Question

Between pyridine and benzyl amine, which is more basic

Answer 1

You can look at the pKb values. It turns out pyridine is more basic. This is difficult to predict from looking at the Lewis structures of the molecules. What you should see is that the lone pair on pyridine is on an sp2 hybridized N. This makes it less basic than an sp3 N. The N in aniline is sp3 but the lone pair is in resonance with the pi electrons of the phenyl ring, lowering the basicity.
Hope you got it