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"And now… a man who shouldn't be up this late… David Letterman!"
—Dave's first intro line from 1982
David Letterman (born 1947) is a late-night Talk Show host famous for defining the genre in the post-Johnny Carson era. Letterman's shows (The David Letterman Show in 1980, Late Night from 1982-93, and The Late Show since then) came to be known as examples of the "Anti-Talk Show", a show that is relentlessly self-aware and intent on deconstructing the conventions of the very medium that gives it life.
From the beginning, Letterman fashioned his persona as a smartass host that was "too hip" for the talk show format, and proceeded from there to make a mockery of the entire genre as a result — for instance, he would often barely hide his contempt for almost every aspect of show business, from his producers and writers, to his wardrobe director, his celebrity guests, his sidekick Paul Shaffer, and even his own fame. All of this pales, however, in comparison to his open contempt for his "rival," Jay Leno, to whom he lost the coveted Tonight Show gig after Carson's retirement, a development about which he is still clearly bitter some two decades later.
Letterman took frequent shots at his network (first NBC, then CBS), and then his network's parent company when NBC was acquired by General Electric. He would intentionally bomb jokes in the monologue, and openly waste network airtime on ridiculous gags whose only purpose served to illustrate simply that, "Hey! I'm wasting NBC airtime here!" He eschewed the typical talk show uniform of a tailored suit in favor of a tie, a blazer, khakis...and white Adidas wrestling shoes.
He dropped random things off roofs, blew random things up on the air, staged impromptu audience competitions (in addition to showcasing Stupid Pet, and Human, Tricks), used "viewer mail" segments as an excuse to break out various non sequitur-style sketches, did stunts in a variety of ridiculous suits (made of velcro, tortilla chips, etc.), and essentially offered a biting parody of the Hollywood machine from the perspective of a Midwestern "everyman" who somehow found himself trapped inside the establishment at the height of its decadence.
As a side-effect, Letterman was sort of feared in the business when it came to interacting with the guests. He was intimidating, and could be somewhat mean to them. Until the late 1990s when he started to mellow down, it was fairly well-known that his only real friend in the business was Julia Roberts. In one interview in the early 2000s, Roberts mentioned the fact that Letterman had softened up and that now every actress was a "lovely girl". Letterman's quip was "Oh, you know I'm just woofing."
Ironically, Letterman's influential "anti-talk show" sensibility ended up saving the talk show format as we know it at some point towards the end of Carson's stint as host of The Tonight Show. Without Letterman mocking the genre in the 1980s, today's genre staples (especially Conan O'Brien's shows) would likely not exist in their current form.
- Andy Kaufman: Frequent guest in the show's early years (until he was too ill to make appearances) — even after the Jerry Lawler Worked Shoot, and even as Kaufman became persona non grata on other mainstream shows such as Saturday Night Live. Simply put, Kaufman's work suited Letterman's sensibilities perfectly.
- Arson Murder And...umm...Jaywalking: As part of Letterman's subversion of the form, as a rule #1 is almost never the funniest joke in the Top Ten List. The studio audience will be applauding anyway.
- Ascended Extra: Many members of he production staff and crew have become familiar faces to viewers and even been utilized in bits, such as stagehand Biff Henderson, production assistant Barbara Gaines, and former producer and director Hal Gurnee and Robert Morton, respectively.
- Big Applesauce: New York-based, unlike the LA-based Tonight Show.
- Biting the Hand Humor: On Late Night, Letterman constantly took shots at NBC and their parent company, General Electric. And he's poked plenty of fun at CBS since his channel hop.
Dave (standing in front of a giant CBS eye) Just between you and me...isn't that eye thing...kinda creepy?
- Body Horror: "Things More Fun Than Reading The Sarah Palin Memoir" consists of Body Horror Stock Footage, mostly from old movies.
- Brick Joke: A relatively recent joke involving newly installed button on Dave's chair. He's told to press it - cue Dave getting blasted out of the building (everyone is then told he's okay). A couple of episodes later, Dave reveals that said button is still there. He pushes the button, and we think we know what will happen next, but instead, the head of the orchestra is blasted outside. Another push of the button, though, and Dave's right behind him.
- The Bus Came Back: Dave made a number of guest appearences on Late Night with Conan O'Brien.
- Calling the Old Man Out: Kirstie Alley got one over on Dave when she appeared on the Late Show in 2011. Having been a Woobie for Letterman in the past, particularly during her run on Dancing With the Stars, she brought with her Dave's cruelest jokes and repeated them back to him. The audience booed the jokes. May count as a Crowning Moment of Awesome for Kirstie.
- Casanova Wannabe: Announcer Alan Kalter.
- Captain Ersatz: Chris Elliot's running characters The Fugitive Guy (The Fugitive) and The Regulator Guy (The Equalizer).
- Catch Phrase: Whenever the subject of drinks comes up, "I don't think there's a man, woman, or child alive today who doesn't enjoy a refreshing beverage."
- "How we doing on time?"
- "I wouldn't give my troubles to a monkey on a rock."
- (When a joke set-up has a fairly obvious punchline coming up) "I think we can all see this one coming down 2nd Avenue."
- Cats: Shortly after moving to the Ed Sullivan Theatre, Dave would parody Sullivan's habit of introducing celebrities in the audience. One night he introduced a confused looking Paul Newman who stood up, said "Where the hell's all the singing Cats?" and walked out.
- Part of the joke here is that the Winter Garden Theater, where Cats spent its Broadway run, is one block down and across the street from the Ed Sullivan Theatre.
- Channel Hop / Executive Meddling: Pissed that NBC execs picked Jay Leno over him to host Tonight, Letterman took his show to CBS, where he had to make a few changes for the 11:30 slot that seemed minor at first but ultimately ended his peak until NBC's Jay-vs-Conan meltdown in 2009.
- Carson never forgave NBC for picking Leno over Letterman, as he always thought that Letterman was the best choice to succeed him. As such, whenever Carson got an idea for a joke while in his retirement, he would send them to Letterman instead of Leno. And Carson himself showed up on-air, the applause was deafening. Both men were clearly overwhelmed by it.
- Chew Toy: Poor Alan Kalter (aka The Announcer).
- City of Weirdos: A recurring Letterman gag is to see "How many guys in X costumes can fit in a Y?", trying to get a rise out of passers-by. People seldom react.
- Cluster F-Bomb: In 1994, Madonna dropped the F-word at least 13 times, which were all censored, during her interview, and tried to get Letterman to smell her panties.
- Coattail-Riding Relative: Dave makes the occasional joke about his uncle Larry trying to capitalize on his success.
- Comic Books: Bizarrely, Letterman was in an issue of The Avengers in 1984. A parody version of Letterman ("David Endochrine") was murdered (along with his audience) by The Joker in Frank Miller's The Dark Knight Returns.
- Complaining About Things You Haven't Paid For: Dave sometimes jokingly tries to preempt complaints from the studio audience saying things like "You didn't pay anything to get in here, you know."
- Also at the midpoint of the show, Letterman would announce the guests booked for the next episode. Sometimes the audience would boo softly if it was a big name guest, leading Dave to say "Oh? Something wrong with tonight's show?"
- Crapsack World: ...Although Letterman's openly-silly style of humor clashes with his seemingly cynical presentation just enough to cause debate on where he stands on the Sliding Scale of Idealism Versus Cynicism.
- Deadpan Snarker
- Deconstruction / Deconstructive Parody
- Don't Try This At Home: Warning disclaimer for many Late Night stunts in the 1980s. Occasionally subverted by Letterman with the addendum "Go to a friend's house instead."
- During Stupid Pet Tricks, "Please....no wagering", which in turn is subverted by Stupid Human Tricks's disclaimer "Go ahead and wager."
- Drum Roll: All upcoming gags receive this, sometimes to intentionally anti-climactic results.
- Dave often also asks Stupid Pet Trick contestants if they want a drum roll or if they think it will scare the pet.
- The Equalizer: Edward Woodward appears in this clip as Dave calls the number in the Equalizer's in-universe ad.
- Expy: Jay Leno's "Headlines" is the exact same bit as Letterman's "Small Town News"...except Leno copies the articles (other people's works) and sells them in book form.
- Letterman's "Small Town News" predates "Headlines" by approximately 10 years. It can be argued that they both stole the concept from Steve Allen's Tonight Show.
- To his credit, Letterman has always credited Allen for insperation for a number of the Late Night/Late Show spots such his Suit of Alka-Seltzer being an Expy of Allen's Suit of Teabags.
- Fake Band: In 1999, Letterman used the faux Boy Band "Fresh Step" to mock groups like the Backstreet Boys and N'Sync.
- Foil: During the rare times that Madonna was allowed to come on, she would happily ruin Letterman's planned schedule of events via grandstanding and showboating.
- Frivolous Lawsuit / Disney Owns This Trope: When Letterman left for CBS, NBC threatened one over the "intellectual property" of Stupid Pet Tricks and the Top Ten list, until both Letterman and Leno's mockery embarrassed them out of it. Among the problems with the lawsuit: Top ten lists had been done for years by people before Letterman, and Letterman actually owned the Stupid Pet Tricks property from an earlier show of his.
- Then-current NBC anchor Tom Brokaw made a surprise appearance during Letterman's first CBS monologue and took one of the cue cards, claiming the jokes were NBC intellectual property.
- After asking Johnny Carson if he can use "Stump the Band", Johnny quips "Stump the Band? Sure, I can hardly claim that as intellectual property!"
- The Frugal Gourmet: The late Jeff Smith almost out-Lettermans Letterman in this clip, and Paul's line might be considered Getting Crap Past the Radar by 1991 standards.
- Game Show: Dave appeared on many games from about 1975-80, and occasionally says "Not a match, the board goes back" when a joke falls flat. He's also done several parodies, which you can watch on the Game Show Appearance page.
- Getting Crap Past the Radar
- Guest Host: Letterman became famous as Johnny Carson's guest host on The Tonight Show. Much later in his career, Letterman would have heart surgery and a bout with shingles that led to famous guest hosts for his show, like Regis Philbin, Bruce Willis, Will Ferrell, Jimmy Fallon, Elvis Costello, Adam Sandler, Tom Green, Megan Mullaly, Vince Vaughn, and Bonnie Hunt.
- I Am Not Shazam: Every so often, you'll still hear someone refer to the current CBS show as Late Night With David Letterman.
- Jerkass: Letterman's interview style was often charitably described as "acerbic" in his early days. Cher told him that for years she didn't want to come back on his show because she thought he was "an asshole".
- Keep Circulating the Tapes: With Late Night co-owned by NBC Productions and Letterman's World Wide Pants, don't expect a "Best Of" DVD anytime soon.
- Left It In: Letterman frequently says "We'll edit that out later." They never do.
- Little-Known Facts: "Fun Facts".
- Logo Joke: The first airing of Late Show was prefaced with the CBS ID of the era playing as normal, except Dave said "This is CBS" instead of the usual V/O guy, and he actually appeared midway through the ID.
Dave (in another promo in front of the eye): Don't you think that eye thing is.....kinda creepy?
- Long Runner: Dave just celebrated 30 years in late night television. However this is split between two shows, Late Night on NBC and CBS's the Late Show.
- Lovely Assistant: Grinder Girl and Hula Hoop Girl in "Will It Float?"
- The pair may also be an example of Ascended Extras as well — both originally showed up in an earlier recurring sketch called "Is This Anything?", during which the audience was treated to a few seconds of someone's offbeat act, after which Dave and Paul would decide whether the act was "anything" worthwhile. ...They really liked Grinder Girl and Hula Hoop Girl.
- Medium Awareness
- One of Us: Dave has made it pretty blatant that he likes classic game shows, among other things.
- Only Sane Man
- Orphaned Punchline: This clip from a 1985 episode has guest Johnny Carson delivering the punchline to a joke that he'd started on The Tonight Show earlier that night: "And the man says to Mrs. O'Hara, 'I'm not so sure about that, he got out three times to go to the bathroom'."
- The Pete Best: Frank Owen, Dave's Musical Director for his Morning Show before Paul.
- Playing with a Trope
- The Rival: Jay "Big Jaw" Leno became this after he beat Letterman out as Carson's successor on Tonight, and Dave moved to CBS to compete directly with Leno in the 11:30 PM slot. The bad blood resurfaced in 2009 after some of the worst Executive Meddling of all time caused Leno to first move out of The Tonight Show and then back in after less than a year because of failing ratings. Letterman joined many others in accusing Leno of "reneging" on his previously-announced "retirement," although the move had been largely forced on Leno and he only reteurned after his ostensible successor, Conan O'Brien (who had earlier succeeded Letterman himself on NBC's Late Night show), had already decided to leave. Despite the bump in Letterman's ratings the events caused, he still tends to come in behind Leno's.
- Although Leno has gotten mileage out of occasional Letterman scandals (notably revelations of Letterman's affair with a staffer), he has been much less inclined to attack Letterman than Letterman has been to attack him. The former friends' relationship remains strained, although Leno has expressed willingness to mend fences.
- Lampshaded to hilarious effect in a promo aired during Super Bowl XLIV.
- Law & Order: Jay Leno Victims Unit.
- Running Gag: Often used to the point of being intentionally unfunny and arguably bordering on Lampshade Hanging.
- One of Dave's more notable phrases, used when a joke falls flat, is "Not a match, the board goes back" — a phrase that should be familiar to anyone who has ever been thanked for playing Concentration.
- Sideboob: On this Very Special Episode, the audience (and later all of Manhattan via the Jumbotron) gets a quick shot of Drew Barrymore's side boob, while Birthday Boy Letterman gets to enjoy the full effect.
- Something Completely Different / Show Within a Show: Late Night would sometimes stage an entire episode in a bizarre, novel way.
- One night, he pretended it was The Morning Show with Dave & Tawny (perhaps a statement on his ill-fated eponymous 1980 series)...and actually seemed like a pretty decent idea.
- Apparently Dave himself was very impressed with this episode. Generally when he would announce that the next night's episode was a repeat, he'd say it's "Just a lousy re-run, don't bother tuning in". But when announcing "The Morning Show" episode's re-showing, he suggested people giving it another viewing.
- On another occasion, he let the audience vote via applause for a "custom-built show".
- Still another episode was an "upside-down show" where the camera rotated 360 degrees throughout the course of the hour.
- One night, he pretended it was The Morning Show with Dave & Tawny (perhaps a statement on his ill-fated eponymous 1980 series)...and actually seemed like a pretty decent idea.
- Star Trek: The Original Series: George Takei narrated "Chris Elliot: Television Miracle".
- Stealth Pun: A staple of Letterman comedy, especially in Top Ten Lists.
- Straw Fan: Predominantly used by Letterman to mock his audience in the "Viewer Mail" segments.
- Studio Audience: Often had a love/hate relationship with Letterman in the mid-1980s; they're all adoration, all the time nowadays.
- Suit Of Awesome: For a while in the 80s David had a number of special suits. Sitting in a giant bowl he was doused with barrels of milk while wearing a Suit of Rice Krispies; Hoisted by a crane he was placed in a giant glass of water wearing a Suit of Alka-Seltzer; And perhaps most famous of all - he jumped off a trampoline on to a wall while wearing a Suit of Velcro to see if he'd stick. He did. As Letterman himself freely admitted, these were inspired by Steve Allen, who during his run as host of The Tonight Show, once sat in a giant tea cup with warm water and 200 lemon wedges while wearing a Suit of Teabags.
- Talk Show
- Teens Are Monsters: "Dwight the Troubled Teen" skits.
- The Eponymous Show: Letterman's first morning show on NBC was The David Letterman Show. But even today, his various incarnations are all lumped together as The Letterman Show.
- Top Ten List: Perhaps Letterman's most well-known Trope. An attempt to eradicate all of those insipid "top ten lists" forever, from the inside, by making lists so intentionally lame that the phenomenon would die on the spot. Ironically, though, the Top Ten actually became one of Letterman's most popular bits, and is his hallmark to this day.
- TV Strikes: Letterman circumvented the 2007 WGA strike by negotiating a special deal that allowed his writers to return to work early.
- Twitter: Dave has composed tweets in mid-show, in full Grumpy Old Man mode commenting sarcastically about how "this is so much easier than a phone call" and spelling out the words "Hash Tag" in the tweet itself.
- Unfortunate Names: For a month in 1995, Dave was absolutely obsessed with a man from Saskatchewan named Dick Assman. Yes, you read that right.
- UST: Between Dave and Julia Roberts, of all people. Also with Gillian Anderson in this appearance.
- Vacation Episode: The crew once spent a week in London, which also marked the only time the series has seen the light of British terrestrial television - BBC2 aired those episodes.
- Vanity Plate: Letterman's company, Worldwide Pants, has a vanity plate that is memorable for the non-sequiteur phrases announced during the display of the plate.
- Vitriolic Best Buds: Dave has had this relationship with several guests, most notably Regis Philbin and Charles Grodin.
- Worked Shoot: Letterman's infamous interview with actor/comedian Andy Kaufman and pro wrestler Jerry Lawler has been confirmed as a staged event in the intervening years. Dave's disastrous chat with Crispin Glover, on the other hand, appears to be all too real.
- What Could Have Been: The Super Bowl commercial with Oprah and Leno was planned to feature Conan O'Brien, but Conan's deal with NBC stipulated that he couldn't appear on television for several months after leaving The Tonight Show.
- Possibly the biggest 'What Could Have Been' ever.... The Tonight Show starring David Letterman.
- Writing Around Trademarks: Due to NBC owning the names (but not the formats) to several of Letterman's skits.
- The World's Most Dangerous Band --> The CBS Orchestra. 
- Viewer Mail --> CBS Mailbag.
- The Top Ten List --> The Late Show Top Ten List.
- Larry "Bud" Melman --> Calvert DeForest.
- Your Favorite: Dave once had his Mother on the show to demonstrate how she made his favorite snack — Fried Bologna Sandwiches.
- (This is either a subtle Take That to NBC's "The NBC Orchestra" and/or a stealth tribute to Carson as The NBC Orchestra, led by Doc Severinsen, was featured on The Tonight Show.)