My Top 10 Favorite Letterman Moments

This week, David Letterman wraps up over three decades of hosting late night TV, handing over his coveted time slot to Stephen Colbert. Letterman has been a fixture of the CBS family for 20 of those years, after moving from a late night spot at NBC.

The sheer number of of unforgettable moments during Letterman’s tenure is way too long to enumerate. That said, here’s a t00-short list of some of my personal favorites.

10. A Young Jon Stewart Jokes About Getting Canceled

In 1995, the “Jon Stewart Show” was canceled after a 2-year run. Letterman and Stewart make fun of the cancellation, but the best part is Stewart yelling prophetically “You’ll see me again!”

9. Warren Zevon Says Goodbye

Music legend Warren Zevon, who was terminally ill at the time, is Letterman’s only guest for the night, and delivers a final public performance.

8. Pacino and De Niro Deliver Top 10 Reasons They Like Being an Actor

Two legends of seventies cinema combined with Letterman’s signature segment? Get outta here…

7. Dave Works at Taco Bell

Letterman takes over the Taco Bell takeout window and has some fun at the customer’s expense.

6. Fast Food Marathon With Zsa Zsa Gabor

Dave completes an item on my bucket list.

5. Joaquin Phoenix… is that you? 

It’s just too crazy not to include.

4. Madonna and Dave, the ultimate duo. 

Between Madonna’s outfit (SO ON TREND), the record amount of cursing, and Dave’s attempts at conversation, this video is comedy gold.

3. Dave Gets Dunked in Alka Seltzer

There were a number of years in the eighties when Letterman would take absurd stunts to ridiculous lengths. This is one of his best.

2. Dave Drops Stuff Off a Five Story Tower

If there’s something more fun than throwing stuff off the top of a building, someone please let me know.

1. Bill Murray’s First Ever Appearance

Bill Murray was David Letterman’s first guest in 1982. Thirty three years later, he appeared for the last time (covered in cake) last night.