Billie Eilish with David Letterman
Billie Eilish with David Letterman

My Guest Needs No Introduction

I've never given David Letterman's lauded interview show's title much consideration until recently. Each guest has a substantial profile, in the heads of millions and, in some measure, a game-changer. When Letterman says to singer Billie Eilish—paraphrasing, "you have a song that has a billion downloads—think of that—1/6th of the planet is a fan of yours; you are known and loved throughout the world." That says it all.

Letterman's quick wit, self-deprecating humour, and fanboy enthusiasm extract miles of intimate knowledge from his subjects with little resistance. It's not the bellwether Barbara Walters in your face shocker, the jolt that leaves the guest with few routes to exit a televised mishap. Instead, Letterman leads his subjects gently through awkward terrain. The survivalist white beard and backwoodsman dress are not the Letterman of old in finely tailored suits and white sneakers. For some, the grandpa act has tired.

The entertainment interview, in my view, is a zone primarily dominated by three non-rivals – Howard Stern, Marc Maron and Letterman. Each is an open book, in need of counselling, and shows a genuine interest in the mechanics and artistry that gives rise to their guests, whether film, television, music or celebrity. And bona fide geeks.

Jerry Seinfeld's Comedians in Cars Getting Coffee offered a glimpse into how to engage what could be a problematic interviewee. Take them to familiar surroundings to neutral ground. Letterman does this throughout season four. Billie Eilish go-carting, Cardi B to The Roosevelt Museum in the Bronx, basketball icon Kevin Durant to a basketball court, comedian Julia Louis-Dreyfus the ocean, Will Smith at a Comedy Club, and Ryan Reynolds baking pizza at home. These simple excursions soften the guest. From there, let's talk as friends and potential neighbours.

Three episodes from season four stand out. First, Julia Louis-Dreyfus talks about growing up with two families: the short takes of SNL - Eddie Murphy, serving Gumby tea, Seinfeld and her immense love, and the role of vice president in the hit series Veep.

Letterman and Dreyfus rough it up. She's no easy mark. The face speaks of a seasoned pro who has endured many storms, including a battle with breast cancer—winning an Emmy one day, the next a catastrophic reckoning. On the celebrity spinning wheel, derailment, chemo, and a year of reflection and recovery. One word connects Eilish, Cardi B and Dreyfus – "Fuck!" Each punctuated conversation with comic timing—"fuck and mother fuckers.” That next level of excitement and possibilities. Letterman senses this and probes deeper.

Eilish and brother FinneasO'Connell are perhaps the most interesting of this allotment of guests. In the early twenties, success in their teens, homeschooled, driven and infinitely creative. Much like modern-day Mozart Jacob Collier, both forgo the manic size of an outside recording studio for the inner workings of a relaxed home space. The large computer screen, banks of keyboards, outboard gear, internal recording program, and high-end microphones are all the gear one needs, a typical basement music-making kid envy. A scene that plays out in millions of homes.

O'Connell layers the tracks from bottom to top, then Eilish painstakingly works her way through the multi-tracked vocals. One revealing sequence shows how the final vocals are cut to pieces and reassembled from dozens of takes. Snippets of various lyrics shaved down to one long-form finale. It's a telling moment where we are today. Sarah Vaughan, Doris Day, and Billie Holiday went the distance during the jazz age, much like the pitching greats of yesteryear, who recorded a dozen or so complete games during a long season.

Eilish identifies sultry American singer Julie London as the voice behind her voice. A genuinely telling moment. The vibe and soul of London accompany almost everything Eilish sings. Much like Canadian singer Sophie Milman co-opting a young Sarah Vaughan.

Canadian Ryan Reynolds is all a Canadian professes to be. Sane, grounded, polite, career-focused and lacking in ego. A good boy who did a few brothers inspired foolish things. With four brothers, the odds of one, two, or three having a run-in with the law are inescapable.

The banter is light and focused on fathers. The dad, who was rarely around, yet a sufficient provider. Not a conversationalist or a small talker. No heart-to-heart soul banter. With that comes the after they are gone questions. What ifs? Why didn't we ever have a real conversation?

The least significant is the Will Smith interview filmed before the Oscars meltdown. Smith is condescending, arrogant, self-absorbed, mouth-cocked and loaded with motivational advice. Even after a dozen or so psychedelic trips courtesy of hallucinogens, Smith comes off as smug even when espousing drug-induced lessons learned about losing his millions, the dream home, the princess bride. Humility is an uneasy fit.

The Rick Rubin segment, April 2018, is still a favourite in this house. At home in Shangri-la (recording studio)—surrounded by gear, music, and newcomer Madison Ryan Ward working out the details to her first single, Mirrors—a shining moment!

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