So if philosophy isn’t preventing conservative comedy from flourishing, what is? Structural, demographic, and financial issues.
Successful comics often rise up out of thriving, crowded standup scenes, which tend to mainly exist in urban areas. Jon Stewart, for instance, spent five years in the New York City comedy world before landing a show on TV. Big cities tend to be liberal, and it stands to reason that so would be the people who attend comedy clubs in them. Funny urbanites who are conservative may decide that there just isn’t much of a market for their political material. One comedian who I was referred to declined to be interviewed because, the comedian said, the conservative label, “has never been good to me.”
Similar impediments exist in the entertainment industry, which has a not-undeserved reputation for being run mainly by liberals. “People always ask why there aren’t a lot of really big conservative comedians but I think the deck is stacked against that and I doubt it will ever happen in my lifetime,” Nick Dipaolo told The Daily Caller, mentioning that he suspected that his politics were why HBO wouldn’t air a recent hour-long special he taped. There just aren’t many outlets for conservative comics. The feeling, as Stephen Kruiser writes on Breitbart, is that “most liberals in the entertainment industry expose themselves to conservatives about as readily as they would a leper colony.”