▲Arguably one of the weirdest interviews ever, let alone on ‘The Late Show,’ Phoenix went through the interview in a complete daze. It was later revealed that it was just a stunt, but it was still a memorable moment.

▲Due to the large number of businesses called “Jimmy’s,” Letterman did a segment where he went to all of the establishments and interviewed the workers about what Jimmy was like.

▲When General Electric bought NBC, Letterman tried to drop off a fruit basket, with some hilarious results.

▲Letterman is known for thinking quick on his feet. A brief, mildly dirty joke, in response to Yue-Sai Kan (pictured) saying that she had eaten the hump of a camel, became a favorite. Jerry Seinfeld even quoted it during ‘Comedians in Cars Getting Coffee.’

▲Letterman was skeptical about doing sketches, however this one was a major success. He tells the "traumatic" story about what it’s like for a teen to find out their favorite show is canceled.

▲Murray was an integral part of both ‘Late Night’ and ‘The Late Show,’ and did everything from pop out of a cake to sing the theme song live. He was also the show’s first guest!

▲In 1984, Letterman got dunked in a water tank while wearing a suit entirely made up of Alka-Seltzer tablets.

▲A German performance artist, Brother Theodore often went on long, angry rants. This allowed Letterman to get a quick ad lib in at the end. “Is that a ban lon shirt?” is a much quoted favorite.

▲This was one of the most iconic regular sketches, but one of the most memorable has to be the first one he ever did, in 1985. The title was, “Things That Almost Rhyme with Peas.”

▲A controversial interview to say the least, some of the highlights included Madonna asking Letterman to smell her underpants, in addition to a whole lot of bleeping.

▲Cher admitted during the show in 1986 that she previously wasn’t Letterman’s biggest fan, calling him a choice word at the beginning of the interview.

▲To celebrate Letterman’s birthday, Barrymore got up on his desk and did a sexy little dance before briefly flashing the talk show host.

▲Letterman is known for his humor, but occasionally we see his sincere side. After his heart operation, he talked about his gratitude to the doctors in a monologue, and brought them out on the show to thank them again.

▲The world was reeling after the 9/11 attacks in 2001. Letterman opened up his show, that aired one week later, with a monologue about what he, and many others, were feeling.

▲Betty White celebrated her birthday during an interview on ‘The Late Show’ with a toast… and vodka. The pair clinked glasses before Letterman drank straight from the bottle and White guzzled from a cup before doing a spit take.

▲Pete Fatovich was the associate producer of ‘The Late Night Show.’ He also played a cranky audience member that complained throughout the taping of the show. Shot from his perspective, the “guest” would provide a running commentary.

▲Much like Joaquin Phoenix, Glover also attended the interview with Letterman in character. And, much like Phoenix, no one knew about it. Glover attended the interview as a character named Rubin from an unreleased film, and tried to goad Letterman into an arm wrestling match.

▲Not one of her better moments, Fawcett was completely oblivious to what was going on around her during this interview. She thought she was actually looking out the window when she glanced at the backdrop.

▲Arguably one of the best Matthew McConaughey impressions, Damon pretended to be the actor on the show with Letterman.

▲A common segment in the show was “Viewer Mail” (later renamed “CBS Mailbag”), and one of the most memorable moments happened in 1986. Colleen Boyle wrote in questioning Letterman’s shoe choice, so he went to find her so they could go shoe shopping together.

▲A sketch with mixed results, Sacha Baron Cohen appeared on the show for an interview as his character, Borat.

▲Andre the Giant is a memorable person in general, even more so when it’s revealed that he once drank 117 beers in one sitting! He also needed a special chair for the interview.

▲One of Letterman’s many sidekicks, the clueless acts of Larry “Bud” Melman (or Calvert DeForest) are a crowd favorite. He popped out of a cake on New Year’s Eve, 1993.

▲Not all memorable moments are good ones. Letterman revealed that a ‘48 Hours’ producer was trying to extort him, so he instead revealed his affairs with various female staff in a monologue during the show.

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The end of an era, Letterman announcing his retirement on air left many emotional. He marked more than three decades on the air, and was succeeded by Stephen Colbert (right).

Now learn about the 30 best comedians in history!

▲Occurring in the first year that the show was on air, near the end of one of the episodes, Letterman appeared on-screen in a pirate hat with a devastated set in the background.

▲Letterman’s mentor, Johnny Carson, took over his seat in a role reversal on the show.

▲Arguably the most memorable moment of the first year of shooting was when wrestler Jerry Lawler slapped Andy Kaufman out of his chair.

▲Carson was Letterman’s mentor, and in the first episode following his death, Letterman paid him a very special tribute. He opened the show with a standard monologue, only to later reveal that Carson had written it for him for the first show.

▲A faux pas worth retelling, Letterman was referencing tattoos and suggested that people were getting the Sistine Chapel tattooed on their body. Bieber responded that he wasn’t thinking of getting anything like the “sixteenth chapel.”

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While David Letterman may have left the late night scene, he's clearly not out of the public eye. His intriguing show, 'My Next Guest Needs No Introduction,' is out on Netflix. Kanye West, Ellen DeGeneres, and Lewis Hamilton are among the A-list interviewees, opening up and laying their heart bare for Letterman. However, Letterman is not new to this, as he has been a brave interviewer for nearly five decades, with too many memorable moments to count. To celebrate the new season, check out the new interviews, plus Letterman's most iconic moments over the years.

▲The Formula One superstar took Letterman for a drive on a race track. But actually, it was Letterman who managed to make Lewis scream in fright, racing around in a station wagon.

▲'My Next Guest Needs No Introduction' episodes feature eye-opening interviews with an array of interesting guests.

▲Touching on #MeToo, West said "we as a society are constantly in fear." Letterman said "I would submit that it's not equal by any equation to the fear women feel being the other side of that."

▲Letterman has a controversial conversation with Kanye West, who talked about Trump, #MeToo, and mental health. "Have you ever been beat up in your high school for wearing the wrong hat? Definitely liberals bully people who are Trump supporters."

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The comedian and movie star danced with David Letterman on the show. She also joked about his new look, "I want to know if you're related to anybody from the North Pole."

Continue clicking to find out more about Letterman's most iconic moments throughout the years!

▲West also invited Letterman to see his fashion collection. He called his new line "the Hermés of sportswear."

▲DeGeneres is used to being in the driver's seat, and interviewed Letterman on her show. She returned the favor on his show, opening up about the drawbacks of fame.