Comradeship // Freechat

Here's my favorite watching path, which I also started with:

Star Trek: The Motion Picture -> Star Trek: The Wrath of Khan -> Star Trek: The Search for Spock -> Star Trek: The final frontier (hated by many, but one of my favorites) -> Star Trek: The Voyage Home -> Star Trek: The undiscovered Country -> TNG (Series) -> Star Trek: DS9 (Series) -> Star Trek: Generations -> Star Trek: Voyager -> Star Trek: First Contact -> Star Trek: Insurrection -> Star Trek: Nemesis -> Enterprise

Benefits of watching it in this order:

1.) You get to see the original crew from the TOS series in their full glory (without them getting horny), not necessarily needing the context of the original series at all to understand the dynamics and relationships between the characters. The original six movies above (The motion picture all the way to the undiscovered country), lay the ground work for a lot of what you see in TNG, and provides some valuable context for some future episodes, as well as Star Trek: Generations. I highly, highly recommend watching the six before going to TNG, trust me, you won't regret it.

2.) There is some intersection between TNG and DS9, somewhere half way through TNG is technically where DS9 begins (I don't want to spoil, but if you want to watch them side by side, start DS9 after watching "The Best of Both Worlds" episode S03E26).

3.) Star Trek: Voyager before Star Trek: First Contact, is beneficial to watch since you get to see the evolution of the borg, as well as central elements of the borg which later show up in Star Trek: First Contact. It also makes chronological sense, which you will see in the first few minutes after watching First Contact.

4.) Star Trek: Insurrection and Star Trek: Nemesis will wrap up everything, but mind you these are two films that cause wars among Trekkies. Save Enterprise for last, because it is arguably the worst among all of them in overall quality, but technically it plays before any of the above, at the infancy of earth's space exploration. The benefit of watching it last is that everything before will fill the vague contexts and hints in the show about different species and events.

Other notes: Star Trek isn't very "progressive," either. But then again, perhaps one could also say it is a product of its time, in the lens of liberal ideology. There are some very, very problematic representations in the first few seasons that are downright racist, and even the cast themselves regret making those episodes. Other shows I can recommend (although not so great either when looking for non-reactionary media) is The Expanse. That show, had me so hooked, you wouldn't believe. It's not overly pretentious, and it almost feels like it would be the actual consequence of a capitalist dystopian future.

Hope this helps!