‘Late Show with David Letterman’s Most Memorable Moments, Year by Year

After NBC chose Jay Leno to become the new host of The Tonight Show, David Letterman launched Late Show with David Letterman on August 30, 1993, changing the late night television landscape forever. On the verge of becoming the longest tenured host in late night history next year, Letterman has proven that his ironic and cantankerous sense of humor could work and be allowed to evolve at the earlier hour. While he continues to believe that he is living in his shadow, he’s the contemporary equivalent of what Johnny Carson used to be, the standard and implied influence for all current and fast approaching late night talk show hosts.

To celebrate the show’s twentieth anniversary, here are memorable moments from each of the first twenty years of the show’s existence, in chronological order. Events important to the comedy world take precedence over celebrities misbehaving, for reasons that should be obvious.

Dave Works the McDonald’s Drive Thru

From November 26, 1993

While Letterman’s 1996 visit to a Taco Bell is the better known fast food drive thru remote, this bit at a New Jersey McDonald’s is just as funny, as Dave insists that impatient customers convince him that they are happy in order to buy a Happy Meal, and asks too many personal questions when sometimes a very depressed individual just needs a Number Three. Split up into three different segments during a sweeps month episode, the audience couldn’t then appreciate how rare witnessing a Letterman outdoors would soon become.

Johnny Carson’s Final TV Appearance

May 13, 1994

On the final night of a week of shows in Los Angeles, a retired Johnny Carson presented Letterman with the show’s top ten list (after a fake out by Dave and Larry “Bud” Melman). Carson received a long, thunderous standing ovation, and indicated who he felt should have replaced him, without saying a single word.

Also from 1994: Letterman and Bruce Willis stole balloons from T.G.I. Friday’s, and Madonna cursed a lot.

Jon Stewart Finds Out His Show Has Been Canceled

June 7, 1995

1995 was the year in which Letterman infamously hosted the Oscars, saw Leno begin his fourteen year stranglehold on the number one ratings position, and spent an inordinate amount of time focused on a Canadian gas station attendant with the given name Dick Assman. Jon Stewart’s syndicated late night show was canceled in 1995, but thanks in part to Letterman’s support (Dave appeared on the final episode of The Jon Stewart Show), Stewart would hang in there and eventually host The Daily Show, which has currently won the last ten Emmy awards in the Outstanding Variety, Music or Comedy Series category. The program that had won the award five times in a row before that insane streak? That would be Late Show.

Of course, 1995 was also the year that Drew Barrymore gave Dave a birthday flash dance on his desk.

Dave is Elaine Stritch’s New Pool Boy

July 5, 1996

In one of the funniest absurd bits in the show’s history, Elaine Stritch played a cougar who kept interrupting the show to demand David, her new pool boy and piece of delicious eye candy, to give her attention. Randy Quaid coming off as the sanest person in the whole matter is an added bonus.

’The David Letterman Story’

February 3, 1997

With the premise that CBS insisted on doing something special to celebrate his 15 year anniversary in late night, David presented the audience with a three part documentary produced and paid by his bosses about his life. It’s really interesting to see what parts of Letterman’s actual life were not thought to need embellishment or a total rewrite to get people to laugh. For example, Dave and Michael Keaton’s real life stint as song and dance men for a failed Mary Tyler Moore vehicle was something left completely untouched.

Also in 1997: That Farrah Fawcett incident.

Norm MacDonald Calls Don Ohlmeyer Fat

January 7, 1998

Apparently mere hours after finding out he was fired from hosting Weekend Update, Norm MacDonald sat down for an interview with Dave. Letterman joyfully ripped on NBC West Coast President Don Ohlmeyer for firing Norm, and MacDonald proceeded to do himself no favors by admitting that keeping him on the show to exclusively do sketches is pointless because he “stinks” at them. Norm added, egged on by Letterman’s constant name calling, does slip that he thinks his future former boss is overweight. Spoiler: Dave feeling comfortable with commenting on his former employer’s controversial firings will lead to more memorable moments down the road.

John Malkovich Is Creepy On Purpose

October 15, 1999

During the height of Malkomania, one of the most inspired Top Ten lists of all-time, “Top 10 Things That Sound Creepy When Said By John Malkovich,” perfectly capitalized comically on the height of Malkovich’s celebrity and the paranoia of the First Lady becoming a New York Senator. The YouTube clip is from the re-airing of the bit for a “best of” special that ran while Letterman was recovering from quintuple bypass heart surgery the next year.

Letterman Returns From Heart Surgery

February 21, 2000

Dave coming back was a big event, and the impetus for a brand new batch of material. A clip that cannot be embedded proved that a lot of celebrities were more than willing to pretend that they didn’t care about Letterman’s well being, as well as an always timely feud between David Duchovny and Regis Philbin. The clip above has the funny opening monologue and a ghoulish Jerry Seinfeld cameo though, so there’s that.

The First Show After 9/11

September 17, 2001

Letterman was the first late night host to come back after September 11th, and the way he handled it — with heartfelt, unfiltered honesty with little jokes sprinkled in to alleviate the tension — set the template for everyone else. Understandably, David admitted last year that he didn’t initially want to go back when he did, but as the one person who had hosted a show from New York City for nineteen consecutive years, he didn’t really have much of a choice.

In happier times that year, Biff Henderson presented his greatest installment of Fun With a Stopwatch, and Paul Shaffer asked Julia Roberts a really private question.

Warren Zevon’s Goodbye

October 30, 2002

Twenty years after making his first appearance on a Letterman show, musician Warren Zevon became one of the few individuals to be the sole guest on a Late Show episode. Unfortunately by October of 2002, the good friend of the show was diagnosed with terminal mesothelioma. Warren’s frankness and sense of humor was endearing, and therefore heartbreaking.

The Bear Story

September 22, 2003

A couple of years before Stephen Colbert alerted the masses to the constant threat of bears, Letterman recounted a gripping and funny story about waking up to a bear in his Montana home. M-80s and a high school kid named Brandon got involved, making it a desk story for the ages.

Amy Sedaris’ West Village Tour at Four in the Morning

May 14, 2004

Randomly feeling the adventurous spirit of his old Late Night show, Letterman decided to tape an episode at four in the morning. A loopy Amy Sedaris volunteered to show David and the audience around her neighborhood at that ungodly hour.

The Tribute to Johnny Carson

January 31, 2005

On his first show back since the passing of his idol, Letterman dove right into a monologue comprised entirely of jokes that had nothing to do with Carson’s death, or any other current events. Risking the chance that people changed the channel thinking it was a rerun, Letterman finished his monologue and sat down before explaining that all of those jokes were written by Johnny Carson for David’s show, and that episode was going to essentially be a wake for the man. Camera shy and long time Carson executive producer Peter Lassally and Johnny’s old band leader Doc Severinsen were the guests.

The Michael Richards Apology

November 21, 2006

Awkward for many reasons, including the fact that he was only appearing via satellite, Michael Richards apologized for his use of the N-word in a recorded tirade the previous weekend.

Also in 2006, Richard Simmons was particularly silly, and Emma Thompson instigated the only pie fight in the show’s history.

Bill Murray Celebrates the 25th Anniversary

February 1, 2007

Bill “Mr. Big Shot” Murray came out dressed like he was shooting for Leonardo DiCaprio’s part in The Great Gatsby years before it began casting for the 25th anniversary of Letterman’s chaotic first Late Night show. He was overdressed.

John McCain Doesn’t Show Up

September 24, 2008

Republican presidential candidate John McCain canceled at the last minute on Letterman to get back to Washington D.C. to work on the sudden financial crisis. The problem was that David found out during the broadcast that McCain squeezed in a TV interview with Katie Couric before leaving, giving Letterman the justification to mock him for the majority of the episode. McCain would try to save face by appearing on the show a month later.

Bill Hicks Posthumously Gets Uncensored

January 30, 2009

Bill Hicks had appeared various times on Letterman’s Late Night show with minor censorship, but his lone standup set on Late Show was entirely cut from the broadcast, allegedly on account of a religious joke that would have offended the people behind a pro-life commercial that aired during that night’s episode. It cemented Hicks’ status as a controversial comedian, and he died a year later without anyone having seen his set. Sixteen years later, Letterman dedicated an entire episode to the dead comic, inviting his mother on the show to apologize in person and show the entire routine, taking full responsibility and admitting it was a mistake to cut it in the first place.

2009 was a busy year: there was that whole extortion thing, and that Joaquin Phoenix stuff that turned out to be performance art.

Dave Speaks His Mind About Jay Leno

January 19, 2010

The winner of the Tonight Show fiasco of 2010 was David Letterman, who was able to sit back and comment every night on his own show, secure in the knowledge that it’d still be there waiting for him the next day. Letterman would continue to pick apart all of the strange comments Jay Leno made after shit hit the fan, and then capitalize on the drama he helped stir up and cast Leno in the famous Super Bowl ad for Late Show that ran a few weeks later. Eventually it led to one of David’s funniest desk stories, when Tyler from Utah mistook the very expensive commercial for an advertisement for Tostitos.

Betty White and Letterman Chug Vodka

January 18, 2011

In honor of her 89th birthday, Betty White and Letterman partook in some vodka. Maybe. It was certainly all a set-up, but I would like to think that Dave always has a vodka bottle under the desk for those nights that just won’t end.

Conan O’Brien Appears On Letterman

May 17, 2012

After the “some kind of a mix-up” that Letterman enjoyed talking about two years earlier, Conan O’Brien agreed to talk to Dave about the late night wars after he had settled at TBS and the anger subsided.

Also in 2012, Hurricane Sandy forced Dave to host two episodes without a studio audience, a gimmick that sounds like it came from the minds of the Late Night staff in the eighties.

‘Late Show with David Letterman’s Most Memorable […]