Do we have to go back a whole century for a model of a greatly influential news columnist of philosophical bent?
One from Baltimore, no less.
Can’t imagine him writing from anywhere else.
Who are you reading these days?
Mencken
From Sunrise County to the Universe
Jnana's Red Barn 
His wife Sara was interesting. Southern Album, a collection of stories HLM edited and published after her death. There is an interesting assessment of her and Zelda Sayre Fitzgerald in Essays on Alabama Literature by William T. Going.
Sounds like there’s much more to explore there. Baltimore is, after all, a Southern city, and Mencken couldn’t have sustained his depth long without some strong support and encouragement. Thanks for weighing in.