David Letterman Trivia
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59 free David Letterman trivia questions with answers — entertainment quiz, new questions added Oct 2026.
David Letterman hosted late-night television for 33 years, longer than his hero Johnny Carson, and reshaped what a talk show could be along the way. This quiz walks through the whole run: the Indianapolis weatherman who congratulated a hurricane, the short-lived 1980 morning show, Late Night at 30 Rock with the World's Most Dangerous Band, the move to CBS and the Ed Sullivan Theater, and the 2015 finale with four presidents and Foo Fighters. Expect the famous moments (Madonna, Drew Barrymore, the first Top Ten List) and the details even devoted fans forget: the Carson-imposed rules Late Night had to follow, the $2 million blackmail plot, the Indy 500 wins for the racing team he co-owns, and where he quietly got married in 2009. Every answer was verified against Wikipedia's articles on Letterman, both shows and the people around them. Good for a night-in challenge, a comedy-nerd showdown, or a themed round at your next trivia night.
30 of 59 questions with answers and explanations. Play the quiz
Q 01In which city was David Letterman born?
Indianapolis
Indianapolis: Letterman stocked shelves at the Atlas Supermarket in its Broad Ripple area as a teenager, then worked at a local TV station as a weekend weatherman before heading west.
Q 02Which Midwestern university awarded Letterman's 1969 degree and later named a media building after him?
Ball State
Ball State in Muncie, where he studied radio and television; he returned to campus in 2007 to dedicate the David Letterman Communication and Media Building.
Q 03As a young Indiana TV weatherman, Letterman drew attention for doing what on air?
Congratulating a tropical storm
Congratulating a tropical storm on becoming a hurricane was an early taste of the deadpan humour that later filled his talk shows.
Q 04After moving west in 1975, Letterman began performing stand-up at which Los Angeles club?
The Comedy Store
The Comedy Store: Jimmie Walker saw Letterman on stage there and hired him as one of the joke writers for his own stand-up act.
Q 05Letterman's first NBC show, The David Letterman Show, aired in 1980 in what time slot?
Weekday mornings
Weekday mornings: The David Letterman Show won Daytime Emmys but flopped with the daytime audience and was cancelled within months.
Q 06In a famous Late Night stunt, Letterman wore a suit made of what to stick to a wall?
Velcro
Velcro: on a February 1984 show Letterman launched himself off a trampoline at a wall covered in the fastener and stuck there, one of several 'suit' stunts that also dunked him in water wearing Alka-Seltzer.
Q 07Who was the very first guest on Late Night in 1982, and also the last guest on Late Show in 2015?
Bill Murray
Bill Murray was the first guest when Late Night premiered in 1982 and was also Letterman's final guest in May 2015, when he popped out of a giant cake.
Q 08Late Night was broadcast from Studio 6A in which New York building?
30 Rockefeller Plaza
Late Night came from Studio 6A at 30 Rockefeller Plaza; Conan O'Brien inherited the studio and the time slot when Letterman left for CBS in 1993.
Q 09What was the topic of the very first Top Ten List?
Things That Almost Rhyme With Peas
Things That Almost Rhyme With Peas, also quoted as 'Words That Almost Rhyme With Peas', opened the run in 1985; NBC later claimed the Top Ten as its intellectual property when Letterman left for CBS.
Q 10Which restriction did Carson Productions impose on Late Night to protect The Tonight Show?
No sidekick like Ed McMahon
No sidekick like Ed McMahon was allowed by Carson Productions on Late Night, and Shaffer's band was also barred from having a horn section, to keep the show distinct from Carson's.
Q 11Actor Calvert DeForest played which oddball recurring character on Late Night?
Larry 'Bud' Melman
Calvert DeForest played Larry 'Bud' Melman; NBC asserted rights to the character when Letterman left, so at CBS DeForest appeared under his own name.
Q 12Chris Elliott started on Late Night as a production assistant in charge of which segment?
Stupid Pet Tricks
Stupid Pet Tricks was Elliott's first charge; he was soon promoted to writer and became a recurring on-camera oddball, most famously as 'The Guy Under the Seats'.
Q 13Which former partner of Letterman's was Late Night's first head writer and devised many of its signature segments?
Merrill Markoe
Q 21What was Biff Henderson's job on the Letterman shows?
Stage manager
Stage manager: Biff Henderson first worked with Letterman on his short-lived 1980 NBC show, and the host kept pushing him in front of the camera for stunts and remote reports.
Q 22Which pop star's profanity-laced 1994 Late Show appearance became one of its most notorious?
Madonna
Madonna swore so often that the interview was heavily bleeped, then playfully refused to leave the set when Letterman tried to wrap things up.
Q 23Which actress climbed onto Letterman's desk and flashed him on his birthday in April 1995?
Drew Barrymore
Drew Barrymore climbed onto the desk, danced, flashed him and finished with a kiss on the cheek, all as a gift for his 48th birthday on April 12, 1995.
Merrill Markoe and Letterman were a couple from 1978 to 1988; several bits she invented for his short-lived 1980 NBC show stayed his property when he left the network.
Q 14Which guest nearly kicked Letterman in the face during a bizarre 1987 Late Night appearance?
Crispin Glover
Crispin Glover arrived in platform shoes and a wig, swung a kick that just missed Letterman's face and sent the host walking off his own set.
Q 15When Johnny Carson retired in 1992, NBC gave The Tonight Show to whom instead of Letterman?
Jay Leno
Jay Leno, Carson's regular guest host, got the job in 1992; Letterman answered by moving to CBS the following year, setting up a head-to-head rivalry at 11:35.
Q 16Late Show with David Letterman was taped in which historic Manhattan theatre?
The Ed Sullivan Theater
The Ed Sullivan Theater on Broadway, where Sullivan staged his variety show from 1953 to 1971; CBS bought and renovated the building for Letterman's 1993 arrival.
Q 17Which relative of Letterman's became a Late Show correspondent at the 1994 Winter Olympics?
His mother
His mother, Dorothy, billed simply as 'Dave's Mom', filed nightly reports from Lillehammer and went on to become a recurring guest on the show.
Q 18Who performed the first musical act on Late Show's 1993 debut episode?
Billy Joel
Billy Joel performed 'No Man's Land' on the August 30, 1993 premiere of Late Show, which drew about 23 million viewers.
Q 19Which announcer took over from Bill Wendell in 1995 and stayed until Late Show ended?
Alan Kalter
Alan Kalter became Late Show's announcer in 1995 and stayed until the final episode in 2015; Bill Wendell had announced Late Night at NBC and followed Letterman to CBS for two years.
Q 20Rupert Jee, a frequent Late Show foil, owned what business next door to the theatre?
A deli
A deli: Rupert Jee's Hello Deli sat around the corner from the theatre, and after a 1993 'Meet the Neighbors' segment he became a regular in Letterman's street stunts.
Q 24Which film won Best Picture at the March 1995 Oscars, the only ceremony Letterman hosted?
Forrest Gump
Forrest Gump won six Oscars that night, including Best Picture; Letterman's bits included a taped sketch of stars auditioning for his own tiny role in the film Cabin Boy.
Q 25What emergency surgery did Letterman undergo in January 2000?
Quintuple bypass
Quintuple bypass surgery on January 14, 2000 kept Letterman off the air for more than a month; when he returned in February he brought the doctors and nurses who treated him on stage.
Q 26Which singer-songwriter, dying of cancer, was the sole guest for a whole October 2002 episode?
Warren Zevon
Warren Zevon, then dying of mesothelioma, filled the whole October 30, 2002 episode; his advice to viewers, 'enjoy every sandwich', later titled a tribute album.
Q 27Which news anchor appeared on Letterman's emotional first show back after the September 11 attacks?
Dan Rather
Dan Rather broke down in tears twice on the September 17, 2001 broadcast, which Letterman opened with an unusually serious monologue instead of the usual jokes.
Q 28In 2009 a CBS News producer tried to blackmail Letterman over staff affairs for how much?
$2 million
Joe Halderman demanded $2 million to keep quiet; he pleaded guilty and got six months in jail after Letterman disclosed the plot on air.
Q 29The 2009 extortionist, Joe Halderman, was a producer on which CBS programme?
48 Hours
Halderman was a producer on the newsmagazine 48 Hours; he presented his threat to expose Letterman's affairs as a screenplay treatment.
Q 30What is the name of Letterman's production company, which produced his CBS talk show?
Worldwide Pants
Worldwide Pants owned Late Show outright, which let Letterman strike his own deal with striking writers in 2007 and return to air with them while NBC's hosts could not.