Top 20 Most Memorable David Letterman Moments

On February 1st, 1982, Letterman began his first foray into late night talk shows. It’s an especially good omen that his first guest was the inimitable Bill Murray. Coming off his storied run on “Saturday Night Live,” the actor didn’t disappoint as he brought his engaging and entertaining comic timing to the program. Murray was able to bring out the best of the host’s idiosyncratic humor, kickstarting the “Late Night with David Letterman” show for the better. The comedian even found time for a goofy musical number to button his historic performance. Not only did Murray’s appearance showcase the potential for the show, it also was the first of his many amazing and lovable appearances opposite the late-night personality.

Known for his autobiographical comic strips, Cleveland writer and personality Harvey Pekar graced the original "Late Night" show several times in the ‘80s. The Midwestern man's candid nature made him a cult hero and the perfect person to make an appearance on the irreverent program. Cantankerous and outspoken, the guest spent his sixth appearance railing against NBC’s connections to parent company General Electric. Testing Letterman’s patience, the writer's continued protests led the host to unofficially ban him. Unsurprisingly, Pekar’s endless ranting and pestering was only tolerated for so long. Thankfully for the viewers, the ban didn't last as the guest was invited back in the ‘90s. In retrospect, the grouchy author's riotous behavior made Letterman's show appointment viewing.

During the heyday of “Late Night,” the show was known for breaking the rules of television comedy. This was never more evident than when the comedian donned a Velcro suit. Despite being silly, the skit represents how the host wasn't afraid to make fun of himself. Playing catch, the entertainer can’t help but access his inner child as he spends precious TV time doing lovably dumb things. Somehow, the climax of Letterman jumping and sticking to a wall justifies the entire skit. While there was another entertaining gag involving an Alka-Seltzer tablet suit, this one wins for being the first and more versatile idea. In the end, the Velcro suit opened the door for increasingly absurd ideas that made the show entirely unique.

Few would've imagined that Letterman’s mom not only agreed to be on the show, she also participated in several comedy segments. Most famously, his mother Dorothy traveled to Lillehammer for the 1994 Winter Olympics. Providing the show with sweet and humorous asides, the host’s mom broadcasted via satellite from Norway. If that wasn’t enough, she even got an interview out of Hillary Clinton. Combining a grounded commentary of the event, the show struck gold with Dorothy's engaging take on Olympic coverage. Juxtaposed with her son’s wit, she shines as a truly likable and down-to-earth figure. Through it all, the moment solidifies Letterman as a great son from a family that isn’t afraid to laugh together.

Before the Kardashians, Paris Hilton journeyed through the 2000s as one of THE celebrity it girls-slash-socialites. After spending time in jail, the hotel heiress wound up as a guest on the “Late Show.” Hoping to talk about her professional pursuits, Hilton was instead questioned about her incarceration. Walking the line between intrusive and funny, the comedian manages to keep steering the conversation into controversial waters. Unafraid and unashamed, Letterman showed no signs of backing down in his quest to uncover all the details of Hilton's time in the slammer. In particular, this interview made it clear to audiences that Letterman wouldn’t engage in the usual, safe talk show patter.

One of the many great field pieces for the show, Letterman spent one day working at a Taco Bell. Manning the drive-thru, the host deals with all manner of fast-food conundrums. While helping people order their food, the comedian serves up several pranks and jokes. At the drivers’ expense, the funny man throws a wrench in the typical flow of a restaurant. Somehow, he squeezes every ounce of humor out of the seemingly mundane operations of a fast food franchise. The remote segment was the perfect encapsulation of Letterman’s polite Midwestern speech mixing with his anarchic comedy mind. As customers grow frustrated, it’s hard not to laugh at the unique comic menace on display.

Among the more bizarre guests in Letterman’s history, Brother Theodore represented the show’s obsession with strange guests that made you question reality. Call him philosophical or incoherent, the performer walked a tightrope between a genuine one-man show and unintentional comedy gold. Regardless, his ability to confuse and delight deserves a mention on this list. At times, it’s unsure if Letterman himself knows how to deal with the German performer’s rambling. As the guest walks to his own spotlight, he unleashes a monologue that’s nothing short of unexpected. Turning the program into an off-Broadway oddity, Brother Theodore leaves his mark in one of many unforgettable appearances.

In 2002, frequent guest Warren Zevon returned to the show with a terminal cancer diagnosis. Despite the tragic announcement, the singer maintained his jovial personality even in the face of death. During his interview, the performer was honest about his poor health, but kept the atmosphere light as he joked with Letterman. Having developed a friendship over the years with Zevon, the comedian held back his emotions as he spoke to the singer about mortality. To cap off the appearance, the musician played the piano and sang in an emotional performance. Proving that the program could be as serious as it was hilarious, this interview was among the more enlightening moments in the history of the "Late Show."

Few Letterman moments were as awkward or earnest as when the “Late Show” captain came clean about his affairs with show staffers. In order to thwart a blackmail attempt, the comedian decided to announce the news and explain the million-dollar extortion plot against him. Not making excuses for himself, the funny man was all business as he apologized for his infidelities. While it isn’t humorous in the slightest, the moment speaks to Letterman’s willingness to be upfront and honest towards his audience. Wearing his heart on his sleeve, the host delivered a sobering and no-frills confession that revealed his inner humanity.

During the ‘80s and ‘90s, Madonna stood as one of the leading figures in pop music. It was only a matter of time that her indelible and iconic personality clashed with Letterman. For this appearance, Madonna smokes cigars and speaks as if there's nobody watching. Needling the performer, the host's overbearing and personal questions were no match for the star's quick-witted retorts. Unfortunately for censors, she dropped some f-bombs in the process. Controversial for the time, the pop singer’s outbursts would be considered tame by today’s standards. If anything, her willingness to do so proved Letterman’s show was a place where anything could happen and the rulebook was optional.

The Top-Ten list was arguably the crown jewel of both Letterman shows, first appearing in the early seasons of "Late Night". Many guests presented the segment over the years, from everyday people to high-profile celebrities. One memorable version came when the singer Barry White provided a unique twist on the form. With backup singers, the ‘70s icon delivered absurd lines that “sound better” when sung by his silky voice. Leave it to the Letterman writers to elevate their tradition through the pitch perfect performance of a musical guest. There’s so many awesome lists to choose from, including a classic segment with Alex Trebek. However, White’s delivery makes this one among the funniest Top-Ten lists of all time.

There were few guests in Letterman history that were as energetic as Chris Farley. Nearing the end of his time on “Saturday Night Live,” Farley stopped by to promote his film "Tommy Boy." Unable to do a casual entrance, the sketch performer rolled out doing cartwheels. The most physically gifted comedian of his day, Farley was never one to shy away from a chance to prove himself. More than anything else, the guest’s ecstatic personality meshed well with the host’s rule-breaking attitude. As a meeting of two comedy geniuses, this interview reminded everyone of the freewheeling and infectious atmosphere of the Letterman show.

Drew Barrymore made the most of her 1995 appearance on the "Late Show." Since it was Letterman’s birthday, the giddy actress wanted to give the legend something he would never forget. Shocking everyone, the guest stood up on the desk to do a dance, before flashing Dave. In complete shock, the comedian failed to muster up a response as the crowd cheered. Rarely speechless, the entertainer himself couldn't believe his show could be this wild. It’s fair to say that there was no script for this moment, proving that Letterman was the most unshackled show on the air. Surprising everyone, Barrymore’s split-second decision will forever be remembered as the time a guest took complete control away from the host.

One of the most talked about interviews from his CBS run, Letterman welcomed a dismissive and unshaven Joaquin Phoenix. Despite the actor’s withdrawn presence, the host was able to turn the interview into a hilariously uncomfortable set piece. Considering his experience dealing with extraordinary guests, Letterman was more than prepared to hit the interview out of the park. Later revealed to be a stunt for his mockumentary “I’m Still Here,” Phoenix’s story about quitting his profession was all an act. Despite a later apology, the actor's performance remains an intriguing look into the destruction of celebrity. Luckily for the audience, the comedian had no clue and made the most out of the odd appearance.

While he had many acting roles dating back to the 80s, Crispin Glover might be best known today for his role in “Back to the Future.” In this manic appearance, the actor’s eccentric personality came out in strange outbursts and ravings. Mixing show-and-tell with a variety of non sequiturs, Glover becomes increasingly uneasy as Letterman attempts to calm the guest down. Building to a dramatic finish, the guest launches from his seat and shows off his martial arts moves. During the demonstration, one of his kicks almost hits Dave, which all but ends the interview segment. It's hard to believe this interview ever happened, making it another historic moment for the show.

Performance artist and comedian Andy Kaufman made a name for himself on TV shows like “Taxi,” as well as several appearances on “Late Night.” Pursuing a side career in wrestling, Kaufman appeared on the show with rival Jerry Lawler. Wearing a neck brace, the performer went on to instigate Lawler. While Letterman attempts to officiate the conversation, he’s unable to stop Lawler as he slaps Kaufman. For nearly a decade, the entire event was believed to be real. Tense and unexpected, the entire interview feels completely off-the-cuff. Regardless of it being staged or not, the appearance felt as genuine and awkward as any guest appearance in the history of late-night television.

By the 1980s, Sonny and Cher had long since broken up. It took a program like “Late Night” to bring the two back together again. Cher's return wasn’t a sure thing, since her last appearance on the show involved her calling Letterman an a-hole. This time, she was much happier to join her former partner to reminisce. By the time they sing "I Got You Babe," it’s as if the pair never parted ways. A healthy dose of nostalgia might’ve boosted this moment even higher. Prompting pure joy from Letterman and the audience, the reunion provided one of the happiest moments in the show’s history.

After the events of September 11th, nobody knew how to properly deal with the fallout of such a huge tragedy. Comedy shows like “Late Show with David Letterman” were trepidatious to return and attempt to be funny again. With a calm and heartfelt message, the host opened his show in a tribute to the victims and citizens of New York. Along with his guests, Letterman traded in jokes for a detailed and honest discussion of the harrowing day and its aftermath. Showcasing his ability to adapt to the changing times, the comedian encapsulated the feelings of many fearful Americans into one of his finest moments as a performer.

Few guests were as meaningful to Letterman as his personal comedy icon, Johnny Carson. Having retired from his decades-long stint on “The Tonight Show,” the appearance was especially important for legions of television fans. Allowing Carson to take over, the moment shows the host’s reverence for the man responsible for the success of late-night talk shows. Carson’s signature comic timing hadn’t missed a beat, with the comedian providing laughs and smiles without having to do anything. Years later, the funny man finally paid tribute to Carson after his death in another worthy moment for this list. While he was a comedy genius in his own right, Letterman also knows when it's best to step aside and let someone else take the spotlight.

After a late-night career that started way back in 1982, David Letterman decided to finally retire in 2015. His final weeks on the show included a parade of esteemed guests saying "goodbye," including a particularly emotional tribute from Norm Macdonald. For his final moments behind the desk, the longtime host decides to keep it classy. He thanks his crew and family, reminding everyone of his humor, irreverence, and undeniable likability. To close the show, the Foo Fighters play him out in an emotional crescendo filled with equal parts energy and sentimentality. Even for those who weren't die hard Letterman fans, it's hard not to count this moment as the culmination of his legendary career.