A curmudgeonly farewell to David Letterman

After 33 years of entertaining millions and redefining late-night television, David Letterman is retiring. And while, like the many celebrity guests who have been bidding him farewell, I too appreciate him as a funny, smart, silly and creative talent, I want to offer a curmudgeonly and less generous look at his legacy. In fact, I wonder if his contribution to pop culture might have been, well, too curmudgeonly and ungenerous.

There are plenty of ways Letterman took late-night comedy to unprecedented heights: with crazy street skits and improvised segments, by refusing to ask boring “show biz” questions in interviews and by giving a platform to unconventional comedians like Andy Kaufman. Yet after losing The Tonight Show hosting gig to Jay Leno in 1991, the grumpiness that was always part of his persona took on an added bitterness and mean-spiritedness. And while Letterman has occasionally lowered his guard – in the wake of his quintuple-bypass surgery in 2000, in the aftermath of the 9/11 terrorist attacks – a sense of dissatisfaction still lingered.

Perhaps the perfectionism that his colleagues have spoken of had something to do with this; he’s been described as hard-working and always short of completely satisfied. At the same time, he’s instinctively self-deprecating; Letterman deflects praise better than he receives it. While he has lined up some of the best shows in this closing stretch of his career and every guest without fail has heaped on adoration, Letterman himself doesn’t really speak of his career as an accomplishment or his life to follow as new opportunity. It’s hard not to wonder if, for all these years doing Late Show, Letterman was chasing something he never quite caught. Perhaps now he’s admitting he never will.

When I look at David Letterman after 33 years on television, he looks troubled, as if his cynical edge has deepened. If that’s true, then his guests and fans are smarter than he is. He should feel what they feel: Satisfied. Happy. Joyful. Letterman was always good. Maybe he could have been better if he enjoyed being good. If he was just a little less curmudgeonly and ungenerous, with himself above all.

As a Christian who subscribes to the “priesthood of all believers,” I consider the primary vocation of human beings to be priestly. In other words, we are called to lift up and offer our work, our talents, our sorrows, our joys in all of life to the praise of our Creator. Our work and pursuits, family time and church engagement, play and recreation - all of these we are invited to engage as worship. 

Comedy is no different. In fact, I would argue that comedy is one of the most sacred of priestly vocations. A comedian’s calling is foremost to tell the truth - to expose societal truths and difficult truths about ourselves. Comedy allows us to confront truth, both by revealing it and employing laughter so that we’re able to face it.

But comedy, humor and laughter are also holy because, at their best, they are about joy. Comedy delights in goodness and revels in the wonder of creation. Insert here a dozen clichés about laughter lifting the spirits of the broken-hearted. When love of life and hope disappear, that is the point at which comedy gets swallowed by cynicism.

Comedy is a vocation. The comic is a priest. And we pop-culture participants attend the churches where these priests preside to be told the truth, to have our lies exposed and to have them exchanged for an infusion of joy.

But not all priests are equal. In fact, good priests can be hard to come by. A good priest loves creation. A good priest knows that the Gospel is good news. A good priest knows the delight in offering everything to God as a response to His favor and grace. A good priest knows the freedom of receiving that grace without the shackling pressure of having to merit it.

Unfortunately, many priests in many churches do not know such joy. They have long since given up believing. They go through the motions, say the holy words and perform the necessary rites. To be fair, they are often very good at it. But their heart is no longer in it. When they were younger they were full of hope, thinking they might find their heart’s desire just around the next corner, if they only tried a little harder, worked the angles a little better.

But they never realized that what they needed had been given all along. The priest that is weary became weary from trying to grasp what can only be enjoyed. Frustrated that their efforts didn’t achieve the contentment they sought, they became in danger of developing bitterness and a heightened sense of cynicism.

Late Show with David Letterman is a church that has had many congregants over the years. Now, our old priest, David Letterman, is retiring. He was well loved and will be well remembered. He was smart, witty, talented and funny. Gifted. I wish him love, joy and peace as he steps away from television. Not the kind that comes from 33 years of hard work, but the kind that is freely received.