9 Most Emotional 'The Late Show' Moments, As If Saying Goodbye To David Letterman Isn't Emotional Enough — VIDEOS

David Letterman has been a late night talk show host for well over 30 years and it's still hard to believe that, come Thursday, The Late Show will no longer feature his signature grin. He's done nearly 6,000 shows, which is plenty of reason for him to enjoy the crap out of his retirement. However, that doesn't make it any easier that Wednesday night will be Letterman's last appearance on The Late Show. The show was the off-beat choice to Jay Leno's spoonful-of-sugar-so-it's-easy-to-swallow blend of humor during his reign on The Tonight Show. The 68-year-old has marched to the beat of his own drum, and delivered shows that were thoughtful, sometimes hard-hitting, and always hilarious. That's what made Letterman special; he wasn't afraid to make people a little uncomfortable. Whether it was about his personal life or about what was going on in the world, the talk show host was honest.

Though his run on The Late Show will be greatly remembered for its dry banter with guests, downright silly sketches and bits, and Letterman's Cheshire cat persona, it will also be remembered for how it dealt with difficult subjects. He didn't stray from tough subjects; he met them head on, and tried to be funny when it was appropriate but gravely serious when needed. Letterman is more than a comedian; he's a cultural touchstone of the times.

Relatable, self-aware, and flawed, these are David Letterman's most emotional moments on The Late Show:

1. His Blackmail Sex Scandal

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Being a showbiz vet, Letterman knew that transparency with the public was going to save him.

2. His Apology to His Wife and Staff for the Scandal

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He doesn't defend his actions. Instead, he apologizes for hurting those who didn't deserve to be hurt.

3. His Defense of Conan O'Brien

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In both clips, Letterman rips into Leno and stands by the comedian who got screwed by NBC the same way he did two decades prior.

4. His Return After Bypass Surgery

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He might be all jokes, but the sentiment is still there.

5. His Tribute to Robin Williams

Robin Williams' death left a huge hole in the heart of comedy, and Letterman expresses that so masterfully.

6. His Fatherhood Announcement

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Sometimes, the father of one could be a real sweetie, too.

7. His Response to the Iraq War

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When Letterman has an opinion, you're going to hear it.

8. His Retirement Announcement

The silence from the audience says it all.

9. His First Post-9/11 Monologue

This is where Letterman really showed up. He was the first late night host to go back to work after 9/11, and his raw monologue still sends chills. He is one man trying to make sense out of such grim events, and, even more daunting, he's trying to bring people back together, give them laughter, and give them some shred of hope to keep going. As an entertainer, Letterman's responsibility went well beyond telling jokes, and here he shows just how little he took for granted in his job.