“I’m just trying to make a smudge on the collective unconscious.”
David Letterman has never been shy about making an impact. The acerbic, always-unpredictable, gap-toothed king of late night may have retired from his duties behind the desk in 2015…but that doesn’t mean there’s nothing left to learn about him! Read on to discover 53 audacious facts about the man himself.
1. Average Student
While in school, Letterman was little more than an average student. When he made it big as a late night comedian he decided to pay it forward to average students like himself by creating a scholarship for C students at his alma mater, Ball State University.
2. Foo Fan
In 2000, David Letterman took a break from the Late Show to undergo open heart surgery. Upon his return, he requested that the band the Foo Fighters play their song “Everlong” on his show, as Dave said the song was “special to [him]. It [was] meaningful during [his] heart recovery.” There was only one problem with Dave’s request: The Foo Fighters were on tour in South America at the time. However, this turned out not to be a problem, as the band canceled their tour on the spot and returned to the US to play on Letterman’s show.
3. Even Flow
The Foo Fighters aren’t the only rock band for whom Letterman has an affinity. In 2017, the Late Show star was on hand to give the induction speech for Pearl Jam when Vedder and co. entered the Rock & Roll Hall of Fame.
4. Super Fan
Mark Hamill, Luke Skywalker himself, is a huge fan of Letterman’s shows. Hamill’s fandom reached a point where he had videotaped and cataloged every Letterman late night show ever aired. Late Night producers even asked Hamill to view his collection and notes in order to figure out when the 1,000th viewer mail segment was going to happen.
In 2007, Letterman fell ill with a stomach virus an hour before the show was to be taped. Letterman’s hosting role fell to none other than Adam Sandler, who was already in the building as he was to be a guest on the show that night. Sandler’s last-minute pinch-hosting went off without a hitch; he interviewed actor Don Cheadle and racecar driver Danica Patrick.
6. Good Guy Dave
During the 2007 Writer’s Strike, generous Dave paid the Late Show staff with money out of his own pocket.
After Johnny Carson retired from the Tonight Show, it was expected that David Letterman would be his replacement. Instead, NBC controversially hired Jay Leno to replace Carson, and Letterman moved to hosting the Late Show on CBS.
Though NBC picked Leno to replace Johnny Carson, it’s widely believed that the man himself considered Letterman to be his true successor. He appeared The Late Show more frequently than The Tonight Show—including his final television appearance ever. Not to mention the fact that Carson would occasionally send in jokes for Letterman to tell in his monologue.
You could always tell if a joke was Carson’s because Letterman would do Johnny’s trademarked golf swing after delivering them.
9. Horsin’ Around
When David Letterman retired from the Late Show in 2015, Conan O’Brien penned a tribute to Letterman on his own show, Conan. To express his thanks, Letterman phoned up Conan and told him that he would be sending Conan a gift. O’Brien expected the gift to be something conventional such as wine or chocolates, but he certainly did not expect what soon turned up on the Warner Bros Lot: a horse. Letterman gifted Conan a horse named Dave!
10. It’s Raining Men
Many know that Canadian musician Paul Shaffer was the longtime bandleader and music director on Letterman’s show, but did you know that Shaffer also co-wrote the 1984 Weather Girls anthem “It’s Raining Men”?
11. Merry Prankster
In 1985, a young David Letterman interrupted a taping of the Today Show proclaiming that he was the President of NBC and that he wasn’t wearing any pants.
12. Lost In Translation
Letterman once engineered the dubbing of his show from English to…English. That’s right, on September 25, 1986, Dave re-aired an episode of the show that had previously aired back on February 25—the only difference was that every guest’s voice, as well as that of Letterman himself, was dubbed over by a professional dubber (Letterman was dubbed over by a voice from the cartoon Speed Racer). Reportedly NBC’s call-in line was inundated by over 200 confused viewers of the show who had no idea what was going on.
13. Late Night with Shrek
Regis Philbin once went on Letterman’s show while dressed as Shrek, because why not?
14. High Praise
The late great comedian Robin Williams appeared on Letterman’s show over 50 times. In one episode, Letterman reminisced about the first time he witnessed Williams perform stand up as a new comedian at the Comedy Store in Los Angeles, saying, “He came in like a hurricane” and thinking to himself, “Holy crap, there goes my chance in show business.”
15. Not That There’s Anything Wrong With That
Letterman bandleader Paul Shaffer was handpicked by Jerry Seinfeld himself for the role of George Costanza in the show Seinfeld. Seinfeld was so confident in the decision that he reportedly said “There’s no audition…you’ve got the part. Just call us back!” Shaffer, who was busy at the time, never returned the call. The iconic part was later scooped up by actor Jason Alexander.
16. Don’t Need a Weatherman To Tell Which Way The Wind Blows
Letterman began his professional broadcasting career as a weatherman for an Indianapolis TV station. He was notable for his zany and irreverent on-air behavior, which included congratulating a tropical storm for being upgraded to a hurricane, predicting hail stones “the size of canned hams,” and reporting the weather for completely made-up cities.
17. Learning the Craft
In addition to his early career as a weatherman, Letterman also had stints as a star on a local kids show, hosted a late-night TV show called Freeze Dried Movies (where he once used plastic dinosaurs to act out a scene from the movie Godzilla), and interviewed 4-H members about their projects on an early morning talk-show called Clover Power.
18. Eternal Return
Jerry Seinfeld bookended his first and last appearance on David Letterman’s talk show by telling the exact same material, 33 years apart.
19. Final Set
In 1993, caustic American comedian Bill Hicks appeared on David Letterman’s show for the 12th and final time (Hicks would die from cancer a few months later). The problem was that Letterman never aired Hicks’ final set for reasons unknown (presumed to be network censorship). It wasn’t until 2009 that Letterman finally aired the “lost” Hicks set.
20. First and Last
Bill Murray was Letterman’s first late night guest on Dave’s first show in 1982. Murray remained a recurring guest during Letterman’s 33 year run on late night, and he appeared on both the 30th-anniversary episode in 2012 and the last episode in 2015.
21. Guest Part
Letterman appeared in an episode of the TV show Mork and Mindy (starring Robin Williams).
22. Guest Voice
David Letterman has an iconic voice, but would you believe he lent his famous pipes to the animated film Beavis and Butthead Do America? Well, it’s true. In the film, Dave, under the nondescript alias of Earl Hofert, voiced a Mötley Crüe roadie, because can’t you just see Letterman as a Mötley Crüe roadie?
Letterman registered for the military draft during the Vietnam War in the late 1960s and passed his physical exam. He wasn’t drafted, though, as a result of his very low lottery number (he was 346 out of 366). Just think how the late night landscape would have changed if Letterman had served in Vietnam.
24. Radio Days
Letterman’s first broadcasting experience was as an announcer and newscaster at his college radio station, WBST in Indiana. Foreshadowing the brazen comedic style that would later inform his late night career, Letterman was fired for his “irreverent treatment of classical music.”
25. Comedians in Bars Getting Funny
As a stand-up comedian working at the Comedy Store in Los Angeles in the late 1970s, Letterman was contemporaries with Jay Leno as well as Louie Anderson and Paul Mooney.
When Letterman moved from Late Night with David Letterman at NBC to the Late Show at CBS in 1992, he was prohibited from bringing old Late Night segments onto his new show because of intellectual property disagreements. Letterman sidestepped these issues by simply renaming segments. For instance, his famous Top Ten List simply became the Late Show Top Ten and Viewer Mail became the CBS Mailbag.
27. Praise You
Letterman’s shows have consistently garnered critical praise, being nominated for an incredible total of 67 Emmys, winning 12 times in his first 20 years on late night TV.
28. Hosting Flop
Letterman hosted the Oscars in 1995. His performance as a host was lambasted by critics, who felt that Letterman’s sarcastic mockery of prominent Hollywood figures diminished the traditional significance of the glamorous gala. Some connected the bad publicity garnered by Letterman’s hosting with the subsequent reduced ratings for the Late Show. Letterman, for his part, lampooned the critical response to his performance.
In his first show back, Letterman joked “Looking back, I had no idea that thing was being televised.” Letterman has not since hosted the Oscars—although he has claimed that he has been offered hosting duties by the Academy.
29. Have You Three Met?
Letterman opened his stint hosting the Oscars by introducing Uma Thurman to Oprah Winfrey: “Oprah, Uma. Uma, Oprah…Have you kids met Keanu?” The stuffy room didn’t appreciate that Letterman would be so crass as to make fun of celebrities’ names, and the joke fell completely flat. Well, at least we found it funny, Dave.
In 2000, Letterman endured a quadruple bypass open-heart surgery after a routine checkup discovered he had a blocked artery. While Letterman recovered from the procedure, he permitted prominent guests such as Bill Cosby, Dana Carvey and Janeane Garofalo to guest-host the show. Upon his return in February 2000, Letterman tearfully thanked all the doctors and nurses who he said had “saved [his] life.”
He even brought them up on stage with him in an emotional tribute.
31. Guests Guest Host
In 2003, Letterman again had to take a break from hosting duties as he suffered from a severe case of shingles. Numerous guest hosts took over the reins of the show while he was gone, including Bill Cosby again, Whoopi Goldberg, John McEnroe, Will Ferrell, and Elvis Costello.
32. Last Call
Letterman’s last episode aired in 2015. It featured a send-off from four of the five living Presidents (George H.W. Bush, Bill Clinton, George W. Bush, and Barack Obama), cameos from The Simpsons, Wheel of Fortune, as well as a Top Ten list performed by a slew of regular guests including Jerry Seinfeld, Tina Fey, Alec Baldwin, Chris Rock, Barbara Walters, Jim Carrey, Julia Louis-Dreyfus, Steve Martin, Bill Murray and Peyton Manning.
33. Meet The New Host, Same as the Old Host
In early 2018, a Netflix interview series hosted by Letterman called My Next Guest Needs No Introduction with David Letterman was released. The first installment of the six-episode series featured an interview with President Barack Obama. It was then renewed for a second season, which premiered in May 2019 with a controversial interview with Kanye West.
34. Chit Chat
Letterman appeared in the second episode of Jerry Seinfeld’s Netflix series Comedians in Cars Getting Coffee. The pair drove Letterman’s Volvo 960 that had been equipped with a ridiculous Ford V8 racing engine, and Letterman mused on his natural introversion as well as his love of the smell of hardware stores.
35. Worldwide Pants
Letterman’s production company, Worldwide Pants Incorporated, produced his own show, as well as Everybody Loves Raymond and the Late Late Show. The company also produced its first feature film in 2005, Strangers with Candy, which was a prequel to the Comedy Central series of the same name.
36. Love and Marriage
Letterman married his second wife, Regina Lasko, in 2009 in a quiet courthouse ceremony in Montana (where Letterman owns a ranch). On his show a few days later, Letterman announced his new marriage, while also revealing that he almost missed the ceremony as his truck got stuck in the mud a few miles from his ranch. Letterman and Lasko have been together since 1986, when he was still living with another long-term girlfriend, Merrill Markoe.
37. Sordid Affair
In September 2009, Letterman announced on the show that he was the subject of a blackmail attempt by a person who threatened to reveal that Letterman had had affairs with several female employees on the show (which Letterman admitted to). Letterman revealed on the show that the person had left a package in his car threatening to reveal his affairs unless he paid $2 million. Letterman explained that he immediately contacted the police and cooperated in sting with them in which he gave the blackmailer a phony check.
The man was arrested after attempting to deposit the phony check and was revealed to be Robert Halderman, a producer of the CBS show 48 Hours!
38. Stalking Fame
David Letterman had a stalker by the name of Margaret Mary Ray during the late 80s and early 90s. Ray was schizophrenic and would frequently trespass on Letterman’s property, once stealing Dave’s Porsche from his driveway. Ray served 34 months in jail and psychiatric hospitals for stalking Letterman. When Ray was released in the mid-1990s, her attentions shifted away from Letterman to astronaut Story Musgrave.
Tragically, in 1998 Ray committed suicide by kneeling on the tracks in front of an oncoming train. Both Letterman and Musgrave expressed their sympathy after her death.
39. Lost the Plot
A house painter at Letterman’s ranch in Montana was arrested in 2005 for plotting to steal Dave’s infant son, Harry, and his nanny, and hold them hostage for a ransom of $5 million. The painter was arrested after approaching an acquaintance of his with the idea of the plot.
40. Dark Humor
In August 2011, Letterman was the subject of a death threat from an Islamic militant who posted the threat on a website used by Al Qaeda members. The militant called on American Muslims to kill Letterman because he had joked about an Al Qaeda leader who had been killed in a drone strike in Pakistan. In his typical acerbic wit, Letterman quipped that “State Department authorities are looking into this. They’re not taking this lightly. They’re looking into it. They’re questioning, they’re interrogating, there’s an electronic trail—but everybody knows it’s Leno.”
41. Grizzly Man
Timothy Treadwell—also known as the “Grizzly Man” following the Werner Herzog documentary of the same name—was once on Letterman’s show to discuss his experience living among bears in the Alaskan bush. While on the show, Letterman presciently joked that Treadwell would someday be eaten by bears—a fate that came true in 2003.
42. Like Father Like Son
Letterman’s sense of humor ran in the family. He’s said how he was always inspired by his father, Harry, who was a jokester and “the life of the party.” After Harry had a heart attack at age 36, a young Letterman became crippled by his fear of losing his father. Harry would survived for two more decades, but sadly he was killed at age 57 by another heart attack.
43. Oil In His Blood
Growing up 12 miles from Indianapolis Motor Speedway gave Letterman a life long love of cars and racing. Early in his career, one of his dreams came true when he got to cover the 1971 Indianapolis 500 as a reporter, even getting to interview racing legend Mario Andretti.
44. We are the Champions
Another of Letterman’s dreams came true in 2004 when he purchased a stake in a professional auto racing team, today known as Rahal Letterman Lanigan Racing. Co-owned with former Indy 500 winner Bobby Rahal, the team even managed to win the prestigious race that same year, with driver Buddy Rice taking the checkered flag.
After finally decided that his future lay in comedy, Letterman and his wife Michelle packed all of their belongings into a pickup truck and headed west with Los Angeles in their sights. As of 2012, Letterman still owned that old, beat up truck.
46. If I Could Turn Back Time
Letterman never treated his famous guests with the reverence that they were used to, and not all of them enjoyed his acerbic interview style. Some of the guests who particularly hated him were Shirley MacLaine, Charles Grodin, and Madonna. Legendary singer Cher one even called him an a**hole on his own show!
47. Super Dave
Letterman was at the center of a 1984 issue of The Avengers. The comic, titled The Avengers on “Late Night with David Letterman, had several members of the superteam appear as guests on Late Night. That was probably a little more pleasant for Dave than his “appearance” in the Batman comics: In Frank Miller’s The Dark Knight Returns, a parody of Letterman named “David Endochrine” gets himself and his entire audience gassed to death by the Joker.
48. The Bottle
Though he’s sober today, Letterman was once, in his words, a “horrible alcoholic.” He says that he was drunk “80% of the time” back in the early 80s.
49. It’s All Dave’s Fault
In 2005, Collen Nester of Santa Fe took out a restraining order against Letterman, prohibiting him from making any contact with her. The strange part? Letterman had never contacted her. Nester was utterly obsessed with Letterman, and she became convinced that the host was sending her coded messages through his show. These messages, she claimed, eventually made her go bankrupt and made her suffer extreme emotional stress.
The restraining order was later called “patently frivolous.” You don’t say…
Oprah Winfrey had an uncomfortable experience on Letterman’s show in the 1980s, which resulted in the two feuding for almost twenty years. Once, Letterman even stuck Oprah with a restaurant bill when they weren’t even eating together, thinking it would be hilarious. It wasn’t until 2005 that the two buried the hatchet and Oprah returned as a guest on Dave’s show, with Dave quipping that it was the “Super Bowl of love!”
51. Close Call
Letterman correspondent Rupert Jee had a very close call while performing a man-on-the-street segment in the 1990s in Hollywood for Dave’s show. As part of an interview segment, Jee approached a man with shoulder-length dyed blond hair, sunglasses and a Michael Jordan jersey. Jee attempted to draw attention to the man by yelling “Hey, everybody it’s Michael Jordan!” but the man quickly shooed Jee away. That man happened to be Ramón Arellano, an extremely violent, high-level Mexican drug cartel trafficker who was in hiding in Los Angeles at the time.
52. And Here’s the Kicker!
American actor Crispin Glover was kicked off Letterman’s show in 1987 after showing up in-character as a personality from a then-unreleased film and wearing garish platform shoes and a wig. After challenging Letterman to an arm wrestling match, Glover performed a karate kick inches from Letterman’s head while exclaiming “I’m strong…I can kick!” Letterman walked right off of the stage right after, just as the show was going to commercial.
It’s remembered as one of the strangest appearances in late night history.
53. Friendship Extinguished
Richard Simmons was a frequent guest on Letterman’s show until the two had a falling out over an incident that occurred during the taping of a show. In 2000, Simmons (while dressed as a turkey) was sprayed in the face by Letterman brandishing a fire extinguisher, causing Simmons to have severe asthma attack. Simmons didn’t return to Letterman’s show for over six years after.