Commentary by guest judge Mississippi Fred MacDowell from On the Main Line:
When the talented and lovely Ms. Shpitzle invited me to guest judge the August Caption Contest, I immediately had three thoughts. No, four thoughts. The first thought was, I was flattered. The second was, guess I can’t win that $25. The third was, what do I know about cartoons? The fourth was, what do I know about captions? And the fifth – yes, it was five thoughts – was, what do I know about judging?
Judging is easy. I specialize in being judgmental, albeit generally in a secret way. I am smiling at you, yes, but your shirt is awful. Besides, the Olympics were going on in earnest and I was taking a crash course in how to judge things on a scale of 1 to 17, to the tenth of a point.
Cartoons. Did I not draw a cartoon of Mr. Mufflehandovermymouth in the 6th grade and did he not show it to my parents at the PTA meeting? (And was not my father openly proud?) Did I not have a good 6 or 7 year run going home to read the day’s Calvin & Hobbes, first thing, after yeshiva? Did I not once drop the 50 pound two volume Complete Far Side on my ankle (sharp corner first)? 
Captions. I’ve been blogging for a complete shemitah, and blog post titles are kind of like captions. In addition, I have mentally submitted many winning captions to the New Yorker contests (and even an anecdote or two to Reader’s Digest, although those I actually sent in), but sadly not one winning caption to Oy Vey Cartoons.
So, without further ado I pick a winner.
Whatever I said, don’t use my name.
Congratulations, Groynem! I understand that the key to getting rich is trading. So turn that $25 into $30, and pretty soon you will never forget this day, the day you won the August Caption Contest.
Why this one? There were other good ones, and caption entrer (? entrant?) Joseph Perl deserves an honorable mention simply because of his aptly chosen name, but I chose this one because. Well, the lack of an open critical debate in the frum community is not necessarily funny, but very true. I happen to think that one of the very interesting revelations of the internet was how much dissent and dissatisfaction there actually was among all groups of frum people (yes, and likely all groups of people, period). Yet, offline it seems to me that there is barely a peep. Who are all those people with all these opinions? Sure, there are sometimes small circles and tables where one feels free to speak one’s mind. But in general, everyone walks around and outwardly mostly accepts things as they are. This actually goes for all kinds of criticism, including from the right. Apart for feeling free to complain about talking in shul, there’s just a whole lot of not saying what’s on your mind in the frum societies, when everyone knows who you are, that is, and unless you are an authorized sayer of your views. Of course this begs the question about my own anonymity. So to squarely address this head on, I say mind your own business. Actually, I am getting closer to the big reveal. Stay tuned.
While there has been some very interesting changes in this regard – Facebook comes to mind, and I think if we compare the state of Open Frum Discussion in 2012 with Open Frum Discussion in 2002 we will be shocked by how much more open it is, with people increasingly openly stating what they really think, name and all – Groynem’s caption still rings true. While some may have learned to be more open and confident about their non-conformity in thought, there is little evidence that the collective societies are becoming safer havens for non-conforming opinions. The irony is that if public debate were allowed to be more diverse, or dare I say, free, perhaps the secretive internet debates where every religious and communal leader wonders if the fella who just shook his hand is assassinating him online, would be calmer and more positive. Well, probably not.
Not knowing how to end, I will leave that thought suspended like a mountain in the air.
I find that we can find a reflection of cartoons and caption contests in our tradition, or shall I say, pseudo-tradition. The author of the Mishnah commentary Tiferes Yisrael recounted a legend that Moses was born bad. A true portrait of him was made by a curious king, who heard of the great wonders, and the Royal Portrait Gazers concluded correctly that this man Moses was no good from birth. Not understanding how this famous man, this great leader of exodused slaves could be naturally greedy and lousy at core, he visited the holy encampment in the wilderness, parted the same clouds that the portrait maker had, and personally met Moses. Seeing that Moses was actually the most humble of men, patient with his flock and all of that, he confronted him with his analysts’ analysis. “It is true,” Moses said, of the cartoon. “But I am free to write my own caption.”
And with that, 60 years later a whole slew of rabbonim took to the pen to castigate the Tiferes Yisrael for casting aspersions on Moses’s natural character.
 Wikipedia says 19.5 lb, and Amazon says 19.8, but I seriously doubt it. http://en.wikipedia.org/wiki/The_Far_Side#Other_books and http://www.amazon.com/The-Complete-Far-Side-1980-1994/dp/0740721135
 See Sid Z Leiman “Rabbi Israel Lipschutz: The Portrait of Moses (Tradition 24(4) Summer 1989) for the entire story. http://www.leimanlibrary.com/texts_of_publications/50.%20Rabbi%20Israel%20Lipschutz%20The%20Portrait%20of%20Moses.pdf