Memorable 'Late Show' moments 20 photos
Michael Richards' mea culpa – When you need to make a massive apology, it makes sense to turn to the well-respected Letterman to help you out. That's what "Seinfeld's" Michael Richards ended up doing in November 2006, with help from Letterman's guest of the night, Jerry Seinfeld. Richards, however, wasn't in the studio -- he made his apology via satellite after coming under fire for using the N-word during a tirade at a comedy club. "Awkward" doesn't begin to describe the appearance.
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11 of 20
Memorable 'Late Show' moments 20 photos
Dave and Bill O'Reilly call a truce – Before Bill O'Reilly and David Letterman found a reason to high-five one another in 2011, they'd had a war of words while taping "Late Show" in 2006. The conversation was about the Iraq War, and the debate became so agitated that the light-hearted comments turned into terse insults.
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12 of 20
Memorable 'Late Show' moments 20 photos
Paris Hilton gets grilled – Paris Hilton braved seeing Letterman again in 2008 even after he upset her during her 2007 interview. The late night host grilled her about her jail time to the point that she said she was "sad" she'd even come on the show. The following year, Letterman acknowledged how tough he'd been on the celebutante and made nice.
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13 of 20
Memorable 'Late Show' moments 20 photos
John McCain in the hot seat – After initially trying to skip out on Letterman's show in 2008, John McCain finally made it into the hot seat that October. The politician was faced with chatting up a man who roasted him for his cancellation in an earlier monologue. Both moments were deliciously squirmy TV.
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14 of 20
Memorable 'Late Show' moments 20 photos
Joaquin Phoenix's strange act – Watching Joaquin Phoenix appear on "Letterman" in 2009 was like watching a train wreck -- it was so hard to watch, but you just couldn't look away. Phoenix had drastically altered his appearance and behaved strangely, as Letterman tried to figure out how to navigate the puzzle before him. It was all an act, though, and Phoenix returned to the show in 2010 to apologize.
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15 of 20
Memorable 'Late Show' moments 20 photos
Dave's shocking confession – In October 2009, Letterman made a stunning admission live on the air when he told his audience that he'd had sexual relationships with female members of his staff and that someone had been attempting to blackmail him as a result. The following Monday, he used his show to offer a "heartfelt" apology to his wife and to his female staffers.
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16 of 20
Memorable 'Late Show' moments 20 photos
Richard Simmons goes up in smoke – Richard Simmons and David Letterman have a wonderfully antagonistic friendship, and out of the many times the fitness king has appeared on the program, it's hard to pick a favorite. This moment from 2009, when Simmons and Letterman bickered over how to use a food steamer just before it burst into flames, is the kind of late night gold that other hosts dream about.
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17 of 20
Memorable 'Late Show' moments 20 photos
Dave and Jay Leno team up – Letterman isn't above poking some friendly fun at his rival, Jay Leno, and in the disastrous NBC late night wars of 2010, Letterman kicked it up a notch. But, we assume, it was all in good fun -- Letterman still joined Oprah Winfrey and Leno in a "Late Show" promo during the Super Bowl that year, an ad that was said to be Letterman's idea.
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18 of 20
Memorable 'Late Show' moments 20 photos
Lindsay Lohan gets emotional – Prior to her court-mandated stint in rehab, Lindsay Lohan gave an emotional but also surprisingly endearing and transparent interview. Letterman, of course, didn't take the easy route and asked pointed, frank questions. Although he led her down a road that ended in tears, the host commended Lohan when it was done: "We never thought we'd see you again, honestly, because of the jokes and stuff," he told her. "But you have enough spine, enough sense of yourself, enough poise to come out here and talk to me."
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19 of 20
Memorable 'Late Show' moments 20 photos
Cher keeps Dave on his toes – Cher and Letterman have a storied past, as the singer seems to have a unique ability to confound the comedian. Once in 1996 she told him he looked like "s---," and generally gave him a hard time. However, the singer has appeared on his show several times since, including in 2013, when she gave him a big hug after performing a song off her latest album.
Hide Caption
20 of 20
Memorable 'Late Show' moments 20 photos
Even when CBS' "Late Show with David Letterman" veers into awkward, uncomfortable territory for the guest -- as it often does -- Letterman never loses his cool. In fact, the opposite happens: The show only gets better. As the show winds toward its May 20 conclusion, here are some memorable moments.
Hide Caption
1 of 20
Memorable 'Late Show' moments 20 photos
Passing of the torch – Any moment with legend Johnny Carson and legend-in-the-making Letterman was destined to be a classic, but Carson's appearance on the "Late Show" in May 1994 is the most memorable. The former "Tonight Show" host opted to make his last TV showing with Letterman, who appropriately handed over his desk chair to his idol.
Hide Caption
2 of 20
Memorable 'Late Show' moments 20 photos
Tribute to Johnny Carson – After Carson died in January 2005, David Letterman paid tribute to him in the best way he knew: by turning over his entire monologue to the celebrated comedian and TV personality, composing it of jokes Carson had written.
Hide Caption
3 of 20
Memorable 'Late Show' moments 20 photos
Madonna's F-bombs – In March 1994, Madonna severely tested Letterman's mettle in an exchange that's become a standout late night moment. Letterman introduced Madge as a top-selling pop star who'd slept with some of the biggest names in the industry, which prompted Madonna to go off a very profane deep end. At last count, somewhere around 13 F-bombs were dropped over the course of the interview.
Hide Caption
4 of 20
Memorable 'Late Show' moments 20 photos
Drew Barrymore flashes Dave – When Drew Barrymore showed up on "Letterman" in 1995, she came bearing gifts -- of a sort. The then-20-year-old actress was a ball of "good energy," and when talk turned to her interest in "nude performance dance," Letterman of course had to get a preview -- complete with flashing. It was his birthday, after all.
Hide Caption
5 of 20
Memorable 'Late Show' moments 20 photos
Courtney Love channels Drew Barrymore – In March 2004, Courtney Love tried to pull off what Drew Barrymore had adorably done a decade earlier. Unfortunately, Love's would-be teasing reveal turned into a major -- and memorable -- fumble.
Hide Caption
6 of 20
Memorable 'Late Show' moments 20 photos
First broadcast after 9/11 – Letterman's first show after the September 11 attacks was an understandably subdued and emotional episode. The monologue was skipped in favor of honoring those lost in the attack. Dan Rather was one of the night's guests, and he memorably couldn't hold back tears as he recited "America the Beautiful."
Hide Caption
7 of 20
Memorable 'Late Show' moments 20 photos
Honoring Warren Zevon – In the fall of 2002, Letterman showed his graciousness and tender heart when he dedicated an entire episode to the terminally ill Warren Zevon in a celebration of his music. The singer-songwriter passed away the following year.
Hide Caption
8 of 20
Memorable 'Late Show' moments 20 photos
McCartney performs – Musician Paul McCartney took over the marquee of the Ed Sullivan Theater, where the Beatles made big news in 1964, to performs for the '"Late Show" on July 15, 2009.
Hide Caption
9 of 20
Memorable 'Late Show' moments 20 photos
Dave and Oprah bury the hatchet – It had been 16 years since Oprah Winfrey last set foot on "Letterman" when she finally returned in December 2005. The episode of course brought in monster ratings, as it appeared that the two were making up. The irony was that neither truly knew -- or at least would admit on TV -- what caused their supposed "feud," or if there was ever a tiff in the first place.
Hide Caption
10 of 20
Memorable 'Late Show' moments 20 photos
Michael Richards' mea culpa – When you need to make a massive apology, it makes sense to turn to the well-respected Letterman to help you out. That's what "Seinfeld's" Michael Richards ended up doing in November 2006, with help from Letterman's guest of the night, Jerry Seinfeld. Richards, however, wasn't in the studio -- he made his apology via satellite after coming under fire for using the N-word during a tirade at a comedy club. "Awkward" doesn't begin to describe the appearance.
Hide Caption
11 of 20
Memorable 'Late Show' moments 20 photos
Dave and Bill O'Reilly call a truce – Before Bill O'Reilly and David Letterman found a reason to high-five one another in 2011, they'd had a war of words while taping "Late Show" in 2006. The conversation was about the Iraq War, and the debate became so agitated that the light-hearted comments turned into terse insults.
Hide Caption
12 of 20
Memorable 'Late Show' moments 20 photos
Paris Hilton gets grilled – Paris Hilton braved seeing Letterman again in 2008 even after he upset her during her 2007 interview. The late night host grilled her about her jail time to the point that she said she was "sad" she'd even come on the show. The following year, Letterman acknowledged how tough he'd been on the celebutante and made nice.
Hide Caption
13 of 20
Memorable 'Late Show' moments 20 photos
John McCain in the hot seat – After initially trying to skip out on Letterman's show in 2008, John McCain finally made it into the hot seat that October. The politician was faced with chatting up a man who roasted him for his cancellation in an earlier monologue. Both moments were deliciously squirmy TV.
Hide Caption
14 of 20
Memorable 'Late Show' moments 20 photos
Joaquin Phoenix's strange act – Watching Joaquin Phoenix appear on "Letterman" in 2009 was like watching a train wreck -- it was so hard to watch, but you just couldn't look away. Phoenix had drastically altered his appearance and behaved strangely, as Letterman tried to figure out how to navigate the puzzle before him. It was all an act, though, and Phoenix returned to the show in 2010 to apologize.
Hide Caption
15 of 20
Memorable 'Late Show' moments 20 photos
Dave's shocking confession – In October 2009, Letterman made a stunning admission live on the air when he told his audience that he'd had sexual relationships with female members of his staff and that someone had been attempting to blackmail him as a result. The following Monday, he used his show to offer a "heartfelt" apology to his wife and to his female staffers.
Hide Caption
16 of 20
Memorable 'Late Show' moments 20 photos
Richard Simmons goes up in smoke – Richard Simmons and David Letterman have a wonderfully antagonistic friendship, and out of the many times the fitness king has appeared on the program, it's hard to pick a favorite. This moment from 2009, when Simmons and Letterman bickered over how to use a food steamer just before it burst into flames, is the kind of late night gold that other hosts dream about.
Hide Caption
17 of 20
Memorable 'Late Show' moments 20 photos
Dave and Jay Leno team up – Letterman isn't above poking some friendly fun at his rival, Jay Leno, and in the disastrous NBC late night wars of 2010, Letterman kicked it up a notch. But, we assume, it was all in good fun -- Letterman still joined Oprah Winfrey and Leno in a "Late Show" promo during the Super Bowl that year, an ad that was said to be Letterman's idea.
Hide Caption
18 of 20
Memorable 'Late Show' moments 20 photos
Lindsay Lohan gets emotional – Prior to her court-mandated stint in rehab, Lindsay Lohan gave an emotional but also surprisingly endearing and transparent interview. Letterman, of course, didn't take the easy route and asked pointed, frank questions. Although he led her down a road that ended in tears, the host commended Lohan when it was done: "We never thought we'd see you again, honestly, because of the jokes and stuff," he told her. "But you have enough spine, enough sense of yourself, enough poise to come out here and talk to me."
Hide Caption
19 of 20
Memorable 'Late Show' moments 20 photos
Cher keeps Dave on his toes – Cher and Letterman have a storied past, as the singer seems to have a unique ability to confound the comedian. Once in 1996 she told him he looked like "s---," and generally gave him a hard time. However, the singer has appeared on his show several times since, including in 2013, when she gave him a big hug after performing a song off her latest album.
Hide Caption
20 of 20
Memorable 'Late Show' moments 20 photos
Even when CBS' "Late Show with David Letterman" veers into awkward, uncomfortable territory for the guest -- as it often does -- Letterman never loses his cool. In fact, the opposite happens: The show only gets better. As the show winds toward its May 20 conclusion, here are some memorable moments.
Hide Caption
1 of 20
Memorable 'Late Show' moments 20 photos
Passing of the torch – Any moment with legend Johnny Carson and legend-in-the-making Letterman was destined to be a classic, but Carson's appearance on the "Late Show" in May 1994 is the most memorable. The former "Tonight Show" host opted to make his last TV showing with Letterman, who appropriately handed over his desk chair to his idol.
Hide Caption
2 of 20
Memorable 'Late Show' moments 20 photos
Tribute to Johnny Carson – After Carson died in January 2005, David Letterman paid tribute to him in the best way he knew: by turning over his entire monologue to the celebrated comedian and TV personality, composing it of jokes Carson had written.
Hide Caption
3 of 20
Memorable 'Late Show' moments 20 photos
Madonna's F-bombs – In March 1994, Madonna severely tested Letterman's mettle in an exchange that's become a standout late night moment. Letterman introduced Madge as a top-selling pop star who'd slept with some of the biggest names in the industry, which prompted Madonna to go off a very profane deep end. At last count, somewhere around 13 F-bombs were dropped over the course of the interview.
Hide Caption
4 of 20
Memorable 'Late Show' moments 20 photos
Drew Barrymore flashes Dave – When Drew Barrymore showed up on "Letterman" in 1995, she came bearing gifts -- of a sort. The then-20-year-old actress was a ball of "good energy," and when talk turned to her interest in "nude performance dance," Letterman of course had to get a preview -- complete with flashing. It was his birthday, after all.
Hide Caption
5 of 20
Memorable 'Late Show' moments 20 photos
Courtney Love channels Drew Barrymore – In March 2004, Courtney Love tried to pull off what Drew Barrymore had adorably done a decade earlier. Unfortunately, Love's would-be teasing reveal turned into a major -- and memorable -- fumble.
Hide Caption
6 of 20
Memorable 'Late Show' moments 20 photos
First broadcast after 9/11 – Letterman's first show after the September 11 attacks was an understandably subdued and emotional episode. The monologue was skipped in favor of honoring those lost in the attack. Dan Rather was one of the night's guests, and he memorably couldn't hold back tears as he recited "America the Beautiful."
Hide Caption
7 of 20
Memorable 'Late Show' moments 20 photos
Honoring Warren Zevon – In the fall of 2002, Letterman showed his graciousness and tender heart when he dedicated an entire episode to the terminally ill Warren Zevon in a celebration of his music. The singer-songwriter passed away the following year.
Hide Caption
8 of 20
Memorable 'Late Show' moments 20 photos
McCartney performs – Musician Paul McCartney took over the marquee of the Ed Sullivan Theater, where the Beatles made big news in 1964, to performs for the '"Late Show" on July 15, 2009.
Hide Caption
9 of 20
Memorable 'Late Show' moments 20 photos
Dave and Oprah bury the hatchet – It had been 16 years since Oprah Winfrey last set foot on "Letterman" when she finally returned in December 2005. The episode of course brought in monster ratings, as it appeared that the two were making up. The irony was that neither truly knew -- or at least would admit on TV -- what caused their supposed "feud," or if there was ever a tiff in the first place.
Hide Caption
10 of 20
Story highlights
- "The Late Show with David Letterman" concludes May 20
- Letterman's guests will include Oprah Winfrey and Bill Murray
- Stephen Colbert takes over the slot September 8
Oprah's in there.
So's Bill Murray, George Clooney, Scarlett Johansson, Jerry Seinfeld, Howard Stern, Tina Fey, Michael Keaton and Ray Romano.
On Tuesday, "The Late Show with David Letterman" announced some of the guests for the talk show host's final month of broadcasts.
The last "Late Show" will air Wednesday, May 20.
Among the notables are Oprah Winfrey, with whom Letterman has had an on-and-off faux feudfor years; Clooney, who's starring in "Tomorrowland," which will be released on May 22; and Stern, who's always an engaging Letterman guest.
But longtime fans may be even more intrigued by the appearances of Keaton, an old acquaintance who once shared a stage with Letterman as players on Mary Tyler Moore's short-lived 1978 variety show, and Murray, who was the very first guest on Letterman's old NBC show, "Late Night with David Letterman."
Steve Martin, who's taken part in some of the "Late Show's" best bits, will also be dropping by.
Letterman has been a late-night host for 33 years, close to 22 of them on CBS' "Late Show."
Stephen Colbert will take over the "Late Show" on September 8.
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