David Letterman Trivia
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60 free David Letterman trivia questions with answers — entertainment quiz, new questions added Aug 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 60 questions with answers and explanations. Play the quiz
Q 01In which city was David Letterman born?
Indianapolis
David Letterman was born in Indianapolis on April 12, 1947; he attended Broad Ripple High School there and worked as a stock boy at the local Atlas Supermarket.
Q 02Letterman graduated in 1969 from which university, where he later endowed a scholarship for 'C students'?
Ball State
Letterman graduated from Ball State in 1969, studying in what was then the Department of Radio and Television in Muncie, Indiana; he later funded a scholarship for C-average students.
Q 03As a young Indiana TV weatherman, Letterman drew attention for doing what on air?
Congratulating a tropical storm on becoming a hurricane
Congratulating a tropical storm on becoming a hurricane was one of his on-air stunts at station WLWI, along with reporting hail 'the size of canned hams'; that offbeat delivery foreshadowed his talk-show style.
Q 04In 1975 Letterman moved to Los Angeles and began performing stand-up at which Los Angeles club?
The Comedy Store
Letterman began performing stand-up at The Comedy Store after moving west in 1975; his then-wife Michelle and several Sigma Chi fraternity brothers encouraged the move.
Q 05Letterman's first NBC show, The David Letterman Show, aired in 1980 in what time slot?
Weekday mornings
Weekday mornings at 10 a.m. was its slot: The David Letterman Show ran from June to October 1980, won two Emmys but flopped in the ratings and was cancelled that autumn.
Q 06On what date did Late Night with David Letterman premiere on NBC?
February 1, 1982
Late Night premiered on February 1, 1982, running Monday through Thursday at 12:30 a.m., directly after Johnny Carson's Tonight Show.
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 name of Paul Shaffer's musical group on Late Night?
The World's Most Dangerous Band
Paul Shaffer led The World's Most Dangerous Band on Late Night; Carson Productions barred it from having a horn section, to keep it distinct from Doc Severinsen's Tonight Show orchestra.
Q 10What was the topic of the very first Top Ten List, on September 18, 1985?
Things That Almost Rhyme With Peas
The first list, on September 18, 1985, was 'Things That Almost Rhyme With Peas'; NBC later claimed the segment as its intellectual property when Letterman jumped to CBS.
Q 11Which 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 12Actor 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 13Chris Elliott started on Late Night as a production assistant in charge of which segment?
Stupid Pet Tricks
Q 21Rupert Jee, a frequent Late Show foil, owned what business next door to the theatre?
A deli
A deli: Rupert Jee's Hello Deli sat at 213 W. 53rd Street, steps from the theatre's stage door, and Jee became a recurring on-camera foil.
Q 22What was Biff Henderson's job on the Letterman shows?
Stage manager
Stage manager was Biff Henderson's job, carried over from Late Night to Late Show; he became an on-camera regular in the process.
Q 23Which pop star's profanity-laced 1994 Late Show appearance became one of its most notorious?
Madonna
Madonna swore more than a dozen times during her March 1994 visit, one of the most notorious guest appearances in Late Show history.
He was promoted to writer and became one of the show's most memorable on-camera weirdos.
Q 14Which former partner of Letterman's created many Late Night staples, including the viewers' animals segment?
Merrill Markoe
Merrill Markoe, Late Night's first head writer, devised many of its signature segments; she and Letterman were a couple from 1978 to 1988.
Q 15Which guest's Late Night appearances frightened Letterman with nearly violent, confrontational behaviour?
Crispin Glover
Crispin Glover's 1987 visit, complete with platform shoes and a near-kick at the host's head, made Letterman walk off the set and remains a late-night legend.
Q 16When Johnny Carson retired in 1992, NBC gave The Tonight Show to whom instead of Letterman?
Jay Leno
NBC chose Jay Leno to succeed Carson in 1992; Carson himself had expected Letterman to get the job, and Letterman left for CBS instead.
Q 17Late Show with David Letterman was taped in which historic Manhattan theatre?
The Ed Sullivan Theater
Late Show came from The Ed Sullivan Theater on Broadway; CBS bought the building for about $4 million and spent millions more renovating it before the 1993 debut.
Q 18What was the annual salary in Letterman's first three-year CBS contract in 1993?
$14 million
Letterman's first three-year CBS contract, signed in 1993, paid $14 million a year, about $42 million over the three years.
Q 19Who 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 20Which 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 24Which actress climbed onto Letterman's desk and flashed him on his birthday in April 1995?
Drew Barrymore
Drew Barrymore danced on the desk and flashed Letterman on April 12, 1995, his 48th birthday.
Q 25Letterman hosted the Academy Awards once, in March 1995. What was the Best Picture winner that night?
Forrest Gump
Critics savaged his hosting, but 48 million viewers made it the most-watched Oscars since 1983.
Q 26What 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 27Which 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 28Which news anchor appeared on Letterman's emotional first show back after the September 11 attacks?
Dan Rather
Dan Rather wept on the September 17, 2001 broadcast, which also featured Regis Philbin and was hailed as one of the most honest moments in TV history.
Q 29In 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 30The 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.