For the better part of my adult life, I proudly avoided nerd/nimrod/goober status. I was always just cool enough.
There's very little you could do to prepare to be a correspondent on 'The Daily Show,' because it's not being a journalist, it's not being an actor. It involves elements of both of those things, but they're not required necessarily as job experience. It's helpful if you know how to improvise, but again, not a requirement.
I think when someone who's known for doing drama does a comedy but just tries to be funny, that's a mistake.
I would like for my kids to at least have some familiarity with who I am: 'It's the man from TV!'