The Murray-Reilly school of one-liner-based column-craft demands a bottomless wit and a skill for self-editing. Humorists like Dave Barry and Gene Weingarten spend paragraphs setting up and detonating a single joke; Reilly launches a grenade every other sentence. When you're such an ostentatious jokester, every punch line is a referendum on whether you're still funny. A good way to lose that referendum is to pop in a molar quip every time you can't think of a Murray-esque witticism.
It's no crime to have a taste for all things dental. Sure, tooth jokes are often corny, but bicuspid and gingivitis are legitimately funny words. Mouth metaphors can also be quite apt on occasion—the PGA Tour's Q-school does seem a bit like anesthetic-free dental surgery. In broader terms, no one would deny the comedian or the columnist the use of catchphrases and deliberate repetitions. The great Chicago newspaperman Mike Royko regularly trotted out characters like Slats Grobnik, and the New York Times' Maureen Dowd drops nicknames like "Rummy" and "Poppy Bush" to give her columns a consistent tone and vernacular. Reilly's ESPN colleague Bill Simmons, too, has a list of regular talking points that function as a kind of call-and-response with his readership: trips to Vegas with his team of sidekicks, copious Karate Kid references, and how-sports-work explications like the Ewing Theory and the Levels of Losing.
But that's not Reilly's game. His reaching for the floss is an unconscious tic, not a willful decision to mine the mouth for comedy. In response to an e-mail query, Reilly says he wasn't aware of his dental habit. "I know gingivitis is funny," he writes, adding that "root canals are generally a strong image." He then offers a psychoanalytic explanation: "I was a terrible Sugar Babies addict, so I had more cavities than the surface of the moon. Really, I'd have three and four every time. So maybe I'm taking it out on dentists."
Reilly says this isn't new territory for him: Around 1995, a reader complained that he'd overused the word spleen. "When you've been writing columns for 30 years," he continues in his e-mail, "I suppose you exhaust every body part." (He also asks if I've counted his references to Barcaloungers. I just did: 15.) The not-enough-body-parts defense is a reasonable one. It's also a symptom of how difficult it is to sustain a wisecrack-heavy writing style. At a certain point, your comic imagination will be outstripped by your perpetual need to fill your column with yuks. A good marker for when there's no more toothpaste left in your tube: the day you make your 116th dental joke.
Reilly is a gifted essayist and wordsmith. His long profile of Bryant Gumbel, "The Mourning Anchor," written for SI a decade before he became the mag's featured columnist, is one of the greatest pieces of sportswriting I've ever read. The first column that Reilly wrote for ESPN back in June, about reconciling with his alcoholic father, is a remarkable demonstration of how much you can say in just 800 words. The rest of his ESPN output, though, has shown signs of complacency. In just six months, he's made five tooth jokes and written two separate columns that refer to a rat gnawing on someone's stomach. Both Reilly and his editors need to start giving his copy more attention. He's far too talented a writer to succumb to something as treatable as tooth decay.