David Letterman's greatest jokes and bits from late-night TV

Claiming it’s his annual “part-time summer job,” Dave manned the drive-thru at a Taco Bell in New Jersey. He antagonized and overshared, talking about losing toes in a riding mower accident, refusing to fill soda orders and offering unsolicited food advice. The highlight comes from when he bullies a patron into ordering lunch for him — “We’re not allowed to order our own food, ma’am” — and then charges her $26 for the meatless Burrito Supreme. It’s pretty dumb, but so is a Doritos Locos Taco. Plus, who among us hasn’t wanted to stick their head under the Pepsi machine?

Letterman is great at providing hilariously terrible food service, but ultimately he’s too famous for in-person hijinks. The solution: use Rupert Jee, owner of the Hello Deli, as a surrogate. Rupert wore glasses embedded with a camera and an earpiece, through which Dave could feed him lines from the safety of a nearby van. But they eventually had to stop for Rupert’s safety. As you can see in this segment, Rupert infuriates a diner by putting his finger in her glass – he clarifies that it was his thumb – and then comes back with his rubber gloves inside her glass. These segments are a wonder, but the most wondrous part is that Rupert was never murdered.

Long before he had political aspirations, Donald Trump was the subject of a popular "Late Show" game: “Trump or Monkey?” A volunteer found on the New York streets or inside the Hello Deli is presented with the photos of the tops of three heads. Two are Donald Trump; one is a monkey. It proves surprisingly difficult to choose!

Chris Elliott played a ton of weird characters for Dave over the years, but perhaps the strangest was a guy who lived under the seats of the "Late Night" studio. This character — and honestly, most of Elliott’s characters — would do a simple bit like ventriloquism and then it would fall apart. Something would go wrong, Letterman would deliver a real or perceived slight and then The Guy would fly into a rage, and he — or a dummy — would invariably threaten to make Dave’s life “a living hell.”

One of the principles of judo is to use your opponent’s strength and power against them. It's also a principle of Letterman’s comedy — he sits back, waits patiently and effortlessly counter-attacks — like he did when TV host Yue-Sai Kan talked about Chinese cuisine and asked Dave if he’d ever had “the hump of a camel.” He lets it sink in and answers that he hasn't, “But I must say, when I was younger, I was pretty good!”

The Top 10 list was a deceptively simple recurring Letterman bit, ripped off by hundreds of others since its inception. Ten entries allowed for real jokes, absurd jokes, non sequiturs and running jokes, and sometimes a delightfully weird pastiche like this one from Dec. 23, 1998. The core of this joke is amazingly flimsy — “Danza” sounds like “Dancer” — and Tony Danza always plays a guy named Tony. What really puts a cherry on top of this wonderfully bizarre list is the No. 1 entry: Mustache Comb.

Chris Elliott’s “Cabin Boy” and David Letterman’s gig as an Oscar host were both critically panned, absurdist efforts that have eventually become cult favorites. At the Oscars, Letterman lampooned his acting in the role of “Old Salt,” with this montage of Hollywood greats attempting his signature line, “Want to buy a monkey?” The result was so good, it'll clean your pipes.

Some of the best Letterman jokes were the ones where the punchline deflates the premise. They feel less like punches and more like the rug being pulled out from your expectations — like this look at statistics and the chart-and-poll-heavy USA today:

Every three years, CBS got to broadcast the Super Bowl, and every time, Dave got a precious 15 seconds of Super Bowl commercial time to do whatever promo for the show he wanted. In 2007, with the Bears playing his beloved Colts, Letterman shot a spot with Chicago’s favorite daughter, Oprah Winfrey, poking fun at their alleged feud. But that paled in comparison to the 2010 spot , when Oprah returned — and so did a guy Dave REALLY feuded with, Jay Leno. It was shocking, and in 15 seconds it was over before the surprise even set in. It’s amazing that Dave pulled it off, with Leno traveling in disguise to shoot the spot to preserve the shock. Clearly, it was far from “the worst Super Bowl party ever.”

Two of the most traumatic events in Letterman’s life were when Jay Leno got "The Tonight Show" instead of him, and his life-threatening quadruple-bypass surgery in 2000. He missed five weeks of shows while guest hosts held down the fort, and he returned with a zinger that brought both disasters together: “A bypass is what happened when I didn't get 'The Tonight Show.'”

Joaquin Phoenix appeared on the show with a huge beard and dark glasses, part of what turned out to be a stunt for his woefully misguided mockumentary, “I'm Still Here.” Phoenix mumbled his way through, pretended he was becoming a rapper and delivered a truly bizarre interview, punctuated by Letterman’s quip, “I’m sorry you couldn't be here tonight.” When an apologetic and clean-shaven Phoenix returned and fessed up, Letterman forgave him — but demanded a cut of the movie’s profits.

Why is it hilarious and compelling to watch random objects dropped from great heights? Damned if we know, but it was a Letterman staple for years. Originally, he dropped things off a five-story tower, but after the move to CBS, he used the roof of the Ed Sullivan Theater. He used watermelons, bouncy balls, really anything smashable, and he even had John McEnroe serve tennis balls through a window of the theater. Still, destroying his employee’s crappy car with bowling balls took it to a new level. Galileo would have been proud.

While Dave was a talented interviewer, the greatest moments often came when he was unhappy with a guest — like when Paris Hilton came on after her drunken driving arrest. It was all questions about her arrest and time in “the slammer.” When Hilton eventually exclaimed that she didn't want to talk about her legal trouble anymore, Letterman coolly replied, “This is where you and I are different. This is all I want to talk about.” Paris was chagrined, and the audience was delighted.

Letterman was always a sports fan, particularly of the Indy 500 in his home state. But he consistently tackled all sports. The Jets and Knicks were regular punching bags in New York, but perhaps Letterman’s best sports joke was this one:

Letterman spent plenty of time in Los Angeles as a young Comedy Store hotshot, but did all his TV hosting in the Big Apple. Still, he nailed the spirit of the smoggy City of Angels with this one: “Fall is my favorite season in Los Angeles, watching the birds change color and fall from the trees.”

Of course, New York has its own natural beauty, and thus, its own bird material from Letterman:

The synergy between Letterman and New York was very strong. He was centered in Times Square, and just like most New Yorkers do, Dave showed his affection through brutality. Nothing unites New Yorkers like complaining about New York!

“People say New Yorkers can't get along. Not true. I saw two New Yorkers, complete strangers, sharing a cab. One guy took the tires and the radio; the other guy took the engine.”

Letterman was known for his brainy political humor, but was he above a cheap fat joke every once in a while? No he was not. Just ask Chris Christie, or check out this line from 1994 about radio host Rush Limbaugh:

“As you know now, Rush Limbaugh is the new face of the Republican Party, but they'll probably go with a different body.”

There’s something magical about animals and Dave, especially if they’re doing the stupidest tricks possible. The perfect Stupid Pet Trick is one that’s both impressive and completely useless. Sure, some dogs can sniff bombs or rescue stranded skiers in the snow, but can they double-dutch? One of the most perfect examples of this is Bailey the Beagle, who played dead to an impressive — even haunting — level.

Madonna had a memorably raunchy 1994 appearance on "Letterman" in which she called him a “sick f---,” handed him a pair of her dirty underwear, and all in all, used the f-word 14 times. It turns out she was really, really high. No hard feelings though. A few months later, Dave showed up at the MTV Video Music Awards and escorted Madonna on stage, where he kissed her hand and said, “I’ll be in the car. Just…watch your language.”

Recently, Dave’s favorite Paul Shaffer-free band, Pearl Jam, was inducted into the Rock and Roll Hall of Fame, and after Neil Young bowed out, Letterman stepped in to induct them. Eddie Vedder once memorably stepped in when Dave was incessantly singing “Black,” so Dave returned the favor. Still, he couldn't resist taking a shot at another aging superstar: