The mad crazy world of writing for Letterman

Our 'Late Show' Top 10
David Letterman retires Late Show moments orig_00022110

    JUST WATCHED

    Our 'Late Show' Top 10

MUST WATCH

Our 'Late Show' Top 10 02:25

Story highlights

  • Steve O'Donnell describes 13 years of writing for David Letterman as best and worst of times
  • He fondly recalls heady collaboration with funny writers and a quirky, original boss
  • But it was also a never-ending grind of show after nightly show, O'Donnell says

Steve O'Donnell was a writer for David Letterman from 1982 to 1995. He has since written for Chris Rock, Jerry Seinfeld and Jimmy Kimmel. The opinions expressed in this commentary are solely those of the author. Watch "CNN Special Report: David Letterman Says Good Night" Tuesday, May 19th at 9 ET/PT.

(CNN)For the first 13 of his 33 years on the late-night airwaves (does anyone still say "airwaves"?), I was a writer for Dave Letterman. It was the best of times. It was the worst of times. The best because working with Dave was endlessly entertaining. He was and is the smartest, funniest, quickest and most oddly original utterer of sentences in our vast republic.

Dave rarely made an ordinary statement, always playing with goofy words or ironically invoking or inverting some cliche. ("Another simple pleasure ruined by a meddling bureaucracy!") He got a kick out of dumb, blunt words like ham, fudge, gas leak and pants. (His production company is called Worldwide Pants, after all.) Yet he also routinely savored fancy words like untoward, crepuscular and velleity.
Tina Fey strips for Letterman
Tina Fey strips for Letterman

    JUST WATCHED

    Tina Fey strips for Letterman

MUST WATCH

Tina Fey strips for Letterman 01:04
The guy's complicated -- as is much observed. But in an intriguing way. Assured but shy. Driven but doubting. Spectacularly verbal but deeply private. An ambivert! Sometimes absurdly silly and just as often grimly severe, but always aiming to be of interest.
    Even in the makeup chair before the show, he'd amuse us (and himself) pretending to use precisely placed explosive charges to blow away the tissue paper bibs around his neck, like he was an ejecting pilot blasting away the canopy on his plummeting Sabre jet. Or, preparing to suit up for yet another taping, he'd empty an entire bottle of 4711 cologne on himself (but mostly on the floor) in the character of a Big Heedless Dope.
    As a boss, I'd say Dave is demanding, but always ready with a suggestion or a brand new premise of his own. Choosy as he could be, he still indulged thousands of peculiar joke experiments.
    An unsung favorite of mine: The Actual Size Show. The camera would get a close-up of the desktop coffee mug or telephone and the words ACTUAL SIZE would flash for a few seconds. After a couple of such "demonstrations," we figured the home viewers would deduce they were being had. But they'd be nevertheless delighted (an old P.T. Barnum tactic).
    A great gift giver, Dave Letterman! He once sent me a dozen picnic coolers full of kielbasa because he knew I liked it. My apartment is full of distinctive Dave-sent objects, ranging from a saber-toothed tiger skull to a giant light-up globe the size of a bathyscaphe.
    Obama makes final appearance on 'The Late Show'
    Obama makes final appearance on 'The Late Show'

      JUST WATCHED

      Obama makes final appearance on 'The Late Show'

    MUST WATCH

    Obama makes final appearance on 'The Late Show' 01:04
    OK, now. The worst of times: the relentless, never-ending grind of show after nightly show! An entertainment ocean liner whose roaring boiler room needed ever more tons of comedy coal from Dave and his sooty staffers. I was never so harried, never so nervously alert for icebergs of dead air.
    And yet there was a happiness in being so engaged, so fully occupied. Especially for me, with the funniest men and women I've ever known all working together around me, borderline frantically (correction: actually frantically). Assembling all those Letterman shows was akin to putting out a daily paper combined with mounting a small-town parade every single day.
    Yet out of this pressed atmosphere has come the greatest friendships of my life, the foundation of most of my professional connections and the satisfaction of having done something kind of odd with a singular group of co-workers for years on end.
    The fear and pain, such as it was, had a strange upside: a bonding of those who shared the experience, like rugby teammates or Marine veterans of Iwo Jima; an exhilaration, such as that described by young Winston Churchill -- like having bullets whiz by you but leaving you un-killed.
    When these heady days are long behind us, we'll look back with love and pride on our best/worst times, and with indescribable fondness for our quirky, incomparable Captain.