Suppose that Akira Toriyama had started Dragon ball with the intention of making Goku an alien (Saiyan). At what point in Dragon Ball (not Z) do you think Goku would have transformed for the first time?
I'll hold off on my opinion until the ball gets rolling.






Maybe when Bora dies?
I can't think of anything other than that. No one really dies in the DB series, and as you know, dying is a sure way to get a Super Saiyan. Now that I think about it, Goku never really gets emotional either. The only time I remember him crying is when Ha-chan dies in The Path to Ultimate Strength movie.
その名は・・・ 名探偵コナン!
Sono na wa... Meitantei Conan!
His name is... Detective Conan!
I think after Kuririn is killed by Tambourine would have been a good spot. I think that was the death that hit him the hardest.
When you say emotional, I assume you mean cry. Goku doesn't typically cry so much as get upset and channel his anger. Goku cried twice that I can remember, the first is when he reunites with his grandpa Gohan at Baba's. The second is after he avenges Kuririn and Roshi's deaths by killing Piccolo.
Well Goku does go Semi Super-Saiyan in the 10th Anniversary DB movie Path to Power.
As for the topic itself...dunno...maybe in his battle with Piccalo Jr.
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I can't imagine it happening any other way but the death of friends either, so I'd agree with either Bora's death or Krillin's. But if I had to come up with some place other than that where it could have happened...maybe after Goku hears that Roshi, Chiaotzu, and Shenron are all gone as well. I think that when he came face-to-face with Piccolo again after that, with all of that knowledge and Piccolo obviously not caring, the thought of that would be enough to push him into Super Saiyan state.
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I think that Goku would have gone Super Saiyan during the fight with King Piccolo. He lost Krillin, Choazu, and his master all because of Piccolo. Not only did he lose his loved ones, he also lost the only method to bring them back.
I say when he confronts Tamborine. There is a scene where Goku's tail spikes up and so does his hair in that style if he were to transform into a Super Saiyan.