Skull Boy is a young living skeleton. A man of many talents, Skull Boy is the mansion's official Jack of All Trades. From film directing to painting, cooking to cavern exploring, robotics to private investigating, Skull Boy can pretty much do it all. His only problem is that he can't seem to find one thing and stick to it for any serious length of time. But if Skull Boy doesn't know where he's going, it's mostly because he doesn't know where he's been. There have been subtle hints that Ruby may have a crush on him and vice-versa. For example, in one episode, Skull Boy goes up to Ruby to ask her an important question, but it turns out he was just asking her to turn his book's pages as he was playing. Another time that would show this would be while doing the play that Poe is directing, Basil and Rosemary, Skull Boy was nervous and blushing when Poe wanted him to show more affection to 'Rosemary', played by Ruby. Skull Boy also shows some affection for Ruby. For example, in one episode, Skull Boy is convinced that he is related to a long line of detectives and runs up to Ruby, giving her a hug, chanting, "Oh, Ruby, thank goodness you're OK!"
In Skull Boy's endeavour to discover his roots, he has undergone many personas and occupations. These include:
- Painter
- Pilot
- Film Director
- Private Investigator
- Explorer
- Scientist
- Chef
- Documentary Filmmaker
- Jazz Musician
- Carpenter
- Etiquette Expert
- Astronomer
- Shrink
- Ice Sculptor
- Action Hero
- Army General
- Layabout
- Talk Show Host
- Ringmaster
- Grease Monkey
- Animator
- Architect
- Inventor
- Tailor
- Show Announcer
- R.I.P.’s Drummer
- Star Fleet Captain
- Magician
- R.I.P’s Band Manager
- Misery’s cousin Murky
- Malt Shop Worker
- French Inspector
- Train Conductor / Engineer
- Shakespearean Actor