Risa

Depends how well you tolerate the pacing and quality of older media.

TOS (The Original Series) is wild and fantastical in its own special way. It's not up to modern standards in many ways so I personally wouldn't recommend starting here.

TNG (The Next Generation) holds up much better. Full of space exploration and philosophical dilemmas. This is a good starting point if you want to watch by release order, but be warned that it takes a few seasons to really get good.

DS9 (Deep Space 9) picks up after the events of TNG but is mainly focused on a space station orbiting a contested planet. Less exploration, more politics and the consequences of war. Personal favorite but probably not the best starting point.

Voyager follows the crew of a ship that gets sent to the other side of the galaxy and has to find their way home. More adventurous with the writing because everything here is new, and it mostly works well. Less connected to the other series so starting here works just fine.

Enterprise is a prequel series and it's pretty divisive. Some great characters and history building, but they go hard on the "American space pioneers" theme. Just watch the intro theme. Please don't start here.

Discovery is the first series made for modern audiences and it shows. Fast paced, high action, gorgeous visuals, and woke af. It's Trek for short attention spans. It's actually really good for the first few seasons, then it goes off the rails. Start here if you want it fast and loud.

Picard is a follow up of the captian from TNG but now he's old and retired. Packed full of fan service moments. Don't watch this until you've seen TNG.

Lower Decks is currently airing. It's animated, silly, and has a lot of fun with the franchise. Great stuff here that you will appreciate more if you get the references, but if you want fun, short episodes then go for it.

Strange New Worlds is also currently airing and is quickly becoming my new favorite. It's a prequel to TOS and has found a wonderful balance between old and new Trek styles. I think this is the best place to start if you're used to modern production quality and have never seen anything else in the franchise.

There are a ton of movies you could start with as well but I'll leave it at that for now.

Fellowship of the Ring

Lower decks is the shit! It makes a bunch of references to all the other shows and movies and stuff but stands on its own. Its kinda like rick and morty but a bit more wholesome. If you wanted to dig in to the live action stuff hmm I'm not sure where you should start .. if you don't mind cheesy old scifi then anywhere would be good, if you like more modern stuff try Strange new worlds its excellent and might hook you enough for the old series

The show isn’t a comedy. It’s memes about the characters and situations that are funny.

Strange New Worlds.

Unironically, it embodies all of the best qualities of Star Trek, on top of being funny, incredibly well-made, and generally fun to watch.

Update for everyone - based on these, I'm currently 1/3 through episode 1 of Voyager. I had to pause it to go run some errands but I'm loving it so far.

I say start with either the original series (if you find old stuff charming, it's great), or The Next Generation (the 2nd series).

I'll be the crazy one and say Star Trek Voyager. Lots of insane moments and more creative freedom in the Delta Quadrant. You don't have to learn decades of lore. Janeway is the craziest captain you will have with the exception of Marriner.

The memes are mostly observations and common headcanon stuff. The show itself has humor, but only Lower Decks is intended to be a comedy. There's a lot of cheese and camp in the early shows (TOS, early seasons of TNG) but the later on down you go, the more refined they get.

If you're looking for funny then Lower Decks is hot hot hot. If you're looking for mostly serious but lots of jokes thrown in then Strange New Worlds is the way to go. If you want classic but not campy, the next Generation and skip the first season maybe and go back to it? Or don't skip it idk. The Original Series is a 60s show through and through. It's great but hard for some people to watch. But if you've watched old shows before and liked them then do it! Finally if you're in the mood for something dark to with DS9.

Lower Decks IS funny.

Strange New Worlds is where you should start IMO.

A double feature. First, Casino with Robert De Niro – then DS9.

Master and Commander: The Far Side of the World.

I say this unironically. It's the best Star Trek film ever made, and I am very serious about this.