Bob is member of Jimmy's gang known as 313.
They are involved in a street war with a rival gang known as THE FREEWORLD.
Chedder bob is protrayed as rather dimwitted, but makes up for this by his loyalty.
He is often seen with his friends, and smoking weed.
After the gang is encouraged to destroy an old abandoned house cause a little girl was rapped there, and it might happen again, Chedder, despite his friends telling him not to, sets the house on fire, unaware Jimmy is still upstairs, but Jimmy manages to escape the building unharmed.
He is seen again, when Jimmy any his gang attack the FREE WORLD for talking smack, and during the commotion Bob reveals to have a gun (cause he earlier saw Papa Doc holding one), frightening everyone, and is ordered to put it away before kills someone, Bob dose so but unwittingly shoots himself in the leg, and is rushed to the hospital, where he slowly recovered.
When the others go to check on him the next day he pretends to be sleeping, but Jimmy sees him, and confronts him about it. Bob admits he didn't want them making fun of him, Jimmy understands, and calls him "MC Bob", cause during the ride to the hospital, Bob no longer wanted to be called CHEDDER BOB.
Bob is okay from the incident, but is seen handicapped, for possibly the rest of his life.
Jimmy mentions this incident when rap battling against Papa Doc..