David Letterman’s Top 10 Sports Moments

Luckily for sports fans, David Letterman has long loved the games—he even co-owns an IndyCar racing team. In his 33 years on TV, he’s interviewed countless big-name athletes, and done many goofy bits involving sports. As he signs off on Wednesday night, here’s a top 10 list for Letterman and sports:

10. Little Buddy

As Pete Rose chased Ty Cobb’s all-time hit record in 1985, Letterman poked a little fun at diminutive Kansas City Royals shortstop Buddy Biancalana, who finished his career a .205 hitter. But Biancalana was stellar (for him) in the 1985 World Series, hitting .278 over seven games, and after KC won it all, Biancalana appeared on Late Night for some self-deprecating fun.

9. The Nash Report

Letterman knew when to enlist others for comedy help—look no further than Rupert Jee. Here, Steve Nash covers the 2009 NBA Finals, between the Los Angeles Lakers and Orlando Magic, for the Late Show, and asks analyst Jeff Van Gundy a pretty, er, direct question about his brother, Orlando coach Stan Van Gundy.

8. Albert Achievement Awards

For those of us who grew up without cable or ESPN—some of us really did—Marv Albert’s Letterman appearances were the only place to see sports bloopers. Earlier this year, Marv picked out his all-time favorite follies. Yes!

7. Revenge Pitch

In 1985, Letterman called Atlanta Braves relief pitcher Terry Forster a “fat tub of goo.” Later in the year, Forster paid Letterman a visit, sporting what could only be a 1981 World Series ring, thank you very much (Forster pitched for the champion Los Angeles Dodgers that season). Forster entered the studio chomping on a “David Letterman” sandwich. “It had a lot of tongue on it,” he said.

6. Loosening Larry and Magic

Later in Letterman’s career, he became a master conversationalist, more willing and able to put subjects at ease. He puts his skills on display in this interview with Magic Johnson and Larry Bird a few years back, probing the dynamics of their relationship. Magic, more outgoing, was inclined to be friendly with his rival; Bird, an introvert, wanted none of it. “He’s got that big smile,” Bird said of Magic. “My goal is to take three of them teeth home with me.”

5. Oh, So That’s How You Do It!

In 1987, Minnesota Twins knuckleballer Joe Niekro was suspended for 10 days after an emery board flew out of his pocket while the umps searched him for suspicious items. So naturally, Niekro went on Letterman to show how to scuff a baseball—while coyly denying he did it that night.

4. Cubs Win!

Will Ferrell broke out his Harry Caray imitation in a recent appearance: the legendary Cubs broadcaster asked “what are we going to do about this wall in Berlin?” and shouted the names of players who haven’t been on the Cubs in years. “And the 2-0 pitch is in there to Dunston, strike on the corner!”

3. Spring Training

Dave heads up to Yankee Stadium in 1992 to workout with Yanks manager Buck Showalter and coach Frank Howard. They discuss the fine art of spitting.

2. Olympic Mom

During the 1994 Olympics in Lillehammer, Norway, dispatches from Dorothy Mengering—Letterman’s mom—became appointment TV. Her gentle midwestern demeanor, insistence on calling Letterman “David,” and dry, one-sentence answers to her son’s nagging questions made Mengering an ideal foil. “Tonya! Tonya!” Mengering shouted, barely audible, while Tonya Harding stood a few feet away. She also scored a sit-down interview with Nancy Kerrigan. “Would you like cocoa?” she asked.

1. Baseball Biff

Speaking of comic foils, for my money nobody beats Letterman stagehand Biff Henderson, especially when he interacted with athletes. Somehow, Letterman convinced the staid, secretive New York Yankees to let their home ballpark become a Late Night/Late Show playground. And Biff took advantage: a few hours before a 1998 World Series game—a World Series game!—he was on hand to ask silly questions and lead “Yanni” chants. For viewers, his laryngitis was well worth it.

[https://www.youtube.com/watch?v=geEQjDV_8E0]

Read next: Everything You Need to Know About David Letterman’s Last Show