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From Tom Waits to R.E.M.: The 10 best David Letterman musical guests

Although most notable for his wry, witty sense of humour and silly televised antics, an under-appreciated aspect of Late Night veteran David Letterman’s career is the wide-ranging variety of musicians he had on the show throughout his 33-year career.

With his creation of the Late Night‘s “World’s Most Dangerous Band,” with Paul Shaffer, it’s evident that, from the show’s inception, it was built to emphasise the importance of music, and that’s without even mentioning Letterman’s own love affair with the art.

From booking unknown club bands and giving them their television debut like the Foo Fighters, or commemorating momentous occasions with musical legends like Paul McCartney, Letterman’s taste was spread far and wide. He even managed to secure rare performances from recluse musicians like Radiohead and Bob Dylan — a near-impossible feat.  

Letterman, reflecting on his work, is quoted as once saying: “Why we are here: To tremble at the terrible beauty of the stars, to shed a tear at the perfection of Beethoven’s symphonies, and to crack a cold one now and then.” This mentality encapsulates the beauty of his show. Although it’s hard to condense multiple decades of memorable appearances by musicians, there are certainly some shining stars that deserve to be noted.

Here are the ten best David Letterman musical guests. 

The 10 best performances on David Letterman:

10. Emmylou Harris 

Emmylou Harris first appeared on Late Show in 1989 with a performance of her song ‘Heartbreak Hill’ that ended in Letterman saying, “I hope you come back here anytime you like.” Harris accepted the offer and continued to appear many times, much to the delight of Letterman, who always shared his flattering remarks about Harris. He once regarded her as one of the great icons of country music, giving a glimpse into the wide variety of genres that made up his musical taste.

Harris later reciprocated this by stating, “I did the Late Show a lot. Dave was very supportive of every aspect over the years of everything I’ve done—different bands, different projects. Gillian Welch, Sheryl Crow, and I came on right after 9/11, and it was a totally different, serious thing. The show must go on, but everybody was feeling the tragedy. We were able to do a beautiful gospel song a capella called ‘Bright Morning Stars,’ and I think we did ‘Will the Circle Be Unbroken?’ which was probably Dave’s idea—I think that’s a very special song to him. We’re going to miss him! It’s kind of hard to imagine evenings without Dave.”

9. Tom Waits 

When Tom Waits appeared on Late Night in 1983, Letterman had nothing but praise for the underground, controversial singer. “My next guest is truly one of the most original music talents working today,” says Letterman. “Please welcome—  it’s a real delight to have this man with us tonight— Mr Tom Waits.”

After his first appearance, due to Waits’ wry humour matching Letterman’s own, he appeared on the show several more times. Throughout the years, he promoted his work while on the show caught up with Letterman in witty bits, who was establishing himself to be an appreciator of music’s fringes as well as the mainstream. Wait’s last appearance came in 2012, after the release of his final album, Bad as Me.

8. James Brown

On James Brown’s first and last appearance on Late Night, he managed to solidify a spot as one of the most memorable performances in the show’s history. Before sitting down with Letterman and discussing his new work and Brown’s passion for the importance of firm childhood education, Brown performed a multiple-song set— something often prohibited by Letterman when it came to other artists. 

Shaffer, of the ‘World’s Most Dangerous Band,’ later recounted in his memoir: “When we were back on the air, James said, ‘Hey Dave, you know what I’d like to do right now? Before you close, can we close with ‘I Got the Feeling?’ ‘Sure thing,’ said Dave. ‘Soon as we come back from one more break.’ Once the commercial was over, we hit it: an unrehearsed full-blown version of ‘I Got the Feeling.’ The audience went crazy. Dave joined the James Brown Fan Club.”

7. Warren Zevon

American rock legend Warren Zevon appeared many times throughout Letterman’s career, his first being the opening year of NBC’s Late Night With David Letterman. But perhaps his most memorable appearance was after a 2002 cancer diagnosis.

After hearing about the news, Letterman decided to devote the entire show to his old friend for the last time. 

Zevon used his slot this time to transparently discuss his mesothelioma, sharing: “I might have made a tactical error in not going to a physician for 20 years. It’s one of those phobias that didn’t pay off.” But along with the bittersweet conversation, he performed the three classics ‘Mutineer,’ ‘Genius.’ and ‘Roland the Headless Gunner,’ the last being a request from Letterman.

6. R.E.M.

A perfect example of how Letterman had a natural eye for talent and touching support of the underdog came in the autumn of 1983 when he asked unknown Athens, Georgia-based band R.E.M. to stop by the show. The band performed ‘Radio Free Europe’ and ‘So. Central Rain’, providing an early glimpse into what was to become one of the biggest bands in the world.

Mike Mills later remembered about that night: “The first time we played Letterman, Peter and I had smuggled some beer into the dressing room, and Dave stopped by to say hi. He saw the beer, and he said, ‘Are you guys nervous?’ Peter and I said, ‘Yeah, a little bit.’ He said, ‘Well, don’t worry, it’s not like it’s a real show or anything.’ We laughed and felt better. He put us at ease, and we had a great time. That was our first national TV show ever, so it was very exciting.”

5. Madonna

Madonna’s debut appearance on Late Night is regarded now as one of the most controversial interviews in the show’s history. It began with Letterman’s sexist introduction of the star by saying: “Our first guest tonight is one of the biggest stars in the world, and in the past ten years she has sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry.”

During the interview, the ‘Holiday’ star was counted as saying the word “fuck” fourteen times, making the episode the most-censored in American network television talk-show history. Letterman sarcastically remarked that she had to stop saying the word “because people don’t want that in their own homes at 11:30 at night.” But despite the controversy, this segment became one of the highest ratings Letterman had ever received, and she continued to appear on the show throughout the years. 

4. Paul McCartney

45 years after The Beatles’ legendary Ed Sullivan debut, Paul McCartney came back to the same stage, this time, with Letterman as the host. Letterman began by stating the 15 years he’d been consistently trying to get McCartney on the show, and asked: “I just need to know going forward, are there any problems that we don’t know about?” McCartney replied jokingly, “I don’t like the show.” The pair went on to discussed The Beatles’ American debut and reminisced on their legendary career. 

McCartney went on to perform the Beatles classic ‘Get Back’ and ‘Sing the Changes’, a new song from his 2009 album Electric Arguments. After the show, he headed onto the rooftop as a tribute to The Beatles’ last 1969 rooftop performance and sang ‘Coming Up’, ‘Band on the Run’, ‘Let Me Roll It’, ‘Helter Skelter’, and ‘Back in the USSR’ for the crowd outside the theatre.

3. Cher

From the beginning of Late Night, Letterman had been trying to get Cher as a guest. After years of denying the offer, Cher claimed that she needed to pay for her $28,000 New York City hotel bill and thought she’d appear on the show to cover it after the incessant hounding by Letterman’s producers.

So, in 1986, Cher appeared, and when asked why she never appeared on the show until now, the singer told Letterman: “I thought that I would never want to do this show with you,” Cher said. “Now let’s explore this a little,” replied Letterman, “Why? Because you thought I was a—.” “An asshole,” Cher cut in. 

This encounter would forever go down as one of the most infamous Late Night moments, but from it sparked an odd friendship. In 2015, Cher appeared again towards the end of his Late Show run to pay tribute to Letterman and their strange bond.

“For a number of years, there’s something that I’ve always wanted to get straight between us…this is one thing that I really mean from the bottom of my heart, I’m not kidding, no bullshit — I really love you, and I’m going to miss you,” she said. The two hugged. “That’s very sweet of you,” Letterman told her. “Yes,” Cher responded, “And you’re still an asshole.”

2. Bob Dylan

Much like Tom Waits, Bob Dylan appeared on Late Night many times from the ’80s onward. His first appearance was in the early years of Late Night in 1983 when he showed up with three 20-something punk musicians to accompany him instead of his usual band members. Letterman was more than thrilled to have him on, asking if he’d play two more songs than originally scheduled. 

However, his most memorable appearance was in 2015. Having announced in April of 2014 that he would be retiring after 33 years, Letterman chose for his idol Bob Dylan to appear on the second to last show.

Before the announcement, he revealed that he had taught his son that “the only two things you need to know in life are to be nice to people and that the greatest songwriter of all time is Bob Dylan.” Dylan performed ‘The Night We Called It A Day’ from his recent Frank Sinatra covers album Shadows In The Night.

1. Foo Fighters (2000)

The day after Dylan showed up, on the very last performance of Late Show, Letterman chose the Foo Fighters to appear, a band he has publicly claimed as his favourite of all time. The band performed ‘Everlong’, a song that Letterman credited with helping him get through his heart surgery recovery. The song worked as a soundtrack for a montage of old Letterman clips detailing his long-spanning history. 

The performance is remembered now as one of the most touching moments in the show’s history.

After debuting their new band after Nirvana on Late Night in 1995, The Foo Fighters struck up a long-standing friendship and mutual admiration with Letterman. Dave Grohl called the final appearance ”one of the most flattering moments our band has ever experienced.”