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13 Greatest David Letterman Sports Moments

by: Esteban On  Monday, April 7, 2014

best david letterman sports moments

Last week, late night talk show legend David Letterman announced that, after 35 years on the air, he will retire some time in 2015.

There are a lot of young people out there who probably have no idea what kind of impact Letterman has had on late night television. To them he’s just one of the many people being funny on TV after 11PM, and he doesn’t seem particularly unique. However, when Letterman got started, he was unique. There was nobody on TV like him. The guy broke the mold with his quirky, ironic, and irreverent take on the talk show, and he inspired a whole generation of comics.

Of course, it just so happens that Dave is a pretty huge sports fan, and some of his greatest segments of all-time involve sports in one way or another. So today, in honor of his impending retirement, we’re going to present you with the 13 greatest Letterman sports moments. Some clips are fairly recent, while others are practically ancient. However, they are all classic Letterman, and they will all make you just a little bit sad for the end of an era.

Take a look…


13. USA Olympic Hockey Top 10 (1998)

The 1998 U.S. Olympic men’s hockey team was a huge disappointment, what with all the losing and trashing of hotel rooms. However, their appearance on The Late Show to do the Top 10 hockey player pickup lines was pretty great. I mean, the bit ends with Brett Hull making a double-entendre about a crooked penis. That’s just classic comedy right there.


12. Interview with George Steinbrener and Billy Martin (1985)

You have to know a little context to really appreciate this one.

You see, late Yankees manager Billy Martin  and late Yankees owner George Steinbrener had the most tumultuous and contentious manager-owner relationship in the history of pro sports. The guy was hired in ’76, won the World Series in ’77, but then fired in ’78 after a feud with Reggie Jackson and Steinbrenner culminated in possibly the greatest sports quotes of all time: “the one’s a born liar, and the other’s convicted.” (Steinbrenner, you see, had been convicted of making illegal donations to Richard Nixon in ’72.)

The feud didn’t end there, though. In ’79 the two patched things up, and Steinbrenner hired Martin to manage the Yankees again…then fired him again after the season because he got into a fight with somebody at a hotel.

But wait. There’s more. Martin was hired and fired again in ’83, ’85, and ’88, with the cause for dismissal in ’85 being that he got into a fight with one of his own players. And that’s the context this surprise reunion between Martin and Steinbrenner on Letterman’s NBC show Late Night.


11. Interview with Art Donovan (1988)

In Letterman’s early days on NBC, when he followed Johnny Carson after midnight, he didn’t have to book huge celebrities who were promoting various TV shows, movies, books, or albums. He got to book people that he liked. And one of the people he really liked—because he was one hell of a story-teller—was legendary Colts defensive tackle and Pro Football Hall of Famer Art Donovan. Dave had him on his show a whopping 10 times, and this was one of them.


10. Late Show Holiday QB Challenge

Nothing illustrates the absurdist humor of David Letterman better than the holiday tradition he carried on with Jay Thomas from 1998 to 2012. I have no idea how or why, but in 1998 Dave started topping the official Late Show Christmas tree with a giant meatball skewered on an Empire State building ornament. Then, right before Christmas, he would have Thomas come on and try to knock the meatball off with a football.

This went on for 15 years, and really wasn’t funny from years three to six. But Dave stuck with it, knowing the joke would be eventually be good again, and by year ten or so the absurdity of the decade-long tradition was just hilarious.

That’s commitment to a bit.


9. Dave’s Mom Covers the ’94 Olympics

David Letterman has the cutest little midwestern mom you’ve ever seen, and in 1994 he sent her to be the Late Show correspondent at the Winter Olympics in Lillehamer, Norway. The results were hilarious, and after that she began to make regular appearance on TV, most notably the annual Thanksgiving Day segment, “Guess Mom’s Pies.”


8. Peyton Manning Interview (1998)

Letterman has interviewed a number of incredibly famous athletes over the years. However, three in particular stand out today because they give us a look at legendary athletes before they were legends.

First up we have this 1998 interview with Peyton Manning on the eve of not winning the Heisman Trophy. As you can see, Manning was the same gracious and gregarious man he is today.


7. Mike Schmidt’s Inside Pitch (1988)

This running bit from the fall of 1988 was so ridiculously simple. All it was was Hall of Fame third baseman Mike Schmidt giving a short scouting report on each of the night’s guests…and yet is was so hilarious and wound up stealing the show every night.


6. Wayne Gretzky Interview (1986)

The second of the three athlete interviews that really stand out is this one with Wayne Gretzky from 1986. At the time Gretzky was already considered one of the greatest hockey players of all-time. However, he was not yet The Great One, and looking at it today the interview gives a great insight into sports culture of the 80s.


5. Interview with 23-Year-Old Michael Jordan (1986)

Everything I just said about the Gretzky interview applied to this interview of a 23-year-old Michael Jordan as well. The kid was a star, and he had his own shoe, but he wasn’t yet considered the greatest basketball player of all-time.


4. Dale Earnhardt’s Top 10

Letterman has had a number of athletes and celebrities read his Top 10 list over the years, and many of them—like former NBA Commissioner David Stern—were awful.

The late Dale Earnhardt, however, was fantastic.


3. Dave and Bill Murray Kick Field Goals on 53rd Street (2012)

If anyone is taking bets on who will be the last guest on the last show David Letterman ever does, I’ll put ten bucks on Bill Murray.

Murray has been on the show dozens of times over the years, which has resulted in so many memorable moments. However, without a doubt one of the best was the time Murray dressed up as a New York Giant and then kicked a field goal out on 53rd Street…with Regis Philbin as the referee.



2. Dave Pitches to Mark McGwire on 53rd Street (1998)

Today some people look back at the great MLB home run race of 1998 and  see a steroid-fuelled quest to tarnish baseball’s most sacred record. However, the fact remains that, at the time, everyone absolutely loved it and got totally caught up in all the hoopla surrounding it—including the time Letterman pitched to Mark McGwire out on 53rd Street and he hit a ball 400 feet.


1. Andy Kaufman vs. Jerry Lawler (1982)

This isn’t just one of the greatest sports moments of David Letterman’s illustrious career. It’s one of the moments that defined his show, period.

In 1980, comedian and performance artist Andy Kaufman was engaged in a feud with professional wrestler Jerry Lawler that culminated in this on-air fight on Late Night with David Letterman in 1982.

Of course, it later turned out that the whole feud—including the fight on Letterman—was staged, and that Lawler and Kaufman were friends. But at the time nobody knew that, because nobody knew what the hell was true with Andy Kaufman.

Today, it’s still one of the best segments Letterman has ever done.