- The show itself. It's a show where (about) four people get together and play boardgames. It sounds stupidly boring on paper, but somehow, it works as a show.
- Ryan Higa's god-like performance during episode 3. He won all three games, one of which he won through impossible odds!
- One for the Pandemic game. Near the end, it looks like the players might win.... Cue at least five outbreaks, all at once.
- Bonnie winning at Fiasco which is supposed to be literally impossible.
- The episode as a whole. Everybody really commits to their characters following them to their inevitable bitter ends.
- During the endgame of Last Day On Earth, it looks like Wil and Felicia might lose. Then they roll enough high numbers to kill one of the survivors in one turn.
- Ashley being able to tell that Allison was a spy in the beginning of Resistance only by noticing that her eyes didn't dilate (the reason being, Allison recently had them open to make eye contact with the other spy, while all the loyal players had their eyes closed the whole time).
- And the other spy, Felicia, being able to convince Wil that she was loyal.
- Wil finally winning in an episode on Tabletop, in Shadow Over Camelot. Congratulations buddy! You earned it.
- Troy Baker spelling out "Hope You" in Unspeakable Words, as in "I hope you have fun" with his hand after he wins.
- On Star Trek Catan, Jeri Ryan and Wil Wheaton STILL being able to almost perfectly synchronize the bridge impacts on a Starfleet vessel.
- In the Takenoko episode, Harley Morenstein uses a combination of Obfuscating Stupidity and siphoning good advice from Wil to ultimately take the game by a decisive amount, despite the fact that he had never played the game before. His shit-eating grin at the Wall of Victory says it all.
- Special mention must go to the turn in which he was able to play three scoring cards in a single turn due to having just the right arrangement of yellow tiles on the board.
- Managing to somehow pull out a victory in Castle Panic after drawing two bosses and a Serial Escalation of "draw more tokens" tokens for a total of NINE tokens in one round compared to the usual two.
- Bill basically carried the entire team in the Elder Sign episode.
- It's all over the place in Tsuro of the Seas courtesy of Andy Hull.
"I just made that dragon eat another dragon! No one has done that in this game yet! Who do you think's gonna win?"
- In a situation where it looks like Kevin's boat will be eaten by a newly appearing dragon, Andy points out how they were supposed to put a dragon somewhere else according to the dice, thus saving Kevin and keeping him in the game. Not only that, but the place where the dragon went instead was on the spot where there was another dragon, essentially kicking that dragon out and preparing for the next moment below:
- Andy pulls off a desperate gambit by putting him in a spot where the only valid move is into the dragon's mouth, relying on the others to wake it up and move it out of his way. Sadly, none of the players manage to do so and it's all up to Andy. Wil states that he had a 22% chance of actually waking up the dragons (he has to roll a 6, 7, or 8 with two dice), which makes the odds very slim combined with having a 50% chance of moving the dragon (he has to roll a 2, 3, or 4) Andy wants to move. Not only does he pull the first roll off, but he managed to do the next roll as well. He even lampshades this by saying it'd be a Tabletop Moment. Wil's so amazed with this that he allows Andy to move the dragon.
- Andy pulls this off again. After Kevin sends a dragon his way, he rolls the exact same roll needed to move the dragon out of his way and in the process, makes the dragon kick out another dragon on the same space. Andy puts it like so:
- Wil's downright convinced that he has Daenerys Duke on his boat with all the feats he's pulled. After the above line, he and Kevin begin to talk about Andy's feats like it's The Hero's Journey.
- Everyone save for the winner gets killed off by having a dragon eat them. Two of them gone out with a dragon suddenly appearing and eating them.
- In Fortune and Glory, two players end up with enough potential points to win the game and be able to do so on the same turn. Felicia, who is dragging behind, manages to draw the one card that turns the tide on everything and ensure a winner: Declare any one artifact card to be close-to-worthless. She considers playing it on Wil and Ryon... Unfortunately, Wil points out that Ryon has already sold his artifacts when he got his ally, rendering the moment of power that Felicia had moot... But she managed to get her revenge by giving the card to a third party and ensuring Wil's victory.
- In season 3, the winners get to keep the trophy!
- The level of roleplaying in Dead of Winter was simply awesome, in particular that Wil was genuinely sorry and ashamed at turning out to be the traitor.
- Wil's amazing performance in the last round of Coup. He completely outmaneuvers the other three players, perfectly calling them out on their bluffs and never letting them catch him bluffing until the end.Felicia: What did you have?
Wil: I don't remember my cards
- Wil, again, in Roll For It, quipping "I didn't choose the 1 life; the 1 life chose me" just as he rolls (without looking) the one last 1 on his die that half the table has been competing for for several turns in a row.
- In Mice and Mystics, Ryan winds up one-shotting a spider with a bow and arrow. To give you guys a good idea, we're talking a monster with three health, can poison mice, and has three defense dice to block almost any attack.
- On the topic of Mice and Mystics, Anne murderizing several enemies at once with a single Thundersqueak.
- The lore of Fury of Dracula, at least the lore Wil and his friends made up, was that Mina is the ex-girlfriend of Dracula. One moment, they end up confronting one another, with people pointing out that, if she gets bit, she is as good as dead. What does Mina do? Punch Dracula in the face then run off.
- Wil faces off against a professional Magic player Melissa DeTora in Star Realms. For the uninitiated, Star Realms is a deckbuilder similar to Legendary, only it is player versus player. Wil has a bad start to the game, with Melissa's deck just wailing on him repeatedly, until Wil manages to get a high HP outpost out to defend himself, letting him stall for time. Then he is able to deal a critical blow to her, knocking her down to just six health while he has 24. After a crappy draw from Wil leaves her with just three health to his 22, what does Melissa do? She draws the 'perfect set of cards needed to defeat Wil in one shot!
- The complete one sided beatdown in Codenames, resulting in a 3-0 victory and some utterly impressive, albeit unintentional rule-bending wordplay from one player, which earns the player in question a standing ovation from Wil.
- Eldritch Horror has a few moments, starting with an unintentional one coming from the 'Wil Dice Curse' of all things. In an attempt to secure a token on the Mystery card, (which they need two of to complete the mystery to advance their win count, and there was already a token present) he rolls crap all twice, and ends up not contributing. Cue the Mythos Phase, which would return a completed mystery back to deck, resetting the team's progress. Except, Wil never completed the card, so it is unaffected by the Mythos Card. Wil even travels back in time to ensure the roll is horrifically bad just to ensure the card isn't shuffled back in.
- At one point, the team had three blessings on the table, with each character bar one owning one. Then a card tells one of the owners to gain a blessing (with blessings, if a new one would be gained, you instead flip the original card over). The team braces for a bad thing to happen... And instead discover that he not only gets to keep his blessing, but gains two clues from it in the process!
- A dark moment of awesome was gained by the game's narrative, as the person playing the "(reformed) cultist" gained a dark pact card, which in the short term removes a monster in play for free. Later on, the Mythos Deck tells the cultist to roll for 'reckoning' on their pact. They rolled a 1, a failure, and had to pay the cost... The cultist instantly killed one of their allies! Narratively, the cultist was not in fact reformed, and was still secretly evil and supporting the eldritch gods; and for a game to pull a Mass "Oh, Crap!" on the players, it deserves a spot on this page.
Awesome / Tabletop