- "I ain't scared of nobody, but a motherfucker says he's gonna kill me? Then a motherfucker's gonna die."
- ― Playboy X
The mission consists of two parts; the first part is a cutscene for the player to think about the decision they will make, and the second part is carrying out that decision.
The Holland Play...
Playboy calls Niko and asks for him to meet at his apartment. When Niko arrives, he hesitantly asks Niko to kill Dwayne. Niko, after first refusing, says he will think about it. Soon afterwards, Niko receives a call from Dwayne asking him to kill Playboy. After another call from Playboy, the second part of the mission begins and the player is given a choice as to who to kill.
...The Holland Play
Killing Playboy X
- "I was someone, you know. I made it. I changed the game."
- ―Playboy X's possible last words
Playboy is surprised to see Niko back at his apartment so soon. Quickly learning that Niko was going to kill him instead, Playboy readies his bodyguards and escapes from his balcony. After a short chase on the street, Niko corners Playboy in an alley, beating on a locked door. His Combat Pistol, either jammed or empty, is unable to shoot Niko and he drops it to the ground, surrendering. Niko executes Playboy by shooting him in the throat.
After killing Playboy, Niko calls Dwayne to inform him while adding that Playboy had first asked him to take out Dwayne. Lamenting his death, Dwayne offers Niko Playboy's apartment, refusing to use it himself as it would remind him too much of Playboy. Dwayne asks Niko to stay in touch in the future.
After calling Dwayne, Niko can call Roman. Roman had hoped Dwayne was paying him a lot of money, though Niko explains Dwayne couldn't, and he felt it was the right decision.
- "Fuck you, man. You a fucking snake like the rest of them."
- ―Dwayne's possible last words
Dwayne is saddened by Niko's appearance, as he thought Niko would be on his side in the matter. After Niko fights only one thug with a Baseball Bat, Dwayne puts up no fight. Both Niko and Dwayne face away from each other as Niko shoots him in the back of the head.
After killing Dwayne, Niko calls Playboy to inform him. Niko is paid for his actions but is also criticized by Playboy, as Dwayne was seen as a mentor and father figure to him. Playboy then cuts all ties with Niko.
After calling Playboy, Niko can call Roman. Explaining the situation, he sounds unsure about his choice. Roman tells him not to worry and enjoy the money.
In order to complete the mission the player must:
...The Holland Play
- Kill PLAYBOY X or DWAYNE.
(Kill Playboy X)
- Take down Playboy.
- Take out Dwayne.
(Kill Playboy X)
- Four of Playboy's bodyguards in his apartment.
- Two of Playboy's bodyguards in a Patriot.
- One hooded thug armed with a Baseball Bat.
The rewards for this mission differ depending on who was killed:
- If Playboy X was killed, Niko receives his penthouse as a gift from Dwayne, which also contains Claude's Outfit from Grand Theft Auto III. Dwayne can also become a friend to Niko if he responds positively to Dwayne's email.
- If Dwayne is killed, Niko receives $25,000 from Playboy X, though Playboy X will have a change of heart towards killing Dwayne, telling Niko he is a "cold-hearted killer" and cuts all ties with him.
- If Niko aims his pistol at Playboy X through the window of his loft, his target reticule will show. If fired, the two characters will be transported to the execution area and the cutscene will play. The only difference is that the player can pick up the Combat Pistol, because Playboy died while holding it.
- On very rare occasions, Playboy X may not make the jump from his penthouse to the other building and will fall to his death, simply passing the mission.
- After the first visit to Playboy's home, Niko can place the phone calls to Dwayne and Playboy himself rather than waiting to receive them.
- If the player moves too far away at either execution, there are two special failure phone calls to Playboy. When choosing to kill him, he will taunt Niko. When choosing to kill Dwayne, he will warn Niko that he is now after both of them, and to meet back at his apartment.
- This mission can be played even after completing the main storyline.
- The name of this mission is possibly a reference to "The Scottish Play", a common nickname used in the theatrical community to refer to William Shakespeare's Macbeth. The nickname is used because referring to the play by name inside a theater is considered bad luck.
- If the player chooses to kill Playboy X, as he jumps off his balcony and before his execution, he will say one of these lines:
- "Another motherfucker gone and let the money go to his head."
- "Even if you kill me, you gonna have this whole town after your ass."
- "I showed you the world, gangster. You don't control this shit."
- "I thought you was money, you a low rate bitch."
- "You coulda been someone, Niko."
- If the player chooses to kill Playboy X, after he jumps from his balcony and before his execution, Niko will say one of these lines:
- "It was you or Dwayne, I chose Dwayne."
- "Not such a big man now, are you?"
- "Where are you going, Playboy?"
- "X marks the spot."
- "You shouldn't have asked me to kill Dwayne, Playboy."
- "You're a bad joke, Playboy."
- If the player chooses to kill Dwayne, Niko will say nothing. However, before his execution, Dwayne will say these lines:
- "Damn, son. I'm your friend."
- "Damn, you done fucked me over in the end."
- "Don't play me like that, Niko."
- "Hell, Niko, no."
- "I thought we was close, Niko."
- "Niko, you cold."
- "Shit, Niko, that weren't cool."
- "What you doing, son?"
- After both options, Dwayne will send an email to Niko asking to be friends. If Dwayne is killed, Niko can still reply positively or negatively, although Niko will express sadness and regret in both. Positively, he will reply "Shit, Dwayne. I'm sorry. -N". Negatively, he will reply "Sounds like you're a lonely guy. Maybe what happened was for the best. -N".