♪ The Night shows you the face behind, a curse for endless times ♪
-Smiling Jack and his crew
Smiling jack was an infamous pirate of the seas who was well known for cutting a smile into the faces of his victims whilst looting, pillaging and raping the many settlements he invaded taking anything of value and as captain of the dark pirate ship "The Sea Reaper".
No one knows what became of him and how he had attained immortality through lichdom, though some say that he was killed during his involvement in the Dragon Wars and was branded with the Black Spot by Davy Jones himself after his body was disposed of in the sea allowing his body and soul to enter Davy Jones' Locker.
Jack's soul pleaded for his life back, going so far as to sell himself. Davy enjoyed the sight of his groveling and let him keep his soul in exchange for him to become his personal debt collector.
Now he sails the seas with his crew now given unlife collecting the souls of those who are branded with the spot and have failed to hold up their end of the bargain to Davy Jones.
Note: lyrics for the song Smiling Jack sings created by youtube user kijuubi