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CBS's Late Show with David Letterman regularly featured different sketches that follow the monologue and precede interviews with guests. Often these are repeated absurdist segments, involving various cast members, Dave's friends, audience participation, edited or contrived news or promotional videos, or competitions or stunts staged outside the Ed Sullivan Theater. Many of the same sketches originally debuted on Letterman's previous series, NBC's Late Night with David Letterman and The David Letterman Show. The show's regularly scheduled segments consisted of "Small Town News" on Mondays and "Fun Facts" on Fridays. Thursdays often featured a rotating set of three audience participation segments: "Know Your Current Events", "Stump the Band", and "Audience Show and Tell." "Stupid Pet Tricks" and "Stupid Human Tricks", two of Letterman's trademark bits from Late Night, continued to be presented on the Late Show, though much less frequently. There were also running gags, which may continue for about a month, such as playing José Feliciano's "Old Turkey Buzzard" or other sound effects when a card "crashes through the window" or telephone calls from "Len Easton, California Highway Patrol" or Joe McCain on a telephone that Dave acknowledges is a prop that is not connected. Dave expresses amusement or annoyance during these recurring events. This article focuses on sketches that have been featured on the Late Show with David Letterman.

Announcer Alan Kalter's (and before him, Bill Wendell's) introduction of Letterman, while technically not a skit, assigned a bizarre modification to Letterman's name and appears at the beginning of every show. ("And now: Microscopic Sea Creature, David Letterman!") Letterman's title changes every night and often makes reference to a current event. ("And now: Disenfranchised French Youth, David Letterman!") Prior to September 11, 2001, the first line of Wendell's and Kalter's introductions contained humorous descriptions of New York City ("From New York! Where the rats hate the subways, too!"). Once the Late Show returned to air on September 17, 2001, the introduction changed simply to, "From New York! The greatest city in the world!" This remained the standard introduction for over ten years; however, "The greatest city in the world!" is omitted from episodes with guest hosts, as is the host 'title'. In 2011, Kalter took to shortening 'David' to 'Dave' in his introduction of Letterman. At some point prior to late 2012, he once again returned to using 'David'. Beginning on January 2, 2013, the introduction began "From the heart of Broadway, broadcasting across the nation and around the world! ", while Kalter also included a brief self introduction of himself ("I'm Alan Kalter") after introducing Paul Shaffer & The CBS Orchestra.

While Letterman himself often participated in many of the show's non "desk comedy" routines in its earlier years (as well as on Late Night), over time he has increasingly preferred to have others star in them instead. Letterman is now rarely featured in any of the show's frequent pre taped bits. Kalter, bandleader and sidekick Paul Shaffer, and Hello Deli proprietor Rupert Jee are often used instead in comedy routines, as are stage manager Biff Henderson, stagehands Pat Farmer and Kenny Sheehan, handyman George Clarke, "cue card boy" Tony Mendez, head carpenter Harold Larkin, cameraman Dave Dorsett, assistant Stephanie Birkitt, former writers Gerard Mulligan and Chris Elliott (who almost always appear together), and Johnny Dark (a personal comedy friend of Letterman's). Letterman's mother, Dorothy, also made appearances (via satellite from Indianapolis) from time to time, including each Thanksgiving. She perhaps rose to fame mostly as a result of her nightly reporting from the 1994 Winter Olympics in Norway. Former recurring players from the show include Mujibur Rahman and Sirajul Islam (employees of a nearby gift store which has since relocated), Calvert DeForest (a. k. a. Larry "Bud" Melman), and scenic designer Kathleen Ankers (reprising her Late Night role of "Peggy, the Foulmouthed Chambermaid"; on CBS, she was the equally censored "Helen, the Ill tempered Ticket Lady"). Random cameo appearances were made during the span of the show, most notably in the earlier years by the Tony Randall, with Regis Philbin later filling that void. For a while, Letterman took great delight in making fun of his employer, continuing a tradition established at NBC, with senior CBS Corporation executive Les Moonves often serving as the target of his abuse. In time, Letterman's relationship with Moonves improved; a segment titled "More with Les" featured jocular phone calls between Letterman and Moonves.

When Letterman left NBC and moved to CBS to begin the Late Show in the summer of 1993, several of Late Night's long running comedy bits made the move with him, including perhaps his best known, the Top Ten List. Letterman renamed a few of his regular bits to avoid legal problems over trademark infringement (NBC claimed that what he did on Late Night was "intellectual property" of the network). For example, "Viewer Mail" on NBC became the "CBS Mailbag", and Larry "Bud" Melman began to use his real name, Calvert DeForest. One recurring sketch on both the NBC and CBS shows has been the destruction of household items by various methods including explosives, steamrollers, and most often throwing them off the roof of the Ed Sullivan Theater. While popular with fans, Letterman gradually lessened the frequency of such segments. Letterman also has a knack for consuming food products and drinks that appear on his show. Among the items that he has consumed are: wine from a bottle used for a cooking demonstration; various kinds of liquor (while quipping "We're gonna lose our liquor license"); Popeyes "Full Flavor Green Beans"; "motor oil" (actually chocolate syrup) from a bottle that bore a "Quaker State" label; Red Bull; liquid from a bottle that supposedly contained Wite Out; pills from boxes labeled "Lipitor" and "Cialis" (obviously not really the drugs); and even cosmetic products. On one occasion, Letterman took a healthy swig of "low carb suntan lotion" and immediately spit it out, having discovered that it actually was suntan lotion. The Late Show is well known for its repeated absurdist segments, often taking the form of competitions or audience participation. The charm of such segments is often that they are completely pointless, yet are taken seriously by Letterman and all involved.

The Top Ten List appears almost daily on the Late Show, and remains one of the few regular segments carried over from Late Night. It is often the last comedic segment presented prior to the show's first guest. List topics are often inspired by current news and pop cultural events, with typical lists bearing titles such as "Top Ten Signs " and "Top Ten Reasons " The Top Ten List is compiled by the show's writing staff, and is usually read by Letterman, although the show occasionally uses guest presenters. Some Top Ten List themes reappear seasonally, such as the carolers singing "Top Ten Least Popular Holiday Songs." For a long time, the Top Ten Lists were said to have been written in a so called "Home Office". There were various Home Offices before the part was dropped, but the list included Sioux City, Iowa; Grand Rapids, Michigan; and Wahoo, Nebraska all actual, extant towns. (Late Show staffer Mike McIntee's nightly online recap of the show, the "Wahoo Gazette", is named after the Nebraska town.) The Top Ten List has occasionally been a casualty of time constraints. Letterman may announce that the Top Ten List is coming up, or Kalter will promote it before the first commercial, when, in fact, it is not delivered on that night's show and is instead held until the next morning, when it is broadcast across Westwood One/CBS Radio Network.

Great Moments in Presidential Speeches was a near daily segment which presented a series of three video excerpts. Originally, the first two come from actual famous moments, Franklin D. Roosevelt's inaugural speech ("The only thing we have to fear is fear itself") and John F. Kennedy's inaugural speech ("Ask not what your country can do for you, ask what you can do for your country"). The third excerpt featured President George W. Bush in an unintentionally comical moment, often during press conferences or town hall gatherings. These moments frequently focused on President Bush stuttering, finding himself at a loss for words, or uttering a nonsensical Bushism. The excerpts were also often taken out of context for humorous effect, such as when Bush declared, "My kids can't read! ", "My lawyer's a Latino" or "Why should I care about Africa?" The "Great Moments" presentation also featured Dwight Eisenhower, Harry S. Truman, Jimmy Carter, Ronald Reagan, Bill Clinton, and even President Bush's father, followed by Bush himself. One adaptation was of President Kennedy's Berlin speech, with the words "Ich bin ein Berliner", followed by President Reagan's Berlin speech ("Mr. Gorbachev, tear down this wall") in 1987 (Reagan was also featured in another Letterman skit "The Reagan Diaries"), and as always, an excerpt from President Bush's recent speeches. An Abraham Lincoln impostor (Johnny Dark) has also given the "Tear down this wall" speech. President Lyndon Johnson made his debut on "Great Moments" with his declaration not to seek reelection in 1968. George Washington's, Abraham Lincoln's, Roosevelt's, and Kennedy's portraits were shown in the graphic at the beginning and end of "Great Moments." After a few months into the segment's inception, the Kennedy inauguration clip began to include a Late Show staffer (often dressed in formal period garb) superimposed over the empty seat to Kennedy's right. The staffers included announcer Alan Kalter, "cue card boy" Tony "Inky" Mendez (who showed cue cards to President Kennedy), costume designer Susan Hum (whose actions included taking his picture with a disposable camera, removing lint from his shoulder, stealing his wallet, and eating a jumbo pretzel), associate producer Nancy Agostini, and stage manager Biff Henderson. All "cameos" ended with the staffers clapping along in real time response to Kennedy's speech. After the incident when an Iraqi journalist threw his shoes at Bush, flying shoes were shown in the introductory vignettes of the other Presidents, including shoes thrown at Abraham Lincoln giving the Gettysburg Address. The last airing of the sketch involving Bush was January 16, four days before the inauguration of President Barack Obama. The first airing of the sketch after President Obama entered office was Monday, January 26, 2009, but the Obama speech that was captured appeared to have no comedic value, thus heralding the beginning of the Obama presidency as well as fulfilling the actual purpose of the Great Moments segment. On the next GMIPS, aired January 28, 2009, President Obama's face was superimposed over the body of former President Bush in one of his speeches, pretending that Obama was speaking comically, but it was actually the voice of President Bush. After that, other sketches, such as "This Day in the Clinton Marriage", were substituted in the time slot when "Great Moments" previously appeared.

An item is dropped into a tank of water by two models, often referred to by Letterman as "The Hi Ho Girls." The segment starts out with Kalter identifying a household item that will be tested, and a faux prize that is supposedly at stake. A picture of that prize is flashed on screen for a split second. Letterman and Shaffer debate the buoyant properties of the item before they each decide on whether it will sink or float (a frequent deciding factor is the nature of the item's container). Two models then drop the item into the tank while the Late Show "Hula Hoop Girl" (Anna Jack) and "Grinder Girl" (Kiva Kahl) perform on either side of the tank. Depending upon the outcome, large flashing words appear reading, "It Floats!" (accompanied by a ringing bell) or "It Sinks!" (accompanied by a buzzer). Letterman often espouses the educational merit of the game in jest, citing positive feedback from parents, educators, and clergymen. He has acknowledged that while the segment is not popular with the Late Show staff, he insists on continuing it for his own amusement. Letterman joked that the skit was adapted from a similar BBC programme entitled "Is It Buoyant?" He also often advertises the (fictional) "Will It Float" home game, which "has everything you need in a box to play the game for only $19.99." The game consists only of a list of suggested household items and a bottle of water. Latterly, Letterman also plugged the PlayStation 3 version of the "Will It Float?" home game, and in the past would highlight the Xbox 360 version. At one point, he issued viewers a warning to stay away from the knockoff version, "Does it Sink? ", which could be found being hawked by street vendors on Canal Street. After the game is over, Letterman often addresses the women by saying he will see them at "the big 'Will It Float?' party" after the show.

Often presented on Mondays, Letterman presents a series of actual news items, advertisements, and police blotter excerpts which are shown to be unintentionally humorous. In earlier incarnations, these items would be the setup for a punchline from Letterman, and Letterman would occasionally tell the audience to "please wait for the humorous comment." "Small Town News" was a segment that began on The David Letterman Show in 1980 and continued through his tenure on Late Night and the Late Show. For most of the run of the Late Show, Letterman dropped the punchlines, thereby making the sketch nearly identical to Headlines, a sketch on Jay Leno's programs that relied on the news items themselves being the punchline. Letterman long stated that he believed Leno stole the concept from Letterman.

Usually presented on Fridays, the segment consists of Letterman reading a series of trivia, records, and statistics. Letterman explains that the "Fun Facts" are submitted to the show each week by "Gary Sherman", the head of the fictional "Federal Bureau of Miscellaneous Information" (FBMI) and a supposed acquaintance of Shaffer whom Letterman claims he met at Shaffer's wedding. The segment often begins with Letterman presenting a few real facts to set up the premise (although they are often of a humorous nature in their own right and are mistaken by some audience members as made up). He then presents several humorous, fictional "facts." Most of these are of an absurdist nature, such as "The first pair of binoculars had a 1x magnification", or "For a short amount of time, the rock band The Who broke up, and formed two new bands called The When and The What." An irrelevant fictitious promotional announcement of some kind is mixed in on occasion, much to Letterman's confusion. The segment was initially presented on the show sporadically before being made a regular weekly feature. Letterman is also promoting a Fun Facts book (unlike the Will it Float? game, a real book, ).

A camera crew is sent to Rupert Jee in the neighboring Hello Deli, where Jee is asked to invite a potential player from the crowd outside. The player introduces him or herself, relates his or her background, and is told what prize is to be won. Regardless of the outcome, the player is also awarded a "Hello Deli Platter" by the Hi Ho Girls. Recurring games include "Beat the Clock"—echoing the title of a game show from the early days of television—in which the confused player helplessly attempts to stop a clock from counting down to zero, and "What's on the iPod? ", in which Rupert tunelessly sings along to a song on his iPod and the contestant has to guess what song he is listening to. Other games involve a player searching for a hidden item in the deli, and guessing the nature of an item obscured under an item of clothing worn by Jee (such as a Hillary Clinton esque pantsuit). Occasionally, the supposed player is a "plant" and the segment ends when the "player" appears to be severely injured. Johnny Dark has appeared, under various names, as the contestant, in which case the routine consists of him asking so many questions that there is no time for the game itself. Biff Henderson has hosted similar games on the street.

These segments were carried over from Late Night, and consist of three pre selected participants (or in the case of "Pet Tricks", pets and their owners), who each demonstrate an unusual talent or stunt on the stage. Letterman will often precede the segment with the tongue in cheek warning: "Remember, this is not a competition, it is only an exhibition — please, no wagering." While still a trademark feature of the Late Show, the segment has been featured on a more sporadic basis in recent years. The show's regular "Audience Show and Tell" bit will often include an audience member performing a "Stupid Human Trick" type act.

Explod O Pop is a brand of popping corn, and is usually given as a prize to the participants of the audience participation games. Letterman often describes the product using various slogans such as "America's Only Atomic Popping Corn", "It's Carbolicious", and "It's Contaminated with Flavor!" It was available at CBS's online store, with the proceeds benefitting the American Foundation for Courtesy and Grooming, a charity of Letterman's which contributes its proceeds to a wide variety of foundations, most of which are of a health, youth, or educational nature.

During the mid 1990s a frequent Late Show routine was The Quiz Machine, a large device wheeled out onto the stage, which progressively got bigger and more advanced as weeks went on. The Quiz Machine contained answers to questions that Letterman had on his note cards, and would be revealed by contestants pushing buttons or pulling levers. Frequently the machine failed to work, adding to its humor. In a notable appearance by Bill Gates, dressed in lab coat and hard hat, he joked that if Microsoft would have invented a machine this bad, he would have it recalled.