The second oldest of Jack's Alter Egos, Jackieboy Man is a heroic vigilante. Brave, bubbly, independent and compassionate, he never hesitates to help someone in need and, in fact, relishes the thrill of the chase and the save. There are times that he can be clumsy, dropping or fumbling with his tools, which can make him seem unqualified for his job, but he's intelligent and has a great heart. He first appeared in the video "Jackieboy Man Returns | Welcome to the Game #2", where Jack called upon him to hack the Deep Web because Jack had been scared by the previous run-through of the game and once more in “THE SCARIEST FUN! | Richies Plank Experience VR (HTC Vive Virtual Reality)”, when he allowed Jack to experience flight and put out fires around the city.

Jackieboy Man is loyal, honorable, and optimistic, always ready with a word of advice for his viewers. He's incredibly proud of his successes, usually sings and dances to celebrate, and is never one to back down from a fight, though he can be easily frightened if he's blindsided or ambushed. Impatient and impulsive, he sometimes forgets the necessary tools he needs for his mission or rushes off into danger without fully listening to the rules.

He tends to take most things at face value, trusting what he sees over what he's told, though he does have a vivid imagination. He has a keen sense of competition with other heroes, particularly Spiderman, and wants to prove his worth, often becoming snarky if he thinks he's being disrespected. His powers include x-ray vision, keen hearing, superior agility, and tentative hacking/coding skills, but his tendency to forget things and resulting need to double back and recheck his work can stand in his way.

Very little is known about Jackieboy Man's personal life: His birthday is July 10, 2016. Apparently he has poor eyesight outside of his x-ray vision and owns a pair of "Superhero Glasses" that he needs to see when he is unmasked and even when he is masked if he's attempting to decipher code. He is also an enemy of Antisepticeye.

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