How does he do it?

Everything he does is right: Lil' Wayne is a Red Sox fan.

Various TV appearances by Red Sox

These appearances range from joyous to painfully awkward like a phone conversation with me. I would want it no other way.

Jonathan Papelbon on Letterman (my personal favorite)
Manny Ramirez on Leno (good)
David Ortiz on Conan (a bit odd, but Papi's jacket makes it worthwhile)
Jonathan Papelbon and Doug Mirabelli on QVC (bizarre)
David Ortiz on Regis and Kelly (painful)