The following is a list of notable episodes from Late Show with David Letterman since its inception on August 30, 1993. Late Show with David Letterman is an American late-night talk show hosted by David Letterman that ran on CBS between August 30, 1993, and May 20, 2015.

1993

August 30 The premiere of Late Show,Late Night with David Letterman / Late Show with David Letterman from the Museum of Broadcast Communications featuring actor/comedian Bill Murray and singer Billy Joel, attracts 23 million viewers. Murray, who had been Letterman's first Late Night guest on NBC in 1982, spray-painted "Dave!" on the front of the host's desk.

1994

March 31

On March 31, 1994, pop star Madonna appeared on the Late Show. The "Queen of Pop", who is known for controversy, infamously swore thirteen times throughout the interview and refused to leave at the end. Letterman, who asked her questions on various topics—including her nose ring, music, and love life—was soon branded a "sick fuck", after he suggested Madonna kiss a member of the audience. Madonna went on to ask if Letterman was wearing a "rug", whether he wanted to smell a pair of underwear she brought on the show, or whether he thought the microphone was sexually big. In between this, Madonna often swore and referred to sexual themes, including her vagina, saying: "Did you know it's good to pee in the shower?" Eventually, she swore so much that the producers went to commercials and showed comedic monologues of Madonna. Letterman has since stated, in USA Today: "I'm not pleased with the way I handled it. I should have said, 'You say that word one more time and you're gone. That's it. Adios.' And I didn't." Madonna appeared days later on The Tonight Show with Jay Leno. Although she appeared briefly at the stroke of midnight on Valentine's Day, 1995, to present Letterman with a bouquet of roses, her return to the show as a guest was not until 2000, while promoting her album Music. During that interview, and other subsequent interviews on the show, Letterman joked that he still had the panties that she gave him.

During the September 1994 MTV Video Music Awards, Madonna was a presenter and was escorted onstage by Letterman, who kissed her hand and stated, "I'll be in the car. Just... watch your language," and walked off stage to applause.

May 13 During a week of shows taped in Los Angeles, Johnny Carson made a surprise appearance on the show after leaving The Tonight Show. Carson maintained a friendship with the show for the years that followed, even secretly writing jokes for the monologue. This rare surprise appearance was Carson's final major television appearance before his death, and to many, his way of acknowledging Letterman as his successor (even if Jay Leno was doing his former show at the time). Carson never appeared on Leno's version of Tonight.

December 2 Hello Deli owner Rupert Jee makes his first appearance, on a segment called "Fun With Rupert".

1995

April 12 After finding out it was Letterman's birthday, Drew Barrymore gave him a "little impromptu birthday present": she "hopped up on his desk, did a sexy little dance, turned her back to the camera and flashed her breasts".David Letterman's Top Ten Most Insane Interview Moments, a February 13, 2009 post from the Yahoo! TV Blog

May 16 A week of shows, with most crew and cast, was filmed and broadcast entirely from London, United Kingdom, featuring guests Pierce Brosnan, Jennifer Saunders, Joanna Lumley, and a musical performance by Elvis Costello. A segment featuring Zsa Zsa Gabor was also taped. In addition, sitting in with the CBS Orchestra were Little Richard and Chuck Berry.

1996

September 20 In early September 1996, it was announced that Late Show would experiment with a commercial-free format. The September 20 broadcast of the show did not contain traditional commercials, although there were breaks (within the show) to acknowledge sponsors. Pearl Jam was the musical guest on this night.

1997

June 5 Farrah Fawcett visited the show for the first time promoting a Playboy pay-per-view special and appeared disoriented and incoherent.

1998

February 16 NASCAR driver Dale Earnhardt does the Top Ten List after winning the Daytona 500.

1999

February 23 Minnesota Gov. Jesse Ventura, a former professional wrestler who had assumed office on January 4, visits the show for the first time.

December 31 Late Show broadcasts in prime time for the year 2000 New Year's Eve. Kevin James is the guest, with a performance by the Brooklyn Philharmonic and cameo appearances by Dick Clark and New York City Mayor Rudolph Giuliani. (Under normal circumstances, Letterman does not broadcast a show on New Year's Eve, opting instead for a repeat.)

2000

February 21 On January 14, Letterman announced on Late Show that he was undergoing an angiogram the following day, after doctors had recently been concerned about his high cholesterol and family history (his father died of a heart attack at 57). Soon it was discovered that he had blocked arteries and had to undergo a quintuple bypass. During his recovery, after a few weeks of rerun broadcasts, the show was hosted by guests for several weeks. On his first show after recovering, Regis Philbin was his first guest; Letterman brought out all the doctors and nurses on the show who had helped him during his surgery and recovery. Despite nearly breaking out in tears during the show, Letterman seemed to find humor in his situation; while referring to one of his nurses, he said: "This woman saw me naked!" He continued to joke about the event for weeks after his return.

Additionally, Letterman invited the alternative rock band Foo Fighters as musical guest. The band performed their 1997 single "Everlong", which Letterman personally requested, and Letterman introduced them as "my favorite band, playing my favorite song." During a later Foo Fighters appearance, Letterman said that Foo Fighters had been in the middle of a South American tour which they canceled to come play on his comeback episode. In 2015, the Foo Fighters would play the song again for the final episode of the show, transitioning into the final credits.

2001

September 17 On September 17, 2001, David Letterman was the first major American comedy performer to return to the television airwaves after the September 11 attacks. In his opening monologue, absent the usual musical opening credits and cheering audience, an uncharacteristically serious and very emotional Letterman struggled with the reality of the attacks and the role of comedy in a post-9/11 world, saying:

Letterman went on to praise Mayor Rudy Giuliani and the NYPD/FDNY in the monologue and ended the segment by saying "If you didn't believe it before, you can absolutely believe it now. New York City is the greatest city in the world." From that point on, Alan Kalter's opening narration at the very top of the show, which up until then poked fun at the city, introduces New York as "The greatest city in the world!" However, beginning in January 2013, Kalter's opening was changed to "From New York! Broadcasting across the nation and around the world!" and in early 2015, once again began to feature bizarre openings, minus the derogatory remarks about New York. Moreover, the opening shot of the credits, which at that time was a view of Battery Park and the World Trade Center, was changed to a dynamic helicopter view of the Statue of Liberty (used ever since) and an aerial shot of the Empire State Building.

His first guest that night was then-CBS Evening News anchor Dan Rather, who broke down twice in tears. Letterman's longtime friend and colleague Regis Philbin later joined Letterman to help lighten up the somber mood.

Time magazine named Letterman's return to the air after the attacks the Best TV Moment of 2001.TIME Best & Worst 2001 -- TV, Time Magazine, January 2002 Entertainment Weekly put it on its end-of-the-decade, "best-of" list, saying, "He's snarky. He's snide. But when a solemn Letterman returned to the air Sept. 17, 2001 (his was the first late-night comedy show to air after the attacks), his off-the-cuff monologue showed the shell-shocked audience it was okay to laugh…and to cry."Geier, Thom; Jensen, Jeff; Jordan, Tina; Lyons, Margaret; Markovitz, Adam; Nashawaty, Chris; Pastorek, Whitney; Rice, Lynette; Rottenberg, Josh; Schwartz, Missy; Slezak, Michael; Snierson, Dan; Stack, Tim; Stroup, Kate; Tucker, Ken; Vary, Adam B.; Vozick-Levinson, Simon; Ward, Kate (December 11, 2009), "THE 100 Greatest MOVIES, TV SHOWS, ALBUMS, BOOKS, CHARACTERS, SCENES, EPISODES, SONGS, DRESSES, MUSIC VIDEOS, AND TRENDS THAT ENTERTAINED US OVER THE PAST 10 YEARS". Entertainment Weekly. (1079/1080):74-84

2002

October 30

The musician Warren Zevon was featured as the only guest for the entire hour. The episode concerned his recent terminal peritoneal mesothelioma diagnosis, a rare form of cancer caused from exposure to small asbestos fibers. The band played Zevon's classic song "I'll Sleep When I'm Dead" as his introduction. Zevon performed several songs and spoke at length about his illness. Zevon was a frequent guest and occasional substitute bandleader on Letterman's television shows since Late Night was first broadcast in 1982. (Letterman had also performed some backing vocals on Zevon's "Hit Somebody (The Hockey Song)", with Paul Shaffer on organ.) Zevon noted, "I may have made a tactical error in not going to a physician for 20 years." It was during this broadcast that, when asked by Letterman if he knew something more about life and death now, he first offered his oft-quoted insight on dying: "Enjoy every sandwich". He also took time to thank Letterman for his years of help, calling him "the best friend my music's ever had". For his final song of the evening, and his final public performance, Zevon performed "Roland the Headless Thompson Gunner" at Letterman's request. In the green room after the show, Zevon presented Letterman with the guitar that he always used on the show, with a single request: "Here, I want you to have this. Take good care of it."Dave At Peace, Rolling Stone Magazine Issue 1061 (Sep/2008) Zevon died less than a year later, shortly after the release of his album The Wind.

2003

November 4 Letterman announces that "last night at 11:58, I became a father." The previous night, Letterman's long-time partner, Regina Lasko, gave birth to his son, Harry.

2004

March 17 Singer Courtney Love flashed Letterman while standing on his desk, her bare back to the audience.

March 29 Singer Janet Jackson made her first network television interview following the Super Bowl XXXVIII halftime show controversy.

May 14 Letterman decided to tape the episode for May 14, 2004, at 4 a.m. EST that morning with a full studio audience. The guests for the show included rat expert Robert Sullivan, humorist Amy Sedaris and the indie rock band Modest Mouse. Highlights included Late Show staff member Bob Borden oversleeping, looking for rats with Robert Sullivan on West 53rd Street, Biff spending the night with the NYPD and Amy Sedaris giving a tour of her neighborhood at 4 in the morning. There was also a special version of the show's intro showing a montage of Late Show staffers sleeping on their desks and at their workstations, Letterman riding to the Ed Sullivan Theater on a horse and a video of Hillary Clinton introducing the show.

June 21 The rock band Phish, making their final television appearance before their farewell concert that August, performed an afternoon set atop the Ed Sullivan Theater's marquee for the taping of that evening's episode of Late Show. Although only one song was specifically taped for the show, Phish also performed five additional songs for the hundreds of fans that had gathered outside the theater. Phish would reunite in 2009, but they did not perform on Late Show again until 2014.

2005

January 31