Chaotic DB image because yes
Connections:
-Both are near insane reality warping entities that control their own dimensions (Caine is the ruler of the Digital World and Bill ruled the Nightmare Realm)
-Both dress in a bow tie and top hat
-Both are referred to as male but aren't confirmed to be male (Caine's an A.I. and has no gender, and I vaguely remember reading somewhere that Bill's kind has over 20 billion genders and even he's not sure which one he is)
-Both have a liking for chaos and mischief
Battle Name: Digital Nightmares