pay Dana Snyder on cameo to say happy birthday to a friend of mine because of how much we both love the character. Definitely single handedly makes ATHF.