"Let the challenge begin."
"The challenger is Dream. Once the Master of the Realm of Sleep. As the challenged, I've selected my champion, Ruler of Hell, Lucifer Morningstar, to represent me in a contest of skill, confidence and transformation."
— Choronzon
Morpheus travels to Hell to reclaim his stolen helm, which requires him to defeat Lucifer, the ruler of Hell, in a contest of wits.
John, seeking the warehouse where the ruby is stored, gets a lift from a good samaritan, who becomes increasingly worried the more she learns about her passenger.
At the end of the episode, Morpheus reaches the warehouse first, but the alterations John made to the ruby create a backlash that knocks him unconscious. John arrives shortly afterward and takes the ruby.
This episode contains examples of:
- Adaptational Alternate Ending: The comic book issue "Passengers" ends with a Hope Spot where it seems like John has been impressed by Rosemary's kindness and is going to let her go unharmed, and then he kills her anyway. This adaptation inverts that ending: it seems like John is going to kill Rosemary, but instead he lets her go unharmed because he's been impressed by her kindness. He even gives her the Amulet of Protection as a token of appreciation.
- Adaptational Attractiveness:
- In the comic, John is an emaciated, barely human figure missing most of his hair and teeth. In the series, he's a bit unkempt but basically a healthy human being.
- In the comic, the demon Mazikeen is basically missing one entire side of her head. In the series, half her face has been burned off but she still retains an intact skull.
- The demon Choronzon, while still not great-looking, looks more human than in the comic, where he had an elongated head and an extra mouth.
- Adaptational Backstory Change: The Sandman comic is set in the DC Universe, co-existing with superheroes like the Justice League. John Dee's backstory had him using the ruby to become a supervillain named Doctor Destiny before being taken down by the Justice League and confined in Arkham Asylum. The TV series is set in something more like the real world, with no superheroes or supervillains, so John's backstory involves more generic "arson, murder, and general mayhem" and his confinement is in an unnamed institution in upstate New York.
- Adaptational Context Change:
- Why Dream is able to win the Oldest Game by invoking hope is changed from the comics where Choronzon lost by merely being unable to think of anything that could beat hope. Instead, Lucifer doesn't even try provide an answer to hope and concedes the game by commanding Choronzon to return Dream's helmet, the implication being that to overcome hope would mean Lucifer accepting they had no hope of returning to Heaven.
- Even hope itself is changed; instead of the abstract idea of hope, it is Matthew's specific hope of getting out of Hell in one piece.
- Adaptational Early Appearance: The demon Mazikeen appears in this episode attending on Lucifer. In the comic, her first appearance was several story arcs later, in the issue revealing Lucifer's revenge on Morpheus.
- Adaptational Modesty: In the series, John escapes from the mental institution wearing nothing but his pajamas. In the comic, the institution was more of a Bedlam House and the warders didn't trust him with anything, so he wasn't even wearing pajamas.
- Adaptational Wimp:
- The extent of Dream's weakness without his tools is greater in the TV version. In his interaction with the mocking demon Squatterbloat, Dream telling him to mind his tone to the King of Dreams somewhat comes off as an empty threat, whereas in the comic Dream punctuates his warning by easily overpowering Squatterbloat and sending him flying, making it a legitimate case of Bullying a Dragon. In the comic, he's never seriously threatened during the Oldest Game and plays the winning move without hesitation, but in the TV version he almost gets destroyed and needs Mathew's support.
- Lucifer gets this to some extent by being the one who engages Dream in the oldest game and losing, rather than it being the demon Choronzon. Comic Lucifer Morningstar was never beaten by Dream in any fashion and merely annoyed Dream had got the better of Hell.
- Adaptation Distillation: This episode combines two issues of the comic: "A Hope in Hell", which depicted Morpheus' visit to Hell, and "Passengers", which depicted John's road trip to where the ruby is stored. Apart from trimming incidental details, the main cut is having the helm allow Morpheus to detect and go straight to the location of the ruby; in the comic, his search for the ruby took up the other half of "Passengers".
- Adapted Out: A lot of what was cut out of "A Hope in Hell" and "Passengers" is specific references to and characters from the DC Universe. During Morpheus' visit to Hell, Etrigan is left out, with Squatterbloat taking on his role of leading Dream through Hell, and the episode also leaves out the two other demons who were co-rulers of Hell at that point in DC continuity. After leaving Hell, Morpheus spent half an issue tracking down the ruby, with cameos by several superheroes; all of this is replaced with Morpheus using the helm to immediately detect the ruby's location.
- Alone with the Psycho: Rosemary spends a good part of the episode like this after John reveals he's a murderer.
- Appearance Is in the Eye of the Beholder: As in the comics, when Nada sees Dream and briefly speaks with him, he appears to her as a black man.
- Armor-Piercing Response: At the end of the episode, Lucifer threatens to keep Morpheus in Hell by force, and asks rhetorically what power dreams have in Hell. Morpheus replies that dreams are the most powerful thing in Hell, which would be nothing if the inhabitants could not dream of Heaven.
- Bait-and-Switch: When John tells Rosemary that bad things can happen to good people, it looks like he's going to kill her, but he instead gives her the amulet of protection so she'll always be protected.
- Bloody Bowels of Hell: The bodies of the damned make up much of Hell's landscape.
- Combat by Champion: Dream accepts a challenge to fight for possession of the helm, but Choronzon chooses Lucifer as his champion.
- Composite Character: In the comic, Squatterbloat was just the gatekeeper, and another demon, Etrigan, leads Morpheus through Hell to the meeting with Lucifer. In the series Etrigan is adapted out (due to, like John Constantine before him, being a character from the DC universe that presumably would cause rights issues) and Squatterbloat performs both duties.
- Fallen Angel: Lucifer, as Morpheus reminds Matthew, was once among the greatest of the angels before falling, and still retains some of their angelic appearance.
- Foreshadowing:
- When Morpheus speaks to Nada, she tells him that she will never give up hope of being released, foreshadowing the end of Morpheus' confrontation with Lucifer.
- Just as in the original comic it's very clear Lucifer is not happy in their role as ruler of Hell and holds their "subjects" in contempt. Anyone whose read the comic will know where that leads. Also Dream is reminded of unfinished business in Hell. In the comics that will eventually bring him back there and trigger "Season of Mists."
- Gory Discretion Shot: When the amulet of protection kills the gas station attendant, all the audience sees is a spray of blood splattering against the gas station window, accompanied by a disquieting noise.
- Hope Spot:
- Rosemary gets the gas station attendant to call the police and even draw a gun to protect her from John Dee but he overhears and the Amulet of Protection kills the attendant, leaving her still at his mercy.
- Dream recovers his helm which leads him straight to the ruby... but John's alteration causes it to reject him.
- Hope Springs Eternal: Weaponized by Dream. In "The Oldest Game", Lucifer overcomes the universe Morpheus has become by becoming anti-life. After a pep talk with Matthew, Dream becomes hope, brightening Hell. Lucifer can't top that, as to overcome hope, they would have to admit they cannot return to Heaven.
- Human Architecture Horror:
- The wall around Hell is constructed out of the merged bodies of some of the damned, who are still conscious and twitch and cry out when Morpheus strikes the gong to announce his arrival (using a striker handed to him by part of the wall).
- As Squatterbloat leads Morpheus through Hell, they pass through a forest where more groaning and twitching bodies are merged horrifyingly with the trees.
- I Have Many Names: In the beginning, Dream states Hell is known by many names to mortals, such as Avernus, Tartarus, and Hades.
- Ironic Echo: When Dream and Matthew arrive in Hell, Dream says they have to announce themselves at the gate instead of sneaking in, because there are protocols that must be followed. Lucifer later says the exact same phrase to Dream, demonstrating that the ruler of Hell sees everything in their realm.
- No Good Deed Goes Unpunished: The gas station attendant who tries to shoot John and save Rosemary gets splattered for his trouble.
- Oh, Crap!: When Rosemary gives a ride to John Dee, she at first thinks he's a charming, harmless eccentric... until he starts casually describing the murders he's committed. Her facial expression clearly shows the dawning recognition of what she's got herself into.
- Pet the Dog: John Dee spends the episode being ferried to his Ruby by a woman named Rosemary, who becomes more and more terrified as she realizes the confused man she's trying to help is actually a deranged murderer and tries to call the police on him. When they reach their destination and John obtains the Ruby, instead of punishing her for her betrayal, he gives her the Amulet of Protection, explaining that he understands she had done him a kindness and her moment of dishonesty was understandable given the context.
- Pragmatic Adaptation: The Helm in the comic was little more than a MacGuffin for Dream, giving him a reason to go to Hell and play The Oldest Game. No explanation was given as to what it did or why he needed it back, beyond the vague allusion to it being one of his tools of office. In the show, it has the power to locate the Ruby (and presumably could have done the same for the Pouch had Dream not already obtained it). This not only gives Dream's quest to retrieve the Helm more weight, as he is no longer chasing after a simple MacGuffin to seemingly no end, but it also gives him a way to find The Ruby, since the Fates' answer about its location was much less useful than in the comic.note
- Race Lift: Rosemary was white in the comic, and is African-American in this episode.
- Secret Other Family: When John and Rosemary are bonding over having awful family members, Rosemary says that after she'd been married to her husband ten years and had two daughters with him, she found out that he had another wife and another child in another town.
- Shapeshifter Showdown: The combat between Dream and Lucifer is a semi-metaphorical version of this. They themselves don't actually transform, but they physically affect each other as if they had.
- Spared by the Adaptation: In the comic, John convinces Rosemary he's a harmless weirdo, only to kill her when he reaches the warehouse. Here, Rosemary realizes very quickly how dangerous John is, but in the end John is impressed by her kind spirit and lets her go, even giving her his protective amulet.
- Summon Bigger Fish: Attempted by Choronzon who nominates Lucifer to represent him in the duel against Dream.
- Tranquil Fury: After Morpheus first defeats Lucifer in a duel of wits then manages to turn their own barb back on them — in front of every demon in Hell, no less — the Ruler of Hell is left utterly stonefaced, save for a quivering lip that shows just how angry they really are.
- The Watson: Although there is also an in-story reason for Matthew accompanying Morpheus to Hell (to Bring News Back if things go wrong), the main storytelling purpose of it is so there's someone for Morpheus to explain things to for the benefit of the audience.
- Wizard Duel: The Oldest Game is described as a game of transformation. While Dream and Lucifer don't literally transform into the forms they take, the wounds they inflict onto each other manifest as though they were actually happening. If they weren't immortal, odds are it would have killed them both.
