Which on was the Michaels

...and why was it Deep Space 9?

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Literally never watched Star Trek properly.

Should I watch WCW from the early 90s onwards or Star Trek from the beginning?

Honestly just watch TNG and nothing else. Original Series is alright but doesn't hold up that well. Deep Space has some fun moments but doesn't have the Soul TNG has.

As much as I love DS9 (which is to say a lot) TNG is the Michaels, it lasted longer than TOS and everything after it exists because of it.

TNG > DS9 > V > Everything else.

Sure TNG is best but the original is still essential viewing, super iconic characters and intentional and unintentional comedy abounds at every turn.

The entire franchise is the Jannetty to Star Wars.

Kirk and Spock himself makes the original worth watching
TNG starts a little bit slow but it gets better as the show runners got balls and started doing more conflict storylines
DS9 is really good when it gets to the dominion war
Voyager is trash but still better than Discovery
Enterprise it's kind of meh but the last season was good.

What's the wrestling equivalent of the new Trek? AEW?

How many good TNG movies are there?
And how many good TOS movies?

1 vs 5 TOS is the clear Michaels.