The courts always have trouble with humor. They're serious places filled with serious people in serious clothes doing serious things. Judges demand - and expect -respect, and don't tolerate jokes. Even when they talk about humor, they fall back on Important Satirists like Jonathan Swift, and don't discuss the equally subversive, but much funnier, Moliere.
So Lenny Bruce gets convicted of obscenity and George Carlin gets banned from the airwaves, but the American Nazi Party can march in Skokie and Saving Private Ryan can go on network TV. And if you want to convince a court that your speech deserves protection, you're much better off if there's a serious purpose, no matter how odious, than if you're trying to be funny.
The thing is, the First Amendment doesn't say "Congress shall make no law . . . abridging the freedom of serious speech," or "core political speech" or anything like that. Still, just as Chief Justice Roberts interpolated a pro-drug message into a nonsense phrase, judges seem to interpolate seriousness language into the First Amendment. It makes me think that maybe, just maybe, we would have been better off if Ben Franklin had been involved in the drafting of the Bill of Rights, rather than the other, very serious Founding Fathers. He, at least, understood the value of a good joke.