Captain Kirk's death in Star Trek: Generations remains controversial as many believe he deserved a more heroic death. Some fans have never forgiven the producers of Generations for the anemic way Kirk was killed. William Shatner has regrets about the death scene himself, but it isn't because it was the last time we saw Captain Kirk onscreen. In speaking with Screenrant [via CBR}, the soon-to-be 93-year-old actor says he never quite hit the mark with what he was trying to say in his last two words.
Shatner believes that Kirk was courageous in life (as do we all), and that he would face things with a sense of adventure, even death. And that was what he was trying to portray when saying "oh my." He wanted those final words to be somewere in the middle of dreading death but looking forward to what lay ahead, the next adventure. But he thinks he didn't get across what he was trying to portray.
Shatner went on to say he had a couple of takes with the scene, but he never got the nuance he was looking for. But Star Trek fans understood that would be Kirk's way of approaching death. He was never afraid of what was around the corner, facing the enemy head on. This time, death was the enemy, and he couldn't fight it, but he could choose to embrace whatever new experience it might bring.
"I thought of Kirk as being so courageous in life that when he faced things that he didn't know about, like the strange, the weird, the entities that the writers thought up, when he faced death, he would face death with a sense of adventure. Oh, what's going to happen now?' So I ad-libbed, 'Oh my.' And I wanted that 'Oh my' to be 'Oh my,' like, dreading it, but looking forward to the adventure - somewhere in between, you know, and it would be very obvious to you what he was thinking. And I never quite hit it. I never quite got that nuance that I was looking for. I had another couple of takes, but they didn't understand what I was doing.""William Shatner
It's doubtful that fans will ever look at that death scene and feel anything but dismay, but at least now we know that Kirk's final words indicated he believed death was another journey, and that he was embarking on another adventure at the end of his life.