"Yes," said Willie, "I'll take some orange pop." (1.129)
Does this sound like our Willie? Not too much. The post-alcohol Willie would never talk like that. This line speaks to his complete transformation.
"Gimme a slug." It was the Boss's voice.
"You know where it lives." (1.227-228)
This is about ten years after the first quote we gave you. It's important because it shows how Jack and Willie are bound together at the hip (where Jack's flask lives) by alcohol.
"It's the first time," [Willie] said. "I never got drunk before. I never even tasted it but once before." (2.371)
Willie isn't quite hooked on booze yet. But the day is young. This whole scene is given too us after we know that the Willie of many years later has already made drinking a part of his daily life.
[Jack Burden:] "According to the old folks […], the best way is to put two shots of absinthe on a little cracked ice and float on a shot of rye. But we can't be fancy. Not with Prohibition." (2.403)
We almost forget that Prohibition is on for much of novel. This ceremony also marks another stage of Willie's induction into the drinking life.
"Hair, hell," [Sadie] said, "he must have swallowed the whole dog." (2.432)
Sadie can see just how drunk Willie is. She isn't at all convinced that Jack's "cure" will work. She still thinks Willie is a complete "sap." She'll sure change her tune in a few minutes.
They drank because they didn't have the slightest interest in what they were doing now, and didn't have the slightest hope for the future. (4.10)
That's a pretty harsh assessment of his old college roommates. Jack knew them well, though, and we'll have to take his word for it. What we find interesting is that they use alcohol for a very different reason than Willie does. While they use it to forget their lives, Willie uses it to, in a sense, save his.
[…] I knew that if I didn't drink the bourbon, as soon as I shut my eyes to go to sleep the whole hot and heaving continent would begin charging at me out of the dark. (7.6)
Though we don't all treat it with bourbon, we do all know what Jack is talking about. That combination of exhaustion and having our worlds badly shaken is a good recipe for night terrors.
And as I drive down the night street, I wondered what Anne Stanton would have to say if she'd been there in that room and had seen the Boss piled up there, out blind on the couch. (9.109)
Hey, we wondered that, too. The clean image we have of Anne seems incongruous with the image of the drunken raving Boss. But then again, we don't really know Anne that well. What do you think she thinks about Willie's drinking?