Conjugation dramatically changes an amine's basicity

In aromatic amines, the conjugation with the benzene ring makes the amine a worse proton acceptor, but this phenomenon is strongly affected by any substituents on the aromatic ring.

You should be able to make several comparisons.  First, what effect does the functional group (methoxy, nitro) have on the basicity of the anilines?  Why is cyclohexylamine a better base than the anilines?

Finally, where do you think dimethylaminopyridine will be protonated?  Why?