Donkey Kong

Donkey Kong (also known as The Ape, The Monkey, and The Robot) is one of Nintendo's oldest and most prominent characters, who is part of both his own series and the Mario series. Within the context of Press Buttons and Talk, Donkey Kong has shown up in several games that the group have played. However, most of them are minor appearances, with his most prominent appearances being in the playthroughs of Mario Party 2, Mario Party 3 and Mario Party as a computer-controlled opponent and their most hated enemy.

Mario Party 2 and 3
Within the main Mario Party games, Donkey Kong acts as the fourth player who competes with ProZD, Manky and Anne Marie. He is always set at a Normal difficulty, and his actual performance varies dramatically, from irrational moves to masterful plays. All three of the players alternate in voicing Donkey Kong. His characterization has shifted over the course of the playthroughs. While he was initially just shown as relying on brute force for everything, his characterization later evolved into portraying him as a generally nice guy who values fair sportsmanship and is undeserving of the hostility of the other three players. Some of his irrational moves are explained by him wanting to give other players a chance or just focusing on doing his own thing rather than winning. On occasion, he openly questions and/or complains about the others' treatment. ProZD once referred to himself and his friends as actually being the villains of Donkey Kong's story.

Because he is a computer-controlled player, the human players sometimes refer to him as a robot. This idea first emerged in Mario Party 3, Episode 13 and then became a running gag for several episodes in which Donkey Kong's characterization shifted so that he was obviously a robot trying poorly to disguise himself as an ape (though sometimes it was unclear whether or not this was Donkey Kong pretending to be a robot pretending to be an ape), with a more robotic-sounding voice. However, he later shifted back to his original characterization, and it was retconned that the human players just kept on assuming that he was a robot and treated him as one when he was not.

Over the course of the games, Donkey Kong has managed to win once in each game: Western Land in Mario Party 2, Chilly Waters in Mario Party 3 and DK's Jungle Adventure in  Mario Party.

Mario Party 3 Story Mode: Donkey Kong's Revenge
During the Mario Party 3 playthrough, the game crashed and lost all of its save data shortly after Donkey Kong gained a magic lamp very early in the game. Thus, he was believed to have cursed the game. While playing the game's Story Mode, Donkey Kong showed up as the opponent for the Strength Star Stamp in "Ep. 26: Donkey Kong Punches the Moon", in which he sought revenge for his mistreatment. The players also discussed how Donkey Kong punching the moon was an actual thing that canonically happened in Donkey Kong Country Returns. Donkey Kong proved to be a formidable opponent, if also one that insulted ProZD by randomly showing him mercy at several points. Donkey Kong defeated Wario/ProZD three times before finally losing the Duel Map in "Episode 31: A Different Donkey Kong". He continued to be a pest on several Party Board maps in the Story Mode playthrough and demanded an apology from ProZD for his behavior, which he never received.

Mario Party 1
When the gang played the original Mario Party, their version chronologically took place after the other two games. It was said that the characters traveled back in time, but also lost their memories at the same time, so it was as if they were starting from the beginning anyway. Donkey Kong quickly began to irritate Wario all over again. This time around, Donkey Kong had his normal characterization, except now he openly acknowledged being a robot.

Wheel of Fortune
In Episode 36 of the Wheel of Fortune playthrough, ProZD and Manky discuss a version of Donkey Kong known as the "Tumblr-oo" Donkey Kong. Their jokes involved making up tumblr posts in which Donkey Kong responds to specific situations by making single-vowel sounds, which is based on one actual tumblr post that just consists of Donkey Kong saying "Oo". They go on to discuss his relationship with Diddy Kong and conclude that Donkey Kong pays for Diddy Kong's college while believing that he himself is too old to finish college. They then make a point of establishing that canonically, this Donkey Kong is different from the one in their Mario Party playthroughs.

Quotes
Donkey Kong: So much negativity. First Bowser, Bowser is not ugly. Or smelly. Toad's guitar is fine. I'm not red, I'm brown. Luigi, I just don't understand, do you hear yourself when you speak?

Luigi: You know what I hear when you speak? *fart noise* I'm an idiot. *fart noise*

- Donkey Kong and Luigi in Western Land 

Donkey Kong: I was saying this from the very beginning. I was playing this very diligently, and I don't know what you guys were doing! Being mean the whole time. But I win! Y'know, this just proves kindness and hard work always win-

Wario: Shut the fuck up!!

- Donkey Kong and Wario after Donkey Kong wins Western Land.

Donkey Kong: I took your verbal abuse, and I'm going to cinch the win. You're not the only one who can waterboat a bowl of mashed potatoes.

- Donkey Kong to Luigi after winning a minigame

Donkey Kong: I gotta huge dick. Hello Millenium Star, wanna see my huge dick?

-Donkey Kong while obtaining his second star on Waluigi's Island

Trivia

 * One running gag is that ProZD and co. threaten to end/delete the channel if Donkey Kong wins. The channel has continued despite Donkey Kong's occasional victories.
 * It has been shown that he and Bowser are very close, resulting in Bowser showing favoritism towards him. Bowser is even shown to have a romantic interest in him, but Donkey Kong feels that he is coming on too strong. ProZD later claimed that they are canonically in love.
 * He is often referred to as just "the ape".
 * In Episode 11 of Mario Party 3, it is revealed that Wario once killed his whole family when following up on a threat.
 * In Episode 48 of Mario Party 3, it is revealed that he has two baby boys that he is providing for, named Rutus Kong and Grumpet Kong. Grumpet earned his namesake by crying like a trumpet at night. In accordance with previously stated lore, these children must have been born after Wario's killing spree.
 * He has also been established as a serial killer (or serial keyler) who buys Skeleton Keys and then buries them without using them.
 * He seems to violently vent his repressed rage through some minigames such as "Hey Batter, Batter!"
 * His father was named Shaunkey Kong and died in the ruins of DK's Jungle Adventure.