Trivia: This episode is rare in that Monk doesn't appear in the final scene.
California's actual male death row is located at San Quentin State Prison, just north of San Francisco. In this episode, the prison is called San Juan and is apparently located within the San Francisco police jurisdiction.
There are a number of unrealistic situations portrayed inside the prison. An inmate scheduled to be executed in less than an hour would not be left so unattended as to require the trustee to yell for help when he went into distress, or to allow the inmate and trustee to exchange objects. A chronic rule-breaker like Spyder, who had just "put a guy's head through a wall," would not have gotten just one day in solitary confinement with no other loss of privileges. The Nazis would not be allowed to wear swastika lapel pins.
During the scene where Stottlemeyer and Disher go to see Dale the Whale, Disher is eating a bagel. From shot to shot and point of view to point of view the position and amount of bagel showing, eaten or covered by the napkin changes all the time.
How exactly did Spyder find Monk when Monk was being attacked by the nazis? How did he even know Monk needed his help? What was he doing wandering around the prison in the first place?
Tucker never made it back to his cell the night he died in the freezer. Why wasn't his empty cell noticed that night
Sharona is patted down first. Then the guard unsuccessfully tries to pat Monk down. Sharona physically leads Monk back to the guard so he can try again. Since she had physical contact with Monk after her pat down, and before his, Sharona would have been repatted down at this point to make sure there had been no contraband hand-off.
Death row inmates are not served their last meal by unescorted fellow prisoners.
As the poisoned prisoner is thrashing on the floor of his cell, a close-up shows a white fluid covering his nostrils and trickling down his upper lip. Immediately after he dies, his upper lip is clear.
I don't believe that prisoners on death row are allowed in the prison population, with access to the library and all.
After Sharona explains Monk's obsession with neatness, the cook shares his handshake with Monk, who later shares it with Spyder, but he needs notes to finish it. However, in episode 19, "Mr. Monk Goes to the Theater," he sees the play only once and has it completely memorized.
When Sharona and Monk are checking Kaspo's records and the killer fakes the warden's phone call, the guard says, "You folks are working late," but the establishing shot shows that it's daytime and in the subsequent shots there's lots of sunlight. What kind of prison considers mid-morning or mid-afternoon "late"?
It's remotely possible that a four-time murderer like Spyder might have got some kind of permission slip, but prisons don't generally let their prisoners have personal possessions like wristwatches. They're kept in storage and given back when they're let out.
Type AB blood is the universal recipient (a person with that blood type can receive a transfusion from any other blood type); type O is the universal donor (a person with that blood type can give blood to anyone but receive it only from another type O).
The episode title should be "Mr. Monk Goes to Prison." Jails are for short-term confinement, not long-term imprisonment. the San Juan Correctional Facility is (correctly) referred to throughout the episode as a prison, not a jail.
Who killed Tucker the cook? Whether it was the real killer, or the guys the killer hired, it doesn't make much sense that they would have left the money in Tucker's pocket.
As the guard is patting Monk down for the last time, he begins at Monk's middle before Monk jumps away, but when the camera angle changes for that same shot, the guard is at his legs.
The TV in the prison looks too old to be remote-controlled. An inmate mentions that the knobs are broken, but I've never seen a TV with knobs being remote controlled, and there doesn't appear to be a sensor to pick up the remote commands.
Dale: Bon voyage, Mr. Monk! Ha, ha, ha.
Dale: Sweetheart, I am Dale the Whale!
Dale: Well, there's the Adrian Monk we know and love. Your fear is huge, but your curiosity is huger.
Dale: Is that a bagel?
Disher: Yeah, want some?
Dale: Oh, no thanks, I can't. I'm on a low-carb diet.
Dale: Don't make me laugh. It hurts!
Monk: I'll tell you people something. Prison changes a man.
Sharona: I wish.
Monk: Sharona, I hate this place. I can't breathe in here. It's like a prison.
Sharona: It is a prison.
Stottlemeyer: What do you think?
Monk: I think I'm out of here. I'm going home.
Monk: I'm not sure it matters who killed this guy. He was going to die in forty-five minutes anyway.
Monk: (patting his pocket) Wait. What's this? Whoa. Hey. Hold on a second. Nail clippers? Where do I think I'm going with those?
Monk: How about this? I'll pat myself down.
Dale: I know you've always blamed yourself for her (Trudy's) death. Now you don't have to. (makes the sign of the cross) I absolve you, Adrian Monk. That's my good deed for the decade.
Monk: Thank you, Dale. It was your faith in me that kept me going in my darkest hour.
Monk: I see you've got your window.
Dale: Mmhmm. Yep. Now I can see the world--but still not be part of the world. Something else we have in common.
Monk: Sharona, I figured out . . .
Sharona: I know, I know-–I did the whole summation.
Nazi: You'd side with a cop over us?
Spyder: I'd side with a cucaracha [cockroach] over you.
Monk: (to attacking Nazis) All right, boys. Come on. You know violence--violence is not the answer. (sprays them with hot water)
Monk: (on the phone) Hello! Nazis here in the rec room. This is a Nazi alert!
Nazi: You're gonna wish you'd never been born.
Monk: I'm way ahead of you.
Monk: (straightening the Nazi's swastika pin) You'll thank me later.
Stottlemeyer: I understand Ray Kaspo owed you some money.
Dale: Twelve hundred dollars. I wouldn't bend down to pick up twelve hundred dollars. I mean--even if I could.
Dale: Well, if it isn't Captain Shottlemeyer and his cabana boy.
Spyder: (looking at Trudy's photo) Is that your old lady?
Monk: (softly) Yeah.
Spyder: She waiting for you?
Monk: Yeah. She is.
Spyder: You sharpened my shiv. You made my bed. What are you in here for?
Spyder: What happened to my bed? Have you been touching my stuff?
Monk: No, no, no. Maybe. A little. I--I--I--Your sheets were all piled. . . .
Spyder: You are a dead man! I am gonna gut you like a fish!
Sharona: Why was he [Spyder Rudner] in solitary?
Warden Christie: He put a guy's head through a wall.
Warden: The guy touched his stuff.
Sharona: (to Rastafarian cook with a dreadlock escaping his hairnet) My boss has a jones for neatness, okay?
Monk: (mournfully) It's my jones.
Sharona: And he needs a fix real bad.
Monk: (to Sharona) This is about Trudy now. I need you to help me focus.
Dale: (in a rage) I want my window! Get me my window!
Dale: One hand washes another. Now there's a metaphor I know you can relate to.
Dale: Your fear is huge, but your curiosity is huger.
Monk: It seems prison agrees with you, Dale.
Dale: Well, and why wouldn't it? After all, I've been inside this prison [his body] all my life.
Monk: (almost sarcastically) That's very poetic.
Dale: Well, of course, it doesn't compare with the prison you've built for yourself.
Monk: You're looking . . . well.
Dale: What a smooth talker.
Dale: Come in! It's always open. Apparently they don't consider me much of a security risk.
Dale the Whale: . . . the irrepressible Sharona Fleming.
This is the second time the series uses the motif of a window in prison: Wendy Maas specifically asked for one in "Mr. Monk and the Red-Headed Stranger."
Archvillain Dale Biederbeck (aka Dale the Whale), who resurfaces as Monk's fellow inmate, is played this time around by Tim Curry rather than Adam Arkin.
Kathy Baker's character, Sylvia Fairbourn, refers to a prisoner as "Jimmy." When she played Jill Brock on Picket Fences, that was what she called her husband, Sheriff James Brock, using the exact same inflection.