Letterman's Top 10 Controversial Political Moments

Wednesday will mark the final episode of Late Show With David Letterman, which has been on the air since 1993. Over the last 20-plus years, host David Letterman has made millions of viewers laugh to their hearts' content, but once in a while he's also shocked audiences with his divisive comments, especially pertaining to politics. In honor of the late-night talk show host and his long career, and borrowing a format that he made famous, here are David Letterman's top 10 most controversial political statements that proved he was as fearless as television personalities come.

Before I get into the top 10 list, let's take a look at Letterman's gradual foray into political opinions, of which he has many, and which set him apart from other late-night hosts. While there's an unspoken understanding among the late-night elite to come off as apolitical, or at least nonpartisan, as possible, Letterman began to veer from that safe neutral zone a few years ago and has become increasingly and unabashedly opinionated ever since.

A 2009 New York Times article examines this shift, which the paper says was marked by President Obama's September 2009 appearance on the Late Show as the first sitting president to ever visit the show. The night after, Bill Clinton made an appearance. But the shift might have started earlier that year when Letterman cracked a highly controversial joke about Sarah Palin's daughter, which many first believed was about her 14-year-old, Willow.

Alan Schroeder, an associate professor of journalism at Northeastern University told the Times:

I think when Letterman became a target of the right wing over Palin, it energized him politically.

Robert Thompson, professor of television and popular culture at Syracuse, echoed:

When he began in television, Letterman was virtually apolitical. Now he’s moved to the point where he could be called a political comedian.

Indeed, Letterman was never short on the political jokes. In the most appropriate way to send the host off, here is the definitive top 10 list of Letterman's most controversial political statements.

10. He Said Donald Trump's Obama Comments 'Smack Of Racism'

During an interview with Dr. Phil in January, the topic of Donald Trump randomly comes up. While Dr. Phil tried to stay above the fray, Letterman dove in headfirst, slamming Trump's questioning of how Obama got into Harvard and how he was able to write his memoirs. Letterman asserted that it "smacks of racism."

9. Anti-Gun Control Stooges

In 2013, Letterman began running a recurring skit called "Stooge of the Night," in which he awards that title to a different senator who voted against gun control in spite of constituent support for more regulation. Some of the senators he featured as the "Stooge of the Night" include Republican Sen. Saxby Chambliss of Georgia, Democratic Sen. Max Baucus of Montana, and Republican Sen. Kelly Ayotte of New Hampshire.

8. Letterman Takes On Rand Paul

In 2011, Letterman wasn't afraid to push back against Kentucky Sen. Rand Paul, who is now a Republican candidate for the presidency. When he asked whether lowering taxes on the wealthy would hurt middle-class citizens, Paul said:

Not necessarily. I think you have to ask yourself where is a function better handled. Is it better that late night comedy be done by private business or by the government? And we say who would do it better? If there is a question, maybe government does it but most of the time the answer is the private sector does it better.

Letterman opposed this view, saying:

What would be so wrong then in terms of leaving the public sector alone and reducing tax benefits for the wealthy and large corporations? ... Who peoples the government sector? We’re talking about firemen, policemen, teachers. ... Am I misunderstanding here? You want to shrink that strata of American worker and give tax breaks to people who well could afford to pay a higher tax rate.

7. The Top 10 Things Heard At Rush Limbaugh's Wedding

In 2010, Letterman poked fun at Rush Limbaugh by making his Top 10 List imagined overheard things at the conservative radio host's fourth wedding. Some of these included "Mrs. Palin, please, enough with the celebratory gunfire," "Do you take this woman to be your future ex-wife?" and "Oh crap. I'm sitting next to Ann Coulter."

6. His Comments On Bush's Post-9/11 Priorities

When Letterman interviewed NBC's Brian Williams in 2012, the host brought up 9/11, criticizing Bush and Cheney, praising Obama, and making Williams slightly uncomfortable all in one go. Letterman passionately stated:

The day after the 9/11 attacks, the number-one priority in America, if not the world, was we gotta get bin Laden. ... So eight years go by, we still haven’t gotten bin Laden. George W. Bush at one point said, well, he doesn’t really think too much about bin Laden. In the interim, we invaded Afghanistan and we invaded Iraq, because Cheney wanted to help out his buddies Brown & Root and Haliburton. ... So, now, Osama bin Laden finally is gunned down by Barack Obama, displaying great courage and great intelligence.

5. Letterman's Rant About John McCain

Letterman's feud with John McCain went beyond politics and into personal territory. In 2008, McCain canceled a scheduled appearance on the Late Show, saying he had to stop his campaign to help deal with the financial crisis. But then Letterman found out that McCain participated in an interview with CBS News' Katie Couric instead. In retaliation, Letterman dedicated basically his entire episode to skewering McCain, calling him "the running mate of Sarah Palin" and questioning his real motives for suspending his campaign. "Are we suspending it because there's an economic crisis," Letterman asked, "or because the poll numbers are sliding?"

4. "Dick Cheney Doesn't Care About Americans"

Dick Cheney has been the target of Letterman's ire on more than one occasion. In 2009, when interviewing White House tell-all author Scott McClellan, Letterman used the opportunity to spout his own opinion of Bush and Cheney, but mostly Cheney. He starts out the interview on a more jocular note, asking, "Is Cheney, is he — is he a goon?" He adds, "I don't mean that to sound like a smart-ass. He seems like he might be a goon."

But then he rips the then-vice president a new one:

My feeling about Cheney and also Bush, but especially Cheney, is he just couldn't care less about Americans. And that the same is true of George Bush. And all they really want to do is somehow kiss up to the oil people so they can get some great annuity when they're out of office. "There you go, Dick, nice job. There's a couple of billion for your troubles." ( applause ) I mean, he pretty much put Halliburton in business, and the outsourcing of the military resources to private mercenary groups, and so forth. Is there any humanity in either of these guys?

3. Letterman vs. Bill O'Reilly

Over the years, Letterman has slammed Fox News host Bill O'Reilly over and over again, like when he stated, "I have the feeling about 60 percent of what you say is crap" and "In my mind, I think of you as a goon" to his face. But one of the most notable instances, which summed up Letterman's feelings about conservative pundits like O'Reilly, came in 2009 when he criticized O'Reilly, Rush Limbaugh, and Glenn Beck for dramatizing their public personae.

You guys know exactly what you’re doing. You’ve been very successful at it. But the truth of it is, you’re not speaking your conscience.

2. That Questionable Palin Joke

Perhaps one of the most controversial jokes that has ever come out of Letterman's mouth was the one about Sarah Palin's daughter, made in June 2009 during his opening monologue:

One awkward moment for Sarah Palin at the Yankee game, during the seventh inning, her daughter was knocked up by Alex Rodriguez.

In response to the questionable joke, Palin issued a searing statement:

Laughter incited by sexually perverted comments made by a 62-year-old male celebrity aimed at a 14-year-old girl is ... disgusting.

Letterman tried to do damage control by explaining that he thought the daughter at the game was 18-year-old Bristol, not 14-year-old Willow, and apologized to the Palin family.

1. Al Qaeda's Hit List

In 2011, a death threat against Letterman emerged on a website supporting al Qaeda in which a follower urged other militants to assassinate the host for joking about an al Qaeda leader getting killed in a drone strike. Letterman had the best response ever:

So now, State Department authorities are looking into this. They’re not taking this lightly. They’re looking into it. They’re questioning, they’re interrogating, there’s an electronic trail — but everybody knows it’s Leno.