Stupid Pet Tricks

On Paul Westerberg and David Letterman forty years later.

What kind of song is "I Will Dare?" With its winsome, spring-loaded riff and cheerfully busy bassline pattern, its aw-shucks country shuffle, its chiming mandolin solo and its rubicon-crossing sentiment: self-effacing humor narrowly masking a vaulting ambition. This last part is, of course, the central paradox of the Replacements, in place from their debut and destined to play out until the end, or if you will, "The Last." But what other songs sound like it? I can't really think of another in their catalog to compare it to, and I struggle to think of ANY direct analogues in anyone else's either. I guess it sounds like something that might have slid on or off of Between the Buttons — a second cousin to the shrugging, offhand "Connection" maybe — but even that doesn't seem quite to nail it. Paul Westerberg once wrote that the Replacements wanted to be the Faces, but they were too angry, and that seems true. But not on “I Will Dare.” They sound hopeful, wide-eyed, excited to startling possibilities that are seemingly accruing around them.

Released in 1984, “I Will Dare” revels in a kind of double game that can feel narrowly legible four-plus decades later. Lord knows that ambivalence about fame is not an unusual topic in music these days — this seems in fact to be the preeminent preoccupation of many of our most well-known artists — but there is something different at work in say, Taylor Swift or The Weeknd's stuck-in-the-terrarium laments. Whatever the relative merits of either artist, their point of view is, necessarily I suppose, something on the order of Alexander the Great in Egypt or Peggy Lee singing “Is That All There Is?” It is the ennui of the total victor. It is said that General Douglas MacArthur became insane following his triumph in WWII, fired by Truman from his command in Korea, his extreme paranoia fed in part by his celebrity. Imagine how The Weeknd feels!

Relative to 1984, all of the neural pathways, in terms of how to feel about media, finance, politics, principle, scruples and ethics feel plowed over in 2025. “I Will Dare” is playful in its contemporary context, a teasing romance but also a wink in the direction of the mainstream that said they’d jump if the call came through. “Meet me anyplace/ Or anytime/ Or anywhere/ If you will dare/ I will dare.” It verged on slutting it up. But the stakes were so much smaller — almost silly. They moved from the respected and well-enough distributed indie Twin-Tone to the better capitalized but still rad and hip Warner Brothers subsidiary Sire. A small lateral move, A little more money. Survive and advance.

I found a paperback tradebook from 1987: The David Letterman Story, an unauthorized biography of the then ascendant, astringent host of the 12:30 NBC show Late Night, then-a newish-after-Carson variety program that had captured the public imagination sufficiently to necessitate the kind of explanation that could be easily found in a grocery store in the first year of Reagan’s second term. Written by Caroline Latham, it is incredibly sharp and insightful. I sincerely cannot recommend it more as an inexpensive eBay option. She’s got a read on him.

Page 151: “Is David Letterman a nice guy who sometimes gets carried away with a joke? Or is he a sadistic wit who doesn’t care who he hurts, as long as he gets a laugh?”

Page 175: “It seems probable that David Letterman is uncomfortable in the grown-up world of serious relationships, intimate feelings, and real problems that give people real hurt feelings.”

Could anything be more true of the man in 1987? The book is full of this stuff, and Latham’s clearly a fan. Just a clear-eyed one.

The front cover boasts a quote from eccentric cast member Larry “Bud” Melman: “This show is the reason television was invented.” On the back, Dave’s high school guidance counselor is quoted as saying: “I don’t think Dave was funny then, and I still don’t think he’s funny.” It’s strange. For a book so well-written, the packaging feels designed to ward potential consumers off.

Early Letterman and the Replacements of the same era represented the shock of the old repackaged as the shepherd of the new. Letterman's very funny, slightly absurdist, rage-adjacent schtick owed a monumental debt to Steve Allen and Ernie Kovacs, figures far removed then and now from contemporary culture. There is considerable talk in Latham’s book — replete with portent — about who will eventually fill Johnny Carson’s shoes. This is presented as something Letterman both wants and doesn’t want. The major question is the elephant in the room: is he temperamentally suited to comfort America at 11:30? It’s not ultimately wrong to say he wanted to be Carson, but he was too angry. His ostensible friend, Jay Leno, evincing no ambition, provides many supportive quotes.

One strange thing about Letterman and Westerberg is the level of contempt they seemed to reserve for whoever had faith in them. Letterman waged a strangely savage and personal-feeling on-air war against then-chairman and CEO of NBC Grant Tinker, a long-time network executive who had worked his way up the org chart after helping to produce hits like The Mary Tyler Moore Show, Hill Street Blues and The Bob Newhart Show. At one point he was married to Mary Tyler Moore. Staid and corporate in a formal sense — he was born in 1926 — Tinker seemed at least initially to be a Letterman fan. Then Letterman kept bringing him up, night after night, in ever more savage terms. Here’s a particularly cruel “We Are The World” parody that starts with a cold open of an episode of Late Night where a pretend Tinker insists on a more positive beginning to the show.

What exactly was happening here? The Letterman show in ‘85 and ‘86 was a pretty anarchic, punk rock affair — it’s difficult to imagine a more ragtag, what-the-fuck enterprise in contemporary television forty years later. Lashing out at Tinker was perverse and funny — a forerunner to the comic foil that Jack Donaghy would become to Liz Lemon on 30 Rock. But it was totally unnecessary and unproductive in any greater sense. If Late Night was not as raw or authentic as Letterman wanted, he had only himself to blame.

Legend holds that the Replacements stole their master tapes, including “I Will Dare,” from the Twin-Tone offices and dumped them into the Mississippi River, after signing their major label deal, in an act of wanton destruction apparently directed at some feeling of royalty withholding from their former label. When I first heard of this legendary mischief in my teens, I was tickled. I had no way of knowing I would end up signed to the indie-label Bar-None as a singer-songwriter or end up interviewing Peter Jesperson as a journalist: the Replacements’ one-time faithful manger, Twin-Tone label head and still seemingly broken-hearted old friend, decades after all the contretemps and capers. For what it’s worth, I think the tapes-in-the-river gambit was probably a tall tale. Nothing that happened that day has prevented the band from reissuing an absolute barge load of their early work.

As I get older, I inextricably link Letterman and Westerberg more and more in my mind. Like Carson and DEVO, they were weird, ambitious Midwesterners, pathologically dedicated to the notion of subversion at any cost. I related as a suburban Long Island girl to the sense of light contempt that us country folk can feel for the landed gentry. I also recognize that, as they both publicly acknowledge, they were both struggling through terrible depression. I lived for a while in the Midwest too — Bloomington, Indiana, Louisville, Kentucky, the Ohio River Valley region — enough to have a flavor for Midwestern sadness, its quiet, salient ever presence.

What kind of song is “I Will Dare?” What kind of show was Late Night? “I’m generally uncomfortable around people,” Letterman vouchsafes on page fifty-nine of The David Letterman Story. “Don’t matter much/ If we keep in touch,” Westerberg laments on the later Replacements’ late-night jazz odyssey “Nightclub Jitters.”

Meet me any place. Two drifters, off to see the world.