Jake’s Take: A Tribute to David Letterman’s Late Night Career

David Letterman retires

After entertaining audiences for 35 years, David Letterman will retire from television on Wednesday. (Photo property of CBS & Worldwide Pants, Inc.)

By: Jacob Elyachar, jakes-take.com

Tonight, David Letterman will be retiring from Late Night for good!

I had the honor and privilege of being in the Late Show with David Letterman audience twice in my life. (Both times were two years apart from each other and in October) Seeing Mr. Letterman work his magic at the Ed Sullivan Theatre twice will truly remain two of my all-time favorite highlights of this decade.

In honor of Mr. Letterman’s retirement, here are some of my favorite moments from his career in Late Night:

Music legends celebrate “Late Night’s” sixth anniversary with “Sweet Soul Music” (1988)

Probably the greatest musical moment in David Letterman’s 35 years of hosting talk shows came when longtime musical director Paul Shaffer rallied an all-star group of musicians for Late Night’s sixth anniversary. Billy Joel, Carole King, Cyndi Lauper, Warren Zevon, Ben E. King, Joe Walsh, Ashford & Simpson, Roberta Flack and Clarence Clemons brought Radio City Music Hall to its feet with their rousing rendition of “Sweet Soul Music” and a medley of classic R&B tracks such as “Proud Mary,” “What I Say” and “Stand By Me”! This was probably the first and last time late night saw a supergroup of that magnitude perform together.

Dave and Johnny commiserate on “The Tonight Show” (1991)

The King of Late Night wanted his top protégé to replace him on The Tonight Show after he stepped down in 1992. However, NBC had other plans and chose Jay Leno to replace Carson instead of Letterman. When Johnny and Dave had one of their last sit-downs, Mr. Carson asked pointblank-“How pissed off are you?” and the entire room erupted. Fans loved Dave’s classic response to the question and his hysterical laughter that he showcased when Johnny correctly predicted that his top pupil was going to be around for another 20 years.


Johnny Carson's final TV appearance

The “Late Show” audience roared with delight as the King of Late Night made his final televised appearance on his protegé’s talk show. (Photo property of CBS & Worldwide Pants Productions)

Johnny Carson’s final appearance on Letterman (1994)

“This is not the list! Johnny, can I have the Top 10 List?” After David Letterman shouted that phrase, the Late Show audience went into pure pandemonium as Johnny Carson himself hand delivered the night’s Top 10 list. Even after Paul and his band stopped playing the iconic The Tonight Show with Johnny Carson theme, the audience continued to go bonkers for the Master of Late Night, as he briefly took command of the stage…. one final time! Seeing the audience erupt and Johnny’s reaction remains one of the best moments in Late Show history.


Drew Barrymore's striptease remains one of the most talked about "Late Show" moments of all-time. (Photo property of CBS & Worldwide Pants, Inc.)

Drew Barrymore’s striptease remains one of the most talked about “Late Show” moments of all-time. (Photo property of CBS & Worldwide Pants, Inc.)

Drew Barrymore flashes Dave (1995)

One of the show’s most outrageous moments came from Drew Barrymore! After celebrating her birthday, Drew opened up about going nude at a nightclub and gave Dave a little taste of her burlesque act. This brief act also included the 50 First Dates actress flashing the talk show host. This moment not only got people talking about the Late Show, but it also delivered one of Letterman’s most memorable moments from the 1990s.

“Late Show” returns to air after 9/11 (2001)

The United States of America was forever changed by the attacks on New York City and Washington DC. On September 19, the Late Show returned to air and delivered one of his most inspiring monologues. He praised then New York City mayor Rudy Giuliani, the Fire Department and Police Department for the courage and inspiration that they showed through America’s darkest days. Mr. Letterman’s honest views were very welcomed and helped his audience heal from the emotional wounds that horrific day gave to every American.

Dave’s tribute to Johnny (2005)

It all started with a simple monologue that contained brilliant jokes. However, all the jokes had one thing in common: they were all jokes written by the Late Show host’s mentor—the late Johnny Carson. “He was like a public utility,” Letterman stated. “It did not make a difference what kind of day that you had or it didn’t matter who the President was or how the economy was doing, At the end of the day, the guy you wanted there was Johnny Carson.” Letterman’s analytical tribute brought back memories of the Golden Age of Television and his homage to his mentor gave me chills.


The Queen of Talk made TV history when she returned to "The Late Show" after debunking a 16-year feud between herself and Mr. Letterman. (Photo property of CBS & Worldwide Pants Inc.)

The Queen of Talk made TV history when she returned to “The Late Show” after debunking a 16-year feud between herself and Mr. Letterman. (Photo property of CBS & Worldwide Pants Inc.)

Oprah returns to the “Late Show” (2005)

Television history was made when media mogul Oprah Winfrey returned to the Late Show after a 16-and-a-half year “proposed feud” between the two talk show icons. During the first few minutes, Ms. Winfrey clarified that it takes “two people to feud” and Mr. Letterman responded, “I think the world of you.” From revisiting the infamous “Uma-Oprah” incident and Dave’s son, Harry’s Book Club to talking about the history of the Ed Sullivan Theatre and Dave accompanying Oprah to her opening of the Broadway production of The Color Purple, the interview was pure magic!

Homer Simpson does the Top 10 (2010)

The Simpsons’ patriarch appeared to the Late Show to deliver a hysterical Top 10 list focusing on what the Springfield resident learned from 20 years on television. Between Letterman “looking around the stage” for Homer and the zingers that the Springfield Power Plant employee threw at iTunes, Keith Olbermann, the Home Shopping Network and the host himself, this remains one of my favorite monologues done by an animated character!


TV legend Regis Philbin holds the record for the most appearances on "The Late Show with David Letterman" with over 150 appearances. (Photo property of CBS & Worldwide Productions, Inc.)

TV legend Regis Philbin holds the record for the most appearances on “The Late Show with David Letterman” with over 150 appearances. (Photo property of CBS & Worldwide Productions, Inc.)

Dave talks to Regis about his retirement (2011)

The entertainment world was stunned when television legend Regis Philbin announced his departure from Live with Regis & Kelly. Longtime friend David Letterman called and voiced his concern during a taping of the show. The former Who Wants to Be a Millionaire host clarified that he would not be retiring indefinitely from show business, but from his show that he did for 28 years. Regis and Dave’s conversations were always fantastic to watch and put a smile on fans’ faces every time the two TV icons caught up.

Xtina’s tips for aspiring singers (2011)

The Queen of the Voice popped by to deliver a hysterical Top 10 list. While the “Let There Be Love” singer was not feeling several of the jokes (watch out for eye rolls from Ms. Aguilera during tips numbers seven and two), Letterman’s impression of a meowing cat and Christina’s ad-libs left the audience in hysterics.


Bill Murray as Liberace and David Letterman

To commemorate “The Late Show’s” 20th Anniversary, Bill Murray dressed up as Liberace and delivered a over-the-top cover of “I Will Always Love You.” (Photo property of CBS & Worldwide Pants, Inc.)

Bill Murray visits “Late Show” as Liberace (2013)

Bill Murray will go down in Late Night history as the most memorable guest to appear on any Letterman talk show! The superstar comedian was Dave’s first guest on both Late Night with David Letterman and The Late Show; he will also be one of the last guests on Mr. Letterman’s final show. To commemorate the Late Show’s 20th anniversary, Bill dressed up as Liberace, made a grand entrance, tore a hole on the stage and delivered several over-the-top gifts to his friend including a hysterical cover of Whitney Houston’s “I Will Always Love You.”


David Letterman and Joan Rivers

David Letterman “walked out” on the late Joan Rivers during her final appearance on “The Late Show.” (Photo property of CBS & Worldwide Pants, Inc.)

Dave walks out on Joan Rivers (2014)

Sadly, July 8 marked the last time Joan Rivers appeared on Late Show. Mr. Letterman talked to the comedy legend about her controversial CNN interview and just as Ms. Rivers was explaining herself to Dave, the Late Show mockingly walked out of their interview. After he walked off the stage, Joan took over control the show with hysterical results.

Howard Stern’s final visit (2015)

Ever since the King of All Media and “America’s Judge” burst onto the scene, Howard Stern took time to visit Mr. Letterman on his show. Any viewer knows that every time the America’s Got Talent judge visited the show, Howard takes free rein of the show and delivers hysterical insights. I will miss watching the two iconic hosts talk about their aging parents, Howard’s hatred of Jay Leno and their favorite guests on their respective shows.

I do not own any of the clips that were featured in my article.  All clips except the “Sweet Soul Music Medley” belongs to CBS & Worldwide Pants, Inc. The “Sweet Soul Music Medley” belongs to NBC, Carson Productions & Worldwide Pants, Inc.


Copyright 2020 Jacob Elyachar