Canon • 
Dubiously Canon
In Paradox Space[]
On Snapchat[]
Jake Harley is memorialised in Gcatavrosprite's Halloween costume.
In Skaianet Systems Incorporated files[]
The files revealed that Jake was given his name to match Jane's. After arriving on Earth in 1910 and being adopted by the Condesce, Jake ran away with his dog Halley in 1923. He befriended Charlie Chaplin, whereupon he saw a heated argument between Chaplin and Laurel and reported it to Albert Einstein. By 1926, Jake's friendship with Chaplin has turned into a turbulent romance, though Jake eventually abandoned him.
In 1931, Jake inherited Skaianet and ran it while unknowingly being used as a puppet by the Condesce. As the head of Skaianet, he dealt with Adolf Hitler's tantrums by "promoting" him to higher positions, and eventually told Paul von Hindenburg in 1933 to give him some "useless title" like chancellor.
Jake eventually practically abandoned his post at Skaianet to go adventuring to look for Sburbian ruins. While in Kansas in 1942, he had an illegitimate daughter named Ann and took custody of her. He brought her to Hawaii while searching for an island, where she ditched him as a teen and changed her surname to her mother's, Dunham.
In 1952, Jake had a child with one of his wives, and five years later took him and his mother on an jungle expedition. They are ambushed by Chaplin, and Jake hid behind his wife who gets shot dead. The two fight and Jake begins to be beaten senseless before Calamity interrupted. Chaplin then left with Jake's son as Jake lies alone in the jungle.
Jake eventually married A. Claire in the late 70's and fathers Joey Claire and Jude Harley. He then set up the infants Dirk and Roxy with trust funds, and eventually left his family once he discovered the Pacific Island and begins to live there.
In The Homestuck Epilogues[]
Jake visited Barack Obama on his thirteenth birthday, and claimed to be his relative.