The Taoist-ish healing chaos of Bobby Lee

Whenever I take a paper towel I always carefully leave the next one hanging free and breezy, in an easily grabbable position, never maddeningly grafted onto the roll. Because, in my angsty imagination, that could doom later-me to some hellish ordeal of groping about, desperately trying to find where the next loose square begins. Very similar strictures apply to toilet paper. And don't even get me started on rolls of packing tape.

In addition, let it be known that toothpaste must always be squeezed and progressively flattened from the very bottom up with surgical precision. Furthermore, bars of soap must be perched on their sides in our bamboo soap dish to avoid the purgatory of the bar of soap getting bonded immovably to some accursed smooth flat surface (I'm looking at you bathtub and sink).

Also, my 80-gazillion nutritional supplements must all be arranged in their cabinets and drawers with their labels fastidiously turned out and easily readable at a glance.

Pots, pans, bowls, and glasses soaking in the sink must be filled (with moderately soapy water) to the very tippy top which, of course, means they cannot be even slightly tilted or canted at any angle whatsoever, lest some stray bits of brown rice or oats or green smoothie harden into nasty little stalagtites, thereby causing the universe to hurdle wildly out of control which I do not care for one bit.

You get the idea.

In modern days, the term for me is OCD, like Monk in the old TV show or Sheldon in Big Bang Theory. But back in the day we used to just say I was “uptight,” or “anal retentive.”

According to a lot of spiritual wisdom, my neurotic ways are just an exaggeration of what all egos do—“egos” meaning all unenlightened people. Many spiritual masters point out that the ordinary unawakened person makes a fetish out of order, control, and predictability. Here’s a quote from a spiritual master named Adi Da Samraj (note that when he uses the term “Narcissus,” he just means the ego):

“The usual man or woman seeks control by all means, since such a person fears that he or she and even existence itself are out of control. That person makes sublime sighs whenever he or she sees something orderly. But such a one does not understand that all order is an arbitrary design, made of repetitions of like things.

Order is Truth to Narcissus. Narcissus dies for the sake of order. Narcissus dies because of order. He is egoically self-possessed, possessed of the repetition of everything he wants to continue to be. He repeats himself, literally. He is fixed upon himself, the symbol of certainty. At last, unable to yield to what is more than independent self, below thought, above thought, outside the thinker, he contracts on himself, imploded on the instant of thinking.”

In short, pretty much every one of us has a primordial case of OCD, even if it's not as comically extreme as mine. This is one reason (and just one) why so many spiritual masters behaved in a so-called “crazy wise” manner.

The traditions are full of stories of Taoist masters getting snookered and wild in unsuspecting taverns. Buddhist masters storming into brothels. Indian avadhoots wandering naked through the city streets, mumbling nonsensical gibberish to themselves. Fools for Christ engaged in all kinds of weird, crazy behaviors, as did plenty of Sufis. A class of yogis called must saints were infamous for acting in bizarre and irrational ways.

These crazy wise masters behave and speak in such wild, unconventional, and even shocking ways in order to pull our egos’ control-rug out from under us. To throw a Holy Hand Grenade of Antioch into our ossified agendas and rigid dualistic mental models of what “spirituality” is. Because it is those very mental models by which we stay “in control,” and, hence, trapped in the ghetto of the ego.

All of which sort of brings us more or less to comedian, podcaster, and actor Bobby Lee.

I'm not saying Bobby Lee is an enlightened crazy wise sage. But I am saying that, among his arsenal of comedic skills, the one that most sets Bobby apart from his peers is his unparalleled genius for chaos. And it's an extraordinary antidote to those of us on the uptight, over-controlled side of the spectrum—especially if we are into spirituality, and our practice could use a bit of laxity and messiness.

When we think of comedians and comedian podcasters the first skill we usually think of is quick-wittedness. Patrice O'Neal, Conan O'Brien, Nikki Glazer, Mark Normand, are a few who had (in the case of Patrice) or have lightning-fast tongues. Bobby's co-host on Bad Friends (one of Bobby's two podcasts) is Andrew Santino, and Santino has a blindingly quick mind and wit. In any sort of direct insult war Andrew annihilates Bobby—and he does so regularly.

But that kind of straightforward “insult war” is the comedic version of “conventional warfare.” And Bobby rarely engages in anything remotely like conventional warfare (and even when he does, and gets demolished, his reactions to getting demolished are usually orders of magnitude funnier than the insults that demolished him...so even in “losing” he wins, which is a very Taoist thing, by the way—“investing in loss” and all of that—for those of you keeping score at home). Bobby’s is asymmetrical warfare. Guerrilla warfare. And psyops. It depends on unpredictability and sheer weirdness.

But whether in a seeming conflict or not, Bobby’s comedy always deploys a disorienting mayhem, disarming spontaneity, strange broken rhythms and just all-around protean awkwardness (and not the pre-packaged “awkwardness humor” of Rick Glassman, Oliver Tree, or Bobby Altoff that, for me, quickly becomes predictable, wearying, and worst of all, a form of invulnerability because they're doing “characters”). You could say Bobby does improv but it's some trippy mutant cousin of improv, improv on DMT. It's virtuosic chaos. Masterful pandemonium.

That doesn't mean constant hyper-freneticness. That, too, would get tiresome. No, the secret to Bobby's brand of chaos—and just his all-around compulsive watchability on any podcast ever, his own or others’—is his bewildering ability to change moods on a dime, to completely shift his energy, his pace, his intensity, in the blink of an eye. The suddenness with which he pivots his whole disposition is a marvel to behold, from petulance to poutiness to apparent rage to heartfelt revelations to spoiled imperiousness to big-brotherly advice, to an unexpected insult—often an insult too bizarre, surrealistic and silly for the other person to even defend or counterattack.

Often he will instantly activate an almost shocking level of vulnerability, a disarming lack of defensiveness about his own weaknesses, insecurities, selfishness, and dysfunctions (which, by his own description, are legion and vast). It's almost like a comic book superpower.

In one episode of TigerBelly Bobby is on a mad tirade about something when his then-co-podcast-host Khalyla says, “You're such a slimy weasel.” In a flash, Bobby becomes soft and quiet, and with a voice of realization, almost a kind of sad wonder, he says, “Oh my God, I am a slimy weasel aren't I?”

Basically Bobby Lee is like the psychological version of a Tai chi master (returning to our Taoist theme), who is so soft and yielding that, no matter where you try to push or grab him, there is seemingly nothing there, no resistance, like you're trying to push or grab water.

For Bobby, his ample foibles are all just raw material for comedy. And btw, this acceptance of or even indifference toward one's own imperfections is a requirement of authentic spiritual life. The heat of spiritual practice will bring up all of our deepest wounds and worst traits, so we'd better start to cultivate some industrial-grade indifference toward them. For the spiritual practitioner, all of one's craziness and dark elements are supposed to be just “grist for the mill,” as Ram Das put it (Ram Das even has a book by that title).

But most of all, it is this ability to let go of one's self-consciousness and plunge with abandon into artful recklessness and free-flowing spontaneity that seems so relevant to anyone interested in spirituality and general transformation. The ability to let go of control is central to spiritual life. And Bobby Lee is a one-man master class in letting go of control. Check out either or both of his weekly podcasts on YouTube and let the master work his quixotic magic on you, loosening up your egoic rigidities by sheer osmosis. Partake, imbibe, enjoy.