Red suggests getting Andy a gift, and his friends agree. Remembering that Andy had been planning to make his own chess set, he says, "Guy likes to play chess. Let's get him some rocks." Heywood nods agreeingly...but then the phrase sinks in and he looks puzzled, turning to Red like a lost puppy.
While working in the field, the inmates try to find rocks for Andy's project to make chess pieces, and Heywood thinks he's found a good one until:
Floyd: Heywood, that isn't soapstone. It ain't alabaster either. Heywood: What are you, a fuckin' geologist? Snooze: He's right, it ain't. Heywood: Well what the hell is it, then? Red: A horse apple. Heywood: ...Bullshit. Red: No, horseshit. Petrified. [Heywood pulls the "rock" apart, revealing that's exactly what it is.] Heywood(disgusted): Oh, Jesus Chr— [The other inmates crack up.]
The prisoners are helping Andy to set up the prison library, coming across :
Heywood: Treasure Island. Robert Louis— Andy: Stevenson. 'Fiction' > 'Adventure'. What's next? Red: I got here... Auto Repair and... Soap Carving. Andy: 'Trade Skills and Hobbies'. Goes under 'Educational'. Stacked behind you. Heywood: Count of Monte Crisco. Floyd: That's 'Cristo', you dumb shit. [Red grins with laughter.]] Heywood: By Alexandree... Dumbass. Dumbass. [Red finally bursts out laughing.] Andy: ...dumbass? [Heywood shows the book as "proof"] Andy: Dumas. You know what it's about? You'll like it. It's about a prison break. Red: Well we ought to file that under 'Educational' too, oughtn't we?
The day the prison receives a shipment of books, they come with a letter for Andy, who's been sending letters to libraries asking for funding. It closes with, "We now consider the matter closed; please stop sending us letters!" Not only does he not listen, he decides to start sending them two letters a week from then on.
The end result: Andy wins and the library gets expanded.
Tommy: So I'm backin' out the door, right? Had the TV like this... [Mimes his grip] Big ol' thing. Couldn't see shit. Suddenly, there's this voice: "Freeze, kid! Hands in the air!" Well, I just stand there holdin' on to that TV, so the voice says, "You hear what I said, boy?" And I say, "Yes, sir; I sure did; but if I drop this fuckin' thing, you got me on 'Destruction of Property,' too!"
That poor new inmate slaughtered by Hadley in the beginning? In the credits, he's credited as "Fat Ass".
And while we're on the subject of Black Comedy... here's Red talking about Warden Norton after he splatters his brains all over the wall.
Red: I like to think the last thing that went through his head — other than that bullet — was to wonder how the hell Andy Dufresne ever got the best of him.
Norton's Villainous Breakdown after discovering Andy's escape. What makes it so great is when he starts throwing rocks around Hadley and Red, the sadistic prison guard and the old prisoner, have the exact same expression of befuddlement at both the situation and Norton's behavior.
Norton: Lord, it's a miracle! Man up and vanished like a fart in the wind! Nothing left but damn rocks on the windowsill. And that cupcake on the wall. Let's ask her. Maybe she knows. What say there, fuzzy britches? Feel like talking? Aw, guess not. Why should she be any different? This is a conspiracy. That's what this is. One. Big! DAMN! CONSPIRACY! AND EVERYONE'S IN ON IT!! Including HER!
Red: "Andy crawled to freedom through five hundred yards of shit smelling foulness I can't even imagine, or maybe I just don't want to."
Andy's first conversation with Red brings up the Running Gag of the inmates saying they weren't guilty and were only incarcerated because their lawyers screwed them over. When Tommy joins the crew, Andy remembers exactly what Heywood said as a response: "Me? A lawyer fucked me." The look on Heywood's face is an expression that can't really be described with certainty.
Andy offering to help Hadley avoid paying taxes on his inheritance is Hilarious in Hindsight when you realize that Clancy Brown also played Mr. Krabs, who was famously stingy with his money.