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Order sorted chronologically, though, there's a decent argument to be made fitting each member's personality.

And yes, I will count ENT as the tail-end of the "golden era," seeing as VOY's finale was 5/23/01, with ENT's debut on 9/26/01. Pretty short refractory period, if you ask me.

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No, no. TOS would be Daredevil, and the rest would be TMNT
Edit: for those you don’t know, the canister of toxic waste, which transformed the Teenage Mutant Ninja Turtles (and Splinter) into their anthropomorphic form is the same canister of toxic chemicals that hit Matt Murdoch in the face and blinded him, leading to him becoming daredevil. After smacking Matt Murdoch in the face and blinding him, it then rolled into a nearby sewer, where it leaked more, and transformed a bunch of turtles and a rat.
I’m totally serious. A major Daredevil villain? The Hand. In TMNT, it’s The Foot. Who trained Matt Murdock? Stick. Who trained the TMNT? Splinter. The puns and in jokes keep going from there. TMNT was made by fans of the daredevil comics as a spinoff. And it’s awesome for that.
- A purist, I see.
- Who do Bebop and Rocksteady represent in Daredevil? 🤔
  
  the radio station

ENT is underrated. Yeah a little rough at times, but which series isn't. Every day I'm angry that we didn't get more seasons and get to watch the birth of the Federation.
Also, while TOS has a special place in my heart and in Trek fandom, it has not aged well for many reasons.
- I love ENT, but I'll never get over how the dealt with trip at the end. I still want to fight the writers over that.
  
  I pretty much just ignore the series finale of ENT
- I agree, ENT is pretty great. The last season was so amazing, it really hurt to see it canceled.
  TOS was really hard for me to get through. I think season 2 was pretty good, but season 1 and 3 were a struggle.

Order sorted chronologically, though, there’s a decent argument to be made fitting each member’s personality.
I just clicked in specifically to chastise you for assigning TNG to Mikey of all turtles!
- Mikey is the goofiest, but arguably the most skilled. Of the four weapons, he is using the hardest to master.
  
  That's a very good point, but I feel like it would just lead to an argument about which series (DS9) is somehow objectively "best" (it's DS9), and that's really not the sort of argument I'm here to start (because it's obviously DS9).
- TNG starts off all kinds of goofy, which is a shade of how TOS was.
  
  True, early TNG would be a better fit. And I get that having any other series in the leftmost spot feels wrong.
  Still, I'd have to go with:
  TNG = Leonardo
  DS9 = Donatello
  VOY = Michelangelo
  ENT = Raphael

Rocked by the omission
- Mistakes were made.

And yes, I will count ENT as the tail-end of the "golden era,"
i remember seeing ENT reruns as a kid and thinking how it made TNG look ancient by comparison. all these years later with the newer series to compare to, all that stands out is the uniforms and CGI (the latter of which is also all over VOY)
- ENT always felt kind of cheap in comparison to the others here. Lots of obvious Green-Screens for example.
  
  at the time the green screens were what probably made it look so advanced to kid me- it's funny/sad how those effects aged like milk but the practical effects from TNG and DS9 aged like wine

The only two where it doesn't fit the personality, IMO, is TNG and ENT should be flipped. TNG is more cerebral like Donatello, where as ENT is just downright goofy at times like Mikey.
- Fair, so long as we agree Raph is spot on for the wrath of The Janeway.

!lemmySilver
- Thanks
  
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I now want a version of TMNT with Patrick Stewart, Avery Brooks, Kate Mulgrew, and Scott Bakula as the voices of the turtles.

I take it TAS is six feet under?
- That can be the little turtles, I guess.

Any love for SNW?
- Of course, but that's 3rd era alongside Lower Decks, Disco, Picard, and Prodigy.
  
  I'm lazy or I'd add a third row to the meme that has the turtles ushering a scaled-down copy of the second row into the distance.
  Because, you know... It's turtles all the way down.
- Would SNW be Casey Jones or April O'Neil?

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