James Winifred Darkmagic III lived most of his early life in his magically transporting mansion with his grandfather James Darkmagic I. They eventually settled the family house down next to the home of Mr. and Mrs. Owlbear. Mr. Ludvig Owlbear would often take Jim on excursions to search for magical artifacts.
When he was a boy, Jim used to torture Clatterby, an animated suit of armor, and lock his cousin Percival Darkmagic in a closet. According to his cousin, Olivia Darkmagic, she and Jim used to kiss in his bedroom closet.
According to Mrs. Owlbear, Jim once turned himself invisible for an entire year, allegedly on accident.
Little is known of Jim's parents, though in The Last Will and Testament of James Darkmagic I it was revealed that at least since he left home his mother has been in a constant state of delirium in which she refers to non-existent things and people and doesn't recognize Jim or other members of her family.
Jim Darkmagic sees himself as an entertainer rather than an adventurer, and is the star of a show he has named 'The Jim Darkmagic Experience'. He's equally renowned for his adventures as he is for his stage prowess.
Jim Darkmagic was the first employee hired by Omin Dran after he accidentally murdered the other person interviewing for the position. Officially, he's recognized as a co-founder of Acquisitions Incorporated, but this title seemingly holds no power.
Jim is known for being a ladies' man and according to him has had many partners in the course of his life. He dated a high elf professional assassin named Kira for a while but parted ways with her as it turned out he wanted more from the relationship than she did. More recently Jim has been in a sexual relationship with Omen's sister Portentia Dran.
Jim is a fairly slim man with angular facial features and dark black hair. He dresses in purple clothing and perhaps most notably wears a purple cape fastened around the neck with a skull-shaped brooch.
- Grandfather, James Tarthanian Darkmagic I, and grandmother, Dolores Darkmagic nee Wartstaff
- Father, James Darkmagic II
- Mother, Martha Darkmagic nee Shadowbright
- Aunt, Wanda Darkmagic nee Severguile, and uncle, Gaylord Darkmagic (deceased)
- Cousin, Gaylord Darkmagic II (deceased)
- Cousin, Olivia Darkmagic
- Cousin, Percival Darkmagic
- Aunt, Gorgon Darkmagic nee Hellbranch, and uncle, Vance Darkmagic (deceased)
- Cousin, Wretched Darkmagic
- Cousin, Hideous Darkmagic
Jim Darkmagic has appeared in every Acquisitions Incorporated main team game, either as a player character or NPC.