The BOSS has a ton of shout-outs.
- Aside from the characters literally showing up, Undertale also has a number of shout-outs within the game's dialogue.
- One of the lamps in Jack's apartment can cause him to quip "A not-so-conveniently shaped lamp!"
- Since Billy (technically the Irresponsible Dad's son) is a party member, Happy Wheels has a massive one.
- There's a possible shout-out to The Cave in the Portal section, only seen if Jack and Cliff get blown up in the holding chamber. When they respawn, GLaDOS says that they're not allowed to die because it would raise Aperture Science's insurance rates. This is almost a direct quote from the The Cave, as the Cave says this to the spelunkers should they die in the opening section of the game.
- Jenny finds a piece of paper on the wall of the Layers of Fear section which says "To spell a word correctly is to honor its meaning." This is a direct quote from Spelling Jungle, also known as Yobi's Basic Spelling Tricks.
- In the Layers of Fear section, Jenny observes that a substance on the wall looks like tar. She then refuses to touch it, noting that it's a one-hit death in Commander Keen.
- Some other references (that the credits mention are direct references) include:
- Papers, Please: Potato Man, or Jorji as the go by in his game of origin, makes an appearance as a running gag.
- Cleverbot: Evie makes multiple cameos throughout the game.
- Batman: The Telltale Series: This game's iteration of Batman makes a cameo appearance.
- Overwatch: Mei makes a cameo appearance.
- World of Goo: The goos from this game make cameo appearances. Billy also mentioned that at the end of Jack's playthrough, Wireland became flooded with the game's inhabitants.
- Manual Samuel: Death makes a cameo appearance. Also, a painting in Jack's apartment is a direct reference to an identical one in Manual Samuel.
- Shadow of the Colossus: Wander appears in Sans' shop.
- The Last Guardian: The boy appears in Sans' shop, while Trico sleeps on Jack's roof.
- Limbo (2010): Limbo Boy makes a cameo appearance.
- Hello Neighbor Mr. Wilson, or the Neighbour as they go by in his game of origin, makes a cameo appearance.
- Night in the Woods: Mae, Gregg, Angus, and Bea make an appearance.
- Bendy and the Ink Machine: Bendy makes a cameo appearance.
- Kindergarten: Nugget makes multiple appearances, and there is also a passing nod to the other Kindergarten kids during a conversation with Billy.
- Sally Face: Sally makes a cameo appearance.
- Ori and the Blind Forest: Ori makes a cameo appearance.
- Life Is Strange: Max and Chloe are party members in The Escapists section.
- Markiplier: Mark, or a parody of him, makes a cameo appearance.
- PewDiePie: See Markiplier.
- Oxenfree: Alex and Jonas make cameo appearances.
- INSIDE (2016): Inside Boy makes a cameo appearance.
- Little Inferno: Sugarplumps makes a cameo appearance.
- Neverending Nightmares: Thomas makes a cameo appearance.
- Almost every prior Jacksepticeye fangame (Jackventure, 1 Million Party, to the Future, Game, Paradox). The Merchants from Paradox even host a game show, which in turn references the Myers-Brigg test, as well as the time Jack made a taco with Matpat.
- Jacksepticeye: Anti makes a very brief cameo appearance.
- Cryaotic: See Markiplier.
- Totally Accurate Battle Simulator: The Soldiers make very brief cameo appearances.
- Grow Home: B.U.D makes a very brief cameo appearance.
- Riddle School: Phil and Smiley make cameo appearances.
- The Final Station: The Conductor makes a cameo appearance.
- Octodad: The man himself makes a cameo appearance.
- The Last of Us: A zombie from this game makes a cameo appearance.
- The Wolf Among Us: Bigby Wolf makes a cameo appearance.
- Tales from the Borderlands: Rhys makes a cameo appearance.
- I Am Bread: The bread makes multiple appearances.
- Party Hard: Employee 207's game of origin.
- Segway Steve mentions he's selling a Flux Capacitor at one point in the game.
- The literal TARDIS appears during The Escapists section.
- There are multiple references to the Undyrus ship, as well as the Shadamy ship.
- The cut-scene at the start of the game bears a striking resemblance to the start of Thor: Ragnarok.
- In a Freeze-Frame Bonus, one of the e-mails on Jack's computer is from Yandere-Chan.
- Undyne jokes that Jack getting mugged for bytes "sounds like a real dark descent."
- Checking the game console while Undyne is in your party has her mention that she could "kick your butt at Mario Kart!" Also, checking the plants while Undyne is in your party or before you enter Wireland has Jack and/or Undyne ask about where to get some Zombies!
- When you meet Sans, he jokes that Undyne breaking Jack's computer had "a mass effect".
- When the topic of Jack's amnesia is brought up, or when taking to Agnus later in the game, both conversations make the point that the hospital in Wireland is, rather unfortunately, Surgeon Simulator. Even more worryingly, Undyne asks to control the fingers.
- When Papyrus mentions that they're inside Wireland within Wireland due to Jack being inside his own computer, which, in-turn, is also Wireland, Sans responds with:
Sans: wasn't there a movie like that?
- When talking to the Water Cooler of DOOM, Jack retorts by saying:
Jack: Where's a DUPA mug when you need one?
- Many references to the infamous pee-break are made.
- The name "Dan Foster" gets a nod.
- When Billy mentions that Wireland is under martial law, Jack angrily states that he should've played Ace Attorney on the channel. He still hasn't, even after reading this line of dialogue in his own playthrough.
- Despite The Escapists area being based on the first game, Jack does ask about The Escapists 2
- Jack's list of crimes, but only the references.
- Vehicular manslaughter
- Daytime robbery
- Nighttime robbery
- Impersonating a priest
- Performing surgery without a licence (multiple surgery games, but probably Surgeon Simulator or Bio Inc)
- Cruelty to goats
- Breaking and entering (Jack has played a lot of games involving burglary.)
- Blowing up an orphanage (Manual Samuel)
- A portion of The Escapists section has you engage Felix in a roast battle. Some possible combinations (and one from Felix) can include:
- "You played Happy Wheels so badly it should be called "Pathetic Wheels"
- "You played Amnesia 20 feet away from the screen in broad daylight and you know it's true!"
- "You were really jumpy during PT and the holes in your ceiling prove it!" (Felix)
- "Your face is so ugly, Slippy could beat you in a beauty pageant where you're the only contestant!"
- "Your dog Edgar, has actually read his namesake, unlike you."
- When Mark is asked about his pink bed, he replies that "The Warfstache is always in."
- Billy mentions that Frisk and Alphys got locked in a meat freezer together.
- Max mentions going to The Last Guardian to take photos while talking to her after The Escapists section.
- While talking to Angus, Mae mentioned that Gregg snuck up behind him and whacked him with a florescent light. This gets blamed on Freddy.
- While in the Five Nights at Freddy's section, when asked about how many balloons the Pizzeria goes through in a month, Jenny replies "Ninety-nine. And they're all red."
- Jack gives Jenny the advice not to wind up a music box in a Five Nights at Freddy's location, as there's normally an animatronic.
- After Billy makes the point that the Five Nights at Freddy's section is arguably a FNAF universe. Jack takes this as an implication that the game they're in is Five Nights at Freddy's World and is utterly horrified.
- When asked about what happens to the kids normally found in FNAF games, Billy mentions that they all congregate with the other kids in games such as Turbo Dismount, Planet Coaster, or TABS. As for the babies (such as Among the Sleep or Who's Your Daddy?)? Toriel and Asgore run a daycare.
- Checking Pirate's Cove in the FNAF section nets you this interaction:
Billy: There is no man behind the curtain. There may, however, be a homicidal fox.
- Checking a poster as Cliff has him wonder where MatPat is where you need him.
- In the Fran Bow section, checking the fire extinguisher will first have Cliff wonder where a flamethrower is, and then have him joke that Adam and Jamie always say to not try any of there show's stuff at home.
- While in the Fran Bow section, checking the crate in the library has Cliff joke that he has "crate expectations" for it, before chastising himself, since his joke stunk like the Dickens
- While in the Fran Bow section, there is a nod that all dark rituals have been blocked by Educational Degree Number 2,790 by order of the High Inquisitor.
- Checking the books next to the mirror in the Fran Bow section will have Cliff respond sadly that there aren't any issues of Calvin and Hobbes.
- When checking the sacks in the Fran Bow section, Cliff Jones jokes that if ever wants to retrieve a small golden idol then all he needs is a stately name. The name he comes up with? Virginia Smedley.
- If you check Fran Bow's furnace, Cliff will sing Relight My Fire before cutting himself off, as he forgets the lyrics.
- One of Fran Bow's books jokes about how The BOSS went Turbo and ripped off a Disney concept.
- Once Fran Bow's goblet is lit on fire, Cliff states that he swears he didn't put his name in the Goblet of Fire.
- Fran Bow's graveyard has a few in the eulogies:
- Checking the wardrobe in Hello Neighbour has Jenny remark that it looks like it walked straight out of a Dr. Suess book. Only for Billy to respond with "Dr. Who?"
- Jack calls the Jacksepticeye's Paradox merchants Team Rocket knock-offs.
- Checking Jack's game console with Cliff in your party reveals it to be a Nintendo 64.
- After the team name "Possepticeye" is decided on, Jack exclaims "Possepticeye, let's roll out!"
- During The Stanley Parable section, there is a nod towards one of the achievements from the actual game, although instead of an actual achievement, this time it only nets you an easter egg. The broom cupboard also returns, with the ability to make the "Narrator " rage as expected.
- After noticing how similar each of the plants in The Stanley Parable is, Jack counts himself lucky that he hasn't played a game based on Little Shop of Horrors.
- After Employee 207's identity is revealed, GLaDOS mocks his attempt at being the actual Narrator by saying he sounded like a sound-alike auditioning for Saturday Night Live.
- How do you defeat GLaDOS? By turning her into a potato, of course. 207 even calls this out!
- When talking to Jorji after clearing the Portal section, he references some of Jack's old Plague Inc. diseases. Billy even mentions that you can't take an outbreak of "My Ass" seriously. In the same conversation, Cliff brings up the fact that "With great immaturity comes great responsibility."
- Turmoil and Subnautica both appear as posters in the last time you visit Sans' shop. Turmoil would get its time to shine later, in the sequel.
- Monika from Doki Doki Literature Club! makes a very brief, blink-and-you'll-miss-it, cameo, but that was likely because of the fact that Jack's DDLC playthrough came out mere months before The BOSS officially released. It's even said in the developer lounge that the latest game they could fully include characters from was Kindergarten.
- In the goodbyes section, some characters not listed above make a brief cameo appearence:
- Slime Rancher: A Slime is standing in the back.
- Little Nightmares: Six is seen standing next to the Slime.
- Bob and Wade, or at least, NPC's that look like them, make a cameo.
- A character from Party Hard note
- And, when saying goodbye to Billy, he won't let Jack go without a "Screw you, Billy."