- Alternative Character Interpretation: You play as someone who never talks, in a First Person Perspective in a game with video game characters (Or ones related to video games), and who is explicitly identified several times as a man. It is that hard of a stretch?
- Ascended Meme: Of sorts. Winslow gained a reputation of being a Memetic Badass and now he's the only character other than the main four to be voiced and the only Monkey Island character to appear.
- Awesome Music: For example.
- Base-Breaking Character: Tycho. Some players find his arrogance and smug personality annoying, while others find it entertaining. That said, very well-liked amongst the female players though, especially with that sexy voice of his.
- Crosses the Line Twice: Heavy's Engineer Story.
- Foe Yay Shipping: Fangirls seem to interpret the rivalry between Strong Bad and Tycho as this. Search "Poker Night Inventory" on Fanfiction.net or "strong bad tycho" on DeviantArt and you'll see.
- There's possibly one-sided Ho Yay from Tycho towards Max, since he goes into very inappropriate detail asking if Max had sex with a human woman, and tells Max his sexual fantasies about giraffes, visibly disappointed when Max is squicked. This is probably less to do with an interest in Max in particular and more to do with Tycho's... animal-related interests.
- Gateway Series: Many fans of Team Fortress 2 who hadn't played a Telltale game ended up picking up Sam & Max or Strong Bad's Cool Game for Attractive People as a result.
- Same thing with Homestar Runner fans to try Team Fortress 2 or Sam & Max.
- Many people who hadn't heard of Penny Arcade (or at least hadn't read it) got into it thanks to this game. (Look up any Poker Night video on YouTube, it's impossible to find a video that doesn't have a comment asking who Tycho is)
- Good Bad Bugs: Using the right mouse button to skip character dialogue can lead to some humorous happenings, from Strong Bad's mouth disappearing, to the Heavy sitting back with his hand on his lap and an all-too-satisfied smile on his face, to Max outright swearing.Max: Next time I'll rethink my strategy of bitches. note
- Harsher in Hindsight: When Team Fortress 2 went Free-To-Play, Tycho claimed he hated the game. Well, there goes ever seeing a Penny Arcade cameo in a sequel, unless he changes his mind...
- Heartwarming in Hindsight: Or perhaps, more heartwarming in hindsight:Tycho: So this Doctor... he a friend of yours?Heavy (firmly): Yes.
- Hilarious in Hindsight: The Game Central Station in the Disney film Wreck-It Ralph seems to be an expansion of the "World between worlds where video game characters go when you're not playing them" idea- although the film's been in Development Hell for so long that it's debatable who came up with the idea first. Coincidentally, Heavy and Ralph later got together in the PC version of Sonic & All-Stars Racing Transformed.
- In Poker Night, Strong Bad claims the next "Snake Boxer" game will have snakes with fists. Fast-forward to The Aquabats! Super Show!, where Matt Chapman (Strong Bad's VA, and a writer for the show), plays Carl, a blatant Expy of Strong Bad who keeps a giant cobra man with arms as a sideshow attraction.
- Strong Bad making fun of how much Sonic The Hedgehog sucks in front of Heavy, who later cameoed (along with Spy and Pyro) in Sonic & All-Stars Racing Transformed on the PC.
- Strong Bad thinks Max is a Pokémon. The fire-type starter from Pokémon Sword and Shield, Scorbunny, has been compared to Max several times.
- The Scrappy: Winslow is this in particular to players who fold their hands a lot, especially when he announces the blinds when they couldn't care less.
- Ship Sinking: "Sascha is my only love" and Telltale's view (as stated at the recent PAX panel) of Sasha and Natasha as Heavy's girlfriends (they're actually two of his miniguns, Sascha being the stock minigun and Natascha being an unlockable/craftable minigun with different stats), while the gun that the Iron Curtain replaced was supposed to be "the stripper he meets in Vegas". Ambiguous, considering the game's canon status is hazy.
- Tainted by the Preview: "Oh, sweet! Strong Bad, Max, Tycho and the Heavy are going to be tearing it up— wait, what do you mean it's going to be a card game?!"
- That One Achievement: Good luck getting that straight flush or four of a kind.
- That One Boss: Tycho is harder to deal with than the other players.
YMMV / Poker Night at the Inventory