- Adaptation Displacement: One of the conversations Claptrap starts lampshades the fact that most modern Sam & Max fans don't remember the comics.
- Awesome Music: A jazz cover of Still Alive.
- Cargo Ship: Ash and Wendy, who was the Anti-Necronomicon in the guise of a woman. He wasn't aware of it at the time, though.
- Crack Ship: Claptrap has a crush on GLaDOS, and he constantly tries to put the moves on her, much to her chagrin. Even in one of the PS3 unlockable skins, he's where Chell was when GLaDOS awoke in the sequel, offering her a rose.
- Ensemble Dark Horse: Some feel this way about Steve, mostly because of the Borderlands-themed eliminations.
- "Funny Aneurysm" Moment:
- In one full group conversation, Claptrap suggests that the four of them, representing the four main branches of geek culture, should make a conglomerate. When asked about his contract working for Gearbox Software, he launches into an angry rant that gets interrupted by a visible override as he praises his company. Amusing enough in the context of Gearbox, which has done well for itself, but considering the future financial situation and public opinion of the company that made this game, Telltale Games...
- In another conversation, Brock mentions that a video game company used his image for one of their games, which later "went bankrupt... with extreme prejudice". Context aside, it's hard to listen to the line nowadays and not think about Telltale, who featured Brock in this game, announced their bankruptcy years later and due to the numerous controversies that followed, one could say the company's reputation went down in flames. Ouch.
- Claptrap getting hacked by Gearbox to keep him from voicing his dislike towards them is a bit of a funny gag. At least that was the case until years later in 2019 when Claptrap's voiceactor, David Eddings, came forward with stories about abuse and injustices he suffered at the hands of Randy Pitchford, CEO of Gearbox.
- Max giving Claptrap a "Wet Willy" note is significantly less funny if you're aware that Claptrap's voice actor claimed Randy Pitchford pulled the same prank on him during a recording session.
- Gateway Series: Just like the first game, particularly in regards to The Venture Bros. and Evil Dead.
- He Really Can Act: Yes, that is Danny Webber from Birdemic doing a surprisingly good Bruce Campbell impression, good enough to fool many into thinking it was a pseudonym for Campbell himself.
- Hilarious in Hindsight:
- In Poker Night at the Inventory, Max recalled a story about Flint Paper beating up Artie Flopshark (deceased) because he was a teaching a "made-up" game called Omaha and "scamming" people. Guess what's an actual alternative to Texas Hold Em' for Poker Night 2?
- Within the same game: Ash thinks highly of the fact that Brock is like a second dad to Hank and Dean, and Ash says he's thinking of starting a family himself with Wendy, provided his "swimmers" aren't cursed. Once you unlock the full Evil Dead set, GLaDOS mentions to Ash that when he time-travelled back to the 14th century, he did end up getting a woman pregnant, despite sleeping with her "once, twice tops". Said woman ended up being one of Brock's ancestors, therefore, Ash is related to him through time-travel. Whoops!
- Max's new voice actor is known for playing Lexaeus in the Kingdom Hearts series. Sam's old voice actor played Goofy, who assists the hero, Sora, in defeating the Organization Lexaeus works for.
- Ash complaining about not letting franchises die is even funnier after the announcement that more Evil Dead movies and a Evil Dead TV series are on the way.
- The Heavy is in the game, even if The Heavy isn't.
- Ash asks Sam about his car and mentions that it growled at him, with Sam replying that it must have been possessed when they were in Hell. In Ash vs. Evil Dead season 2, "The Classic" gets possessed by demons.
- Ho Yay: Ash speaks to Sam about his 25-year relationship with Max as if he's talking to a couple that's been married for a long time, and seems approving of the (according to Brock, mistaken) idea that Brock and Dr. Rusty Venture are raising Hank and Dean as co-dads.
- When the rest of the table explains to Ash that they know his exploits through comic books, collector's edition DVD's, and other merchandise, Sam mentions that Max has a rare, "Naked Ash" variant action figure.
Sam: You don't even like...whatever gender that is.Max: Call me.
- Max also rewards The Player with a kiss at the end of the Sam & Max 25th Anniversary Tournament, despite both Freelance Policemen admitting that they can't tell what gender The Player is.
- When talking about HELPeR in the Venture Bros table set, Claptrap gets distracted with the idea of a robot head getting stuck in Brock's shirtless torso. And in another conversation, Claptrap flat-out tells Ash that he'll always be "his one true man-crush".
- Sam wishes he had a "manly, dame-swooning jawbone" like Brock and Ash. However, he sounds less interested in making ladies swoon to him and more interested in those two.
- Internet Backdraft: The increased difficulty compared to the first game is a bit of a sore subject on the game's Steam forums.
- Just Here for Godzilla:
- Most Annoying Sound:
- Sam's line "Great day in the morning!" becomes rather irritating after hearing it for nearly every all-in.
- GLaDOS says, "Well, that was a clever move that won't come back to bite you in your ample posterior" WAY too often.
- Name's the Same:
- Tainted by the Preview: The lack of Homestar Runner characters hasn't been met with much warmth from the fanbase desperate for a sign that the site ain't dead.
- That One Level: Well, challenge. Winning with a high card is terrible, because in addition to being entirely luck based, it requires you to win with both the worst condition possible. Get a pair and win? Too bad, you're out of luck. Your opponents fold when you would've won with a high card? Again, out of luck. While also terrible (but not anywhere near as bad) is winning a showdown with at least two players in it, since your opponents will likely end up folding rather than going all in. Unless you have a pitiful amount of money that won't change their stack much even if they lose.
- That One Achievement: Fortunately, unlike the first game, there's none requiring you to get specific hands. Unfortunately, "We are the 1%", requires you to get $1,000,000 in lifetime balance, which means winning several games in a row without losing too much. If you're not good at Poker, you're not gonna be getting this for a long long time.
- It's hard to get by playing honestly, anyway. It's quite easy to get if you cheat by Save Scumming.
YMMV / Poker Night 2