Star Trek: First Contact (1996) — PICK
Star Trek II: The Wrath of Khan (1982) — PICK
Star Trek III: The Search for Spock (1984) — PICK
Star Trek IV: The Voyage Home (1986) — PICK
Star Trek fans, it’s a good time to be on Hulu! Nine of the 10 pre-J.J. Abrams Star Trek films are streaming on the service (the missing one is the skippable Star Trek Generations; most are also on Amazon Prime).
The solidest entries are Star Trek II: The Wrath of Khan (with Ricardo Montalban); Star Trek IV: The Voyage Home (“the one with the whales,” set in 1986); and Star Trek: First Contact (“the one with the Borg,” featuring the Next Generation crew). For my money, you also need Star Trek III: The Search for Spock (the necessary bridge between The Wrath of Khan and The Voyage Home).
Ones to skip: Star Trek: The Motion Picture and Star Trek V: The Final Frontier.
Star Trek VI: The Undiscovered Country: Your call!
Caveat Spectator: Star Trek movies include sometimes deadly sci-fi and action violence and an occasional curse word. The Voyage Home includes mostly humorous (mis)use of bad language and documentary footage of whale butchery.