It’s been hard to write or say anything about David Letterman’s impending retirement that doesn't sound like hagiography. This is a man who was my comedy hero in first grade and remains my comedy hero to this day; a famous person who is probably more responsible for the kinds of things I find funny than anyone I’ve ever met in real life. There have been roughly a bajillion adulatory pieces written about Letterman since he announced he was retiring a little over a year ago, and every single one of them was deserved. Because for more than 30 years, Letterman has been just that goddamn good.

To tick off a (very incomplete) list of things he brought to late-night television is to run down an inventory of groundbreaking and often half-baked ideas that ultimately made comedy goofier, weirder, cooler, and above all, funnier. Pets and humans did brilliantly stupid tricks. Random objects were thrown off five-story buildings. Man-on-the-street interviews took surreal and bizarre turns. Top Ten Lists became cultural reference points. Letterman put a camera on a monkey’s back and then put that monkey on roller skates and let him coast around the studio, because why the fuck not? That thing where you tell a joke until it’s not funny anymore, and then keep telling it until it’s funny again? Letterman basically invented that. He made awkward oddballs like Biff Henderson and Larry Bud Melman (R.I.P.) featured players. Rock bands no one had heard of were booked by the Letterman show before other shows realized it was a cool thing to do. Letterman's repartee with Teri Garr in the 1980s, Sandra Bernhard in the '90s and Amy Sedaris in the oughts remains unmatched. You can draw a line straight from Letterman not just to Fey, Stewart, Colbert and O’Brien, but also to 30 Rock, Mr. Show and Tim & Eric. In his early years, people who didn’t like him said it was because he was acerbic, sarcastic, ironic and smug—which, coincidentally, were the same reasons people gave for loving him.

More recently, he’s been accused of mellowing, though it seems like he’s actually just gotten better at letting his most abhorrent guests reveal their own awfulness without a lot of heavy lifting on his part. When the situation calls for it, Letterman won’t hesitate to call a guest on his bullshit. A prime example of this might be seen during Letterman’s political moments, when he cuts right-wingers, and those who vote with them, down to size. Conservatives accuse him of harboring a liberal bias, to which one might respond, ah, duh. Though monologues feature bipartisan ribbing, Letterman reserves his most sound drubbings for bloviating figures from Fox News and double-talking Republican politicians. Until about a year ago, if you wanted bland, uninspired, middle-of-the-road political humor, you could turn on Jay Leno. If you wanted the opposite, you put on Letterman.

And so, to recognize his exquisite work in taking down some of the right’s worst, and for being a culture-shifting, groundbreaking, trailblazing, brilliant force in comedy, here’s a look at a few of David Letterman’s best anti-right-wing political moments.

1. David Letterman vs. Bill O’Reilly: “Sixty percent of what you say is crap.”

To be honest, it was too hard to consolidate Letterman’s many takedowns of Bill O’Reilly into a single entry, so there are multiple examples on this list. Perhaps the best came during an episode that aired Jan. 6, 2006. O’Reilly kicked things off by complaining about the war on Christmas, a claim Letterman dismissed thusly: “Isn’t this the kind of thing where, once or twice every 20 years, somebody gets outraged and says, Oh, by god, we gotta put diapers on horses!'" He followed that up by stating, “I don’t think this is an actual threat. I think…people like you are trying to make us think that it’s a threat.”

From there, O’Reilly moved on to attack Cindy Sheehan, a prominent figure in the anti-war movement whose son was killed in combat in Iraq. O’Reilly claimed Sheehan and others like her were “putting us all in danger” by “undermining” the war effort and President Bush. “It is a vitally important time in American history, and we should all…be very careful with what we say,” O’Reilly lectured.

Without missing a beat, Letterman shot back, “Â“Well, and you should be very careful with what you say also,” to audience applause. After O’Reilly had waved the flag a bit more, Letterman shut him down completely with this gem: “I have the feeling about 60 percent of what you say is crap.” Just watching O’Reilly seethe is worth the price of admission.

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”599998″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

2. Letterman: “Cheney and Bush…couldn’t care less about Americans.”

In an episode that aired June 11, 2008, while speaking with Scott McClellan, former White House press secretary for George W. Bush, Letterman didn’t mince words: "My feeling about Cheney—and also Bush, but especially Cheney—is that he just couldn't care less about Americans. And 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. (Pantomimes counting bills from a big stack of money.) 'There you go, Dick, nice job! There's a couple of billion for your trouble.' He pretty much put Halliburton in business and the outsourcing of military resources to private mercenary groups and so forth. Is there any humanity in either of these guys?"

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”599999″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

3. David Letterman vs. Bill O’Reilly: “You’re putting words in my mouth. Just the way you put artificial facts in your head.”

Letterman is nothing if not a completist; in this case, he managed to call bullshit not just on O’Reilly, but on Fox News and the entire right-wing noise machine. Seconds after O'Reilly sat down, Letterman asked, “Am I right about one thing? You guys over there at Fox, and guys like Rush Limbaugh, you guys know it’s all just a goof, right?”

When O’Reilly later asked Letterman if he wanted the U.S. to “win in Iraq” (attempting to reduce a complex geopolitical situation to a game of “Are You A Commie?”), Letterman paused, only to have O’Reilly quickly assert that “it [was] an easy question.” Letterman cut him off: “It’s not easy for me, because I’m thoughtful.” (The host went on to state, on the record, that the situation in Iraq was “all about oil.”)

O’Reilly later implied that Letterman and other liberals were seeing the situation in “black and white,” saying, “it isn’t [that] we’re a bad country, Bush is an evil liar.” Letterman, clearly annoyed, fired back, “I didn’t say we were a bad country, I didn’t say he was an evil liar. You’re putting words in my mouth. Just the way you put artificial facts in your head.”

Game, set, match, Letterman.

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600000″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

4. Letterman: Rush Limbaugh is a “bonehead.”

Rush Limbaugh was the closing speaker at the 2009 CPAC convention, where the conservative audience went so gaga for him and his assertion that he “want[ed]…President Obama to fail,” outlets began calling him the “leader of the Republican Party.”

On the heels of the convention, speaking to CBS News anchor Katie Couric, Letterman wondered aloud, “What about this bonehead Rush Limbaugh? Honest to God, I mean, what is going on there?” (“Oh, Dave, don’t do this to me, please,” Couric begged.) But Letterman was just getting started. “He gets up in Washington and he's the keynote speaker at some function and he comes up—he looks like an Eastern European gangster, you know? He's got the black jacket on, the black silk shirt and it's unbuttoned like, oh yeah, when you think Rush Limbaugh, you think, Ooh, let's see a little flesh. Honestly, you know?”

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600001″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

5. David Letterman vs. Bill O’Reilly: “You’re not speaking your conscience.”

In yet another example of Letterman’s endless mockery of O’Reilly, on a 2009 episode, just seconds after the Fox pundit took his seat, Letterman informed him, “In my mind, I think of you as a goon.” Gesturing to the cover of O’Reilly’s book, which featured a photo of him as a sweet-faced young altar boy, Letterman said, “Look at how sweet and adorable that kid is. And it breaks my heart, because I have a sweet, adorable kid like that, and I think, Oh, great. What if he, too, becomes a goon?"

Letterman then turned the conversation to Limbaugh, noting that even Michael Steele, the ostensible head of the Republican National Convention, had to kiss the radio host’s ass. “I want Rush Limbaugh to be the new face of the Republican party,” Dave joked. When O’Reilly asked why, he responded, “for a long time [Rush] had his housekeeper buying illegal drugs. And I thought, if the Republican party needs [that]….”

Near the end of the segment, after an extended speech in which Letterman suggested O’Reilly, Limbaugh and Glenn Beck were basically faking their public personas, he told O’Reilly, “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.”

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600002″,”attributes”:{“alt”:””,”class”:”media-image”,”style”:”font-size: 12px;”,”typeof”:”foaf:Image”}}]]

6. Letterman: “Republicans are unstable.”

On a 2012 episode where he was joined by NBC Nightly News anchor Brian Williams, Letter posed this query: “Let me ask you a general question. And I’m no political expert, certainly. But when did the Republican Party become the party of the emotionally unstable?….Ronald Reagan now looks like the greatest statesman that ever lived! And we got a guy running around named Newt.”

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600003″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

7. Letterman makes Republican heads explode by praising Obama.

I present to you an exchange between a visibly uncomfortable Brian Williams and a wholly unfiltered Letterman:

Letterman: I’ll tell you frankly—and try not to get me sideways on this. The day after the 9/11 attacks, the number-one priority in America, if not the world, was we gotta get bin Laden. 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—

Williams: You’re getting a little sideways here, Dave.

Letterman: —and grab up all the oil. I think they went soft on the project because they were worried about upsetting their Saudi Arabian royalty buddies.

Williams: Easy there….

Letterman: So, now, Osama bin Laden finally is gunned down by Barack Obama, displaying great courage and great intelligence. What more do you want to lead your country than that kind of courage and that kind of intelligence?

Later, in the same conversation, Letterman went a bit deeper, saying: "Remember the Iraq war—'Mission Accomplished'? Well holy goddamn, the mission was not accomplished. It was far from accomplished. They put up a banner on the SS Lincoln aircraft carrier, George flies in, in a thing, and he’s got his little flight jacket on. He was very cute….You know what I mean? It makes me angry that we can’t give this president anything…What more do we want this man to do for us? Honest to god.

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600004″,”attributes”:{“alt”:””,”class”:”media-image”,”style”:”font-size: 12px;”,”typeof”:”foaf:Image”}}]]

8. Letterman shames anti-gun control lawmakers with “Stooge of the Night.”

In a recurring skit in 2013, Letterman began naming a “Stooge of the Night,” a senator who voted against gun control regulation against the overwhelming wishes of his or her constituents. You can check out a bunch of the segments here, but here’s a few examples.

Letterman: Hey, Alan, what time is it, for heaven’s sake?

Alan: Dave, it’s time for Stooge of the Night. Tonight’s Stooge of the Night is Republican Senator Richard Burr of North Carolina.

Letterman: North Carolina Senator Richard Burr—or as I like to call him, “Dick” Burr—voted no on gun reform legislation. Last month, Senator Burr received a $1,000 donation from a British company that manufactures ammunition. Remember, ladies and gentlemen, there is no background check if you want to buy a senator.

Here’s another:

Letterman: Alan, what time is it, for heaven’s sake?

Alan: Dave, it’s time for Stooge of the Night. Tonight’s Stooge of the Night is Democratic Senator Max Baucus of Montana.

Letterman: Montana Senator Max Baucus was one of five Democrats to vote no on gun control despite the fact that 79 percent of voters in his state are in favor of background checks, and also, he’s not running for reelection. Less than a week after the vote, Senator Baucus announced he was retiring. "That’s me, Max Baucus. Look at the glow on the top of my head."

And so on. Check out the clip below, in which Letterman crowns New Hampshire Senator Kelly Ayotte Stooge of the Night for voting against gun reform legislation, even though 89 percent of voters in her state were in favor of background checks.

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600005″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

8. Letterman vs. Rand Paul.

A few choice Letterman quotes, following Paul’s assertion that Republicans “are for shrinking the public sector and growing the private sector”:

“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.”

“What would be so wrong with…leaving the public sector alone, and reducing tax benefits for the wealthy and large corporations? Why couldn’t you make up your money that way?”

“I don’t think it makes sense. You look at these people in Wisconsin…Why don’t we just raise the taxes and let these folks have their collective bargaining, have their union representation and go back to their jobs?”

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600006″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

9. David Letterman vs. John McCain.

Things were fine between Letterman and the senator from Arizona, until in 2008, McCain canceled a scheduled appearance on the show at the last minute, saying he was suspending his presidential campaign to deal with the country’s financial crisis. Then Letterman got wind of the fact that McCain had not rushed back to Washington, DC as promised, but instead had made a beeline for CBS News, where he was set to be interviewed by Katie Couric. Annoyed that he’d been stood up and prone to crankiness in general, Letterman invited Keith Olbermann on the show in McCain’s place and spent the entire episode basically calling out McCain’s stunt for what it was: an empty gesture to distract from falling poll numbers.

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600007″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]

10. Letterman imagines the Top Ten things overheard at Rush Limbaugh’s fourth wedding.

Sure, this is as silly as a typical Letterman Top Ten List (the targets of which were vast and of varying political stripes), but it’s a bit of a bonus knowing Letterman’s attitude toward Limbaugh. Highlights include “Oh crap. I’m sitting next to Bill O’Reilly,” “Mrs. Palin, please, enough with the celebratory gunfire,” and “Do you take this woman to be your future ex-wife?”

[[{“type”:”media”,”view_mode”:”media_large”,”fid”:”600008″,”attributes”:{“alt”:””,”class”:”media-image”,”typeof”:”foaf:Image”}}]]