Why Does Justin Smith-Ruiu Like a YouTube Video of Bing Crosby and Louis Armstrong on the Pearl Bailey Show in 1971?

“There’s a whole history of that era that we’ve just memory holed because it wasn’t cool enough.”

Welcome to Why Do You Like This?, a weekly interview series in which I explore a person’s liking for a specific thing. A song, a book, a film, a street in Osaka, a species of bird: anything goes. Read it for the recommendation, for the person, or simply for the conversation.

My first guest is the philosopher and author Justin Smith-Ruiu. Many of you already subscribe to Justin’s newsletter The Hinternet, which gets described in many ways (because it is hard to describe) including, on its ‘About’ page, as a “fictional magazine.” It’s at least as likely to cover Siberian epic poems or the case for horse telepathy as it is to talk about TV performances by major celebrities. Nonetheless Justin chooses a seven-minute YouTube video of Louis Armstrong and Bing Crosby performing on The Pearl Bailey Show, a primetime variety show of a kind whose days were very much numbered by then. It was originally broadcast, on the ABC TV network, on Saturday 23 January 1971.

Our conversation covers late-stage celebrity, the nature of Bing Crosby, the influence of Louis Armstrong, the memory-holing of mainstream culture, Chilean pop rap, Justin’s YouTube browsing habits more widely, and Edward Said’s notions of late style.

Justin’s latest book is On Drugs: Psychedelics, Philosophy, and the Nature of Reality.

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Read Me: When did you first come across this clip?

Justin Smith-Ruiu: Maybe a year ago. It was during a period when I was watching everything I could find with Bing Crosby and Louis Armstrong together. I’ve been trying to write an essay about Bing Crosby for a long time. I’ve done Brenda Lee, Jerry Lee Lewis, the Beatles… My goal is to cover every 20th century musical icon who matters to me, and Bing Crosby is really top billing for me — as is Louis Armstrong, but in different ways. This particular encounter is fascinating because the two of them are on their last legs. I mean, Louis Armstrong is really on his last legs, and Bing Crosby will live for another six years, and you can see that they’re both just performing out of love for one another. There’s not even really any expectation that it should sound good. They’re just putting their friendship on public display. Then Pearl Bailey comes out, a real performer in her prime, and she saves it with a performance that’s actually good. Bing Crosby and Louis Armstrong are both two of the greatest musical performers of the 20th century, and then to have them saved by her in that way is so poignant to me.

Read Me: Is that why you like it?

Justin: There are so many layers to why I like it, but the core of it is that I’m really fascinated with the way iconic performers get old, and in particular there’s a very poignant life arc for a certain kind of figure who basically went extinct over the course of the 1970s. It’s the people who’d been around since the late 1920s, who were already around in the era of vaudeville in many cases, who were around in the silent film era, and were still there to be hauled out for celebrity galas until around 1975 or so. To watch them in the period between 65 and 75 when the dominant culture is youth culture and counterculture, to watch them just soldiering on anyway, is part of the poignancy for me, and it’s manifested so perfectly in the friendship between these two characters.

Louis Armstrong of course is much discussed as the great jazz innovator, from his recordings in the 1920s which Django Reinhardt then heard a year or so later. It ended up changing the way everything sounded. So in a sense, few people are more important for explaining the sound of the 20th century. Bing Crosby in turn is a peculiar kind of mediator because, well, obviously he’s white, and he speaks to the, kind of, more conservative American audiences. But if you listen carefully, he innovates, with the dropping into ordinary speech patterns, and the riffing, stuff like that. It is extremely ‘American vernacular’ in what I would describe as a, kind of, transracial way. So then you get this intense friendship between the two of them that gets increasingly corny as the decades go on. And by the fifties, by the time you have an emerging consciousness of jazz as a high art form, Louis Armstrong is singing ‘Gone Fishing’ with Bing Crosby and just letting the natural-born cornball inside of him pour out. This did not help his reputation in the mid 20th century when he was doing this simultaneously with the incredibly innovative, revolutionary work of people like John Coltrane and Miles Davis. But again, it’s just that friendship that amazes me every time I see it.

Read Me: But what is this repeated line of “I don’t want to sing that song”? Is it a real song or a self-referential thing they’ve made up for the night, or what?

Justin: I haven’t done the research on it. I think it doesn’t matter. One of the things that fascinates me about this period, ’65 to ’75, is the proliferation of this very particular kind of television entertainment. You’ve got the Pearl Bailey Show, the Dinah Shore Show, the Johnny Cash Show, the Dean Martin Show, and they all involve these extremely jovial encounters with invited guests who sing medleys with the host.

Read Me: Were these shows still at the core of the mainstream, or something more niche at this point?

Justin: It’s the aging mainstream, the people who couldn’t hack it with the hippies. On some of the looser, younger shows, like Rowan and Martin’s Laugh-In, you see some symbolic gestures opening up to the hippies but on Pearl Bailey you don’t see any of that. You really see that alternative America that is kept alive in the fantasies of John Wayne, Ronald Reagan, Charlton Heston. I was thinking recently, after watching Tarantino’s Once Upon a Time in Hollywood, which is set in 1969, how the soundtrack wasn’t Jimi Hendrix, Janis Joplin and so on. It was, like, Neil Diamond, right? And if you look at the top of the charts from August 1969, it was Neil Diamond. It was Henry Mancini, and Neil Sedaka. There’s a whole history of that era that we’ve just memory holed because it wasn’t cool enough.

Read Me: Too popular to remember?

Justin: Exactly. I guess my love for this stuff has a lot to do with age. I was born in 1972, so some of my first memories are the TV on in the background at my grandparents’ home in ’75 or ’76, and it was typically shows like this one. That is, in a way, my permanent representation of what celebrity life is.

Read Me: Are you aware of the British TV programme Strictly Come Dancing? It’s a direct descendant of these shows. They still have the glossy stage set, it’s still on Saturday nights, but ultimately it’s had to bow to the reality TV revolution.

Justin: Yeah, like Dancing with the Stars and America’s Got Talent, and whatever. I mean, I’ve only seen little snippets here and there, and I find the lighting and the scenery and the aesthetics so repulsive that I can only look at the screen for a second or two. But I would say the big difference is that everyone implicated in these productions is hyper aware of the screen-based nature of their performance.

Read Me: Maybe that brings us to the status of this item which isn’t its original context but its afterlife as a 7-minute YouTube clip. It has had 17,000 views, which isn’t really a big number by YouTube standards.

“watch?v=H3vfqpt4iU4”

Justin: But of course all the comments are just 100% positive. Let me just say something about my media consumption habits. I read a lot of 19th century French literature and then, late at night, if I can’t sleep, I put on headphones and I go to what I think of as the great media archive, which is YouTube. I pull up old clips of Bing Crosby and Louis Armstrong, and the more obscure and often the lower quality the better, as far as I can see. Sometimes, if it’s someone who’s still alive I’ll mention it — in Substack Notes, say — that I’m really enjoying a video of some performer who’s been around forever, and someone will say, “oh yeah, they’re in concert this spring. You can go and see them in Paris.” And I’m like, “I don’t want to go and see them in 2026. I want to go and see them in 1970. Who cares if they’re still performing?” I have hopelessly backward-looking sensibilities about popular culture and I don’t even want to know what the surviving vestiges of the things I love are. But let me get back to the “we don’t have to sing that song” thing. It keeps coming up as part of a medley. They’re just doing one familiar tune after another but then I do like the poetry of this late stage refusal, so to speak. And of course Louis Armstrong is laughing about it.

Read Me: It’s this hybrid of singing but also having a chat. They face towards the camera but also a bit towards each other, and everybody’s constantly smiling.

Justin: Louis Armstrong is just the most genial person you could imagine and it’s disarming, especially because you can tell he is quite sick and feeble here. Bing helps him off the stage and it’s fascinating because it is 100% still them — they would have been performing together 25 years ago — and at the same time, it’s just a dim echo of what they once were. So it’s this great example of late style, in the Edward Said sense, in that it’s obviously decline but at the same time their essences are still entirely there. I also love it when Pearl Bailey comes out, and actually starts performing well, but then it takes this strange meta twist where she addresses the producer of the show by name — his name is Michael or something — and she’s like, “no, Michael, I ain’t going to sing that song.” You get the sense of they’re protesting against the corny bullshit that has made up their professional lives as performers.

Read Me: What struck me is that they’re not that slick either. The camera isn’t quite centred. The dancing is a little bit loose. Maybe that was slick by the standards of the day but not compared to watching a performance now, where it’s been produced to within an inch of its life and where every movement is so precise.

Justin: It’s completely sloppy, and that obviously adds to the delight of it. Again it’s this idea of late style. There’s a point in the Nick Cave documentary 20,000 Days on Earth where he’s talking with one of the Bad Seeds about going to see Jerry Lee Lewis in concert, when he’s quite old and feeble. At some point Jerry Lee tries to mount the piano but he can’t, because he’ll break his hip. The other guy — I forget which Bad Seed it is — observes that he has the persona and the history behind him such that even the failure to mount the piano is a thing of genius. If you do the iconic performer thing right then you should arrive in old age still performing and manifesting your genius even in what you can’t do. I love that idea. What explains the painfulness of seeing a Scorpions reunion tour versus the genius of seeing Jerry Lee Lewis failing to mount a piano? I would say that Louis and Bing on the Pearl Bailey show are up there beyond Jerry Lee Lewis, in terms of how their incapacity reflects their lives of superhuman capacity.

Read Me: You chose this video. You like this video. How often do you go back to this video? Weekly? Daily?

Justin: Every few months. But just to flesh out my YouTube habits, sometimes I do really peculiar things like asking myself, “What kind of music would I like if I were not me?” I imagine I was just randomly some other person among the 8.5 billion people in the world, and I go and I find what’s there in the way of low quality pop rap from Chile, something like that. What would it be like if I were doing a home stay in a high-rise apartment with a random family in Santiago? What would be on the TV in the background? That’s what I want to experience, and that’s one kind of YouTube deep dive, which is categorically different from my journey through the archive of the 20th century where I’m really concerned about understanding the significance of the way media looked shortly before and shortly after my appearance in the world, the way it looked and the way that shaped my perception of reality. The ’65 to ’75 period uploaded so much content into my mind in my first years. It established a template that I just can’t break away from, even though, in another respect it looks extremely archaic and I find myself thinking: I can’t believe people used to look like that.

Read Me: Do you log your browsing in some way?

Justin: Sometimes I write about these things on Substack, and typically when I write about music there, I do it under the pseudonym Mary Cadwalladr. She’s a Welsh former indie musician, who runs a donkey sanctuary in New Mexico. She was in a band in Cardiff called the Shoo-Fly Complex in the early ’90s. I use her to compile links to what has been most interesting to me in my YouTube explorations recently but no one clicks on that. If 11,000 people read a piece and I put in a link to a Bing Crosby and Louis Armstrong duet, it might get 15 clicks. So it is a rather thankless effort. I don’t know what to do to get people to click these things.

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Quirks of this conversation:

1. There is a fourth performer in this clip, Andy Williams! We don’t mention him at all here. Weirdly I barely noticed him when I watched the video, despite him being entirely part of the performance and not at all in the background. This is partly to do with the intensity of Justin’s interest in Armstrong and Crosby specifically, but it is also to do with the metadata surrounding the video, especially how it’s titled.

2. I have sent this first instalment of Why Do You Like This? on 26 December, which seems an absurd date to launch something but I don’t know, there’s something quite Christmassy about it isn’t there? The kind of thing you might have watched with extended family, maybe? And Armstrong and Crosby have festive associations.

3. The creation of Why Do You Like This? is also a way of recalibrating Read Me. It is intended to complement the original format, which will return soon. Partly this new strand is my answer to the realisation that I couldn’t produce the core Read Me newsletters at the pace I had hoped. Thanks for understanding!

4. For more from Justin Smith-Ruiu, Mary Cadwalladr and the rest, subscribe to The Hinternet.

8:30pm, Saturday 23 January, 1971