David Letterman's 10 Best Political Moments

May 20th 2015

Sarah Gray

Tonight is David Letterman’s last time hosting CBS' “The Late Show.” After 33 years on late-night television — the majority of those on “The Late Show” — David Letterman is stepping down and passing the torch to Stephen Colbert, who takes over later this year.

Though “The Late Show” was not an explicitly political late-night program — unlike “The Daily Show” or “The Colbert Report” — Letterman still dipped his toes into political waters and was often unabashedly left-leaning. He interviewed presidents, created infamous mash-ups, and even crafted some memorable candidate “Top 10” lists. Here are ten amazing political segments on "The Late Show":

1. This compilation of President George W. Bush clips.

Letterman was relentless in his poking fun of President George W. Bush:

2. Which was not to be outdone by the "Top 10" list read by then-Texas Gov. Bush in October of 2000 -- just a month prior to his election as president:

3. Ridicule has been a bipartisan affair for Letterman.

Here he is mocking Hillary Clinton's campaign "Scooby" van.

4. He has also interviewed Hillary Clinton back in 2008 during her first presidential campaign.

5. Of course, we can't forget Letterman interviewing President Bill Clinton multiple times.

6. Long after President Clinton's two terms ended, Letterman eventually apologized for his role in ridiculing Monica Lewinsky.

7. David Letterman also spent time speaking to another man named Bill -- Bill O'Reilly, who he once called a "goon."

The two also recently discussed the 2016 election.

8. Letterman has his own thoughts about Ted Cruz, and he made a great "Top Ten" list for the Texas senator

9. And of course, Letterman has spoken to our current Commander-in-Chief, President Barack Obama. President Obama made history as the first sitting president to appear on "The Late Show." Here's their most recent chat:

10. Letterman's response to the attacks on the World Trade Center and Pentagon on September 11 is also worth adding to this list.