Robert allows his brothers to go to his Portal Room, and they all decide to go through the Hell Portal. There, they meet the unsettling inhabitants (Zombie Labmen and Espouses) and unsafe materials (Hellrack, Fluorescent Rock, and Spirit Sand). They eventually take refuge in a brick castle someone built, which serves as a bar people go to. However, when they go in a basement, they encounter gold and an Espouse, but quickly kill it. They then go to Buccaneer Bay and defend against enemies and go fishing. They then chase the Headless Horseman through his castle, a pirate ship, a tomb, a mine, and Robert eventually cuts the head off of Pumpkin Head and kills him. Robert and his brothers do the medieval version of Trick or Treating afterward, even though they are adults.
Robert has dark brown hair, brown eyes, beige skin, and he wears a reddish-brown jacket (dark gray in Venture: Revolution, Venture: Bounty and Venturian Battle) with a white undershirt and a red and white striped necktie, and dark blue jeans (also dark gray in Venture: Revolution, Venture: Bounty and Venturian Battle), and brown shoes. Robert is above average height, standing at 6'1" and weighs 175 lbs.
- Hair: Cocoa Brown
- Skin: Peach Orange
- Trench Coat: Dim Gray (VCU), Baker's Chocolate (Ingame)
- Pants: Dim Gray (VCU), Catalina Blue (Ingame)
- Robert Jacob won the "Character of the Year" award in the LMMCU Awards on February 14, 2019.