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Notes -
Do you have any recommendations on which series is best (1959-1964, 1985-1989, 2002-2003, 2019-2020)?
Are there any episodes that you felt stood out above the rest?
The original is the best but 1980s version might have more like the 90s Outer Limits.
In checking on something, I saw there's a 60s era Outer Limits so you might see if there are any writers in common and start with those episodes.
If not, The Invaders might be a twilight zone episode that would give you a nice taste of the show while fitting well within your list.
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I looked through and downloaded IMDB's top rated original (1959-1964) TZ episodes a while ago. I ended up with 9 episodes from S1, 8 from S2, 9 from S3 and 4 from S5. There's lots of other selected Twilight Zone episodes lists out there to browse, they're all roughly in agreement. If you're not bothered about filtering the best of the best you can't go far wrong by starting at the start as that's where the benchmark that justified the additional series and reboots was created.
I don't know about the '80s and '00s reboots but I'd avoid Jordan Peele's 2019 reboot, it's more concerned with moral commentary on $current_year American culture war than it is the human condition.
Like Atelier says TZ is lacking in the sci-fi aspect compared to The Outer Limits. You could try 2017's Phillip K Dick's Electric Dreams but I haven't seen any of those. TZ is a bit dated and unsophisticated compared to modern counterparts like Black Mirror but like OG Star Trek it's classic television that stands the test of time.
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The Twilight Zone has some episodes that are absolute classics of the genre (and written by some of the best SF authors), the best approach would probably to try and google one of the lists that notes great episodes and go from there.
For follow-up you can watch SFDebris episodes on the content.
In case you didn't know The Outer Limits is basically TZ's younger brother.
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