* AlternativeCharacterInterpretation: 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. [[VideoGame/HalfLife It is that hard of a stretch?]]
* AscendedMeme: Of sorts. Winslow gained a reputation of being a MemeticBadass and now he's the only character other than the main four to be voiced and the only ''VideoGame/MonkeyIsland'' character to appear.
* SugarWiki/AwesomeMusic: [[https://www.youtube.com/watch?v=w3x3DR7LGeQ For example]].
** The music from the trailer is a minute and half of funky [[https://www.youtube.com/watch?v=Q-ipUrT7JME smooth jazz]].
** The music also has a ''porn groove'' to it, intentional or not.
** And how can we forget the music from the [[https://www.youtube.com/watch?v=71B11mBOw0A teaser that started it all]]?
* BaseBreakingCharacter: 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.
* CrossesTheLineTwice: [[https://www.youtube.com/watch?v=7E0y2ZDnkps Heavy's Engineer Story.]]
* FandomSpecificPlot: The very concept of the ''Poker Night'' series has inspired many concepts about all sorts of characters from different franchises crossing over to play poker.
* FoeYayShipping: 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 Website/DeviantArt and you'll see.
** There's possibly one-sided HoYay 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.
* GatewaySeries: Many fans of ''VideoGame/TeamFortress2'' who hadn't played a Telltale game ended up picking up ''Sam & Max'' or ''VideoGame/StrongBadsCoolGameForAttractivePeople'' as a result.
** Same thing with ''Homestar Runner'' fans to try ''Team Fortress 2'' or ''Sam & Max''.
** Many people who hadn't heard of ''Webcomic/PennyArcade'' (or at least hadn't read it) got into it thanks to this game. (Look up '''any''' ''Poker Night'' video on Website/YouTube, it's impossible to find a video that ''doesn't'' have a comment asking who Tycho is)
* GoodBadBugs: 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 [[DoesThisRemindYouOfAnything 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]]The actual line is "bet every time my bellybutton itches."[[/note]]
* HarsherInHindsight: When ''VideoGame/TeamFortress2'' went Free-To-Play, Tycho claimed he hated the game. ''VideoGame/PokerNight2'' ended up having no Webcomic/PennyArcade representation, not even a cameo.
* HeartwarmingInHindsight: Or perhaps, ''more'' heartwarming in hindsight:
-->'''Tycho:''' So this [[TheMedic Doctor]]... he a friend of yours?\\
'''Heavy:''' (firmly) Yes.
** Later, in "[[VideoGame/TeamFortress2 Meet The Medic]]", Medic refers to Heavy as ''his'' friend, with genuine fondness in his voice. In fact, a lot of "Meet The Medic" could potentially be a CallBack to ''Poker Night'' - Heavy's fondness for RussianHumor, birds...
* HilariousInHindsight: The Game Central Station in the Disney film ''WesternAnimation/WreckItRalph'' 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 long DevelopmentHell makes it debatable who came up with the idea first. Coincidentally, Heavy and Ralph later got together in the PC version of ''[[VideoGame/SegaSuperstars Sonic & All-Stars Racing Transformed]]''.
** In ''Poker Night'', Strong Bad claims the next "Snake Boxer" game will have snakes with fists. Fast-forward to ''Series/TheAquabatsSuperShow'', 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 ''[[VideoGame/SegaSuperstars Sonic & All-Stars Racing Transformed]]'' on the PC.
** Strong Bad thinks Max is a Franchise/{{Pokemon}}. The fire-type starter from ''VideoGame/PokemonSwordAndShield'', Scorbunny, has been [[https://twitter.com/VelvetyF/status/1100826316247584768?s=19 compared]] [[https://knowyourmeme.com/photos/1465782-pokemon-sword-and-shield to]] [[https://www.newgrounds.com/art/view/arkvayth/scorbunny-max Max]] [[https://twitter.com/Boo_Rad13y/status/1100766016970391552 several]] [[http://tredlocity.tumblr.com/post/183094530745 times.]]
* QuirkyWork: Take four characters no one would ever expect to see in a crossover. Now do just that. Now make it a ''poker game''. This is what you get.
* TheScrappy: 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.
* TaintedByThePreview: "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?!"
* ThatOneAchievement: While the game is already luck-based to a degree, the achievements for winning with a straight flush or four of a kind are the worst due to the statistical improbabilities involved.
* ThatOneBoss: Tycho is overall the hardest person to bust out due to his very conservative strategy of folding or calling only low bets and blinds with all except the best of hands, and his ability to get into the player's mind in doing so in part due to the fact that it's both not impossible for him to bluff and that his AI will take increasingly more risks as the game goes on, making it unclear whether he's just trying to scare you or is about to destroy you with a killer hand.
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