The 9 Lives of Alexander Baddenfield by John Bemelmans Maricano

Alexander Baddenfield is the last of a long line of Baddenfields.  And the Baddenfields are bad people.  They are mean, spiteful, cranky, rude, bullying jerks.  As the last of the Baddenfields, Alexander has incredible wealth with which to be as bad as he wants to be.

But there's one problem Alexander would like to overcome: because they are so bad, the Baddenfields always die grisly deaths at an early age, despite the efforts of their traditional protectors, the Winterbottoms (you can read more about them for yourself in the book).  So Alexander comes up with a plan: he'll have his cat's nine lives transplanted into himself - that'll give him lots of opportunities to be bad!

After finding a doctor to perform the operation, does Alexander become more cautious?  NO! He becomes more reckless!!  Despite the pleas of his faithful Winterbottom, Alexander cooks up scheme after scheme, each of which results in his untimely demise.  You can read about his nine lives (and his nine deaths) in The 9 Lives of Alexander Baddenfield, by John Bemelmans Marciano (the grandson of the author of the original Madeline stories).

The book is full of dark humor, and the illustrations by Sophie Blackall are a great complement to the text.  This isn't a feel-good book about a bad boy learning the error of his ways and becoming a better person.  This is about a bad boy getting what's coming to him - nine times!  A really fun read.