David Letterman will hang it up this week after more than three decades as one of the nation’s pre-eminent talk show hosts.
The “Late Show” comedian saw presidents, vice presidents, first ladies, presidential candidates and lawmakers of every stripe pass through his studio at the Ed Sullivan Theater in Manhattan.
Here are some of his most memorable political moments:
Sen. John McCain (R-Ariz.) was neck and neck in the presidential race with Sen. Barack ObamaBarack ObamaObama promotes new airline regulations Is Georgia turning blue? Five takeaways from money race MORE (D-Ill.) when he canceled a scheduled appearance on CBS’s “Late Show” in September 2008 at the last minute.
Letterman went ballistic, opening his show with a nine-minute broadside against McCain, who had suspended his campaign because of the financial crisis.
In a moment where the left-leaning host might have had a significant affect on a presidential race, Letterman questioned McCain’s temperament at a time of crisis.
The host also cut to a live feed of McCain giving an interview with CBS’s Katie Couric, just down the hall.
It all went poorly for the GOP candidate, who acknowledged upon returning to the show a month later: “I screwed up.”
2. Poignant after 9/11
Letterman spent his entire 33-year late night career in New York City, first at NBC and then at CBS.
After the Sept. 11, 2001, attacks, his was the first late night talk show to return to the air — and it was one of his most memorable moments.
At a time when people were questioning whether it was OK to tell jokes, Letterman launched into an emotional eight-minute monologue paying tribute to his adopted hometown and American resiliency.
“If you didn’t believe it before, you can absolutely believe it now,” he said. “New York City is the greatest city in the world.”
3. Hounding Dan Quayle
Letterman’s late night career spanned five presidencies, beginning with Ronald Reagan’s and ending with Barack Obama’s.
But his first memorable political target might have been former Vice President Dan Quayle.
Between August 1988 and Election Day that year, Letterman ran six Top Ten lists assailing Quayle as a know-nothing pretty boy.
In one list, Letterman said Quayle might someday make a great president because he “would not seem like a brainy egghead when visiting the nation’s injured professional wrestlers.”
Quayle had a good sense of humor about the perpetual ribbing and eventually appeared as a guest on the show in October 1999.
4. Regrets over Monica Lewinsky
The 1998 sex scandal in the White House was comic gold for late night talk show hosts and remains a standby even today.
At the time, Letterman relished the opportunity to cast former President Bill ClintonBill ClintonBill Clinton: We're entering era that will 'make the 90s look like small potatoes' Trump son: Talk like father's leaked 2005 tapes 'a fact of life' Is Georgia turning blue? MORE as an insatiable sexual deviant, but he also relentlessly mocked Monica Lewinsky.
The jokes were always sexually charged and full of innuendo, and occasionally even touched on Lewinsky’s weight.
In a 2014 interview with Barbara Walters, Letterman said he regretted the “relentless jokes about the poor woman.”
“I feel bad about my role in helping push the humiliation to the point of suffocation,” he said.
5. George W. Bush’s Top Ten list
In October 2000, a month before voters went to the polls in an election that would trigger a recount and ultimately be decided by the Supreme Court, George W. Bush delivered the “Top Ten Changes I’ll Make In the White House.”
Bush vowed not to “get sick on Japanese leaders like other President Bushes have.”
Just for fun, he said, he’d “issue an executive order commanding my brother Jeb to wash my car.” He also said his mother would get her face on Mount Rushmore.
The Top Ten list also jabbed at Bush’s intellect, which would become consistent fodder for Letterman throughout his presidency.
“Make sure the White House library has lots of books with big print and pictures,” Bush said.
6. Apologizing to Sarah Palin
Not all of Letterman’s jokes ended well.
The host landed in hot water for an off-color 2009 joke that one of former Alaska Gov. Sarah Palin’s daughters had been “knocked up” by Alex Rodriguez.
Palin’s daughter Willow, who was 14 at the time, had just been in the news for attending a New York Yankees game.
Palin was furious, denouncing the “laughter incited by sexually perverted comments made by a 62-year-old male celebrity aimed at a 14-year-old girl.”
Letterman said the joke was meant as a reference to Bristol Palin, who was 18 at the time and had just given birth to a son, but he later offered a direct apology to the Palins.
“It’s not your fault that it was misunderstood — it’s my fault,” he said.
“I’m sorry about it, and I’ll try to do better in the future.”
7. Obama appears
Obama had already been on the “Late Show” five times before making history in 2009 as the first sitting president to appear on the show.
Obama would visit the show three times in total while he was in the White House. His performances were typically light, but his last visit in May was notable because the two spoke at length about the unrest in Baltimore that followed the death of a black man in police custody.
“This is not just a policing problem,” Obama said during the sober conversation. “What you have are pockets of poverty, lack of opportunity, lack of education all across the country. And too often, we ignore those pockets until something happens.”
8. Sparring with Bill O’Reilly
Letterman has made no effort to hide his contempt for Bill O’Reilly, the host of Fox News’s “The O’Reilly Factor.”
“I think of you as a goon,” Letterman deadpanned to O’Reilly in a 2009 interview.
Letterman told O’Reilly he believes the Fox News anchor is playing the part of a conservative showman and doesn’t actually believe the things he says on his show.
O’Reilly typically plays along and fires right back.
“Why am I so popular?” he asked Letterman. “Are the folks out there stupid?”
9. Running for office
Sen. Al FrankenAl FrankenGretchen Carlson to testify before Congress Great Lakes senators seek boost for maritime system Court ruling could be game changer for Dems in Nevada MORE (D-Minn.) told Letterman earlier this year that he should run for office.
Letterman, who is from Indiana, was furious with Gov. Mike Pence (R) for signing the state’s controversial “religious freedom” bill, which critics said would allow businesses to discriminate against gays.
Franken offered the suggestion after Letterman asked what he could do to “make the governor of Indiana uncomfortable” over the law.
“As a matter of fact, there’s an open [Senate] seat there,” Franken responded. “I think you should run.”
10. Rick Perry’s ‘oops’ mea culpa
In November 2011, then-Texas Gov. Rick Perry (R) had some serious cleanup to do after the mortifying debate gaffe that became known as his “oops” moment.
Perry went on Letterman’s show to read his Top Ten “excuses” in an attempt to humanize the moment and prove he could laugh at himself.
“Actually, there were three reasons I messed up last night,” Perry said. “One was the nerves, two was the headache and three was, and three, uh, uh. Oops.”
But the damage was done, and Perry pulled out of the race for the Republican presidential nomination weeks later.