As an additional tip, when jacking the 3 bosses, it seems it only counts 1 jacking per life and not multiple.
I jacked each boss about 15 times each while still on the same life and couldn't get the achievement to pop. But once I died between each jack, it counted as 1 each time and the ach popped on the 5th time jacking Yucktopus.
I.e. Jack them once, die, jack again, die, etc....5 for each boss.
Hopefully this helps anyone who was confused like I was when it wouldn't pop.