Not much is known about Ghostly Bob life before or how he died, other than he is a captain of a small band of pirates that enjoy haunting other pirates. He and his crew where somehow imprison within a wooden crate and sent to the bottom of the Never Sea.
Ghostly Bob is the most aggressive of the three pirate ghosts even when confronted by Jake,Captain Treasure Tooth and Peg-Leg Peg when Bob was not intimated and refused to leave Captain Hook's ship and not even Jake and his friends had the power to get rid of him and his men. Ghostly Bob's only fear ironically is scary ghosts.
Role in the series
Ghostly Bob first appeared in the episode "Stowaway Ghosts" ,after the wooden crate they where sealed in was found by Captain Hook and his scurvy crew and brought aboard the Jolly Roger,believing the crate contained treasure Hook open it releasing the mischievous ghost pirates who soon cast Hook and his crew off Jolly Roger. Hook was desperate to reclaim his vessel he was forced to ask Jake and his and crew for help, but the pirate ghosts prove to be quite tricky for Jake and his crew to get rid of alone. Jake knew if anyone could help rid Hook's ship of ghost is Captain Treasure Tooth. Using the ghost call shanty Jake and his mateys summon Treasure Tooth and Peg-Leg Peg. Jake soon explains their polite to with the three ghosts haunting the Jolly Roger, Treasure Tooth knew of the silly spirits and the only means to rid themselves of them is by tricking them. Treasure Tooth and Peg-Leg Peg are last seen after Jake and his crew trick the mischievous ghost pirates back into their crate, Treasure Tooth and Peg-Leg Peg decide to take them back to Pirate Paradise so they can't haunt any more ships.
Ghostly Bob and his crew reappear in the episode "Phantoms of Never-Nether Land", still causing mischief in Pirate Paradise. The trio ends up stealing Peg-Leg Peg's Spirit Key locking the gates to Pirate Paradise preventing Peg from leaving and Treasure Tooth from entering. With the help of Jake and his pirate crew Treasure Tooth was able to track down Ghostly Bob and his crew. Bob informs Jake that they took the key to free Captain Wraith from Never-Nether Land who they got a message from in a bottle. Jake and his crew warn Bob not to trust Wraith after dealing with the fiendish pirate once before and the dangers of unleashing the evil spirits of Never-Nether Land on Never Land. Bob agreed to return the key but it was too late, Pranky accidentally sets Wraith free. After Wraith is locked away once more Bob and his crew apologized for the trouble they caused and returned to Pirate Paradise with Treasure Tooth to free Peg-Leg Peg.