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Top David Letterman "Late Show" moments

David Letterman is departing late-night television with a star-studded goodbye that has included guests ranging from Dave Matthews Band and Julia Roberts to Tom Hanks and Bill Murray.

During his final "Late Show" episode on Wednesday, Letterman, 68, is expected to give his final Top 10 list. The show is also poised to feature highlight clips and a few surprises.

When he retires, Letterman will have hosted 6,028 late night talk show broadcasts over 33 years between his time on "Late Night" and the "Late Show" -- more than any other late-night talk show host. Over the years, Letterman and his broadcasts have received 16 Emmy Awards and 112 Emmy nominations, a 1992 Peabody Award and a 2012 Kennedy Center Honor.

To commemorate his retirement, we look back at some of the most memorable Letterman segments.

Madonna drops the F-Bomb

Madonna tends to make heads turn wherever she goes for one reason or another. The year was 1994 and the Material Girl showed up on the "Late Show" -- cigar in hand -- ready for, well, it's hard to say what. The result is a varied conversation, some tension and plenty of F-bombs, censored of course. It was network TV after all.

Cher calls Letterman an a-hole

Madonna wasn't the only one who gave Letterman a piece of her mind. Cher waltzed onto the "Late Show" stage in 1986, and her chat with the "Late Show" host centered on why it's taken her four years to appear on the show. "I thought that I would never want to do this show with you," she said. Why? Well, she thought Letterman was an a-hole. Yikes. The moment comes around 3:57.

Bill Murray is Letterman's first guest

On Feb. 1, 1982, Bill Murray was the first celebrity guest to grace the "Late Show with David Letterman" They talked about everything from comedy and fame to lint balls.

Drew Barrymore flashes Letterman

Letterman was in for a real treat in 1995 when actress Drew Barrymore not only got up and danced for the late-night TV host, but also flashed him.

First Post-9/11 Episode

Letterman had quite a different monologue on his first new show after the 9/11 attacks. Taking a serious tone, Letterman praised then-Mayor Rudolph Gulliani, acknowledged the lives lost and spoke about the chaos that resulted in the hours and days after the deadly attacks.

"If you didn't believe it before, you can absolutely believe it now. New York City is the greatest city in the world," he said, to a round of applause.

Letterman returns from heart surgery

In 2000, Letterman returned to the "Late Show" from heart surgery -- and of course, managed to make a joke of his ordeal. "Wait 'til you hear what happened to me!" he said at the opening of the show, adding, "I've been away for a while. While I was gone I quintuple bypass surgery on my heart. Plus, I got a haircut."

The first Top 10 list

In 1985, Letterman did his first-ever Top 10 list, starting a popular "Late Show" tradition.

"We've decided tonight, we're going to start our own Top 10 list...."And tonight we have a good one...Tonight's will be the top 10 words that almost rhyme with peas," said Letterman -- launching what would be come a long-running and career-defining sketch.

Where's Joaquin Phoenix?

He was in the chair, but was actor Joaquin Phoenix really there? In 2010, Phoenix gave one of the most dazed and confused appearances ever seen on the "Late Show."

Retirement Reveal

On April 3, 2015, David Letterman announced he would be retiring from the "Late Show."

"What this means now is that Paul [Shaffer] and I can be married," he joked. "Some time in the not-too-distant future -- 2015 for the love of God -- in fact, Paul and I will be wrapping things up and taking a hike."

There were plenty more moments over the years -- as this list barely scratches the surface. As for what's next for the Indiana native, it's unclear. But Letterman did say saying goodbye is going to be hard.

"I'm not looking forward to it at all. I don't want to go to a party. I recognize that it's good for, cathartic perhaps, for all of us to be together, because it's not been easy on anybody who's been here any length of time for this to end," he told CBS News' Jane Pauley.

Tell us: What's your favorite Letterman moment?

Lauren Moraski

Lauren Moraski is managing editor of entertainment at

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