Jake Harley/Dubiously Canon

In Skaianet Systems Incorporated files
The files reveal that Jake was given his name to match Jane's. After arriving on Earth in 1910 and being adopted by the Condesce, Jake runs away with his dog Halley in 1923. He is befriends Charlie Chaplin, where he sees a heated argument between Chaplin and Laurel and reports it to Albert Einstein. By 1926, Jake's friendship with Chaplin has turned into a turbulent romance, though Jake eventually abandons him.

In 1931, Jake inherits Skaianet and runs it while unknowingly being used as a puppet by the Condesce. As the head of Skaianet, he deals with Adolf Hitler's tantrums by "promoting" him to higher positions, eventually telling Paul von Hindenburg in 1933 to give him some useless title like chancellor.

Jake eventually practically abandons his post at Skaianet to go adventuring to look for Sburbian ruins. While in Kansas in 1942, he has an illegitimate daughter named Ann and takes custody of her. He brings her to Hawaii while searching for an island, where she ditches him as a teen and changes her surname to her mother's, Dunham.

In 1952, Jake has a child with one of his wives, and five years later takes him and his mother on an jungle expedition. They are ambushed by Chaplin, and Jake hides behind his wife who gets shot dead. The two fight and Jake begins to be beaten senseless before Calamity interrupts. Chaplin then leaves with Jake's son as Jake alone in the jungle.

Jake eventually marries A. Claire in the late 70's and fathers Joey Claire and Jude Harley, sets up the infants Dirk and Roxy with trust funds, eventually leaving his family once he discovers and begins to live on the Pacific Island.