Playboy X offers Niko some money if he helps out his recently released friend Dwayne. Dwayne wants Niko to recover some money from a guy named Jayvon Simson. Dwayne has a feud with Jayvon as he was the man who informed the police of Dwayne's illegal activities, resulting in Dwayne being sent to prison. Jayvon is also the current boyfriend of Dwayne's ex-girlfriend, Cherise Glover. Dwayne says that he was sending this money to Cherise from prison to help pay her rent, but now that he knows that she was giving the money to Jayvon instead he wants it back. Niko agrees to help out the melancholic Dwayne, saying that Dwayne "reminds him of himself".
Niko heads to the Videogeddon arcade in Chinatown and sees Cherise and Jayvon together. Jayvon spots Niko and fires at him with a Micro SMG. Niko dodges the bullet and Jayvon escapes on a Hellfury.
After either killing or sparing Cherise (player's choice), Niko steals a nearby NRG 900 and chases Jayvon through the city, eventually killing him and retrieving Dwayne's money. Niko phones Dwayne, who asks Niko to meet him at the Cluckin' Bell near Star Junction. Niko meets Dwayne there and returns his money. Dwayne also asks about Cherise: If she is spared, Dwayne will say he is happy she isn't dead due to her being "just an idiot". If she is killed, he will also say he is happy, due to her being "such a bitch".
"Jayvon Simson's body was one of the many collected by coroners in Algonquin recently. It wasn't a knife or a gun or a rocket launcher that killed this man though... he was killed by video games. Witnesses report a heated argument outside Videogeddon arcade, an establishment where addicts pump quarters into computers to get their fix of horrific violence. The argument was followed by a chase on motorbikes then his grizzly murder. It is no surprise that upset community leaders are pointing to games as the cause of this death: the pattern of altercation, vehicle chase, murder, rebirth and try again is common in video games. Although Mr. Simson was a known drug user and dealer with several convictions, we are certain this case is due to polygons and pixels not parole boards."
Transcript[]
This section/page depicts all cutscenes and dialogues in the mission Ruff Rider in Grand Theft Auto IV.
Sure, just got out of the pen, old friends aren't paying him no mind.
Playboy X:
Yeah, that's what he think. He got friends all over the shop but he living in the past. I need you to go over to the Governor Greg Johnson Projects over in Northwood, he holding up there and needs help with some shit. You assist his broke ass, I'll send some paper your way. I owe that fool - ain't payback a bitch? Peace out, money.
Dwayne's Apartment
Niko knocks on the door of Dwayne's apartment. Dwayne opens the door.
Dwayne ushers Niko inside the apartment, then chacks the hallway before closing the door.
Niko:
Yeah... it's hard living with the past. Eh?
Dwayne:
Yeah. Especially when the present has turned into an asshole. Fucking bitch... nobody wants to roll with me no more. It's like I'm tainted.
Niko:
What do you mean?
Dwayne:
Playboy don't wanna hang no more. He pays for you to come over instead. My girlfriend, the love of my fucking life... man, I was pulling moves in the joint so this bitch could pay the rent. Now, she won't answer the phone. Man, I gave her everything when I was inside. Cars, houses, apartments, bank accounts. Everything. I heard she hanging with Jayvon now.
Niko:
Who?
Dwayne:
Some punk who fucking talked. He swears he wasn't involved in me going down, but I knew. I knew his ass was lying. Now motherfucker's fucking my girl? For real? Shit is fucked up, man. Sometimes I just wanna end this shit.
He points the Micro-SMG he's holding to his head briefly.
Dwayne:
Just... bam. But I ain't there yet. Mm-mm. Not quite.
Niko:
Listen, why don't you go talk to her?
Dwayne:
Ain't shit to say.
Niko:
Then I'll go speak to both of them. I'll ask for your money back... and if they don't agree, I'll make them. Where do they hang out?
Dwayne:
At some arcade in Chinatown. Uh, look, man, don't bother.
Niko:
No. I'll bother. I'm getting paid. And besides... you remind me of me.
What? Dwayne must a finished his bid. Shit, he going to be mad angry.
Jayvon gets on a motorcycle and flees. If Niko stays near Cherise, she begs him not to kill her.
Cherise:
Don't kill me. I know I fucked Dwayne over real bad but he wouldn't want me dead. He too much of a gentleman for that. He ain't like that Playboy X punk, he's only chasing paper. You do right by Dwayne he gonna stick to you for life. I didn't mean it. Girl get lonely when her man's inside for a long time. I thought Playboy was gonna look out for me but he didn't answer my calls. Punk didn't wanna know me. I did what I did to survive. Please. I don't wanna die. Come on! Dwayne wouldn't ever hurt no one he loved, even if they screwed him like I did. Please. I'm only human. Come on.
They paid up? I guess my name still means something out there. People are still scared of me.
Niko:
They are, I got rid of Jayvon for you but I let your ex go.
Dwayne:
That fool Cherise? She just couldn't help herself. She always told me she'd burn me good. I guess I shoulda listened. Happy she ain't dead, though - she just an idiot. Peace, man.
Niko:
I collected on that debt for you.
Dwayne:
They paid up? I guess my name still means something out there. People still know me.
Niko:
I had to explain things to them. They didn't listen so good.
Dwayne:
You slept Cherise? She were a bitch, weren't she? This fool falls real hard for them. That's why he gets burnt. Thanks for getting this paper, Niko. It helps.
If Niko killed Cherise, some time after completing this mission, Niko gets a call from Dwayne.
Dwayne:
Niko, man. I was out today and I saw this bitch coming out a nail place. She looked just like my old girl, Cherise. The one you said you killed with Jayvon outside the arcade. You sure that was her?
Niko:
Dwayne, it was her. She screwed you over while you were inside. She's dead now.
Dwayne:
Shit, man. I coulda sworn it was her.
Niko:
Sorry, man. She's gone. Maybe things coulda been different in another life.
Dwayne:
Word.
Video Walkthrough[]
Trivia[]
The mission's name is a reference to the real-life Ruff Ryders motorcycle club.
The post-mission article in the Liberty Tree accusing video games of being the primary reason for Jayvon's death is likely a parody of the various claims of video games instigating real-life violence, with the Grand Theft Auto series being a frequent target.