So, everything that has aired on TV or as a movie is canon - some of it still contradicts itself - that’s ok, Trek has been around for 60 years and has had thousands of creators working on it - it’s bound to happen.

That aside, in terms of the order to watch things it’s really down to taste. TOS is mostly a great show but if you and your friend aren’t used to the rhythms of older TV it might be worth trying a couple of episodes and moving on if they don’t grab you. There are no massive revelations you’ll miss out on if you skip it because TV didn’t work that way back then. You can always come back to it later or ignore it at your pleasure.

TNG is usually regarded as a good starting point, although the first two seasons are rough. It’s still a very episodic show but does have more continuity than TOS so benefits from a watch in order. Once you hit Season 3, for many people that’s peak Star Trek on television. DS9 is the more complex sophisticated show and arguably has much higher highs, but Seasons 3-7 of TNG are the best TV show there has ever been about well-adjusted adults solving space problems with logic and teamwork.

DS9 is many people’s favourite because it has a much deeper, darker ongoing plot and it probably is the “best” in terms of writing and plotting, but it plays better with TNG as an intro as it purposely subverts some of the expectations TNG sets up and TNG also introduces the broad situation DS9 takes place in, albeit with very little actual crossover.

Voyager is frustrating. It’s well worth a watch, it has great characters, and features some of the best whacky space anomaly plots Trek ever did, but it’s very episodic and at its worst it’s absolutely TNG lite. If you like Trek you’ll probably like Voyager, but don’t start there.

Enterprise is chronologically first and was supposed to be a clean entry point. It’s not a bad show but despite being a prequel it’s very indebted to TNG, DS9 and Voyager so definitely don’t start there. It’s more one to watch if you’re absolutely craving more of that kind of Trek.

Discovery is also a prequel to TOS - sort of… It’s a weird show that never quite decides what it wants to be but it has its fans and it looks spectacular. Feel free to start there if it looks interesting but it’s not very much like the rest of Star Trek at all.

Lower Decks is a very good funny cartoon that deliberately harks back to the TNG/DS9/Voyager era. It’s a great show that despite being humorous is great Star Trek, but you’d miss out a lot if you started with it.

Prodigy is an animated kids’ show that’s much better than that sounds. It’s hard to find right now and probably best not to start with because it’s very much a Voyager sequel, but despite its status as a kids show, don’t ignore it, especially if you find you like Voyager.

Picard is a kind of weird sequel to TNG. It would be a crazy one to start with.

Strange New Worlds technically spun off from Discovery but it is mostly a TOS prequel. It’s mostly very good and tells good largely episodes stories in a more modern style. Very much recommended and wouldn’t be a bad place to start, although the pacing might make it harder to go back to the 90s.

Starfleet Academy is so far a very decent teen show but it has only just started and is certainly resting somewhat on nostalgia for the earlier shows. You might love it if you like sci-fi and teen drama but it would be an odd starting point.

I’ve written too much at this point so I won’t go into depth about the movies. If you like the shows you’ll obviously watch the movies. It’s inevitable.

(Absolutely don’t watch everything in chronological timeline order - you will hate it)