The only part of the haggadah that ever interested me was the four sons. It seems to me that the part of the text that deals with the four sons is the most honest part of the seder. Here we sit down and divide people into groups. There are smart people and bad people and simple people and boring people. This is what we teach our children. Pigeonholing is apparently the best way to deal with fellow Jews.
The Four Sons as Four Books: David Weiner and Yonah Weinreb, The Haggadah in Memory of the Holocaust, 1988
In a way, it’s astonishing that this is a message we’re comfortable giving to kids, but then, it’s not like every family doesn’t have obvious and often predictable roles for each child. The perfectionist, the rebel, the nerd, the misfit, the genius, the drama queen, and so on. You know your role, and you know that no matter what you do and how much you change, you’ll always be the baby of the family, the one everybody considers irresponsible and temperamental. A second cousin of mine once said to me, “You’re the troubled sister, right?” And I shrugged and said yeah, because I was troubled when I was 14, and I know I’m going to live with the label at least until I have kids of my own.

But beyond the unfair labeling that goes on, the actual distinctions between the sons make me crazy, especially the wicked and the wise.

The wise child asks: "What mean the testimonies, and the statutes, and the judgments, which the Lord our God hath commanded you?" (Deuteronomy 6:20) To that one, you explain all the laws of Passover, down to the very last detail about the Afikoman.

The wicked child asks: "What mean you by this service?" (Exodus 12:26) By saying "you," and not "we" or "me," he excludes himself from the group, and denies God. Answer that child plainly: "This is done because of that which the Lord did for me when I came out of Egypt." (Exodus 13:8) For me, not for you: had you been there in Egypt, you would not have been redeemed.

Notice that both the wise and wicked sons refer to “you,” excluding themselves. But somehow the wicked son gets bitched out, and the wise son gets to be teacher’s pet. Why? Because the wise son had enough background to ask a specific question, and the wicked son was brought up in the dark about “this service.” So basically, if you didn’t get a stellar Jewish education you’re not worthy of being redeemed.

It seems to me that there are times when we all should be the wicked son. There are times when standing back and saying, “What is all this?” can be helpful, and instructive and important. Yes, we need to be loyal to each other and our traditions, but sometimes we also need to step back and assess the direction we’re heading. What are we doing here, exactly? It’s a fair question, and when we forget or refuse to ask it we end up in trouble. (See: Israel).

I put together a gallery of different portrayals of the four sons from a variety of haggadahs. Check them out and see everything from a wicked son who boxes to a wise son modeled on Groucho Marx.