32 Of The Funniest Moments On David Letterman’s Talk Shows

History has seen many great late-night TV hosts, but David Letterman is really someone special. As the host of NBC’s Late Night from 1982 to 1993 and CBS’s Late Show until 2015, he brought an unprecedented energy and perspective to the world of comedy that has served as a clear inspiration to his peers ever since. As a tribute to the Letterman era, let’s look back on some of his greatest hits.

Dave Works The McDonald's Drive-Thru

One of the most iconic remote segments from David Letterman's days on Late Show saw him employed by McDonald's for a day, where he worked at the drive-thru window. Instead of simply taking orders, he indulges in giving the customers a hard time, asking one woman to drive around the building because they are too busy to answer for her at the moment and telling another guy asking for two #3's that he will give him a #6 instead.

Dave Visits General Electric

In 1986, when Letterman was still hosting Late Night on NBC, the network was purchased by General Electric, which gave him the idea to visit his new bosses' headquarters with a basket of fruit as a welcoming gesture. However, he would not make it past the front lobby, thanks to a security guard enforcing the building's strict laws against letting cameras inside.

Dave's Mom Reports The Olympics

Letterman enlisted his mother, Dorothy Mengering, to present a number of remote segments. The first instance of this was in 1994 when she was sent to Lillehammer, Norway, to cover that year's Winter Olympics for Late Show, during which she interviewed the likes of figure skater Nancy Kerrigan and then-First Lady Hillary Clinton.

The Top Ten Words That Sound Romantic When Said By Barry White

Barry White had the kind of voice that could make anything sound smooth and enticing, as demonstrated by one of David Letterman's most ridiculous Top 10 Lists. Accompanied by a trio of backup singers, the legendary R&B musician forever changes the way you might hear words like "jazzercise," "doo-hickey," and the Number One choice, "Oprah."

Joaquin Phoenix "Couldn't Be Here"

In 2009, Joaquin Phoenix appeared on Late Show to promote his film, Two Lovers, but he did not do much promoting and passively mumbled through most of the interview, which David Letterman capped with the perfect quip, "Well, Joaquin, I'm sorry you couldn't be here." The future Academy Award winner would later return to explain himself after it was revealed that his scraggly-haired aspiring hip-hop artist persona was all an act for his brother-in-law, Casey Affleck's, mockumentary, I'm Still Here.

Dave Hangs Out With Richard Simmons

Sometimes, just partnering Letterman with somebody whose personality greatly opposes his own was enough to conjure comedy gold. For instance, the time when the host shot a remote segment chronicling the day he spent with flamboyant fitness guru Richard Simmons, which consisted of visiting random people in their homes and searching for the latest Barbara Streisand album.

Crispin Glover Nearly Kicks Dave In The Face

One of David Letterman's most infamous interviews from his Late Night days, let alone his entire career, saw Crispin Glover from the Back to the Future cast seem to nervously struggle through the entire conversation, culminating in him performing a kick that came uncomfortably close to the host's face. The actor would later return only once more, but this time, he dodged any opportunities for a substantial explanation of his behavior and awkwardly giggled for much of it.

Biff Henderson's Fun With A Bullhorn

David Letterman's longtime stage manager, Biff Henderson, participated in many classic bits. One of his own personal favorites was a remote segment in which he travels the streets of New York yelling at random people with a bullhorn, and often providing them with valuable information, too.

Dave Wears A Velcro Suit

On Late Night, Letterman participated in many a ridiculous stunt that involved him wearing a funny suit constructed with some unusual material or substance. One of the more famous was a suit of velcro, with which he leaped onto a velcro wall and got stuck face first.

Jerry Lawler Slaps Andy Kaufman

In 1982, David Letterman had Andy Kaufman and wrestler Jerry "The King" Lawler on Late Night to discuss their feud, which grew heated before Lawler slapped him across the face, causing the already injured comedian to fall out of his chair. It was revealed years later that this infamous TV moment was not so authentic, as the pair were really good friends pulling a gag on the world.

The Long Debate Around The World's Largest Vase

On Late Night, David Letterman invited on the show a man who claimed to have the world's largest vase, which another person from Canada challenged, claiming his was taller. This inspired a lengthy debate involving polygraph tests and legal experts, before Dave decided to put it all to bed by placing a 35" radio transmitter on top of the vase they had in the studio, bringing its final length to 9'8".

Dave Assures "No One Is Blaming Conan"

David Letterman left NBC after losing the chance to host The Tonight Show to Jay Leno, who would, in 2010, leave the network's leading late-night program for Conan O'Brien to step in, only to take it back just months later. The Late Show host commented on the debacle, mentioning how Leno insisted that fans should not blame O'Brien, which prompted Letterman to point out that no one was pointing fingers at him in the first place.

Dave Is Startled By A Monkey

Like any other late night host, Letterman was known to bring animals on his show from time to time, but he did not enjoy his experience with a monkey on Late Night. The primate continuously lunged toward the host, causing him to exclaim, "She's gonna leap at me and pull a vein out of my neck and kill me!" To make matters even funnier, the monkey was wearing a dress.

The Final TV Appearance By Johnny Carson

David Letterman maintained a strong relationship with Johnny Carson even after both of them had left NBC. In fact, the former Tonight Show host made his last-ever appearance on television in 1994 to present Letterman with that night's Late Show Top 10, much to the audience's delighted surprise.

Dave Presents The Flashing Party Horses

Similar to saw horses with flashing lights placed around accidents or road construction sites to ensure safety, the "Flashing Party Horses" are smaller in stature and used to surround a party guest who has had a few too many and has collapsed on the floor. Future SNL one-season wonder Chris Elliott helps Letterman demonstrate the faux product by donning a tuxedo as the inebriated party guest.

Kamarr The Discount Magicians Puts Paul Shaffer In A Guillotine

One of the most amusing recurring guests that Dave Letterman would have on Late Night was Greece's own Kamarr the Discount Magician, whose illusions were always worth the price of admission. One of his most memorable appearances saw him place band leader and music director Paul Shaffer in a guillotine that he promised would pass right through his neck, leaving him unharmed, but would chop down on the cucumber beneath him.

John Candy Takes On Wasps In The Studio

One funny Late Night-era bit sees comedy legend John Candy interrupt his interview with David Letterman when a wasp appears on the back of his neck, prompting him to take care of the studio's infestation. He returns from his interspecies quarrel with a bag full of winged pests and a few gross clusters of stings on his face.

Dave's Shocking Diet Tip

In response to a fan letter asking for tips on how to lose weight, Dave presents a solution in the form of a visual demonstration. He takes a 12-volt car battery, attaches one clamp to his earlobe and the other to his soup spoon, and indulges in his meal, experiencing a shock that just "melts the fat" right off.

Camping With Barry White

After joking for several episodes about what it would be like to camp with Barry White, David Letterman invited the "Can't Get Enough of Your Love, Babe" singer onto the show for an official demonstration. He opens an episode of Late Night with a lesson on how to treat a snake bite, using White as his subject, and presents a few products essential for the occasion, including a walkie-talkie equipped with a woofer powerful enough to match the singer's deep baritone.

Dave Hounds Paris Hilton About Her Prison Stint

David Letterman himself has admitted that he could be a little too mean to his guests for the sake of getting a laugh, and one of the most notorious examples is when, in 2007, he repeatedly asked Paris Hilton about her 22 days in prison for violating parole. At one point, she pleads that she does not want to talk about it anymore, to which he responds, "This is where you and I are different because it's all I want to talk about." The following year, he brought the heiress back to apologize for offending her.

Dave Wears A Suit Made Of Alka-Seltzer Tablets

One of the strangest stunts that Letterman ever performed involving an unusual suit was the time he donned an outfit covered in Alka-Seltzer, which is a brand of effervescent tablets used to treat heartburn, indigestion, or even headaches. Also equipped with an oxygen tank, the stunt sees the host lowered into a vat of water, causing the tablets to dissolve and create a rousing fizz.

Larry Bud Melman's Hilarious Lack Of Interview Skills

Comedian Calvert DeForest recurred on Late Night as his comically average and inept character, Larry Bud Melman, whom Dave would send out into the world for various remote segments, such as one in which he interviewed tourists at New York's Port Authority. The mundane manner of his questions is funny enough, but what makes the bit especially hilarious is the way he continuously brings the microphone away from his mouth too early with each question.

Dave Visits A Store Called Just Bulbs

One of Dave Letterman's most amusing Late Night era remote segments sees him visit a New York store called Just Bulbs, where he asks an employee if they sell anything other than what the name suggests, constantly receiving an emphatic no. When he asks the remarkably patient employee if they sell lampshades, she suggests he "try a store called 'Just Shades,'" at which point the scene immediately cuts to the front of a store called Just Shades.

Dave Meets A Man Who Claims To Have Been Buried Alive Three Times

Letterman discovered and conducted an interview with a man who invented a device that would allow a person who is accidentally buried alive to notify loved ones that they are still breathing. The man was inspired to develop this product after he was mistaken for dead and placed underground more than once.

Brother Theodore's Perplexing Rant

Theodore Gottlieb, better known as Brother Theodore, appeared on Late Night with David Letterman several times, never inspiring a dull moment. The German-American comedian would indulge in an assertive and combative interview with the host before delivering one of his signature, riotous stream-of-consciousness monologues.

Chris Elliott As The Guy Under The Seats

Late Night writer and performer Chris Elliott participated in various recurring segments on the show, including one in which he plays a man living under the studio bleachers who interrupts the show. David Letterman would go meta by making comments about Elliott's approach to the segment that the comedian would immediately take great offense to and respond with petty, threatening remarks.

Paul Shaffer's Freudian Slip

Paul Shaffer is responsible for one of the most infamous moments in SNL history, being the first person to accidentally drop the F-bomb on the live program. However, it was no accident when David Letterman's musical director told the host that he meant to ask his mother to pass the salt, but instead gave an explicit, insulting admission that she ruined his life. It was only a joke, but it inspired Letterman to get Shaffer's actual mother on the phone. After she corrects his grammar, Letterman turns to Shaffer and says, "I see what you mean now."

Gerard Mulligan Fills In For Levon Helm

In 1983, Levon Helm was scheduled to appear on Late Night with David Letterman but did not show up for the interview. Instead, Letterman and segment producer Gerard Mulligan discussed what they would have asked the drummer and vocalist for The Band, inspiring much laughter from the audience over what could have been.

Chris Farley Cartwheels Into The Studio

Iconic '90s Saturday Night Live star Chris Farley never failed to make a grand entrance, just like when he showed up on Late Show with David Letterman and inspired a rousing round of applause by kicking off his appearance with a triple cartwheel.

Biff Henderson Gets Hypnotized

For one fun Late Show segment, David Letterman invited a hypnotist to put members of his staff under his spell, including Biff Henderson, who was supposedly still under hypnosis and fell into a deep sleep on the show. In a YouTube video recalling his favorite moments, the long-serving stage manager did not confirm whether or not he was truly hypnotized, but he did reveal that he saw the hypnosis as an opportunity to relax at work.

Drew Barrymore Flashes Dave

One of the most surprising moments from David Letterman's entire career saw guest Drew Barrymore stand on the host's desk and lift her shirt up right in front of him.

Madonna's Expletive-Filled Interview

Pop star Madonna's 1994 appearance on Late Show gave the censors a lot to worry about. In fact, due to her use of 14 F-bombs, the episode became the most censored in talk show history, according to EW.