ABOVE: Watch David Letterman announce his retirement on Late Show.
TORONTO — David Letterman announced Thursday he is retiring next year — wrapping up more than three decades on late night television.
The Late Show host, who turns 67 on April 12, is the longest-running late night host ever and he’s had Canadian Paul Shaffer as his band leader the entire time.
There are, of course, hundreds of extraordinary moments from Letterman’s career — from Bill Murray spray-painting his desk and Andy Kaufman getting socked to Stupid Pet Tricks and visits from Larry “Bud” Melman.
Still, to mark Letterman’s retirement revelation, here is a Top 10 list of memorable moments from his shows.
10. The No. 1 Top Ten list
Letterman introduced his first Top Ten list on Sept. 18, 1985. The topic: “Things That Almost Rhyme with Peas.” The No. 1 word was “meats.”
9. Drew Barrymore’s birthday surprise
On the Late Show on April 12, 1995, guest Drew Barrymore gave Letterman a birthday surprise. She danced on top of his desk, flashed her breasts and gave him a kiss.
8. #awkward
In 1987, actor Crispin Glover appeared on Late Night in character — but Letterman didn’t seem to be in on the joke. The result was an awkward and uncomfortable interview that ended with Glover almost kicking Letterman, who got up from his desk and walked away. After a commercial break, Letterman told the audience: “I would have loved to have chatted a little bit more with Crispin Glover but I understand he had a cab to catch and … we wanted to ensure every possibility that he would get wherever he was going on time.” Letterman called Glover a “goofball” and a “dork.” Glover returned to the show a couple of weeks later and tried to explain his behaviour.
7. Sex, lies and extortion
In 2009, Letterman got personal on Late Show when he confessed to having had sexual relations with female members of his staff. More shockingly, the host said he was the target of an extortion plot by a man seeking $2 million. “Would it be embarrassing if it were made public? Perhaps it would. Especially for the women,” said Letterman, who had a son in 2003 with longtime partner Regina Lasko. Robert Halderman, a CBS producer, pleaded guilty to grand larceny and was sentenced to six months in jail.
6. Grilling Lohan
In April 2013, troubled actress Lindsay Lohan appeared on Late Show to promote Scary Movie 5. Letterman used the opportunity to read some of his best monologue jokes about her. He also asked her some tough questions. “Do you have addiction problems? Do you drink too much?” “Aren’t you supposed to be in rehab now?” “Yes or no, do you steal stuff?” Despite the laughs, Letterman showed genuine concern for Lohan, who was in tears by the end of the segment.
5. A host with heart
Letterman underwent quintuple bypass heart surgery on Jan. 14, 2000. He returned to Late Show on Feb. 21 and opened his monologue with: “Wait ’til you hear what happened to me.” Letterman later introduced the doctors and nurses who took care of him.
4. Fawcett runs wild
3. Madonna gets tough
Letterman sparred with Madonna on March 31, 1994. “You do irritate me sometimes,” Madonna told him. “Well, you kind of irritate me, too,” he replied. The pop star swore repeatedly, smoked a cigar and criticized Letterman. “You used to be kind of cool,” she said. “You kiss up to everybody on your show now.” The audience, firmly on Letterman’s side, booed and hissed Madonna.
2. Name game
This memorable Letterman moment didn’t happen on one of his talk shows but while he hosted the 67th Academy Awards in 1995. Letterman introduced Oprah Winfrey to Uma Thurman with: “Oprah. Uma. Uma. Oprah.” He added: “Have you kids met Keanu?” The bit fell flat and haunted Letterman for years.
1. Back to normal?
Late Show returned to the air on Sept. 17, 2001 — a week after the terrorist attacks in New York City. Letterman’s guests were Regis Philbin, Dan Rather and the Boys Choir of Harlem. He opened the show with an emotional speech. “If we are going to continue to do shows, I just need to hear myself talk for a couple of minutes, and so that’s what I’m going to do here,” he began. Later, he explained: “We’re going to try and feel our way through this, and we’ll just see how it goes… take it a day at a time.” When Rather apologized for breaking down, Letterman said: “Good Christ, you’re a human being.”
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