Last Call in the Underworld
Last Call in the Underworld
A trio of entrepreneurial villains descend into the Underworld to pitch Death himself on a bartending gig at their criminally dubious restaurant. Death, deeply unimpressed and thoroughly annoyed at the interruption of his eternal coffee break, kills them on the spot. Now trapped in the Underworld as undead misfits, the party must complete a ridiculous quest across the afterlife to prove their worth — and maybe, just maybe, convince Death to pour a drink for the living.
Read Aloud
You stand at the yawning obsidian gates of the Underworld, armed with a laminated business proposal, a PowerPoint scroll, and entirely too much confidence. The air smells of brimstone, stale regret, and, inexplicably, a faint whiff of burnt espresso. Across an enormous desk of carved bone sits DEATH himself — a towering skeleton in a rumpled cardigan, reading spectacles perched on his nasal cavity, cradling a mug that reads "World's Okayest Reaper." He looks up at you with hollow eye sockets that somehow still manage to convey profound, bone-deep disappointment. You clear your throat, unroll your proposal, and begin your sales pitch. He does not look enthused.
Description
This is the comedic cold-open scene. The party has somehow — through a ritual, a wrong turn, sheer audacity, or all three — arrived in Death's personal office in the Underworld. The office is cluttered with filing cabinets stuffed with soul paperwork, a motivational poster that reads "Hang in There" above a skeleton dangling from a noose, and a single dying potted fern. Death listens to the entire pitch in silence, refills his mug, and then, without a word, snaps his fingers. The party immediately dies. Cut to black.
DM Notes
Play this entirely for laughs. Let each player describe how their character contributes to the sales pitch. Death should respond only in flat, deadpan one-liners — "No." "Still no." "The fern has more promise than you." No skill checks are needed here; this scene is pure narrative setup. Death is not evil, merely extremely irritable. When the snap happens, describe each character's death in a hilariously undignified way — the Druid trips on their own staff, the Fighter's sword falls on their own foot, the Wizard is bonked on the head by a falling filing cabinet. No saving throws allowed. Death is CR infinity.
Read Aloud
You wake up on the cold stone floor of a dimly lit processing chamber that smells strongly of mildew and bureaucratic despair. Fluorescent soul-light flickers overhead. A laminated sign on the wall reads "WELCOME TO THE UNDERWORLD — PLEASE TAKE A NUMBER." Yours is 4,000,003. The number currently being served, according to a distant ding, is 7. You look down at your hands — except they are not quite your hands anymore. The Druid's bark-like skin has gone grey and crumbling, the Fighter's armored body clanks with a hollow metallic rattle, and the Wizard's robes billow around a form that is, unmistakably, mostly translucent. A nervous, clipboard-clutching imp in a vest scurries over and squeaks: "Ah! The special cases! Right, so — you're not fully dead. Not fully alive. We call it... probationary deceased."
Description
The party wakes up as undead. The Druid is a Ghoul (grey, twitchy, compelled to sniff everything), the Fighter is an Animated Armor (their soul is literally piloting their own now-empty suit of armor, which has a habit of falling apart at inconvenient moments), and the Wizard is a Specter (partially incorporeal, keeps accidentally phasing through floors). The imp, Piffle, serves as the party's reluctant guide and quest-giver on behalf of Death. He explains that Death has left them a sealed scroll — a quest. Complete it, and he'll hear their pitch again. Fail, and they get filed permanently under "D" for Disappointment.
DM Notes
Encourage players to roleplay their new undead quirks for the whole session — the Druid (Ghoul) must make a DC 12 Wisdom saving throw whenever they smell fresh souls or risk being distracted for one round; the Fighter (Animated Armor) falls apart and must spend a bonus action reassembling if they take more than 15 damage in a single hit; the Wizard (Specter) can walk through walls but keeps accidentally falling through the floor at dramatically inconvenient moments (once per scene, DM's choice). Piffle is cowardly and unhelpful but technically informative. The sealed scroll reads: "Retrieve the Ledger of Lingering Debts from the Vault of Unfinished Business. Return it to my desk. Try not to cause more paperwork." Signed with a small skull doodle.
Read Aloud
You follow Piffle down a winding corridor of cracked obsidian tiles — several bearing the fossilized footprints of something enormous — until you emerge onto the docks of the River Styx. The river is the color of old dishwater and smells worse. Dozens of confused souls mill about the pier, clutching their death-certificates and arguing with each other about whose fault it was. A rickety sign hanging over a ramshackle dockside establishment reads "THE LAST DROP — Fine Spirits for Departed Spirits." The ferry is delayed. Indefinitely. The ferryman, a hunched skeleton in a raincoat named Gerald, is on strike, waving a small placard that reads "FAIR COINS OR NO FERRY." He spots you and narrows his eye sockets. "You," he croaks. "You're the lot who bothered the boss. I'm not taking you anywhere until you sort out my union dispute. And possibly buy me a drink."
Description
The party must cross the River Styx to reach the Vault of Unfinished Business on the far shore. Gerald the ferryman is on a one-skeleton labor strike against Death's management. He wants three things: a coin for his troubles, someone to resolve a petty dispute between two squabbling souls on the dock, and a decent drink from the Last Drop tavern (which has been out of its best stock since a poltergeist raided the cellar). Resolving Gerald's demands is a social and skill-challenge scene with comedic overtones.
DM Notes
This is the session's non-combat social challenge. Structure it as three mini-tasks: 1. THE COIN: The party has no gold — they died. DC 13 Charisma (Persuasion) to convince a nearby soul to donate their coin, DC 15 Dexterity (Sleight of Hand) to pickpocket one, or DC 11 Intelligence to remember that Piffle always carries emergency petty cash and talk him into surrendering it. 2. THE DISPUTE: Two souls — a baker and a tax collector — are screaming at each other about a debt from 40 years ago. DC 14 Charisma (Persuasion or Intimidation) or a creative argument settles it. On a failure, both souls start crying and the argument escalates into a full dock brawl of confused ghosts. 3. THE DRINK: The Last Drop's poltergeist has barricaded the cellar with flying bottles. DC 13 Wisdom (Perception) to spot its weak spot (a leaky bottle cork it's using as a security blanket), then DC 12 Dexterity or a clever plan to retrieve the stock without breaking everything. Reward a creative approach with advantage. If the party succeeds all three, Gerald weeps a single spectral tear and says "Fine. Get on." The Animated Armor Fighter keeps clanking loudly the entire time, giving disadvantage on any Stealth checks.
Read Aloud
Gerald's ferry deposits you on the far shore with a sullen wave of his oar and immediately turns back without a word. Before you looms the Vault of Unfinished Business — a squat, sprawling building that looks like a tax office designed by someone who deeply hates people who visit tax offices. The walls are plastered with sticky notes, each one a regret: "Should have called Mom," "Never finished that novel," "Left the oven on in 1987." The front door is ajar, and from within comes the sound of distant shuffling, the scraping of restless chains, and what might generously be described as off-key humming. A plaque beside the door, slightly crooked, reads: "All debts unresolved. All business unfinished. Do not feed the Wraiths."
Description
The Vault is a cluttered, labyrinthine building stuffed floor-to-ceiling with filing cabinets, floating debt ledgers, and the restless remnants of souls who simply could not let things go. The Ledger of Lingering Debts is locked in the deepest filing room — Room 13B — guarded by the Vault's self-appointed custodians: a pair of Wraiths who take their filing duties extremely seriously, several Ghouls who were once auditors and still act like it, and a Specter who is the ghost of a man who died before finishing his strongly-worded letter and has been writing it ever since. The party must navigate to Room 13B and retrieve the Ledger.
DM Notes
Split this scene into exploration and combat. The Vault has three notable rooms before Room 13B: ROOM OF REGRETS: Walls covered in sticky notes. DC 13 Wisdom (Insight) to notice that touching a note causes a one-minute vision of the regret — harmless but disorienting. The note "Should have never opened this door" is on Room 13B's entrance. THE FILING MAZE: Cabinets rearrange themselves. DC 14 Intelligence (Investigation) to find the correct path, or DC 12 Wisdom (Perception) to follow the faint smell of old ink toward the Ledger's location. ROOM 13B: The combat encounter happens here. Afterward, the Ledger is found inside a cabinet labeled "DO NOT TOUCH — THIS MEANS YOU." The Wizard (Specter) can phase through the cabinet to grab it, but must make a DC 12 Constitution saving throw or accidentally drop it through the floor, requiring a second fumbling retrieval attempt.
Read Aloud
You emerge from the Vault clutching the Ledger of Lingering Debts, slightly singed, moderately disheveled, and in the Druid's case missing a hand — which is scuttling along behind you of its own accord and refuses to reattach. Gerald is waiting at the ferry dock, somehow already aware you are coming, drinking something hot from a thermos. The return crossing is silent except for the lapping of the Styx and the occasional sound of the Fighter's shoulder pauldron falling off. Death's office looms ahead, the obsidian gates swinging open as if expecting you. Inside, Death is exactly where you left him — same cardigan, same mug, now reading a small paperback titled "How to Deal With People Who Won't Stay Dead." He looks up. He sighs. He sets down his book.
Description
The party returns the Ledger to Death. This is the climactic negotiation scene and the comedic payoff of the entire session. Death reviews the Ledger, makes a few notes, and then leans back and says "You completed the task. Marginally. With unnecessary property damage." He then reveals he was going to say yes to the bartending job all along — he just wanted to see if they were worth the paperwork. He pulls out a signed contract, a name tag that says "DEATH — Staff," and a bartending apron. He does, however, have one condition: he works Tuesday through Thursday only, no doubles, and absolutely no birthday cocktails.
DM Notes
Let the players roleplay the second pitch freely — Death should respond with dry amusement rather than hostility this time. Each creative, funny, or heartfelt argument earns a point of "Approval" (track 0-3). At 2 or more Approval, Death agrees with minor conditions. At 1 Approval, he agrees but keeps the apron as collateral. At 0 Approval, he agrees anyway but mails them a bill for the paperwork. Then he snaps his fingers and sends them back to the land of the living — but each character retains one minor cosmetic quirk of their undead form as a permanent reminder: the Druid's left eye glows faintly grey, the Fighter's armor occasionally rattles on its own at night, the Wizard can still accidentally phase a hand through a table when distracted.
Monsters
Tactics
The Wraith (Senior Archivist) acts as a middle manager and shouts bureaucratic justifications for all attacks — "That is a violation of Vault Code 7, Section 12!" It prioritizes the Wizard Specter first, insisting they are "in the wrong department." It uses Life Drain on the most heavily armored target (the Fighter's Animated Armor, which is hilariously immune to the necrotic damage since it has no life to drain — the Wraith must make a DC 10 Wisdom saving throw or become visibly flustered and waste its action rechecking the rulebook). The two Ghoul Auditors move to flank and try to paralyze the Druid with their Claws, prioritizing the one who has been sniffing things. The Specter of the Strongly-Worded Letter does not attack combatants — it floats around reading excerpts from its unfinished letter aloud (DC 12 Wisdom saving throw or be annoyed into disadvantage on Concentration checks for 1 round). It will stop if anyone expresses sympathy for its grievance and makes a DC 10 Charisma (Persuasion) check, at which point it drifts away happily, whispering "finally, someone gets it."
Terrain
Room 13B is a cramped filing room packed floor-to-ceiling with cabinets. The space is difficult terrain everywhere. Flying enemies (the Wraith and Specter) ignore this. The cabinets provide half cover (+2 AC) to anyone standing behind them. There is one narrow corridor through the center — a choke point that rewards the Fighter's melee dominance but clusters enemies for the Druid. The Ledger sits in a glowing cabinet at the far end labeled "DO NOT TOUCH." Three cabinets in the room are labeled with ominous warnings and, if opened by curious players, release harmless but distracting swarms of filing confetti (DC 11 Dexterity saving throw or blinded until end of next turn). Note: the party themselves are undead this session — they cannot be paralyzed by the Ghoul's claws (Ghouls only paralyze living creatures) and the Wraith's Life Drain deals half damage to the Specter-form Wizard (who has no life force to drain). Play up these quirks for comedy.
Monsters
Tactics
The Poltergeist does not want to fight — it wants its cork back (its emotional anchor, hidden in a crate of suspiciously labeled bottles). It hurls bottles telekinetically at anyone who enters the cellar (Force of Will: ranged attack +4 to hit, 3d6 bludgeoning from bottle impact, 10-foot range). If anyone locates the cork (DC 13 Wisdom Perception) and either returns it or sincerely promises to protect it, the Poltergeist immediately calms, weeps, and hands over the Last Drop's best stock — a bottle of Stygian Reserve that Gerald will accept as payment. If the party simply tries to brawl it down, it works fine (AC 12, HP 22, immune to all physical damage — requires magical attacks or the Wizard's cantrips), but all the bottles in the cellar shatter, denying them the Stygian Reserve and requiring them to find another way to satisfy Gerald's third demand.
Terrain
The Last Drop's cellar is low-ceilinged and cluttered with crates, racks of bottles, and a suspicious number of barrels labeled "NOT EVIDENCE." The Poltergeist starts invisible (DC 14 Perception to detect by the sound of rattling bottles). The narrow aisles between racks provide half cover but also create excellent bottle-throwing lanes for the Poltergeist. The cork is wedged in a crate in the far corner under a banner reading "STAFF PICKS." Smart players can use the Fighter's bulk to shield the others while the Wizard uses magical detection or the Druid sniffs out the cork (their Ghoul form gives them advantage on Perception checks involving smell).
A formally notarized contract signed by Death himself, agreeing to serve as Head Bartender at the party's restaurant on Tuesdays, Wednesdays, and Thursdays. No doubles. No birthday cocktails. The contract is written in elegant calligraphy on vellum made from something the party chooses not to examine too closely. Functions as a legal document of cosmic authority — any magistrate, crime lord, or supernatural entity who reads it becomes immediately cooperative (one use, then the magic is spent). Death's name is signed with a small doodle of a frowning skull.
The Last Drop's finest vintage, recovered from the poltergeist's cellar. A deep grey liquor that smells of cold stone and forgotten memories. Drinking a bottle functions as a Potion of Heroism (grants 10 temporary hit points and the Blessed condition for 1 hour) but the imbiber also temporarily forgets one embarrassing memory of the DM's choice for the duration. Worth 250 gp per bottle to the right buyer.
A small embroidered pouch containing 47 gold pieces, 3 Underworld transit tokens (no longer valid above ground but make excellent conversation pieces), and a crumpled receipt from a place called HADES QUICK-PRINT. Piffle will ask for it back. Loudly.
Each character retains a cosmetic undead trait as a permanent souvenir: the Druid's left eye glows faint grey (advantage on Insight checks against undead creatures, they recognize you as one of them momentarily), the Fighter's armor rattles on its own when danger is near (advantage on Initiative rolls, the rattling cannot be silenced), and the Wizard occasionally phases a hand or foot through solid objects when distracted (can pass one hand through a locked container once per long rest to retrieve a single small item).
Story Hooks
Death's Bartending Contract will inevitably draw attention — a rival crime lord hears that the party's restaurant has Death on staff and wants the contract stolen or voided. Additionally, the Stygian Reserve has a mysterious label on one bottle that reads "Property of — name scratched out — DO NOT OPEN UNTIL THE END OF THE WORLD." The Underworld transit tokens, if brought to the right fence, could open a smuggling route between the Underworld and the material plane — which a certain necromancer might pay handsomely to exploit.
Conclusion
Wrap Up
Death snaps his fingers, the world goes white, and the party wakes up in a heap outside their restaurant's back door — fully alive, slightly confused, and clutching the signed contract. The restaurant staff stares at them. Piffle was apparently also sent back and is clinging to the doorframe, shaking. Death's apron is already hanging behind the bar, freshly laundered, with a note pinned to it: "Tuesday. Do not be late. — T.E." (The End). The session closes with the party hearing the first customer of the night walk in and ask the now-empty bar, "Is anyone working tonight?" A cold wind blows through the closed windows. Somewhere, a glass polishes itself.
Cliffhanger
As the party finally gets Death's signed contract framed on the wall, a well-dressed stranger steps into the restaurant, slides into a barstool, and sets a black envelope on the counter. "I heard you have a new hire," she says, smiling pleasantly. "I'd like to extend a counter-offer." Her shadow, cast by no light source, is shaped like a crown.
Next Session Hooks
- The mysterious woman with the crown-shaped shadow turns out to be a rival cosmic entity — perhaps Life herself, or a deposed Underworld noble — who wants Death under contract for her own purposes, setting up a bidding war between cosmic forces with the party's restaurant as the prize.
- One of the Stygian Reserve bottles bears a scratched-out name that, when revealed by a magical ink or Identify spell, turns out to belong to a living person who is not yet dead — someone powerful who made a deal to delay their soul's arrival indefinitely, and who will do anything to keep that secret.
- Piffle, now technically Above Ground, discovers he has no way back to the Underworld and has been reassigned to the party as a permanent administrative liaison. He is devastated. He brings a great deal of forms. The party owes Death eighteen separate pieces of paperwork from the property damage they caused in the Vault.
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