01of 20

August 1993

Alan Singer/CBS

Image

02of 20August 1993Alan Singer/CBSOn night two of the show, Robin Williams did what he did best – make people (in this case, Letterman and the not-pictured audience) laugh.

02of 20

AUGUST 1993

On night two of the show, Robin Williams did what he did best – make people (in this case, Letterman and the not-pictured audience) laugh.

03of 20September 1993Alan Singer/CBSWith N.Y.C. in the background, Letterman grinned from the seat at his new post. As he should have: That month alone, he welcomedDemi Moore,Bruce Willis, Al Gore,Sarah Jessica Parkerand Rod Stewart to his stage.

03of 20

September 1993

SEPTEMBER 1993

With N.Y.C. in the background, Letterman grinned from the seat at his new post. As he should have: That month alone, he welcomedDemi Moore,Bruce Willis, Al Gore,Sarah Jessica Parkerand Rod Stewart to his stage.

04of 20September 1995Alan Singer/CBSAlong with the actors, actresses, models, politicians and comedians, there have been plenty of musical visitors to theLate Show, too. Here, David Bowie performs in the show’s early years.

04of 20

September 1995

SEPTEMBER 1995

Along with the actors, actresses, models, politicians and comedians, there have been plenty of musical visitors to theLate Show, too. Here, David Bowie performs in the show’s early years.

05of 20April 1995Alan Singer/CBSA young, wild andfreeDrew Barrymoregave Letterman quite a shock when she jumped on top of his desk, danced – and flashed him.His reactionsaid it all.

05of 20

April 1995

APRIL 1995

A young, wild andfreeDrew Barrymoregave Letterman quite a shock when she jumped on top of his desk, danced – and flashed him.His reactionsaid it all.

06of 20November 1995Alan Singer/CBSLetterman cracked up while interviewing a 34-year-oldGeorge Clooney, then the hot new star ofER.

06of 20

November 1995

NOVEMBER 1995

Letterman cracked up while interviewing a 34-year-oldGeorge Clooney, then the hot new star ofER.

07of 20July 1996Alan Singer/CBSDemi Mooresported her buzzed-about shaved head (for her role in the filmG.I. Jane) during a trip to the Ed Sullivan Theater to talk up another of her controversial flicks,Striptease.

07of 20

July 1996

JULY 1996

Demi Mooresported her buzzed-about shaved head (for her role in the filmG.I. Jane) during a trip to the Ed Sullivan Theater to talk up another of her controversial flicks,Striptease.

08of 20November 1998Alan Singer/CBSALate Showguest many times over, Steve Martin stood with Letterman on the show’s fifth anniversary.

08of 20

November 1998

NOVEMBER 1998

ALate Showguest many times over, Steve Martin stood with Letterman on the show’s fifth anniversary.

09of 20January 1999Alan Singer/CBSItalian actress Sophia Loren brought a little bit of home to the Ed Sullivan Theater in 1999, teaching Letterman how to make tiramisu on stage.

09of 20

January 1999

JANUARY 1999

Italian actress Sophia Loren brought a little bit of home to the Ed Sullivan Theater in 1999, teaching Letterman how to make tiramisu on stage.

10of 20September 2001John P. Filo/CBSThough generally light, theLate Showhad its serious moments: Dan Rather, then-anchor ofCBS Evening News, got choked up while discussing the Sept. 11 terrorist attacks.

10of 20

September 2001

John P. Filo/CBS

SEPTEMBER 2001

Though generally light, theLate Showhad its serious moments: Dan Rather, then-anchor ofCBS Evening News, got choked up while discussing the Sept. 11 terrorist attacks.

11of 20

November 2002

John Paul Filo/CBS

NOVEMBER 2002

12of 20September 2003John Paul Filo/CBSSynonymous with both LettermanandtheLate Showis the program’s set at the Ed Sullivan Theater in Midtown Manhattan. In 2003, the New York Philharmonic performed on the building’s roof.

12of 20

September 2003

Image

Synonymous with both LettermanandtheLate Showis the program’s set at the Ed Sullivan Theater in Midtown Manhattan. In 2003, the New York Philharmonic performed on the building’s roof.

13of 20November 2005John Paul Filo/CBSIn preparation forOprah Winfrey’sfirst-everLate Showvisit, Letterman posed with a portrait of the two of them. At the 1995 Oscars, he made a dud of an “Oprah, Uma, Uma, Oprah” joke, “introducing” the talk show hostess to Thurman, so Winfrey’s 2005 appearance on his show was seen as a burying the hatchet of sorts (though she insisted there was never a feud).

13of 20

November 2005

NOVEMBER 2005

In preparation forOprah Winfrey’sfirst-everLate Showvisit, Letterman posed with a portrait of the two of them. At the 1995 Oscars, he made a dud of an “Oprah, Uma, Uma, Oprah” joke, “introducing” the talk show hostess to Thurman, so Winfrey’s 2005 appearance on his show was seen as a burying the hatchet of sorts (though she insisted there was never a feud).

14of 20February 2009John Paul Filo/CBSLetterman’s hilariously awkward interview with Joaquin Phoenix went down as one of his weirdest. The nine-minute chat touched on Phoenix’s hip-hop aspirations and an injury to Letterman’s thumb, among other topics. It later came out that the whole thing was just promotion for Phoenix’s bizarre pseudo-documentary,I’m Still Here.

14of 20

February 2009

FEBRUARY 2009

Letterman’s hilariously awkward interview with Joaquin Phoenix went down as one of his weirdest. The nine-minute chat touched on Phoenix’s hip-hop aspirations and an injury to Letterman’s thumb, among other topics. It later came out that the whole thing was just promotion for Phoenix’s bizarre pseudo-documentary,I’m Still Here.

15of 20July 2009Jeffrey R Staab/CBSTwo icons in one shot: the Ed Sullivan Theater, home to both Letterman and theLate Showfor more than 20 years, and Paul McCartney, who performed on the theater’s marquee. McCartney and his band The Beatles made their U.S. debut in 1964 on the theater’s hallowed stage.

15of 20

July 2009

Jeffrey R Staab/CBS

JULY 2009

Two icons in one shot: the Ed Sullivan Theater, home to both Letterman and theLate Showfor more than 20 years, and Paul McCartney, who performed on the theater’s marquee. McCartney and his band The Beatles made their U.S. debut in 1964 on the theater’s hallowed stage.

16of 20

August 2009

Jeffrey R. Staab/CBS

AUGUST 2009

17of 20December 2010John Paul Filo/CBSSmooches all around! Dustin Hoffman planted one on Robert De Niro’s head as they promoted their filmLittle Fockerstogether.

17of 20

December 2010

Image

Smooches all around! Dustin Hoffman planted one on Robert De Niro’s head as they promoted their filmLittle Fockerstogether.

18of 20

September 2013

SEPTEMBER 2013

19of 20April 2014Jeffrey R. Staab/CBSThe past and the future came together as Letterman snapped a selfie with Stephen Colbert, who eventually replaced him as the host of theLate Show.

19of 20

April 2014

APRIL 2014

The past and the future came together as Letterman snapped a selfie with Stephen Colbert, who eventually replaced him as the host of theLate Show.

20of 20October 2014John Paul Filo/CBSTaylor Swift’s1989was one of the most talked-about albums of 2014 – and just a day after its release, she sang a few tracks on theLate Show.

20of 20

October 2014

OCTOBER 2014

Taylor Swift’s1989was one of the most talked-about albums of 2014 – and just a day after its release, she sang a few tracks on theLate Show.

source: people.com