Memorable Moments from David Letterman’s Late Show
David Letterman’s Late Show has provided audiences with countless unforgettable moments, featuring both celebrities and the host’s unique sense of humor. Below are some standout appearances that showcase the show’s impact on late-night television.
Even when CBS’ Late Show with David Letterman veers into awkward, uncomfortable territory for the guest, Letterman never loses his cool. The show only gets better as it winds toward its conclusion.Any moment with legend Johnny Carson and legend-in-the-making Letterman was destined to be a classic, but Carson’s appearance on the Late Show in May 1994 is the most memorable.After Carson died in January 2005, David Letterman paid tribute to him by turning over his entire monologue to the celebrated comedian and TV personality.In March 1994, Madonna severely tested Letterman’s mettle in an exchange that’s become a standout late night moment, dropping several F-bombs during her interview.When Drew Barrymore showed up on Letterman in 1995, she brought unforgettable energy and a teasing reveal that became a memorable highlight.In March 2004, Courtney Love’s attempt to recreate Drew Barrymore’s playful appearance turned into a memorable fumble that left audiences laughing.Letterman’s first show after the September 11 attacks was a subdued and emotional episode, where the monologue was skipped in honor of those lost.In the fall of 2002, Letterman honored the terminally ill Warren Zevon with an entire episode dedicated to celebrating his music.Musician Paul McCartney performed on the Late Show, taking over the marquee of the Ed Sullivan Theater, where the Beatles made big news in 1964.Oprah Winfrey returned to the Late Show after 16 years, creating a moment that drew huge ratings and intrigue about their past.Michael Richards made a notable apology on the Late Show via satellite in November 2006, following his controversial tirade at a comedy club.Bill O’Reilly and David Letterman had a contentious but memorable debate over the Iraq War during one of their Late Show appearances.Paris Hilton returned to the Late Show in 2008, overcoming a tough previous interview with Letterman that had left her in tears.John McCain faced the heat on the Late Show in 2008, confronting Letterman after the host roasted him for canceling a prior appearance.Richard Simmons and David Letterman showcased a humorous friendship when they had a playful argument over a cooking appliance during a Late Show segment.
