David Letterman’s 10 Most Memorable ‘Late Show’ Moments

The late-night veteran will host the ‘Late Show with David Letterman’ for the last time on Wednesday, May 20th.
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David Letterman Photo

Late Show host David Letterman on the 'Late Show with David Letterman,' Friday May 15, 2015 on the CBS Television Network. (Photo: Jeffrey R. Staab/CBS ©2015)

It’s the end of an era as a TV titan signs off for good.

After 33 years in late-night television and 22 years at CBS, David Letterman says goodbye this week as he retires from the Late Show with David Letterman.

The final three broadcasts feature some Letterman favorites. On Monday night, Tom Hanks made his 60th appearance with Dave, while Eddie Vedder was the musical guest. Bill Murray, who holds the distinction of being the very first guest on both of Letterman’s late-night shows (at CBS and NBC), was on deck for Tuesday, marking his 44th visit overall. Bob Dylan also appeared on Tuesday’s show in his first Late Show performance in over 20 years. There aren’t any announced guests for Letterman’s final show tonight, but it will feature “surprises,” memorable highlights and the final Top Ten list. Ever.

In honor of the more than 4,600 “Top Ten Lists” Dave has delivered over his career, we couldn’t help but present our own featuring the Best of Dave.

And now, David Letterman’s Most Memorable Late Show Moments:

10. Anything with Larry “Bud” Melman (Feb. 1, 1982)

David Letterman Larry Melman Photo

Calvert DeForest wishes everyone a Happy New Year on the 'Late Show with David Letterman,' December 31, 1993 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo: Alan Singer/CBS ©1993)

Letterman has had a lot of trusty sidekicks over the years, from stage manager Biff Henderson and bandleader Paul Schaffer to Dave’s own mom Dorothy Mengering (who adorably always insisted on calling him “David”). But our favorite of all time was Larry “Bud” Melman (real name: Calvert DeForest), a struggling actor whose clueless bit was always a hit, ever since he was first introduced on Letterman’s Late Night NBC show.

Watch a clip of Larry Melman in action, starting at the 1:05 mark:

9. Madonna Talks Dirty (March 31, 1994):

While Dave was always in command, he couldn’t always control his guests. Like the time Madonna got pissed at him for introducing her as someone who’s “slept with some of the biggest names in the entertainment industry.” The pop star decided to swear up a storm, reportedly dropping the F-bomb 14 times, in a heavily censored — and highly rated —controversial appearance. She would not return to the show for six years.

Watch a part of the uncomfortable exchange:

8. Bill Murray’s Graffiti (Aug. 30, 1993):

David Letterman Bill Murray 1993 Photo

Bill Murray spray paints Dave's desk on the first taping of the 'Late Show with David Letterman,' August 30, 1993 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo: Alan Singer/CBS ©1993)

It’s sweet how these two grumpy old men go way back: Murray holds the honor of being Dave’s first-ever guest twice, on his NBC Late Night show and his CBS Late Show. Murray memorably helped Letterman mark his late-night territory when the Late Show debuted…by spray-painting his name on his talk-show desk.

Catch the graffiti moment at the 28:52 mark:

7. Warren Zevon’s Final Appearance (Oct. 30, 2002):

David Letterman Warren Zevon Photo

Warren Zevon talks to David Letterman when he visits the 'Late Show with David Letterman,' Wednesday, Oct. 30 on the CBS Television Network. On the show, Zevon also performed three of his legendary songs. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo: Barbara Nitke/CBS ©2002)

A Letterman favorite, Warren Zevon made his final public appearance on the Late Show, which dedicated the entire hour to the musician, when he was dying of cancer. During the candid interview, Zevon told Letterman what he now knew about life and death: “Enjoy every sandwich.”

Here's the first part of the one-hour tribute:

6. Dave’s Brush with Death (Feb. 21, 2000):

Letterman’s first show back, five weeks after his quintuple bypass surgery, found the host as self-deprecating as ever: “A bypass is what happened to me when I didn't get the 'Tonight' show.” Then he brought out on stage the entire medical team that saved his life for a heartfelt thank you. Capping off Dave’s return was a cameo by Jerry Seinfeld, who walked up to Dave at the end of his monologue and said, “What are you doing here? I thought you were dead.”

Watch the opening act of his return:

5. Johnny Carson Tribute (Jan. 31, 2005):

While it was always an on-going “joke” over the years how Letterman was denied inheriting The Tonight Show, which went to his frenemy Jay Leno instead, Dave got seriously sentimental when he paid tribute to his mentor Johnny Carson in the first Late Show following Carson’s death.

Letterman retells jokes sent to him from Carson:

4. Joaquin Phoenix’s Bizarre Interview (Feb. 11, 2008):

David Letterman Joaquin Phoenix Photo

Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the 'Late Show with David Letterman,' Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo: John Paul Filo/CBS ©2009)

Donning dark shades, a black suit and a big bushy beard, Joaquin Phoenix sat in Dave’s guest chair for one wild interview. During the awkwardly hilarious disaster, Phoenix claimed he was retiring from acting and becoming a rapper, among other outrageous and, at times, unintelligible ramblings. (It was later revealed to be a stunt for the Casey Affleck mockumentary I’m Still Here.) Always quick on his feet, Letterman wrapped the chat by quipping, “Joaquin, I’m sorry you couldn’t be here tonight!”

Here's a clip of the weirdness:

3. Letterman’s Sex Scandal (Oct. 1, 2009):

Okay, so Dave did a bad thing. But it was how he handled the blackmail bombshell that stands out. The audience had no idea what they were in for that day when Letterman came out during his traditional monologue time and turned it into a jaw-dropping confessional, in which he admitted to having affairs with female staff members. Dave decided to come clean on-camera to foil the 48 Hours producer who tried to extort him. Brutal for him and his family, for sure, but Dave’s directness helped him save his reputation and he came out of it relatively unscathed.

Catch the bold-move confessional here:

2. Drew Barrymore’s Flash Dance (April 12, 1995):

David Letterman Drew Barrymore Photo

Drew Barrymore turns to the audience after flashing host David Letterman during the April 12, 1995 taping of the 'Late Show with David Letterman' in New York City. This show was taped on Dave's Birthday. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo: Alan Singer/CBS ©1995)

Who could forget wild child Drew Barrymore, then 20, jumping up on Dave’s desk to wish him a Happy 48th birthday … by flashing him! When Barrymore returned to the show years later, Dave joked about the spontaneous peep show, saying: “I’m very grateful for the opportunity. It was lovely.”

Watch Dave's reaction after the big reveal:

1. We Love New York (Sept. 17, 2001):

David Letterman was the first late-night host to go back on-air following the Sept. 11 attacks on New York City. With a heavy heart, Letterman gave a choked-up, emotional and inspiring eight-minute monologue to a grieving nation about “the greatest city in the world.” It was a sharp reminder that Letterman always was the one who could handle not just comedy but tragedy with eloquence and gravitas.

Watch the emotional moment unfold:

Watch Dave’s big send off when the final broadcast of the Late Show with David Letterman airs Wednesday, May 20th at 11:35 p.m. ET/PT.