The Undiscovered Country is the final appearance of all the major cast members from the original television series as a group. For the new characters, casting director Mary Jo Slater loaded the film with as many Hollywood stars as the production could afford, including a minor appearance by Christian Slater, her son. Meyer was interested in casting actors who could project and articulate feelings, even through alien makeup. Producer Ralph Winter said, "We were not looking for someone to say 'Okay, I'll do it', but people who were excited by the material [...] and would treat it as if it [were] the biggest picture ever being made."
• William Shatner as James T. Kirk, the captain of the USS Enterprise. Despite his personal hatred of the Klingons for killing his son David, Kirk is ordered to escort the Klingon High Chancellor to Earth. Shatner felt that though dramatic, the script made Kirk look too prejudiced.
• Leonard Nimoy as Spock, the Enterprise's science officer and second-in-command. Spock first opens negotiations with the Klingons after the destruction of Praxis and volunteers Kirk and the Enterprise to escort Chancellor Gorkon to Earth.
• DeForest Kelley as Leonard McCoy, the chief medical officer of the Enterprise. Kelley's appearance as McCoy in The Undiscovered Country was his last live-action role before his death in 1999. With Leonard Nimoy as the film's executive producer, the 71-year old Kelley was paid US$1 million for his role, assuring a comfortable retirement for the actor. Kelley and Shatner shot their prison scenes over the course of six to eight nights; the two actors got to know each other better than they ever had.
• James Doohan as Montgomery Scott, chief engineer aboard Enterprise. Scott discovers the assassins' clothing hidden in the dining room shortly before the two men are found dead.
• George Takei as Hikaru Sulu, captain of the USS Excelsior; despite having taken his own command, Sulu remains loyal to his old friends aboard the Enterprise. The Undiscovered Country marked the first canonical mention of Sulu's first name, which was first mentioned in Vonda McIntyre's 1981 novel The Entropy Effect. It was included when Peter David, author of the film's comic book adaptation, visited the set and convinced Nicholas Meyer to insert it.
• Walter Koenig as Pavel Chekov, navigator and second officer on Enterprise. Chekov finds Klingon blood by the transporter pads, leading Spock to widen his search of the ship.
• Nichelle Nichols as Uhura, the Enterprise's communications officer. Uhura was supposed to give a dramatic speech in Klingon during the film, but midway through production the speech was scrapped and a scene where Uhura is speaking garbled Klingon while surrounded by books was added for extra humor. Nichols protested the scene, wondering why there were still books in the 23rd century, but accepted the change since it would be the last Star Trek film she would appear in. Being African-American, Nichols was uncomfortable with some of the dialogue's racial undertones. …

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The Final Frontier, the previous film in the series, was a critical and financial disappointment; Paramount was worried that the franchise would not be able to recover from the blow. With the looming 25th anniversary of the original series in 1991, producer Harve Bennett revisited an idea Ralph Winter had for the fourth film: a prequel featuring young versions of Kirk and Spock at Starfleet Academy. The prequel was designed to be a way of keeping the characters, if not the actors, in what was called "Top Gun in outer space". Bennett and The Final Frontier writer David Loughery wrote a script entitled The Academy Years, where Dr. Leonard McCoy talks about how he met Kirk and Spock while addressing a group of Academy graduates. The script shows Kirk and Spock's upbringing, their meeting McCoy and Montgomery Scott at the Academy and defeating a villain before parting ways. The script would have established that George Kirk, James T. Kirk's father, was a pilot who went missing—presumed dead—during a warp experiment with Scott. The script is set before the "enlightenment" of the Federation; slavery and racism are common, with Spock being bullied because he is the only Vulcan student. Nurse Christine Chapel cameos in the script's climax.

Actor James Doohan claimed that Paramount chief Frank Mancuso had fired Bennett following negative reaction from the core cast, Roddenberry, and fans. Bennett claimed that after he rewrote the script to include Shatner and Nimoy, Paramount had still rejected it and that he decided it was time he left the franchise. He said, "My term was up. I was offered $1.5 million to do Star Trek VI and I said 'Thanks, I don't want to do that. I want to do the Academy.'" Actor Walter Koenig approached Mancuso with a new script outline codenamed "In Flanders Fields"; in it, the Romulans join the Federation and go to war with the Klingons. The Enterprise crew, except Spock, are forced to retire for not meeting fitness tests. When Spock and his new crew are captured by a monstrous worm-like race of aliens (which Koenig described as "things that the monsters in Aliens evolved from"), the old crew must rescue them. In the end, all of the characters except McCoy and Spock die.

Mancuso asked Leonard Nimoy to conceive the new film to serve as a swan song for the original cast. Nimoy, Mark Rosenthal and Lawrence Konner suggested Kirk meeting Jean-Luc Picard, but Star Trek: The Next Generation's producers refused to end their show. Nicholas Meyer, who directed The Wrath of Khan and co-wrote The Voyage Home was also approached for an idea for the sixth film, but had none. Ralph Winter was brought on to the project as producer shortly after Bennett's departure, and said Paramount's mandate was to produce a 25th anniversary film that would not cost a lot of money.

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The Undiscovered Country's Cold War allegory and references to literary history were recognized among researchers and cultural historians. Scholars have noted that it is the Klingons, not the humans, who quote William Shakespeare; Gorkon claims at one point in the film that "You have not experienced Shakespeare until you have read him in the original Klingon." In reality, the reverse—translating Shakespeare into Klingon—proved problematic because Marc Okrand had not created a verb for "to be" when he developed the language. Shakespeare scholar Paul A. Cantor argues that this association is appropriate—the warlike Klingons find their literary matches in the characters Othello, Mark Antony, and Macbeth—but that it reinforces a claim that the end of the Cold War means the end of heroic literature such as Shakespeare's. According to Kay Smith, the use of Shakespeare has meaning in itself and also derives new meaning (underscoring cultural politics in the film) by its rearticulation in a new form. Meyer said the idea for having the Klingons claim Shakespeare as their own was based on Nazi Germany's attempt to claim the Bard as German before World War II.

According to scholar Larry Kreitzer, The Undiscovered Country has more references to Shakespeare than any other Star Trek work until at least 1996. The title itself alludes to Hamlet, Act III, Scene 1, the famous "To be, or not to be" soliloquy. Meyer had originally intended The Wrath of Khan to be called The Undiscovered Country. Whereas the undiscovered country referred to in Hamlet (and its intended meaning in The Wrath of Khan) is death, Star Trek VI's use of the phrase refers to a future where Klingons and humans coexist in peace.

Chang recites most of the lines from Shakespeare used in the film, including quotes from Romeo and Juliet and Henry IV, Part 2 in his parting words to Kirk after dinner. During Kirk's trial, Chang mocks Kirk with lines from Richard II. The final battle above Khitomer contains seven references to five of Shakespeare's plays. Two references are drawn from the title character's lines in Henry V ("Once more unto the breach"/"The game's afoot"), while two more quotations are from Julius Caesar ("I am as constant as the Northern Star"/"Cry 'havoc!' and let slip the dogs of war"). There is a single reference to Prospero from The Tempest ("Our revels now are ended"), and Chang shortens the wronged Shylock's speech from The Merchant of Venice: "Tickle us, do we not laugh; prick us, do we not bleed; and wrong us, shall we not revenge?" The final line spoken by Chang before he is obliterated by torpedo fire is lifted from Hamlet's famous soliloquy: "to be, or not to be..." Flinn was initially unsure about the numerous classical quotations, but when Plummer was cast, Meyer enthusiastically added more. He said, "Whether it's pretentious or not, I think it depends on how it's used. [...] I don't quite agree with using too much of that sort of thing, but once you get Plummer, suddenly it's working."

In addition to Shakespeare, Meyer's script includes references to Arthur Conan Doyle. "The game's afoot", originally from Shakespeare's Henry V, is spoken by Sherlock Holmes to Dr. Watson in a short story by Doyle. As the Enterprise crew works to identify Gorkon's assassins, acting Captain Spock invokes "an ancestor of mine" who maintained that when the impossible is eliminated, what remains must be true, no matter how unlikely it is. This statement was made by Holmes in several works by Doyle; Meyer, too, has written Holmes novels, an…

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