A Fifth of Jack: Goodnight Dave Letterman, Late Night’s Class Clown

It was the late 1980s, I was in junior high, and we had to do an oral book report for English class on a biography. I was at the public library just going up and down the aisles of books, trying my damndest to come up with someone I cared enough to read anything about, in order to write this report. Then, there it was, an unauthorized biography The David Letterman Story by Caroline Latham.  This book jumped out from the shelf, and since there were no other important people in my life at the time, it was decided. I was going to do my oral book report on my favorite television personality, David Letterman.

Let’s go back to when I was fourteen. We had moved away from my beloved Peoria, Illinois hometown and were living in tiny Vero Beach, Florida at the time, because that’s where my father’s radio career had taken our family. It was 1989, and I was about as uncool and as much of a misfit as a teen could be. I had bad hair, acne, braces, crazy gapped teeth, and a weird sense of humor. I was pretty much just a smarter version of Beavis, really. I had only a handful of friends at this school I was attending in our temporary Florida home, and girls thought I was weird and wanted nothing to do with me. I wasn’t into surfing, skating, or really anything most kids my age were into, and as a matter of fact, I am pretty much into the same things today I was into then which involve music, radio, comedy, and cuttin’ up. It’s very natural that a fourteen year old me was way into someone like David Letterman, and I started to learn just what kindred spirits we are.

My love affair with Letterman began several years earlier when during the summer months, I’d stay up really late to watch The Tonight Show Starring Johnny Carson with my father. Now, Dad was a broadcaster and loved Johnny, and the old time Hollywood scene that Tonight was back then. For those of you too young to know what that show was like, today’s Jimmy Fallon Tonight bears little resemblance in style or form, but I digress. Johnny was handsome, smooth, really funny, a true player, and he was the most important man in show business back then. The Tonight Show… it was a big to-do.  Staying up late to watch Carson was something all adults did, and even kids felt very grown-up when their parents let them stay up late with them to watch Johnny. I’m not sure that will ever happen again.

Following Johnny, was the show everyone in the 1980s and 1990s talked about… everyone cool, that is. Late Night with David Letterman broke all the rules of television and broke all the ground there was. When Dave began his show, Carson’s people forbid him from doing a real monologue, having an orchestra, and insisted this new show for 12:30 look nothing like Tonight. Fair enough, Letterman and his young and hip writers found their way, and paved new roads. The eccentric nature of Letterman’s personality, and the edgy antics made it okay for people to embrace off-beat humor, if they hadn’t before. Dave’s interview style was unlike anything else seen on television. He was charming, self-deprecating, honest, and could not have been more sarcastic. Sometimes celebrities didn’t like being on with Letterman for fear that he’d ask an inappropriate question, or not treat them with the respect they may have been used to. The comedy bits were crazy, the humor was equally irreverent, intelligent, intellectual, and downright idiotic at times.   All of these things caught my eye when I was a child, and my infatuation with and admiration for this man began.

When school started up in the fall, I had mastered how to set our VCR’s timer (no easy feat in the mid 80s) to record Late Night, so I could watch it after school every day. I mean, I never missed it, and I loved this even more later when I was a teenager, and I could talk about the episode with adults I thought were cool, like-minded, and hip, and could lock minds with them, as opposed to the kids in school I was invisible to. Watching Dave gave you a cool card. You were hip to his lingo, his regular bits, you knew who the recurring players were, you were part of a society of other people who watched this show because it was unlike anything else on TV.

Who will Dave piss off tonight? What will Dave say about this or that? Where will Dave take the studio cameras… into the halls of the RCA Building or the streets of Manhattan for his spontaneous comedy piece? What crazy letters will he read on Viewer Mail?  Ooh, it’s Stupid Pet Tricks!  Ooh, it’s Small Town News!  Oh, here comes Chris Elliott again!  What’s tonight’s Top Ten list? Will all ten be funny, or just a couple, or will it be dumb and can Dave make it funny by making fun of the bombing jokes and/or himself?

In fact, it was Dave’s self-effacing manner I loved the most.  Through David Letterman, I learned how to make fun of myself a little better.  Although none of us ever got to know the real Dave, we got know and like the one we saw on TV, because he was just so… soreal. This was not a showbiz phony or kiss up kind of guy.  When you were a guest on Late Night, you had to be on your toes, because the sharpest tongue on TV would get you if weren’t measuring up to his expectations. By today’s sad soft standards, Letterman is “mean” and a “bully”, but for his first twenty-five years on the air, David Letterman made television interesting to watch every night he was on it.  Most of the time when he was making sport of his guests, or his audience members, they too were in on the joke.  It was the ones who weren’t hip, that he’d antagonize, and keep pressing for a cheap laugh which would make him look mean.  As a guy who has done this on the radio himself, and unintentionally hurt people, I know what he was going for.  Not everyone is funny or in on the joke… and sometimes it takes risks for laughs, and risky he was.  NBC couldn’t hang with that style at 11:30, as it was far too risky for advertisers, and Dave remained at 12:30 for about a year and a half after Johnny Carson hung it up.  The rest is history, and soon… so is David Letterman.

After Jay Leno was named host of The Tonight Show in 1992, and Dave jumped ship for CBS, to start Late Show with David Letterman, his style softened a bit, but he still remained Dave, but this time to a much broader audience.  Since more people finally got to enjoy him at an earlier hour than they ever did before, his style became mainstream, even. People had a license to be sarcastic and silly, everywhere it seemed, because of Dave. Also, as his CBS show was taking off, America was going through a cultural revolution thanks to alternative rock, which was just as self-deprecating as Dave’s sensibilities were. It seemed his humor, that music, that edgy culture that was creeping into the mainstream through radio airplay and MTV melded well with Letterman and he sort of became a spokesman for Generation X in addition to late Baby Boomers who had already appreciated the intelligent, eccentric dry wit of America’s new Mark Twain when he was on NBC.

I loved watching David Letterman become mainstream with society. I finally felt like I could talk to anyone I knew about Dave, for the first time ever. “Did you watch Dave last night? Wasn’t that bit he did at the Taco Bell drive thru hilarious?” “Did you see Stupid Pet Tricks last night? Oh my GOD!” “Wow, what about that crazy interview with Madonna last night on Dave?” If you were a fan of late night talk shows in the 90s and 2Ks, you were either Team Dave, or Team Jay. I was Team Dave all the way, and I still am.  I honestly can’t think of any reason to watch anything after 11:00, except to see what kind of hat Mara MacDonald is wearing on Local 4 News.  There were some tough times I endured personally and professionally in my twenties, and on days I didn’t feel I had a friend in the world, I had Dave.  Dave always made me smile, even at my darkest hour.  I always wondered how I’d handle his inevitable retirement, and this week, I’ve been flooded with a color of emotions and even unreasonable sadness over the selfish loss of a man I never met, never will meet, and will miss like crazy from my television for the rest of my life… and even took for granted.

Oh, dammit… here come those tears again.

Back to English class and my oral report on The David Letterman Story. We had to make a poster board which would hang in the classroom for several weeks about our subject, and I drew a big gap-toothed smile on my poster, and on each tooth I posted a photo of Dave and his life and antics on the show.  At the top read “Dave Letterman.  Late Night’s Class Clown”.  I learned that he was very much like me growing up, a middle-class Midwestern misfit who had a weird sense of humor, a sense of adventure, a curious nature, and liked to cut up and attract attention to himself. Also like me, he enjoyed his high school grocery store job, loved radio and television, and wanted to pursue it as a career one day. He was also kind of a dorky looking kid who didn’t score with the ladies in high school any more than I did. There were a lot of reasons I was drawn to Dave, but knowing he was kind of like me at the time, was comforting to this alienated kid lost in Tinytown, Florida, missing Illinois terribly, and wasn’t sure my post high school dreams of radio or television stardom would ever equate his.  I also share Dave’s famous insecurity.

I got an A+ on my report, which I remember had the class laughing as I added my own humorous anecdotes while I told the story of Dave’s life those five minutes (we were timed).  This oral report was also the first time in my life I ever stood in front of a class and had their attention on a positive level as opposed to the disruption I usually was known to be, and I absolutely loved it. Mrs. Simpson said to me at the end of my report, “I see many parallels with you and David, Jack. I think you’ll go far with your dreams.” Thanks Mrs. Simpson. Most of all, Thank you David Letterman. I sure hope you know how much you are loved by the world tonight.

Jack Shell – Radio Personality, Denture Wearer

99.5 WYCD – Detroit, Michigan

CBS Radio

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