Top 10 David Letterman moments of perfection

Saying good-bye to David Letterman by remembering 10 perfect moments in a very long career

David Letterman - CBS Promotional Image
David Letterman - CBS Promotional Image

HOUSTON, May 21, 2015 – After 33 years, over 6,000 shows and hundreds of thousands of jokes, David Letterman is now a former television host. Letterman was always a paradox. He got celebrities to divulge their deepest secrets while attempting to zealously guard his own privacy.

At his best, Letterman was hysterically funny and brilliantly innovative.

At his worst, he was an angry, grumpy man who was harsh with others and even harsher with himself.

He never lost the bitterness that infected him when he lost out on Johnny Carson’s “Tonight Show” to Jay Leno. He even stayed on the air just long enough to outlast Leno.

Letterman the man is a complex if not tortured soul. His personal life showed him to be somebody who was far less than admirable. He even was the victim of a stalker who would repeatedly show up and break into his home.

Rather than relive Dave himself, let us celebrate the best of what he brought to television.

Here are the top 10 contributions that David Letterman, through “Late Night on NBC” and “The Late Show” on CBS, brought to television.

10) Down the stretch they come – Letterman was obsessed with the Kentucky Derby. Every year on the Friday before the race, he would have the radio announcer on as a guest. Letterman would repeatedly yell, “and down the stretch they come” throughout the show. He would make his guests say it.

9) Paul Shaffer, Don Pardo and Alan Kalter — On some nighttime talk shows, the host is the only one who matters. Craig Ferguson used a robot as a sidekick. Carson had Ed McMahon, who was either a brilliant straight man or a talentless lump depending on who was asked. Letterman made stars out of his team.

Paul Schaffer was a star in his own right, and in later years Letterman took delight in mocking Schaffer’s outrageous outfits. Don Pardo’s introductions were classic, but when Pardo was locked into his NBC contract, Alan Kalter became the voice on CBS.

Walter was hilarious in skits, often playing a guy who got beaten up for no reason.

8) Annoying the bosses — Letterman loved burning bridges. There was the time he was stopped by General Electric security in the lobby when he tried to give the bosses a fruit basket. He was constantly joking about GE lightbulbs burning out.

GE owns NBC, and when the 1992 Olympics Triplecast was failing miserably in sales, Letterman harassed Bob Costas on the air into buying a subscription. At CBS Letterman would frequently mock and antagonize executive Les Moonves.

7) The Oprah obsession – Letterman was at his best when interviewing guests he disliked (Bill O’Reilly) or who disliked him (Cher). After he offended Oprah Winfrey with his “Oprah, Uma” routine at the Academy Awards, he became obsessed with getting back in her graces. He had his “Oprah log” to monitor whether she would call. “Oprah? N’Oprah.”

He sparred with Dr. Phil, jealous that Oprah did like him. He and Dr. Phil walked off the set holding hands to the Aerosmith tune “Walk this Way.”

6) The Top 10 List — Letterman’s nightly ritual is now a staple of American culture. His best one contained the top 10 Prince Charles Pickup Lines. “Would you like to play with the royal sceptre?” “Well, if you think my ears are big…” “Let’s put the bucking back in Buckingham Palace.”

His viewer mail was also funny. Later would scream out the number of the letter being read. “Dear Dave, I’ve moved. Please make the change in your address book.”

5) Self-deprecating jokes — When the show was at its worst and everything was going wrong, Letterman knew how to dig out of the hole. When ABC tried to steal the show from CBS, Letterman remarked, “Can you believe two networks are fighting over this crap?”

When jokes failed, he would ask, “What time is rehearsal?” If Schaffer made a joke Letterman did not understand, Dave would say, “See me after the show, Paul.”

He once remarked that he could not effectively interview Bill O’Reilly. “I don’t think he knows what he’s talking about, and I know I don’t know what I’m talking about.”

4) Ridiculous skits — He sent bunny rabbits into an H&R Block on April 14, and they were thrown out by stressed-out accountants. He traveled to Los Angeles and threw tacos on the 405 freeway at motorists. He had Super Bowl winning kicker Adam Vinatieri kick field goal kicks across the street to Donald Trump. He had a guy dressed as a bear stop a New York City cab driver in the middle of the street to dance the waltz. Then of course there were the stupid pet tricks and stupid human tricks.

3) Biff Henderson — Letterman took ordinary people and made the celebrities. Stagehand Biff Henderson was an Everyman who once stripped down and got into a bed with a baseball umpire. The skit was called “Biffy the Umpire Layer.” The Christmas tree gag saw the red light in the tree burn out. Letterman and Henderson quickly stole a red light from a nearby traffic light. As they fixed it to the tree, the background featured the sound of cars crashing. Tony the cue card guy would curse at Letterman in Spanish. Letterman even sent his mom to Lillehammer, Norway, to cover the Olympics.

2) Comedian appearances — The greatest comedians of the past 33 years all made repeated visits to Letterman. Billy Crystal, Robin Williams, Jerry Seinfeld and Howard Stern all made memorable appearances. The best was Bill Murray. He was Letterman’s very first guest in 1982 and again in 1993 when Letterman moved to CBS. Murray came in breathing heavily, announcing that he accidentally went to the NBC studio by mistake.

Murray was Letterman’s very last guest in 2015. He jumped out of a cake and hugged Letterman, getting cake all over his expensive suit. Worldwide Pants is Letterman’s production company, and Murray led a chant on the streets of New York City. To the tune of John Lennon’s “Give Peace a Chance,” Murray sang, “All we are saying, is more Worldwide Pants.”

He also read the final joke of Dave’s last Top 10 List.

1) Sept. 17, 2001, interview with Dan Rather — Letterman was not just a comedian. His background was broadcasting, and he was a very good interviewer. He asked probing questions and could get very serious when needed. After the devastating Sept. 11 attacks, comedians everywhere took a few days off. Although from Indiana, Letterman embodied New York. Letterman used to have a different introduction for New York every night, making fun of the smell, the hookers and the rats.

After the 9/11 attacks, it was just “Live from New York, the greatest city in the world.” Six days after the attacks he and Dan Rather discussed the worst terrorist attack on foreign soil. Rather broke down crying and Letterman consoled him.

Letterman even snuck in a couple of jokes, asking if the terrorists hated us because they did not have cable. The interview was masterful and helped heal a reeling nation. Leno and the other comedians soon returned to work, but they needed Dave to pave the way.

There is plenty more to say about Letterman, but the self-effacing comedian ended his last monologue by reminding the audience to save some words for his funeral.

Goodbye, Dave. You were the very worst…and the very best.

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  • Andy

    Eric, this is a great column! Good recollection … and perspective.