In both the first and third acts of The Empire Strikes Back, Chewbacca wails because Han Solo is going to be frozen.
In the first act, Han is stuck in a snowstorm as night falls on the ice planet Hoth. When Princess Leia Organa makes the decision to close the doors of the Rebel base, likely dooming Han to freeze to death outside, Chewbacca wails in sorrow.
In the third act, Han is captured by the Empire and lowered into the carbon freezing chamber on the planet Bespin. Han's imprisoned friends watch helplessly as the freezing process puts him into a state of deep hibernation – a sleep like death – and once again, Chewbacca wails in anguish.
The animal-like Chewbacca, who is covered in warm fur and "always [thinks] with [his] stomach" (as Han says in Return of the Jedi), generally represents the warmth of passion, over and against cold, hard reason. It makes sense, both emotionally and symbolically, that he would wail over Han being frozen. However, in both cases, Chewbacca's friends overrule his passionate nature for altruistic reasons. Leia must shut Han out of the base on Hoth in order to preserve the safety of everyone inside, and on Bespin, Han forbids Chewbacca from helping him for Leia's sake: "Save your strength. There'll be another time. The Princess – you have to take care of her." Though it may seem cold, there are times when right action requires that the passions be subdued.
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Characters: Chewbacca / Han Solo / Leia Organa
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This is awesome! Another reason Irvin Kershner is and will always be the greatest Star Wars director