I’m an originalist.

IV, wait 3 years.
V, wait 3 years.
VI, wait 16 years.
I, wait 3 years.
II, wait 3 years.
III, wait 10 years.
VII, wait 2 years.
VIII, wait 2 years.
IX.

You watch the original trilogy and then you stop.

R1 (Double feature with IV to see the jarring transition from a 2016 film to a 1977 film, I think its funny)

IV

V

I

II (feel free to skip parts of I and II)

III

VI

I classify VII+ as the redacted trilogy and would rather watch the holiday special.

My preference is sort of a modified & extended machete order, though be warned that this is probably going to be a months-long undertaking so you have to be in for the long haul, and may involve searching out some fan edits

For the OT, there are some fan edits that use ports of the special editions and such where they’re appropriate for better effects and such, but use the original versions where the changes made are stupid (so han shoots first) I’d use those if possible.

IV
V

You get the “I am your father” reveal then it’s flashback time

I, some say it’s optional, but the duel of the fates is badass, and you need to introduce Maul somehow
II

Squeeze in at least a “best of” selection of The Clone wars here, I won’t blame you for not doing the whole series.

III (there’s a fan edit that mixes in the parts of the last season of clone wars and Bad Batch that happen concurrently with the movie, use that if possible, if not, save the last season for after this)

Bad Batch
Solo (optional, I enjoyed it for what it was, but it’s optional)
Kenobi
Andor
Rebels (probably do another “best of”) Rogue one (I suppose you could also do rogue one first, but I’d let episode IV stand on its own, so maybe immediately after IV)

VI

Mando
Boba Fett (very optional)
Ahsoka

Then I guess the sequel trilogy if you really want to

If they’re not in it for the long haul, and just want to do the movies

If you just want to do the main series movies

IV
(After considering my above advice, I’d probably slot R1 in here if you want to include it even though it’s not main series)
V
I (more optional here, I’d still do it for completions sake and to lay the groundwork if you think they may want to do TCW and/or Rebels later)
II
III
VI
Sequels if you want to

Personally, I prefer release order, especially for first-time watchers, but whatever you do, don’t start with TPM. The prequels are a terrible introduction to Star Wars, and if they’re watched before the viewer has an emotional investment in the franchise, it can cause them to lose interest in continuing.

If they know the “I am your father” line (which is quite possible, since it’s so prevalent in pop culture) I would go chronological. Otherwise release order or Machete+TPM.

In chronological order Anakin’s fall and Palpatine’s transition to Emperor are the big twist for the audience. “I am your father” still works as an emotional twist for Luke.

release order is the way this series hooked the world, that’s the most likely way for it to hook your friends too