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Series / The Late Show with David Letterman

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The Late Show with David Letterman is an American late-night Talk Show hosted by David Letterman on CBS, the first iteration of the Late Show franchise. The show debuted on August 30, 1993. The show's music director and leader of the house band, the CBS Orchestra, was Paul Shaffer. The head writer was Matt Roberts and the announcer was Alan Kalter.

In 2014, Letterman announced his retirement and the final episode of Late Show aired on May 20, 2015. The show was then succeeded by The Late Show with Stephen Colbert, hosted by Stephen Colbert, which premiered on September 8, 2015.

In 2002, Late Show with David Letterman was ranked No. 7 on TV Guide's 50 Greatest TV Shows of All Time. As host of both Late Night and Late Show for more than 30 years, Letterman surpassed Johnny Carson as the longest running late-night talk show host in 2013. That same year, Late Night and Late Show were ranked at #41 on TV Guide's 60 Best Series of All Time.

"From the home office in Wahoo, NE, it's tonight's Top Trope List":

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    Tropes A to D 
  • Affectionate Parody: Shortly after moving to the Ed Sullivan Theatre, Dave would parody Sullivan's habit of introducing celebrities in the audience. The first night he introduced a confused looking Paul Newman who stood up, said "Where the hell's all the singing Cats?" and walked out.
  • The Announcer: Bill Wendell (1993-95, as a carryover from Late Night), Alan Kalter (1995-2015)
  • Annoying Laugh: He often employs this deliberately.
  • Arson, Murder, and Jaywalking: Jokes aside,Explanation  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 director and producer Hal Gurnee and Robert Morton, respectively.
  • Ashes to Crashes: Paul Rudd described his surreal experiences with his father's ashes in Ireland. Yes, he got "Lebowski'ed".
  • Back for the Finale: The show's final top ten list was delivered by frequent guests and good friends of the show, such as Jerry Seinfeld, Steve Martin, Julia Louis-Dreyfus, Tina Fey, and Bill Murray, who was Dave's first guest on NBC in 1982 and on CBS in 1993; and Foo Fighters, a frequent musical guest on The Late Show, also came back to perform "Everlong", just as they did years prior (and cancelled a tour to do it) after Letterman's heart surgery.
  • Badass Boast: After 2008 Republican Presidential Nominee Senator John McCain told Letterman that he couldn't appear on the show in September 2008 due to his campaigning schedule,note  only to turn up on The Tonight Show with Jay Leno, Letterman proclaimed, "The road to the White House goes through me!"
  • "Balls" Gag: One of Letterman's recurring jokes were his observations about the squirrels in Central Park — which inevitably led to some sort of Double Entendre about what they were doing with their nuts.
  • Big Applesauce: New York-based, in contrast to the L.A.-based (prior to 2014) Tonight Show.
  • Big Budget Beef-Up: CBS lured Letterman away from NBC with a huge pay raise, along with seemingly unlimited resources and technological advances, starting with moving him from a cramped studio at Rockefeller Center to the fully-refurbished Ed Sullivan Theatre on Broadway, and he responded by turning the show into more of a spectacle than Late Night had been.
  • Big "WHAT?!": Anything that results in a look of mock horror and him proclaiming "WHAT! WHAT!"
  • Biting-the-Hand Humor: 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.
  • Book Ends: Bill Murray was Dave's first interview guest on both Late Night and Late Show. Guess who his final Late Show interview guest was? What's more, Letterman introduced Murray for the last time using virtually identical language to when he introduced him for the first time:
    David Letterman: It's a pleasure for me to introduce my first guest. With credits that include Saturday Night Live, the films Meatballs, Caddyshack, Where the Buffalo Roam, and Stripes, Bill Murray has become one of the top box-office draws in show business, and besides that he's a very funny man, and it's a pleasure to have him [on our first program / as our next-to-the-last show guest]. Ladies and gentlemen, Bill Murray.
  • Brick Joke: A joke relatively late into his run 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.
  • Buffy Speak: Any time he'd ask about a segment, "Did we open the thing?" or "Did we open the deal?"
  • 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.
  • Canada, Eh?: Paul Shaeffer is a proud Canadian who wears the "Snowflake" lapel pin that signifies him as a Member of the Order of Canada at all times. When Michael J. Fox made an appearance without his own pin, Shaeffer called him out and Fox made sure to wear it for subsequent interviews.
  • Casanova Wannabe: Announcer Alan Kalter.
  • Captain Ersatz: Chris Elliot's running characters The Fugitive Guy (The Fugitive) and The Regulator Guy (The Equalizer).
  • Catchphrase
    • 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."
    • (Wiggling some blue cards) "If these weren't actual letters from actual viewers....could I do this?"
    • "Did we open the thing?" (in reference to the Top Ten List theme song/graphic. Letterman has said this on practically every episode for years).
  • The Chew Toy: Poor Alan Kalter (aka The Announcer).
  • Christmas Carolers: During many a Christmas season he'd bring on a group of carolers to sing the "Top Ten Least Favorite Christmas Carols" (which are traditional Christmas carols reworded to reflect current political satire topics).
  • Cigar Chomper: For many years Letterman was known for his love of cigars, although he's apparently given them up.
  • 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 Batman: The Dark Knight Returns. Funnily enough, David Endocrhine was voiced by Conan O'Brien in the animated adaptation, and come 2015, the cast of Avengers Ageof Ultron would feature heavily... on Jimmy Kimmel Live!.
  • 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?"
  • Couch Gag:
    • The opening introduction for Dave ("And now, a man who...") was different for every episode.
    • Until September 2001, New York City was always introduced differently ("From New York, pony rentals not included..."). After the show's first post-9/11 episode, New York City was introduced as "The greatest city in the world". The gag would be revived towards the end of the show's run as introducing the show from pretty much anywhere.
  • Crossover:
  • 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. Letterman quipped that he couldn't believe Brokaw used "intellectual" and "NBC" in the same sentence.
    • 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!".
  • Disposable Intern: In one episode of The Late Show a man who had invented a new super-powered pogo stick is demonstrating it outside the theater. Dave has the man pogo stick over a row of interns, since even if he does accidentally hurt one it won't matter.note 
  • Don't Try This at Home: During Stupid Pet Tricks, " wagering", which in turn is subverted by Stupid Human Tricks's disclaimer "Go ahead and wager."
  • Drum Roll, Please:
    • 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.

    Tropes E to M 
  • 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 incarnation of The Tonight Show. To his credit, Letterman has always credited Allen for inspiration 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"note  to mock groups like the Backstreet Boys and *NSYNC.
  • 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. This was likely out of revenge for Dave introducing her as someone who "slept with some of the biggest names in the entertainment industry."
    • Perhaps Dave's most mis-timed joke happened one evening in 1989, when he welshed on a restaurant bill and left his unsuspecting dinner partner (Oprah Winfrey) to pay, ho ho. Oprah froze him out for almost twenty years (and it was suggested, by Roger Ebert and other guests, that many doors were shut to Letterman as a result), but eventually accepted Dave's three bajillionth apology. They are now friends again.
    • Cher famously called him an "asshole" during an interview, to his face.
    • In what is becoming a rite of passage for pop stars, Lady Gaga ate his note cards after Dave asked about her lingerie buying habits.
  • Fourth-Wall Mail Slot: "CBS Mailbag", in which he reads mail from viewers.
  • Freak Out: Dave was witness to Craig Nicholls from The Vines having one of the biggest freak-outs ever during a 2003 appearance, creating some incredibly uncomfortable television in the process. Even Dave couldn't play that one off. note 
  • Fridge Logic: Invoked this in a joke about the Angelina Jolie movie Salt, saying that it is so compelling you don't realize that it makes no sense until you are walking back to your car.
  • Funny Foreigner: Foreign correspondent Graham Fenwick-Jones, who spoke almost without exception in impenetrable British slang with no subtitles.
  • Genre Deconstruction: Letterman's entire schtick is based around deconstructing the traditional TV talk show and its conventions.
  • Greeting Gesture Confusion: In 2012, he took to fist-bumping some of his guests, specifically the "exploding" variety. Most of the time his guests are confused - often thinking he's going for a traditional handshake - but every once in a while someone (who has probably been prepped beforehand, or is a regular viewer) joins in on both the bump and the explosion, at which point Dave is both impressed and amused.
  • Grumpy Old Man: 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.
    • Once during a segment in the audience, the first two people he talked to were an advisor and an analyst.
    "One guy's an advisor, one guy's an analyst, doesn't anybody work anymore?"
  • 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, Bill Cosby, Will Ferrell, Jimmy Fallon, Elvis Costello, Adam Sandler, Tom Green, Megan Mullaly, Vince Vaughn, and Bonnie Hunt.
  • Heh Heh, You Said "X": From "Top Ten Reasons Mills College Students Don't Want Men Attending" (May 18, 1990)
    "7. Guys often whoop and holler when words like breast appear in sensitive poetry."
  • Impossibly Cool Clothes: 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.
  • Insignificant Anniversary: Early in the show's run Dave announces with great fanfare that it's the 1,000th show, along with a large graphic. Dave then says "oh, wait, that's a typo. It's actually our 100th show." A much smaller "100" graphic is shown, along with a much more subdued fanfare from the band
  • Jumping Out of a Cake: Bill Murray on the second-to-last Late Show episode.
  • Lampshade Hanging: His explaining away jokes that didn't work.
  • 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?
  • 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.
  • Man on Fire: When the movie of the same name was coming out, Dave would have a guy running around the stage screaming with his shirt on fire until he ran to the back and the fire was extinguished.
  • Manipulative Editing:
    • Played for Laughs, of course. Dave once cut up a John McCain speech to make it seem like McCain was calling Franklin D. Roosevelt his "close personal friend."note  Dave even once called it "Great Moments in Unfair Editing."
    • Sarah Palin was also a frequent subject of this during the 2008 U.S. Presidential Election. In one instance, Dave manipulated a Palin speech to make her sound incompetent (hyphens indicate jump cuts): "It's so clear I have—no—experience; John McCain should—get rid of—me."
  • Memetic Psychopath: Invoked, as Letterman for a time had a bit called "Dr. Phil's Words of Wisdom", which were quick out of context clips from his show intended to make him look as bad as possible, including such quotes as "Let's just kick her ass," "Children hate me," and "I would eat some Fruity Pebbles if I got hungry enough." Usually, Dave would end the bit by saying, "Someday they're going to close down that little parlor game and put that man in jail."
  • Men Are Uncultured: From "Top Ten Reasons Why Mills College Students Don't Want Men Attending" (May 18, 1990)
    "9. Annual production of Chekhov's Three Sisters replaced by 3-day Stooge-a-Thon."
  • Must Make Amends: In October of 1993, Bill Hicks made his last TV appearance before his death, on Late Show, and performed a set that didn't make it to air due to its content. Bill was, uh, not pleased with this, and made no secret of his bitterness during his final months. Sixteen years later, on January 30, 2009, Dave discussed the incident, took the blame for the decision, and had an interview with Bill's mother, Mary Hicks, where he profusely apologized. He then presented Bill's unaired set in its entirety.

    Tropes N to R 
  • Once a Season:
    • Every time Rosh Hashanah (the Jewish New Year) comes along, Dave mentions what year it is on the Jewish Calendar (for example, 2014 was 5774), and that he's still writing the previous year on his checks, with Paul saying "You crazy nut."
    • He makes similar jokes about the Chinese New Year, mentioning that it's the year of some particular animal, and say that he's still writing the previous animal on his checks.
    • The show's Christmas Episode always featured a few regular bits: Paul Shaffer reminiscing about an episode of the Sonny & Cher variety show and Cher's performance of "O Holy Night," complete with an imitation; Jay Thomas telling his famous story about an adventure with Clayton Moore of The Lone Ranger, followed by Thomas and Dave competing to see who could knock a meatball off a pizza on top of a Christmas tree by throwing footballs at it; and a special performance by Darlene Love singing "Christmas (Baby Please Come Home)," Letterman's favorite Christmas song.
  • One Extra Member: On the "Small Town News" segment, one of Dave's self-described favorite categories of news is things like "Classical Trio performs" with a picture of 4-6 members.
  • Orphaned Punch Line: Once he and Paul had been talking about "Ventriloquists' Week" and he threw in, "Wednesday we'll be having Dick Cheney and George W. Bush!"
  • Outside-Context Problem: As part of the show's Rule of Funny, many times someone will just walk over to Dave, say something insulting, and promptly disappear and never be seen or referenced again.
  • Politicians Kiss Babies:
    • In a joke about New Jersey Governor Chris Christie, Letterman said when running for office Christie "got confused. Kissed a blintz, ate a baby!"
    • Another Letterman gag: in "Top 10 signs [then Presidential candidate] Herman Cain is losing it."
      Kissed a picture of himself and signed a baby
  • Precision F-Strike: In re Leonard Tepper walking out in a giant squirrel costume:
    Dave: I know what you're thinking. This (bleep) better be funny.
  • 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 returned 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. For his part Letterman has expressed grudging respect for Leno's skills, characterizing him as a great standup comic. Letterman has never considered himself as such, which is why he stopped touring basically as soon as he could get a TV show. During a 2012 interview with " fellow Leno victim" Conan O'brien, both got their shots in, Letterman stating that in the 70s all the stand up comedy circuit admired Leno's talent, but all knew that deep down he was just 'a big brat' whenever he wanted something. Lampshaded to hilarious effect in a promo aired during Super Bowl XLIV.
  • Rule of Cool: From the January 5, 1994 show:
  • 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.
    • The "Countdown until Bernie Madoff's Release".
    • "It's always the horn section!"
    • This exchange:
      Dave: Hal, can you [do something technical] for us?
      Hal: Sure, Dave.
      Dave: [to the audience] Our director, Hal Gurtner.
      Hal: That's Gurnee, Dave.
      Dave: Oh, right! Gurnee.
    • Constant reference to his unruly hair, often pretending it was actually a wig.
    • Whenever Gene Siskel and Roger Ebert are guests, David will ask them why the Academy Awards keeps snubbing Barbra Streisand. (answer: She's ineligible because she didn't make a movie that year)

    Tropes S to Z 
  • Sad Clown: He's famously guarded about discussing his private life, but in interviews during his final weeks on the air he candidly talked about his long struggles with depression and alcoholism when he was younger.
  • Santa's Sweatshop: One Top Ten list ("Top Ten Elf Complaints") implies this trope. Entries include "Santa's union-busting goons killed a guy last spring," "Workman's comp doesn't cover mistletoe lung," and "dead elves just tossed out on tundra."
  • Sassy Black Woman: Parodied without mercy with "Pat and Kenny Read Oprah Transcripts," with the very white, very male Pat and Kenny doing Dramatic Readings of transcripts of Oprah's interviews with celebrities, which always start with "Girl, girl, girl, girl, girl..."
  • Self-Deprecation:
    • All the damn time, especially when the Top Ten List is read by any kind of guests. It will ALWAYS include some reference to the guests wanting to be on Leno or a comment on how old Dave is.
    • His notoriously unsuccessful stint hosting the 1995 Oscars immediately became joke fodder on The Late Show. Two years afterward he turned up on the Oscars again in a parody of The English Patient that climaxed a montage of spoofs featuring that year's host, Billy Crystal. Crystal finds himself running for his life from a crashing plane piloted by Dave, who suggests that Billy use the "Oprah...Uma" bit that more or less summed up how badly Dave bombed.
    • In response to NBC putting up a billboard in New York City proclaiming The Tonight Show the #1 show in late night, Letterman had CBS put up a bigger billboard, declaring his show #3 in late night. (At the time, ABC's Nightline finished in second.)
  • Shout-Out:
    • The World's Most Dangerous Band is a reference to 1960s-1970s pro wrestler Dick the Bruiser, whose Red Baron was "The World's Most Dangerous Wrestler" and was the owner and top star of the World Wrestling Association in Dave's hometown of Indianapolis, IN.
    • The "CBS Mailbag" segment opened with Perry Como's "We Get Letters."
    • Dave opened the February 18th 2015 show's monologue by introducing a shot of the audience and saying "These people, dressed as they are..."
  • The Show Must Go On: While New York City hunkered down for the imminent arrival of Hurricane Sandy in October 2012, the show was recorded without a studio audience and a skeleton crew. A mannequin was "operating" one of the cameras and an intern held up handwritten text cards for the Top Ten List. (Jimmy Fallon, also in NYC, did a similar show.)
  • Show Within a Show: Chris Elliott's The Fugitive Guy complete with opening and closing credits, theme song, 'Tonight's Episode' Quinn Martin type titles, and a final episode in which Dave and Chris hunt down The One Legged Man.
  • Sideboob: On a 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.
  • Spell My Name with a "The": The show's title was during Dave's tenure was indistinctly spelled as either "The Late Show" or just "Late Show", although the latter ultimately seemed the prefered spelling, as it was spelled that way on the show's graphics. His successor Stephen Colbert's tenure in contrast always spelled the show's title as "The Late Show".note 
  • Stealth Pun: A staple of Letterman comedy, especially in Top Ten Lists.
  • Studio Audience: Often had a love/hate relationship with Letterman in the mid-1980s; they're all adoration, all the time nowadays.
  • Take That!:
    • To absolutely anyone and anything you can possibly imagine, including himself.
    • During the Tonight Show controversy between Conan and Leno, Dave took many, many shots at NBC and Leno. When Dick Ebersol complained, Dave publicly responded that he was only doing it because he enjoyed it tremendously.
  • Teens Are Monsters: "Dwight the Troubled Teen" skits.
  • Title Confusion:
    • The Late Show is often mistakenly referred to as Late Night and vice versa. In reality, Late Night still exists at NBC and is hosted since February 2014 by Seth Meyers. Oddly enough considering that Conan O'Brien had a 16-year stint hosting the show after Letterman.
    • It gets worse...during the second to last episode's monologue, Dave showed a series of clips from local CBS station newscasts (his own network no less) noting Dave's retirement from The Tonight Show.
  • Top Ten List: Perhaps Letterman's best-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.
  • Unfortunate Names: For a month in 1995, Dave was absolutely obsessed with a gas station employee from Saskatchewan named Dick Assman. Yes, you read that right. He eventually even got the guy on the phone, first talking to his business partner before saying "I'd love to keep talking to you, but your name isn't silly enough."
  • Unresolved Sexual Tension: Between Dave and Julia Roberts, of all people. Also with Gillian Anderson in this appearance.
  • Unusually Uninteresting Sight: 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.
  • 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.
    • He did a week of shows in Hollywood in 1994, during which Johnny Carson made a couple of cameos that turned out to be his final television appearances.
  • 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.
  • We Used to Be Friends: For all the vitriol Dave directed towards Jay Leno in later years, the latter had actually been a frequent guest when Dave was still with NBC. They seem to have fallen out at some point before Jay was selected to host The Tonight Show, but that incident certainly drove the final nail in the coffin of their friendship.
  • 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, though only Lawler and Kaufman knew what was going to happen. As a result, Letterman's look of surprise when Lawler and Kaufman started fighting each other was completely genuine.
    • Dave's disastrous chat with Crispin Glover, on the other hand, appears to be all too real.
    • Dave wasn't in on Joaquin Phoenix's bizarre in-character appearance in 2009, but Joaquin's subtle laughing at a couple of Letterman's quips probably tipped him off as to what was going on (He was pretending to have a Creator Breakdown invoked as a commentary that Celebrity Is Overrated). In a later appearance Phoenix pointed out that he actually broke character at the very end, getting up and shaking his hand with surprising energy compared to the lethargic interview.
  • 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. note 
    • Viewer Mail --> CBS Mailbag.
    • The Top Ten List --> The Late Show Top Ten List.
    • Larry "Bud" Melman --> Calvert DeForest (his real name).
  • Your Favorite: Dave once had his Mother on the show to demonstrate how she made his favorite snack — Fried Bologna Sandwiches.

"Now, stay tuned for [The Late Late Show with] Craig Ferguson! This is Alan Kalter speaking! Good night, everybody!"