I liked to bust a gut laughing, even though I was sad to see this, one of Letterman's best bits in years, go packing. Taking a joke to its logical conclusion and then stretching it (and his audience's patience) far, far beyond all reasonable tolerance is a Letterman specialty. Stevie Wonder once said something like, "First, I do it right. Then someone else will come along and do it neat." Wonder was referring to his trademark over-long songs, wherein he hammers the listener with a hook for seven minute stretches, bludgeoning the listener into picking up the irresistible melody. 

And, that's Letterman: drilling us with the same joke, relentlessly, week after week after month, going on hiatus and coming back with the same gag, wearing out our patience beyond all reason, until, finally, the joke morphs into a tribal experience. It becomes greater than itself, humor on a whole new level, as America (at least Dave's America) assimilates the phenomena into its cultural lexicon.

Dave is the real deal. A cranky social misfit, the rapidly aging (scary, ain't it, how the very short hair makes him look positively fossilized) Letterman's savage skewering is practiced, first and foremost, on himself. He becomes terribly uncomfortable with praise of any kind (especially the critical and emotional accolades given him at his triumphant and deeply moving return to television after the attacks in New York on September 18). A very public figure who has learned some very bad habits from fellow social cripple Johnny Carson, Letterman (it is widely rumored) hates to leave the house, despises parties and other social gatherings, and does none of the "Hollywood"  social moves one would expect of an entertainer worth $14 million per year (just from The Late Show; this estimate doesn't include profits from his company, World Wide Pants, Inc., producers of the hit CBS comedy Everybody Loves Raymond).

I closely identify with Dave, as I have adopted a bunch of bad social habits, following him as he follows Carson, I suppose. But I'm not worth $14 million per year, and, frankly, nobody misses me at parties. I guess I like Dave because Dave more or less validates my point of view, letting me know I'm not so alone out here on the ledge after all.  Thanksgiving at Dave's family home, back in Indianapolis, is much like any number of familial horror scenes from my past. Dave thinks stupid things are stupid, and he makes it all right to actually use the word, "stupid," for which I am continually criticized by the ever-increasing fragile souls in my orbit.

I tend to withdraw from a world I neither understand nor fully appreciate, and from a society so riddled with hypocrisy and stupidity, much of it enrapt in sentimental social custom that serves no effective or productive purpose in our lives. If I had Dave's money, I'd withdraw so far I'd likely vanish, but, alas, I am still forced to be somewhat functional amid all of this screeching of monkeys.

Oprah Winfrey, conversely, is the antidave. The sentimental big sister who has built an empire around her own fruitless attempts to achieve closure with a stolen youth. Winfrey's energized zeal is frightening to me in that her apparent arrogance— she knows she's right and she's gonna tell you how to get yourself straight— is blatant overcompensation for deep-seated insecurity.

If Winfrey had any sense of humor at all, She'd have flown to New York and barged in on Letterman in mid-taping, telling him to shut up already. But she has no sense of humor. She's a black woman (watch me get in trouble now), and to my experience, black women have absolutely no sense of humor beyond the tip of their own noses. There are exceptions to every rule, but I've met more than my fair share of black women who are so unbelievably self-possessed and arrogant that Letterman-style irreverence doesn't even register. The overwhelming majority of black women I've met are suffering post-traumatic distress from some jerk guy that bounced them on their head at some point. There's always The Jerk Guy, because the black woman is, nine out of ten times, drawn to The Jerk Guy, not The Good Man. And then she gets bounced and what does she do? Take it out on The Good Man, building her force field and armoring herself with intemperance, especially towards men. The loud-mouthed, histrionic Aunt Esther stereotype of black women is broadly based on their need to protect themselves and/or overcompensate for feelings of inadequacy or vulnerability. It is a largely self-reinforcing pathology that drives away The Good Guy, leaving only The Jerk Guys on their radar screen.

These women don't watch Letterman or Leno. They watch whatever black crappy ignorant mess is on UPN or The WB. They don't watch the news. They don't know who Alan Greenspan is. And their sense of humor runs exactly along the lines of films like Soul Food and Waiting To Exhale. Rent those films and see for yourself: none of those women in that film would even understand a man like David Letterman. Dave's humor is as lost on them as it was on the incredibly stiff and incredibly pompous crowd in 1995 at the 67th Annual Academy Awards, where host Letterman introduced Winfrey to Uma Thurman by gesturing from the stage and lyrically pronouncing, "Oprah? Uma. Uma? Oprah." It was hilarious. And almost nobody laughed, least of all the inhaled Winfrey. This incident was likely the beginning, or near the beginning, of the Letterman-Winfrey "feud," which consisted mainly of cruel jokes at Winfrey's expense.

And, see, that's probably why Letterman did it. He likely taunted Oprah knowing Oprah has no sense of humor about herself, that Oprah (putting the lie to her Me Am So Very Together snake oil show) is incapable of poking fun at herself, or of extending herself in any way that might even seem like it ridicules her or her work. To Dave, it was a gag. To Oprah, an insult, one she wouldn't even dignify with a response, which makes Winfrey seem all the more pathetic. 

I pause parenthetically to observe that Jay Leno's Tonight Show regularly trounces Dave in the ratings. Which really scares me about America and makes me want to withdraw all the more. Leno is so unbelievably un-funny— his range moves from not funny to not tasteful— I can't believe he's still on the air. Still on the air and clobbering all comers with his rigormortis inducing monologues (I mean, the audience is barely laughing), sophomoric skits and impotent attempts to rise to Letterman's manic genius (Dave is actually best when he throws the script out the window and starts making it up on the fly).

Leno, as a stand-in for Johnny Carson, was hilarious. Probably the best stand-up comedian I've seen. But, once he got the desk for himself, he seemed to adjust, moving into the comfortable middle so as to not offend Ma and Pa Carson viewers. But it's all bland cooking, no spice, obvious (and groan-inducing) punchlines, and, paradoxically, hideously poor judgment (The Dancing bin Ladens).

Leno, of course, has been on Oprah. That's more of an Oprah-approved guest, Oprah, perhaps, conveniently forgetting Leno's gross exploitation of the great racial tension and divide of the Simpson trial. Letterman, sadly, succumbed to OJ jokes after first taking the high ground, shutting guest Howard Stern down with the withering disclaimer, "Double murders just don't crack me up the way they used to." Thunderous and sustained applause. Letterman forced Stern to keep his coat closed, to cover a Simpson parody tee-shirt, and Letterman has not, to my knowledge, ever re-run that segment. I wish he'd stuck to his guns, letting Leno be the jerk, but after a few test shots across the bow, Dave was fully in the Simpson gag reel, though still not to the gutter level of Leno.

But, I digress...

MacDave: Letterman working the drive-through window at MacDonald's

We are likely not to hear from Oprah, ever.
Which, I think, is a shame. Being an educated black person, a dignified black person, a spiritual and moral black person should not and must not become equated with having no sense of humor. We should not become so culturally insulated that we think, somehow, protecting our dignity is worth sacrificing our humanness. Like it or not, what one black person does is, more often than not, received by the majority of white America as indicative of our culture as a whole. I don't want White America thinking our mark of high calling in humor is limited to Arsenio and Chris Rock. That all we laugh about is fried chicken and old church ladies, drunks and junkyard owners. In 1988, Jesse Jackson went on Saturday Night Live and spent the better part of two hours disemboweling himself, skewering himself, his speech patterns, his looks, and his mission, while at the same time surgically implanting the message he wants us to hear and the questions he wants us to ask. It was a brilliant move, widely criticized by, well, everybody who widely criticizes things, but it de-stiffened Jackson, made him human and approachable, de-mystified "The Black Thing," and, I have no doubt, won him thousands if not millions of new sympathizers.

Oprah, by contrast, has squandered her opportunity. Whether it was years of Letterman fat jokes, the Uma thing, or just her distorted sense of self, Oprah has clearly retreated to a place many black women go to justify doing stupid, dumb and immature things. Maybe she's popping a champagne cork tonight, declaring victory. She showed him. But I get no sense at all that Winfrey has any clue about the opportunity she missed: to swim with the sharks. To show she can take a joke, that she can even have fun at her own expense, and most of all, to use the opportunity as a platform to advance the things she cares deeply about. To get Dave under the lights and just ask him why there's hardly any blacks in his audience and precious few on his staff (to my knowledge, stage manager/sidekick Biff Henderson and guitarist Felicia Collins, whom Dave routinely referred to as "Felicia Collins-Schaffer, Felicia and Paul married in a quiet ceremony with family and friends," a running joke until  Collins nixed it because people were taking Dave seriously (which I find ghastly and implausible) and it was, so the story goes, encroaching on Collins' love life). 

I don't claim to actually know what goes on in Winfrey's head, but from where I sit, she seems consumed by ego. Tonight she has broken the back of Letterman. applause and cheers. And maybe black women all over America are high-fiving and "yeah, sister"-ing. Without thinking about the opportunity missed. White America will, largely, go to bed tonight assuming we're all like that¾ too black for Dave. That Dave and Jay are a refuge for White culture and White America, and that people like Winfrey (by extension, black women ipso facto black people) are to be dismissed as uptight, humorless superegos with massive chips on narrow shoulders. Winfrey's silence has sent a terrible message to an America struggling with a post-apocalyptic identify crisis. She let Dave not understand her or her motives. 

She let Dave be frustrated, puzzled and confused by her and, while I hesitate to assume that translates to all of Black America for Letterman, it very well may for Letterman's audience. Dave's writing and production staff (with the notable exception of the brilliantly put-upon Henderson) is apparently all white. Dave probably doesn't "get" Oprah (by extension, black women ipso facto black people) any more than Winfrey gets Dave, the white guys who love him, and the culture of irreverence that produced people like Andy Kaufman, George Carlin and, yes, Jerry Seinfeld, who made an entire episode of his hit show Seinfeld  a virtual confession that he doesn't understand blacks or black culture (the one where Elaine spends the episode trying to discern the race of her new boyfriend), and that he doesn't care. That's what I liked about the episode: its honesty. None of the Seinfeld characters actually cared about The Black Thing, they just wanted to know how to deal with the guy. In the scheme of things, the racial question was no more important to Jerry than whether or not he had the proper level of milk in his bowl of Cheerios. To me, that felt right. That felt honest. I hate whiny liberals falling over themselves to be numbingly PC and take up our causes. Jerry doesn't get us. Dave doesn't really get us. And, more to the point, it doesn't (apparently) bother them. I find the honesty refreshing. I prefer the honesty to the condescension of false concern.

Which brings me back to Oprah, a bastion of both condescension and false concern, and, despite years of teary-eyed confession,  far more plastic than either Letterman or Seinfeld. I sort of understand where Oprah is coming from, but I really wish she had done something— anything— to respond to and/or one-up Dave. Scanning the audience in Dave's show, I am hard-pressed to spot any black people at all, while Oprah's crowd is predominately black. One-upping Dave would have been so funny. Having Dave on the Oprah show would have introduced Dave to a whole audience that has absolutely no clue about him. Despite all of Winfrey's sermonizing and Dr. Phil-iphying, she (by the scant evidence available) apparently turned a blind eye and deaf ear to what she may have perceived as a sophomoric affront, but what was, actually, a tremendous opportunity for continued post-OJ, post-9.11 healing. A national Oprah-Dave Day, where millions of people, divided by both race and sensibility, are forced to co-mingle and deal with one another and see one another for more than the stereotypes we've collectively bargained for. Dave was clearly running with a gag, but Oprah could have gagged him with a run, if she'd have only gotten out of her own way.

Dave ran these mock-ups of his head pasted on the body of an Oprah guest, Dave and Oprah sharing a warm laugh and an intimate moment. What Winfrey could have had was an embarrassed and squirrelly Letterman melting under the lights as housewives of all races put the screws to him while a collected Oprah calmly sips Evian and waits for straight answers from him. And, failing to receive said answers, Winfrey then would have rolled in Dave's Mom (who said she'd appear) to further stick it to him, and then Dr. Phil to earnestly (Letterman would try and dismiss him as a joke) slap around Letterman's inner child, making Letterman squirm all the more by hitting way too close to home, unearthing some of the issues that drive Letterman to be Letterman: a virtual recluse who goes on national TV every night . It would have been fabulous. It would have been hilarious. She could have so mopped up the floor with Letterman, but she seemingly chose to appear frostily humorless, allowing what could have been a great national moment (it certainly would have made news) to pass her by. Am I making much of this? You bet. And she should have, too.

Worse, Oprah allowed Letterman to mock her and get away with it, the racial subtext to Dave's snarky campaign grounded somewhere in months of OJ jokes. I think she made a bad call. I think she put ego before intellect and, rather than advance the goals she tirelessly promotes, she allowed both camps—  Oprah and Dave—  to remain polarized in their generally erroneous perception of one another. And that, to me, makes Oprah a Doprah.