Howard Stern's “Hollyweird Squares” Are the Funniest 79 Minutes in the History of Television

Wow, where to even begin with this one?... I was just watching some random clips of Beetlejuice when I happened to stumble upon this legendary day of old. What first got my attention was Shirley Phelps' demonic grin on the thumbnail picture there, a grin I had definitely seen before, but then I noticed Megan Phelps, now Phelps-Roper, making a distinct gesture of teenage embarrassment, and her sister Grace beside her with a look of strange distrust. What I'm trying to say here is that even the thumbnail of the video is a work of art... So I clicked on it, I skipped ahead to watch a random bit and I immediately knew I had to watch the whole thing from beginning to end. And since I first saw it, which was a few days ago now, I've been rewatching it nonstop, both in full or in random bits. So yeah, it's been a fun, and very controversial, couple of days.

In case you haven't seen it or know nothing about it, it's a sort of parody of Hollywood Squares, a gameshow where celebrities are filmed in a tiny studio so as to have their faces appear on a tic-tac-toe board. The host then asks them questions of general knowledge to which they give their best guesses, and the contestants have to agree or disagree with the answer. If they get it right, they place their symbol on the board, hoping to make a straight line. It's simple enough, and Howard decided to do the exact same thing, but he just so happened to fill the squares with some very interesting people indeed.

In the top left square we had Gilbert Gottfried who is one of the funniest comedians around and a guy who simply cannot be offended. He can make fun of absolutely any topic, no matter how racy, because he can simply find humor in the most wicked things. He simply doesn't care, as seen, for example, in his podcast with the great Norm Macdonald. At the center top was a black man from Howard's sales team, probably the only normal person of the group. At the top right was Jeff the Drunk effortlessly wearing a cowboy hat and, of course, with a beer in hand, and he was handcuffed to a woman named Jenny as part of a side contest they were playing. On the center left were the aforementioned Phelps trio who spent the entire show sparring with pretty much everyone, except for Grace who looked understandably shifty all throughout. In the center square was Daniel Carver, a mild-mannered man of few words, though the words he does speak tend to be a little bit blunt. Daniel was the man Gilbert laughed the most at, and with good reason. On the center right was Elephant Boy, who just seemed like a nice guy with an unfortunate speech impediment. On the bottom left was Bobby Trendy, a flamboyant gay man who, understandably, did most of the sparring with Shirley. Center bottom were Caressa Kisses and Rebecca Love, two sex workers who, aside from being participants in the show, were also the prize. And lastly, on the bottom right were Gary and Wendy, whose innocence and wholesomeness really tied the whole square together.

Playing the game were Randy and Adam, two seemingly random dudes who not only knew almost none of the answers but they were also weirdly analytical of each question, Randy by overthinking every friggin' thing to the point of annoying Howard, and Adam by taking an ungodly amount of time to meditate and ponder on every single answer when in reality the best thing to do would be to almost always disagree because the chance of the participants' guess being wrong is of course way, way higher than the chance of them being right. And at one point he even agreed with a complete and total guess given by the sex workers... It seemed like, because Adam was legally blind, Howard was trying to aid him in getting the big win, but the man sure didn't make it easy on him... Not to mention how neither contestant knew the very basics of the game and almost always neglected the center square, not so coincidentally occupied by Daniel, whose funny outfit really drew attention to the game, or they just went for random choices that most certainly didn't make a straight line... Anyway, beside the board was Greta, a pretty gameshow lady wearing a stunning black dress and black heels combo who would often hesitate about which tile to put up on the board, and at times seemed positively distant, and when I say distant I mean ever so slightly intoxicated... I guess what I'm trying to say here is that the whole thing was a total mess from beginning to end, and that's why it was so funny.

The show started by each participant introducing themselves and the sparks flew right off. Daniel for one opened with a bang of hate and then immediately threw a right uppercut at Shirley and at how she makes a living, but then, in an unexpected twist, he made an endearing “my wife” joke... That's when I knew this show was something else. A bit later, Gary and Wendy were introduced and that was when, not even ten minutes into the show, Megan made that gesture of embarrassment, the typical “what have I gotten myself into” reaction... Sooner rather than later, because of Gilbert, the conversation shifted gears into anti-semitism, and Shirley sounded almost human when acknowledging the love her kids have for Gilbert's voice in Aladdin. And on that note, Daniel made his feelings known about Gilbert's and Howard's heritages but I couldn't quite catch what he said. That's a recurring theme by the way, both me and Gilbert were quite hard of hearing throughout the show, especially regarding Daniel's various interventions, which if I were to relate I'd do so in incomplete or mistaken ways... Eventually, Jeff the Drunk was properly introduced, and his cool demeanor of not giving a damn tied in beautifully with all the crazy controversial talk going around, namely Daniel's loving-kindness and Shirley picking a fight with everything that moved. In some ways, he was in perfect contrast with Gilbert in the sense that neither of them really cared about the actual stuff being talked about, but Gilbert made fun of the various contestants, whereas Jeff mostly didn't care, except at one point when he got weirdly offended by Shirley and thus hilariously misquoted scripture in what was perhaps the greatest moment in the whole show.

I could go on and on, mentioning Gary's confusing admissions of prejudice or how in the laconic Grace decided to throw two hilarious shots, but seriously though, what can I say that wouldn't best be experienced by your own self? In fact, telling it, aside from the whole inappropriateness of it, would actually make it lose all humor. But while this is a beautifully hilarious mess, it's also a bit more than that, in all honesty. By getting all of these crazy people together, Howard managed to create a situation where they got to freely confront each other's beliefs by openly stating their views in complete and utter confrontation with one another. So when I say they were sparring, I don't mean it all that figuratively. My point is that freedom of speech ought to be like this, a mess where people fight with words, getting all of “their truths” out there so that the ensuing clash can result in the real truth coming out. And these days that's precisely what's missing... Howard had a gay man and a black man interacting with very aggressive opponents and, not only did nothing come of it, but both men held their own. In fact, the black salesman, whose name I believe wasn't ever mentioned, made repeated offers to take Daniel out to lunch, which he obviously, and sadly, refused. Maybe that was naive of the salesman, but you know what? That takes some guts that I wholly admire.

And regardless of the outcome, speech should always be free, because no alternative is ever good enough... No, they don't even come close. And whatever happened to a thing like this, a show where we get the craziest people arguing, being as honest as they wanna be? Because the way I see it, all that came of it was good – people got to express their views with words rather than with violence or subversion, everyone else got to confront the opposition and defend themselves, becoming stronger and smarter in the process, and all the while, Gilbert got to laugh and even ironically clap at some incredibly wicked things, as did we I'm sure... And when that happens, we realize that hatred, when mocked, dies.

But whatever, I don't wanna get too serious up in here. I just had to write something about this because if I didn't I wouldn't be able to get it out of my head, and also because it's quite a gem of comedy. Not that well hidden though, the video currently has four hundred thousand views, but still, it's a gem from a different age, from a time when I barely knew how to read but that I now almost long for, wishing comedy was still so crazy and speech was still so free.

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