Bike cuck guy is a spineless weasel with negative self-respect, and will rationalize all misfortune that happens to him as somehow being his fault. His "friendgroup" constantly bullies him as a result, as evidenced by the reaction to a tweet saying "political disagreements shouldn't merit ending friendships".
New Guy artist is a narcissistic asshat who presented a person feeling sympathy for someone else getting robbed as being a dopey idiot, and presented themselves as the virtuous hero for taking perverse glee in it. Bike cuck guy is leagues better, if only because his mental issues are pathetically directed inward instead of against others.
It's because sports games took off during the PS1 and the kids who bullied him in middle school started playing vidya in high school on it. I can't remember where he let that particular bit slip but it's one of the most revealing things Bob's ever said. He hates "hardcore" gaming, FPS games, and Sony products because they embody the era where he wasn't the cool outsider for playing video games anymore, and, even worse, his precious Mario still wasn't popular as playing video games became more mainstream.