1) Great Wrym Red Dragon + 20 levels of Druid.
2) Wild Shape into something fun
3)No none core
4)20th level druids are only cheesy in so far as druids are cheesy in general.
5) Dragon wins.
There we go. I should also point out that you never said the dragon had to be CR20 in return. My result has a CR46 monster fighting a CR20 wizard.