Since he first debuted on television as the inaugaral Late Night host in 1982 (the same show that became the Tonight Show) and onto his time as the host of CBS’ Late Show, David Letterman has been entertaining audiences. His tenure on the tube has seen him not only offer his hilarious commentary on multiple phases and generations of pop culture, but also see him become an influential multi-generational pop culture fixture himself.
On the heels of the exit of Letterman’s time-slot nemesis Jay Leno on NBC’s Tonight Show and the successful emergence of Jimmy Fallon as the new host of that program, the Late Show host announed his impending retirement – making room for another evening talk show legend in Stephen Colbert to take over in May 2015.
Since Colbert just bid adieu to his eponymous Colbert Report on Comedy Central before the 2014 Holiday season, the countdown to Letterman’s departure has officially commenced. So, now seems as good a time as we’re ever gonna get to reflect on the television career of Letterman that spans over three decades and countdown his top moments the way he would – in a Top 10.
10. Jay Leno Makes a Late Night Appearance
Before he went on to host more episodes than any other host of the Tonight Show, Jay Leno was just the young stand up comic, popularized in LA, who would fly to NY and often make visits to the 30 Rockefeller Center and the then host of the Late Night Show – David Letterman. The interviews serve as a fascinating capsulization of time, wherein Letterman and Leno share a fantastic rapport, not very indicative of their future rivalry that incited Letterman’s departure to NBC and Late Night.
9. Letterman Announces His Retirement
On the evening of his 4,014th broadcast of the Late Night Show, David Letterman announced his soon to come retirement to the world. In classic Letterman fashion, his detached and snarky outlook on his own fate as the host of the program brings the yuks. “If you spend your day trying to ID birds, should you really be running a network television program?” Letterman asks.
8. Letterman Leaves NBC
Serving as an interesting reflection of the situation that would affect fellow Late Night showman Conan O’Brien in 2010, Letterman’s last broadcast of Late Night was filled with jabs and bites aimed at the NBC brass that did not see him fit for the Tonight Show hosting gig.
7. Joaquin Phoenix’s Meltdown
Diminished only by its being revealed as a part of Phoenix’s odd Docu-Dramedy I’m Still Here, Joaquin Phoenix’s bizarre Late Show meltdown was one of the first clips of any show to “break the internet.”
6. Denzel Washington and Letterman live, from an empty Ed Sullivan Theater
A lasting and effective testament to Letterman’s dedication to being the fantastic showman that he is, on October 30th, 2012, David Letterman hosted his program with his guest Denzel Washington in the wake of Hurricane Sandy. We’re talking a full-fledged production while the rest of New York City was going underwater. The show opened with a shot of Denzel entering the theater in a raincoat and leading into commercial breaks, the camera would pan over the empty seats of the theater.
5. Drew Barrymore Gives Letterman the Ultimate Birthday Present
It’s legitimacy still debated, on David Letterman’s birthday broadcast of the Late Show in 1995, Drew Barrymore gave Letterman a birthday present – well two birthday presents – by flashing her breasts to him on network television.
4. Johnny Carson’s First Post-Tonight Show Appearance
A few years before making his last television appearance ever on Letterman’s program, Carson made his first appearance after retiring from the Tonight Show on Letterman’s young Late Show. In a hilarious television moment, Johnny Carson brings out his own desk to feel more comfortable talking to Dave.
3. Crispin Glover’s Infamous Late Show Appearance
Character actor Crispin Glover, perhaps best known for roles in Back to the Future and Charlie’s Angels, appears on the Late Show in what appears to be a drug-fueled frenzy. During the middle of the interview, Letterman goes to a commercial and when the program comes back, Glover was kicked off the show and nowhere to be found.
2. Andy Kaufman and Jerry Lawler Brawl
In another instance of the lines between reality and fiction being blurred, Andy Kaufman and professional wrestler Jerry Lawler brought their wrestling storyline to Letterman’s program and engaged in an on-air battle of fisticuffs. The incident would later be reenacted in the Jim Carrey film Man on the Moon.
1. David Letterman Pays Tribute to Johnny Carson
In the first broadcast after the passing of the late night legend Johnny Carson, Letterman dedicated the January 31, 2005 episode of the Late Show to his hero. Going off on a heartfelt monologue completely devoid (or perhaps unaware of his own) ego and having Tonight Show Starring Johnny Carson executive producer Peter Lassally and band leader Doc Severinsen as his guests.
