Top Ten Musical Moments With David Letterman

By Daniel Margolis

When one thinks about David Letterman and music, the first person to come to mind is Paul Shaffer. The musical director and bandleader, himself a Hollywood veteran, plays the affable yet acerbic foil to Dave's dry sarcasm, playing guests in and out of every commercial break and through the credits five nights a week. In between the music, Shaffer has stood behind his keyboards, hugging himself while wearing sunglasses and quipping back and forth with Dave.

But beyond the lengthy tenure of Shaffer and the World’s Most Dangerous Band (later dubbed the CBS Orchestra), Letterman’s musical legacy is more broadly defined by the artists and bands he’s had perform as guests over the last 33 years.

When it debuted in 1982, Late Night with David Letterman was a forum for great new artists and established ones going through some weird streaks in their careers—you weren’t going to see Captain Beefheart on the couch with Johnny Carson. This didn’t change with Letterman’s earlier time slot, larger audience, and advancing age when he went to CBS to host Late Show with David Letterman in 1993.

Letterman, for his part, genuinely seems to enjoy it all; even as, from his vantage point, the past three decades must feel like a parade of music that came and went. So here, in chronological order (Dave’s Top Ten Lists have never really been ranked anyway), from the home office in Lebanon, Pennsylvania, is tonight’s Top Ten List.

When Letterman had Captain Beefheart on in his first year on air, it was actually as an interviewed guest. Don Van Vliet was promoting what woulds become his last album, 1982’s Ice Cream For Crow. Vliet comes out with a bottle of Perrier in a bag and immediately uses the bottle and the bag to mock Letterman’s lack of other guests—probably the whole reason he’s being interviewed at all.

Letterman is amused by a musician on Vliet’s new album listed as Richard “Midnight Hatsize” Snyder, which Beefheart tries, and fails, to explain. It goes about as well when he’s asked about the meaning of Ice Cream For Crow’s title—something about Reagan? They even throw to a clip, which is basically Beefheart and his band freaking out in the desert.

Letterman is polite about all this, flitting through topics such as Vliet’s work as an abstract painter and his pre-fame stint as a manager of a Kinney Shoes store. All of this was apparently not viewed as a disaster; Letterman brought Captain Beefheart back on the following year—though it was mainly to discuss his paintings.

Imperial Bedroom, which Letterman refers to as Elvis Costello’s eighth album (in fact it was his seventh; Dave’s staff must have counted the 1980 odds-and-sods comp Taking Liberties), was his big prestige move—a huge production that almost boasted the songs to match. Costello even had to break with his longtime producer Nick Lowe to make the album, for fear of taxing the producer's patience.

A New York Times review of the album compared Imperial Bedroom to George Gershwin, which led to his brother Ira Gershwin—to Costello’s horror—acquiring and listening to a copy. Columbia Records had marketed it with the tagline, “Masterpiece?” which Costello later admitted “was really asking for it.”

All these great expectations arrived on late night television, right into David Letterman's lap. Elvis does a note perfect version of Bedroom’s “Kid About It,” followed by “Man Out Of Time.” Between the two songs, Dave has Elvis over for an amusing interview. Asked what it was like recording his country album, Almost Blue, in Nashville, Costello relays a story in which the producer and engineer brandished guns in front of him. Letterman asks him to say where he’d fit in high school—somewhere between honors society and shop class—and Costello just blinks, protesting that he doesn’t understand how the American education system works.

Beginning with 1983’s Swordfishtrombones, listeners were introduced to a very different Tom Waits—one more likely to sing something resembling a sea shanty while bashing on junkyard trash than a piano ballad, as had been his style during the previous decade. So Letterman, in his second year on air, caught Waits at just the right time.

Waits walks out to Shaffer grooving on his trademark dated organ (a sound he’s stuck with through the decades) playing “Frank’s Wild Years.” It's a perfect choice, because to modern ears this song already sounds like a commercial break intro/outro on an old talk show. From there, Tom essays Frank’s fate just has he had on record, mining audience reactions and laughs missing from the studio recording.

During the interview between songs, Letterman has specific knowledge of Waits’ past, aware that he used to live at the Tropicana Motel on Santa Monica Boulevard and hang out somewhere called Duke’s Coffee Shop, where he kept his piano in the kitchen, and that he lived in a house trailer, as well as in his car—and even that he was born in a cab in Dave’s native Indiana.

After a commercial break, Waits floors the audience and viewers at home by reaching back just one album in his catalog, a wide gulf in his evolution as an artist, to “On The Nickel” off 1980’s Heartattack and Vine. Waits’ festive, reflective performance of the song proves that to whatever extent he was willing to smash form in his music, he knew where his strengths were.

Even among the weirdest stories in Bob Dylan’s mythology, this is one of the weirder ones. In 1984, Dylan enlisted the Plugz, an L.A. post-punk band best remembered for their appearance on the Repo Man soundtrack, to back him as he promoted his recent album Infidels on Late Night.

They did so in style, first with a cover of “Don’t Start Me Talkin’” by Sonny Boy Williamson, and “License to Kill” and “Jokerman” off Infidels. “Jokerman,” in particular, kills. It sounds like the new wave blast it was perhaps always meant to be. The entire appearance follows a historic tendency for Dylan: his best musical impulses aren’t always reflected on his album cuts, but they tend to emerge in his live performances. Dylan had a long-running habit of shelving his best songs, only to let them slip out years later.

His involvement with the Plugz was never documented in the studio and never really explained. All we have is these appearances on Letterman—not that the host himself doesn’t appreciate it. At the conclusion of “Jokerman,” Dave asks Dylan, “Is there any chance you guys could be here every Thursday night?” and Dylan laughs and insincerely agrees.

When the Beastie Boys first appeared on Late Night with David Letterman in 1992, Dave spent most of the episode talking it up. He confirms they’d never been on the show before but, in conversation with Paul, recalls some flap in which the Boys started a fight on the morning show across the hall, which sounds very much in keeping with the Licensed To Ill-era Beasties. He also accuses them of stealing his coffee and trick-or-treating him—though none of the jokes really land with Shaffer, the studio audience, or guest Bryant Gumbel.

Things switch gears when the Beastie Boys actually come out to perform. Letterman holds up a long box of Check Your Head to introduce them, and when he attempts another joke at their expense, he’s met with a groan from the group itself. What they do next is rather unexpected—the Check Your Head album cut “Live at P.J.’s.” Money Mark introduces the song from behind Shaffer’s keyboard and the Beastie proceed to unleash an awesome performance with the help of Shaffer and the entire Late Night band, complete with Mike D on drums, Ad-Rock on guitar, and MCA on bass.

It feels like a proto-version of them doing “Sabotage” on every television show imaginable a couple years later. At the time, however, this probably confused viewers who hadn’t seen Beastie Boys since “(You Gotta) Fight For Your Right (To Party).” After the commercial break, Dave says to Paul, “The Beastie Boys were here. I just hope to hell they’re not neglecting their schoolwork.” Paul shoots back, “They’re traveling with a tutor!”

When Weezer hit Late Show with David Letterman in August 1995, the dust had settled on the grunge-fueled, alternative rock shake-up that rearranged popular music in the first half of the decade. The band was over a year into promoting its celebrated debut and visited the show to perform their third single, “Say It Ain’t So.”

River Cuomo’s stage presence is far from involved; a casual viewer flipping through channels could have been forgiven for mistaking bassist Matt Sharp as the lead singer of the band. But what Cuomo lacked in stage presence, he made up for in pant size: he gives Letterman—at the time known for sporting huge khaki slacks—a run for his money.

Regardless, when we hit the chorus, as was so often the case in those days, things get loud and the band practically jumps through the screen. They own the crowd by the time they get to the bridge, with its climactic declaration of, “like father, stepfather, the son is drowning in the flood…”

When The Strokes first appeared on Letterman, he introduced them by saying, “Our next guests are one of the most talked about new bands to emerge in the past year.” He certainly got that right. At that time, there was simply no avoiding it; whether you loved or hated them, you had to have some sort of a take on The Strokes.

They even spawned a trend: the record industry began spitting out one stripped-down rock band after another—The Hives, The Vines, too many to count. Sum 41 spoofed this with a video that began with their manager telling them they were now called “The Sums.” This was a rock band having broad impact on a level that would likely never come again. Speaking to the A.V. Club in 2004, rock legend Lou Barlow pointed out even that only went so far. “Even The Strokes, who are huge, they’re not a household name, you know?” he said. “Only among pockets of hipster kids. It just happens to be a pretty big country, with a lot of pockets of hipster kids.”

All of this makes The Strokes’ 2002 appearance on Letterman so remarkable, watching over a decade later. Removed from the outsized expectations surrounding them (they’d even named their debut Is This It), it is clear The Strokes were simply a great band that did everything right to ascend to a national stage. They wisely rip into an album track—the closer, in fact—rather than a single, avoiding fatigue that may have set in surrounding their three singles to date.

From there everything unfolds perfectly; the band is as tight or loose as it needs to be in either direction. Julian Casablancas is well backed but could carry the song himself with his casual croon on the verses and urgent shout on the chorus. He and the band careen together into the bridge, at which point Casablancas slams down his mic and exits the stage for a note-perfect solo from Albert Hammond, Jr., then returns just in time to spank the guitarist and resume singing. All this was either choreographed or impressively spontaneous. Letterman is visibly pleased as he comes over to shake hands with the band.

Janelle Monáe’s May 2010 appearance on Letterman was her network television debut. Watching her performance, this comes as a bit of a shock. Performing “Tightrope” off her first full-length album The ArchAndroid, Monae seems to have emerged fully formed from some sort of genre-defying-singer assembly line.

Leading a ten-piece band as Shaffer lurks in the dark behind his keyboards, Monáe places every note precisely where it needs to land and dances as if she was computer-programmed. (Appropriate, considering she was promoting a concept album about a female robot.)

She apparently couldn’t get Big Boi to appear to replicate his verse from the studio version, but Janelle made the most of that time, channeling James Brown with a cape routine (Letterman and Shaffer had a version of this themselves).

Letterman is right there to shake her hand as soon as the song’s over; effusively praising her work and asking after Monáe’s “buddy Sean.” Diddy then emerges from backstage to playfully bow before her. By the next time Monáe appeared on the show three years later, she’d grown sufficiently emboldened enough that she danced right on Dave’s desk.

In the summer of 2010, M.I.A. was suffering through a public-relations headache that—it’s difficult to believe now—actually involved a contentious dish of truffle fries ordered in the presence of a writer from New York Times magazine. This was the climate surrounding her third album, which sharply divided critics.

But just as she released Maya, she appeared on Letterman with a performance seemingly designed to shut everyone up. Even Pitchfork, which had given the album a scathing 4.4 review, admitted “M.I.A. can still pull off pretty amazing things.”

She wisely selected for her appearance the album’s first single and standout track: the raging, Suicide-sampling “Born Free,” backed by Suicide’s Martin Rev himself—that's the way to own a sample. More visually impressive, though, she was also backed by nine women dressed exactly like her, all also holding live microphones on stands. The message seemed to be that people can try to displace or imitate her, but there is still only one M.I.A. She sings the song with the casual cool of someone who’s never heard of Lynn Hirschberg, much less tweeted her phone number, all as her army of M.I.A. impersonators vaguely mimic her moves—except when she moves to the vanguard to air-hump one of the monitors. Letterman is as pleased as he always is whenever anyone does something truly unique on the show. After the song, he walks over chuckling and says, “Seriously, Happy Halloween!”

“Rusty,” off Tyler, the Creator’s second studio album Wolf, has Odd Future member Domo Genesis rapping first, followed by Tyler himself, then Earl Sweatshirt. But when the three appeared on Letterman shortly after the album’s release in April 2013, Tyler switched up this order. It was probably for the best, since the studio version had Tyler taunting Earl during his verse before ending it by shooting Earl dead. For the taping, it went Domo, Earl, Tyler.

Dave mines some humor from their rap names; grinning and pausing for laughs after saying "Earl Sweatshirt." From there the three rappers prowl Letterman’s stage; Tyler and Earl amuse by falling into a simple dance routine behind Domo.

Tyler finishes it off with a long, sublime verse that was a bold choice to perform on a national stage. He efficiently runs down the state of the world and his life and answers his myriad critics. “In a world where kids my age are popping mollies with leather. Sitting on Tumblr, never outside or enjoying the weather,” he raps. “Look at that article that says my subject matter is wrong. Saying I hate gays even though Frank [Ocean] is on 10 of my songs.”

At the conclusion of the track, Tyler drops his mic and the three unceremoniously exit stage right. Letterman, to his credit, coaxes them back out, joking, “Now we’ll never be able to open the teen center.” Tyler bats away Letterman’s offered handshake and takes a selfie with him. Then, in a moment that speaks to how Letterman’s sense of humor perhaps doesn’t translate with a millennial audience, Dave asks the three, “You guys ever been to Bend, Oregon?” Tyler innocently protests, “I don’t know what that is!” Dave tells him, “Don’t worry about it.”