Then in the spring of 1949, after two years of imprisonment (the worst in Red's memory for Andy due to continual rapes from the Sisters), Red and Andy are selected from volunteers to begin a week's work ("outdoor detail") to resurface the roof of the license-plate factory. Red orchestrates, through his black market dealings in packs of cigarettes, their selection. In the fresh air of the outdoors - without walls, fences, or bars - while the cons pour and spread bubbling tar on the roof, Captain Hadley complains bitterly about exorbitant government inheritance taxes that he will owe after receiving money from his rich brother's estate. Out of a million bucks, Hadley will only see $35,000 and most of that will be taxed: "Uncle Sam, he puts his hand in your shirt and squeezes your tit till it's purple."

After overhearing the bitching, Andy boldly saunters over to the Captain and inquires: "Mr. Hadley, do you trust your wife?" Furious with his audacity, Hadley grabs Andy and jerks him toward the edge of the roof to throw him off, dangling him there precariously, with Andy's arms outstretched in a Christ-like pose. The ex-banker proposes a solution that would require some legal paperwork - that he could complete, of course:

Because if you do trust her, there's no reason you can't keep that thirty-five thousand...If you want to keep all that money, give it to your wife. The IRS allows a one-time only gift to your spouse for up to sixty thousand dollars...tax-free...you do need someone to set up the tax-free gift for ya, and it'll cost ya, a lawyer for example...I suppose I could set it up for ya. That would save you some money. You get the forms, I'll prepare them for ya, nearly free of charge.

For his part of the bargain in the uplifting scene [often interpreted as a Biblical Last Supper with Jesus and his dozen disciples], Andy victoriously requests "three beers apiece for each of my co-workers...I think a man workin' outdoors feels more like a man if he can have a bottle of suds. That's only my opinion." The walls dissolve for the men as they sit in the sun and drink cold bottles of beer from iced buckets - feeling like free men again, and appreciating one of the simple pleasures of life - for a short while. Andy doesn't partake of the alcohol, but sits on the side with a beatific smile on his face:

And that's how it came to pass, that on the second-to-last day of the job, the convict crew that tarred the plate factory roof in the spring of '49 wound up sitting in a row at ten o'clock in the morning, drinking icy cold Bohemia-style beer, courtesy of the hardest screw that ever walked a turn at Shawshank State Prison...The colossal prick even managed to sound magnanimous. We sat and drank with the sun on our shoulders and felt like free men. Hell, we could have been tarring the roof of one of our own houses. We were the Lords of all Creation. As for Andy, he spent that break hunkered in the shade, a strange little smile on his face, watching us drink his beer...You could argue he'd done it to curry favor with the guards, or maybe make a few friends among us cons. Me? I think he did it just to feel normal again, if only for a short while.

While playing checkers with his 'friend,' Andy asks Red to help acquire alabaster and soapstone rocks from outside the prison yard to be carved into chess pieces: "The years I got. What I don't have are the rocks." In his bunk later that night, Andy carves a chessman for his new chess set - the piece is a noble-looking knight. [Andy relishes chess and considers it a "civilized, strategic" game but Red hates it.] With one end of his rock-hammer, he carefully scratches his name into the concrete wall, adding his mark to the other names there. The wall crumbles as the first letter of his name, "A", is imprinted there. [An important plot point is missing from this sequence in the film - shown later.]

In an abrupt scene change, the film Gilda (1946) is being projected - within a bright shaft of light - for the entranced prisoners in the prison's auditorium/chapel, who are transported out of their prison surroundings into the world of cinema. The film clip begins when casino owner Ballin Mundson (George Macready) shows off his singing "canary" - his new 'caged' wife named Gilda (Rita Hayworth) to his right-hand man Johnny Farrell (Glenn Ford). One of Red's earlier flashbacks/recollections was that Andy had asked for "Rita Hayworth" (a wall poster of the pin-up Hollywood star) in 1949. [The choice of this film seems entirely appropriate, given that the film was based on Stephen King's 1982 novella Rita Hayworth and Shawshank Redemption.] In an anxious tone during the screening, Andy makes his request: "Can you get her?" Distracted by Rita flinging back her red mane of hair ("when she does that s--t with her hair"), Red exclaims, smiling: "God, I love it." Soon after, he replies that he can work his 'magic': "It would take a few weeks...I don't have her stuffed down the front of my pants right now, I'm sorry to say. But I'll get her. Relax."

On his way out of the auditorium, Andy is again ambushed by the Sisters and dragged into the projectionist's booth [a symbolic place to confront his evil enemies]. The film's dialogue, faintly heard in the background, is cleverly juxtaposed with Bogs' leering taunts toward Andy, who fights back valiantly and breaks Rooster's (Gary Lee Davis) nose with a heavy 35mm film reel:

(Gilda) What are you supposed to say to the bride?
Bogs: (To Andy) Ain't you gonna scream?
(Gilda) Good luck...
Andy: Let's get this over with.
(Gilda) My husband tells me you're a great believer...

Then, Andy is threatened with a sharp steel spike in his ear if he doesn't perform oral sex for them. Bogs demands: "I'm gonna open my fly and you're gonna swallow what I give you to swallow." Using his wits to save his dignity, Andy counters with a description of a strong bite reflex that would result from a sudden, serious brain injury: "Anything you put in my mouth you're gonna lose." Instead of being sexually brutalized - an apparent victory over them, "they did...beat him within an inch of his life. Andy spent a month in the infirmary. Bogs spent a week in the hole." When Bogs returns to his cell after a week in solitary confinement and suddenly flips his light on, Captain Hadley is there to protect his legal advisor - and to pummel the defenseless predator and turn him into a crippled vegetable: "Two things never happened again after that. The Sisters never laid a finger on Andy again. And Bogs never walked again..."

As a "nice welcome back" for Andy when he returns from the infirmary, the cons gather chesspiece-sized rocks for their now-respected hero: "By the week Andy was due back, we had enough rocks saved up to keep him busy till Rapture. Also got a big shipment in that week. Cigarettes, chewing gum, sippin' whiskey, playing cards with naked ladies on 'em, you name it, and, of course, the most important item..." - wrapped in a long, circular cardboard tube - "Rita Hayworth herself." Andy finds the wall-sized poster/pin-up of the 1940s love goddess in the tube on his bed with a small note: "No charge. Welcome back."

During a surprise inspection (termed "tossin' cells") of Andy's room by the imperious Warden - with his Rita Hayworth poster exhibited on one wall, Andy's cell is torn upside down in a futile search for contraband - the only thing slightly illegal is his rock carvings. The hypocritical Warden takes Andy's Bible out of his hand and expresses support for the prisoner's devotion to Scripture. They both exchange their favorite Biblical passages, in a game of one-ups-manship. Andy's favorite passage in the good book is slyly shared with the 'master' Warden:

Watch ye therefore, for ye know not when the master of the house cometh. (Mark 13:35)

The Warden prefers to be Andy's 'light' and savior:

I am the light of the world. He that followeth me shall not walk in darkness, but shall have the light of life. (John 8:12)

The Warden, after noticing that Andy is "good with numbers" (because he identifies the Warden's scriptural selection), strolls over to the poster and mildly disapproves "...but I suppose exceptions can be made." The Warden fails to notice that the word 'MOTHER' is scratched above the poster - a hint that the wall can be weakened. As he walks off, he almost forgets to return Andy's Bible. At the last moment, he remembers, and hands it back with a extremely meaningful, smugly-delivered phrase: "Salvation lies within." [This entire scene, in particular, contains details which - only in retrospect - are extremely significant and hold many layers of meaning.]

Shortly thereafter, Andy (#37937) is summoned to the office of the Warden, where his wife's framed, needle-point sampler is prominently displayed on the wall, reading: "His Judgement Cometh and that Right Soon..." To better use his education (but more to exploit Andy's accounting skills), Andy is transferred from the laundry area and "reassigned" to Brooks - the prison's librarian for over 37 years. The broken-down prison library is stocked with cast-off reading material: "National Geographics, Reader's Digest Condensed Books, Louis L'Amours, Look Magazine, Erle Stanley Gardners." Another guard named Dekins (Brian Delate) requests financial help - "settin' up some kinda trust fund for my kids' educations." Later, Brooks regales the other cons with Andy's re-birth as a respected financial planner who has regained some of his former status in life:

All Andy needed was a suit and a tie and a little jiggly hula gal on his desk, he would've been Mister Dufresne, if you please.

Now as the library's curator, Andy has unrealistic hopes about expanding the library's book acquisitions when he considers asking the Warden for funds. Norton is reluctant to "spend the taxpayer's hard-earned when it comes to prisons." Usually, additional prison funding is only approved for "more walls, more bars, more guards." Although not directly supportive, the Warden promises to mail persistent Andy's weekly letters to the State Senate. Now valuable as a financial accountant, he is allowed to set up an office in the library where he "did tax returns for half the guards at Shawshank. Year after that, he did them all, including the warden's. The year after that, they rescheduled the start of the intramural season to coincide with tax season. The guards on the opposing teams all remembered to bring their W-2's." At tax time during the month of April, Andy uses Red as an assistant tax preparer.

Then one day in the year 1954, Brooks goes beserk when his parole comes through - he holds a knife at Heywood's throat so he'll be judged crazy and not be released into the frightening real world: "It's what they've done. I got-I got no choice...It's the only, it's the only way they'd let me stay."

He's just institutionalized...The man's been in here fifty years, Heywood, fifty years. This is all he knows. In here, he's an important man, he's an educated man. Outside he's nothin' - just a used-up con with arthritis in both hands. Probably couldn't get a library card if he tried...these walls are funny. First you hate 'em, then you get used to 'em. Enough time passes, it gets so you depend on 'em. That's 'institutionalized'...They send you here for life and that's exactly what they take, the part that counts anyway.

Just before he departs the prison the next dawn, Brooks also releases his full-grown pet crow/raven Jake at the library window: "I can't take care of you no more, Jake. You go on now. You're free." The old con steps cautiously through the main gate of Shawshank, clutches the bar on the bus seat in front of him as he is transported to Portland where it is even terrifying to cross the street. The outside world presents itself as a new 'prison':

(voice-over) Dear Fellas: I can't believe how fast things move on the outside. I saw an automobile once when I was a kid but now they're everywhere. The world went and got itself in a big damn hurry.

A montage follows Brooks through his new life on the outside. He is placed in a half-way flop house called the Brewer, and is employed as a grocery-bagger at the Foodway Market. Lonely, afraid, melancholy, and disoriented in the outside world, he has difficulty sleeping. He worries about the fate of Jake as he feeds pigeons in the park. He even contemplates shooting the Foodway manager (to force a return to Shawshank), but he's even too old for that. As he packs his few belongings into a bag, he narrates, in voiceover, that he plans on leaving: "I don't like it here. I'm tired of being afraid all the time. I've decided not to stay." He climbs up onto a chair and then onto a table and carves a message into the wall with his pocketknife: "BROOKS WAS HERE." And then he kicks out the table from under his weight and hangs himself - his feet dangling. The end of Brooks' 'Dear Fellas' note is read outloud by Andy in the prison yard following his death. [Everything about Brooks' departure from Shawshank will later be mirrored in Red's own exit.]

To Andy's amazement after six years of request letters, boxes of books ("a charitable donation") are delivered to the Supervisor's office accompanied by a check for two hundred dollars from the State Comptroller's Office. One of the guards, Wiley (Don McManus) grins and congratulates him: "Good for you, Andy." When the guards leave momentarily, Andy savors his victory - he leafs through a stack of used record albums in a wooden crate and finds a boxed set of Mozart's opera "The Marriage of Figaro" - Le Nozze de Figaro. [Symbolically, The Marriage of Figaro was about a valet/servant Figaro who outwitted his master Count Almaviva.] In another redemptive act similar to the one on the rooftop, he places the record Duettino: Sull'Aria on a phonograph player in the office, locks the doors and broadcasts the opera on the P.A. system throughout the entire prison to share a moment of freedom and make the prison walls dissolve.

Guards in a bunkhouse and prisoners on the open yard are stunned and hypnotized in place by the music as it floats from the loudspeakers over them and breaks the routine of prison life. The music transcends the day-to-day numbness - Andy reclines back in his chair, with his arms on the back of his head and a sublime smile on his face (resembling the look on his face on the tarred roof earlier), ecstatically experiencing the gift of music to the other inmates, while dreaming of freedom:

I have no idea to this day what those two Italian ladies were singin' about. Truth is, I don't want to know. Some things are best left unsaid. I like to think they were singin' about something so beautiful it can't be expressed in words and makes your heart ache because of it. I tell you, those voices soared, higher and farther than anybody in a gray place dares to dream. It was like some beautiful bird flapped into our drab little cage and made those walls dissolve away. And for the briefest of moments, every last man at Shawshank felt free.

The Warden is incensed ("pissed...off") by Andy's disobedience - Andy's response is to increase the volume rather than turning it off. The Warden punishes Andy with "two weeks in the hole for that little stunt." Andy is unphased by the harsh consequences since Mozart's music freed his soul, but Red is fearful of Andy (now nicknamed "Maestro") becoming too hopeful:

Andy: I had Mr. Mozart to keep me company...(He points and taps his head) It was in here. (And he gestures over his heart) And in here. That's the beauty of music. They can't get that from you. Haven't you ever felt that way about music?...Here's where it makes the most sense. You need it so we don't forget...that there are places in the world that aren't made out of stone, that there's, there's somethin' inside that they can't get to, that they can't touch. It's yours.
Red: What are you talkin' about?
Andy: Hope.
Red: Hope? Let me tell you something, my friend. Hope is a dangerous thing. Hope can drive a man insane. It's got no use on the inside. You'd better get used to that idea.
Andy: Like Brooks did?

In 1957, Red is brought before the parole board for his annual review after thirty years as an inmate serving a life sentence - and again is rejected - in a scene that is a virtual re-run of a previous one. A red stamp marks his file REJECTED. Andy has also served ten years of his own sentence: "You wonder where it went. I wonder where ten years went." Andy presents Red with a "parole-rejection present" - a harmonica - something Red played as a younger man but then lost interest for in prison. To mark the passage of time through various poster-girls, Andy also receives "a new girl" for his ten-year anniversary - Marilyn Monroe astride a subway grating with her dress blowing up - from The Seven Year Itch (1955). In the dark anonymity of his cell at lights out, Red holds the harmonica briefly to his mouth and only dares to blow into it once - he reacts by gripping it inside his clenched hand, frightened by the thought of music that frees the soul.

When a work crew knocks through a wall during the library expansion and creates a huge gaping hole through which light shines [a significant foreshadowing of a future escape], Red narrates how the State Appropriations Committee voted an annual payment of five hundred dollars to Andy on account of his persistent letter-writing campaign to improve prison life:

And you'd be amazed how far Andy could stretch it. He made deals with book clubs, charity groups. He bought remaindered books by the pound.

The convicts sort through the books for the new, 'resurrected' library to be named in Brooks' honor: Brooks Hatlen Memorial Library. Heywood mispronounces: "The Count of Monte Crisco...by Alexandree Dumb-Ass" - a book that Andy reminds is "about a prison break." [The parallels between the plot of the film and the Dumas novel are many: the literary classic was about a wrongly-accused and falsely-imprisoned Frenchman who daringly escaped from prison through an escape tunnel, then acquired 'treasure' learned about in prison, and plotted revenge on those who wronged him.]

By 1964, "Andy had transformed a storage room smelling of rat turds and turpentine into the best prison library in New England, complete with a fine selection of Hank Williams" - Heywood's favorite singer. Due to Andy's efforts in improving the prison and freeing the minds of the inmates, Warden Norton sanctimoniously takes all the credit for his "famous Inside-Out program" with the media, in a public speech delivered in front of the walls of the prison:

...no free ride, but rather a genuine, progressive advance in corrections and rehabilitation. Our inmates, properly supervised, will be put to work outside these walls performing all manner of public service. These men can learn the value of an honest day's labor while providing a valuable service to the community - and at a bare minimum of expense to Mr. and Mrs. John Q. Taxpayer!

The "valuable community service" program is a scam for the devious Warden - the real criminal - who skims money off the top from different building projects, and accepts bribes and kickbacks for not using his "slave labor" to "underbid any contractor in town." Andy becomes a valuable asset as he keeps the laundered, financial records for the rich, power-broking Warden: "And behind every shady deal, behind every dollar earned, there was Andy, keeping the books." Manila envelopes with money are stashed in the Warden's wall-safe - hidden behind the religious slogan sewn in the needle-point sampler with the apt saying: "His Judgement Cometh and that Right Soon." [Both Andy and the Warden conceal things behind a covering or picture!] Andy's function is to camouflage the "river" of corrupt, ill-gotten money:

What you hear isn't half of it. He's got scams you haven't even dreamed of. Kickbacks on his kickbacks. There's a river of dirty money running through this place...I channel it, filter it, funnel it - Stocks, securities, tax-free municipals - I send that money out into the real world and when it comes back...by the time Norton retires, I will have made him a millionaire.

To avoid the inevitable paper trail that would lead the FBI and IRS to Andy or the Warden, the smart ex-banker/convict creates a guilty and "silent, silent partner" named Randall Stephens - a phantom person only on paper:

He's a phantom, an apparition, second cousin to Harvey the rabbit. [Another reference to a classic film: Harvey (1950).] I conjured him out of thin air. He doesn't exist, except on paper...Mr. Stephens has a birth certificate, driver's license, social security number...The funny thing is, on the outside, I was an honest man, straight as an arrow. I had to come to prison to be a crook.

When the sirens sound and a new busload of prisoners are brought in with a new generation of modern-day prisoners (in a scene reminiscent of Andy's arrival), one of them is black side-burned Tommy Williams (Gil Bellows) who "came to Shawshank in 1965 on a two-year stretch for B and E. That's breakin' and enterin' to you. Cops caught him sneakin' TV sets out the back door of a JC Penney. Young punk, Mr. Rock 'n' Roll. Cocky as hell." At a meal, Andy - now one of the paternal old-timers - suggests that Tommy find "a new profession" since his thieving career hasn't been very successful. With a "young wife and new baby girl," Tommy seeks Andy for help in fulfilling "a high school equivalency" education. Andy, who doesn't "waste time on losers," rejects Tommy's call for rehabilitative help until he promises "one-hundred percent - nothing half-assed." To pass the "slow-time" of the prison, Andy adopts Tommy as his "new project" or disciple. As his mentor, he teaches him the alphabet to restore his hopes and dreams through education - it was "a thrill to help a youngster crawl off the s--theap...In prison, a man'll do most anything to keep his mind occupied."

In a slow pan around Andy's cell, marking the passage of almost twenty years of incarceration, all of the rock chess pieces on his chessboard are almost entirely carved, and a new, colorful poster-girl ("fantasy girlies") adorns the wall - Raquel Welch as a fur-bikinied cavewoman from the film One Million Years, B.C. (1966).

But Tommy has a short fuse when he fears he has failed the equivalency exam in the same year. During a conversation with Red in which he is told the reasons for Andy's imprisonment, Tommy divulges that in Thomaston prison four years earlier, a high-strung, mad cellmate named Elmo Blatch (Bill Bolender) admitted murdering a golf pro and his lover:

Big twitchy f--ker. Kind of roomie you pray you don't get. You know what I'm sayin'? 6 to 12 for armed burglary. Said he pulled hundreds of jobs...So one night like a joke, I say to him, I say, 'Yeah, Elmo? Who'd you kill?' So he says: 'I got me this job one time busin' tables at a country club. So I could case all these big rich pricks that come in. So I pick out this guy, go in one night and do his place. He wakes up and gives me s--t. So I killed him. Him and this tasty bitch he was with. (He laughs insanely.) That's the best part. She's f--kin' this prick, see, this golf pro, but she's married to some other guy! Some hotshot banker. And he's the one they pinned it on.'

The Warden cannot believe this "most amazing story" when told - he believes that Williams fabricated the revelatory tale to "cheer" Andy up. "With Tommy's testimony," Andy knows that he could get a new trial, but the Warden isn't convinced. [The warden doesn't want to believe Tommy's story, probably because if he did, the result would be that he would lose his invaluable money launderer-accountant.]

Exasperated and awe-struck, Andy calls the stonewalling Warden "obtuse" but also assures the corrupt prison head: "Sir, if I were ever to get out, I would never mention what goes on in here. I'd be just as indictable as you for laundering that money." For his insolence and fearing that Andy will be paroled if his conviction is dismissed, the warden places Andy in solitary for a month - the "longest damn stretch" most of the cons had ever known - especially for an innocent convict "going on nineteen years."