David Letterman—Our Top 10 Tennis List

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By Bill Simons

The dictionary says a letterman is a “student who has earned a letter in an interscholastic or intercollegiate activity, especially a sport.” We say the definition of Letterman is a TV whiz who gained our admiration through comedic activity, especially late at night.

In honor of his final show after 33 years, here’s our David Letterman Top 10 list:

10. Some initially shy away from Dave. For instance, at first Lindsay Davenport chose not to go on the show for fear of his sometimes blistering barbs. But Serena, who loves the spotlight and high-profile banter, has been on many times. She often chatted about grunting, and said Monica Seles was “the first person I knew who used to grunt really loud, so [she’s] who I modeled my grunt after.” Then there was the show where she blasted a forehand through the window of Letterman’s neighbor Rupert Jee’s much-celebrated Hello Deli.

9. Not surprisingly, there have been many references to drink on The Late Show. After Novak Djokovic asked if Dave can do splits like he does, Letterman said, “Well, when I used to drink.” Then there was the charming Marat Safin. The Russian, who had one of the best deadpan senses of humor in tennis, told Letterman that he drank vodka everyday: “Breakfast, lunch and dinner.”

8. After John McEnroe‘s short-lived CNBC-TV talk show failed, we wrote, “Sadly, from the beginning, the hour was saddled with too many clunky moments, with little of the seamless spontaneity, conversational aplomb or comedic genius that we take for granted on Leno and Letterman.”

7. In 1989, Letterman spoke to Jimmy Connors about auditioning to become the host of Wheel of Fortune and then said Ilie Nastase “was the first solid goofball in tennis.” Connors interrupted and said he was Nastase’s “student.”

6. Andy Roddick confided that when he tossed the first pitch out at Yankee Stadium, he went for “disaster control” and threw “a high powder puff” pitch. But it went over the catcher.

5. After Rafa Nadal told Dave that the people in Spain don’t understand Mallorcans like him because they speak too fast, Letterman asked, “Ever been to Trenton?”

4. The Late Show went from sultry (pop sensation Lorde singing a version of “Tennis Court” in 2014) to silly (our favorite Stupid Pet Trick: a golden retriever from Houston who lifted a tennis ball with his paws) to serious and thoughtful. Reflecting on his childhood in Belgrade, Novak Djokovic contended that “most people would agree that war is something that doesn’t bring any good to anyone … You see the planes flying over and you hear the bombs and people running away and crying and buildings burning … You were worried for your survival. But most importantly, we stayed together as a people and and a family and it made us stronger … It has been a big part of my mental strength.”

3. After talking about how he was once his own worst enemy, was depressed, and hated tennis, Andre Agassi discussed his use of crystal meth and then told the tale of how his mullet hairdo was actually a wig. He confided that the night before his first Grand Slam final in Paris, he used the wrong conditioner and the wig began to disintegrate. Andre said he used 50 bobby pins just to secure it and he prayed it would stay on. His brother Philip comforted him, saying, “I think it will stay on—just don’t move.” Letterman responded by saying, “It’s tennis, try not to move around. They’ll hit it right to you.” Andre asked, “What better way to hide your inner self than to wear a mullet?” Then a mullet was dropped down on a hook from the rafters of the Ed Sullivan Theater. Later, Dave spoke of meeting Agassi’s wife Steffi Graf, saying, “The aura of this woman, she’s so perfectly constructed as an athlete,” at which point Agassi interrupted and said, “Watch out, you’re getting pretty close, Dave.” Letterman continued, “I’ve never seen a woman with this aura in my life … and I thought this was a wonderful experience for me.”

2. Our favorite Letterman-like Top 10 list that we concocted was Steve Wanczyk’s “Top 10 Advantages to the Davis Cup Being Played in Las Vegas.” The list included such items such as “Nuclear test sites can double as press area,” “Everyone can stay at Agassi‘s house,” “Before serving, players can have fans blow on tennis balls for good luck,” “Chair Ump Wayne Newton,” “Two words: radioactive balls,” and “Line judges dress like Elvis.”

1. Pete Sampras once confessed, “I know I’m not David Letterman when it comes to interviews.” But he was great on the show. After Dave asked what made him upchuck at the the US Open against Alex Corretja, Pete said it was because he had “watched Jay Leno the night before.”