The Hardest Thing for A Musician to Do
The Hardest Thing for A Musician to Do
Sure, making a classic is hard. Imagine doing it for 40 years.
In a 2011 piece for the AV Club, music critic
defined a new metric for musical greatness: the five-albums test. An artist passes this test if they release at least five consecutive masterful albums. According to Hyden, very few artists pass this test. The Beatles do. So do Queen. That said, Bob Dylan and The Rolling Stones come up short. Inspired by Mr. Hyden, I want to propose a test of musical greatness that is even more stringent: the 40-year test. As always, this newsletter is also available as a podcast. Listen on Spotify and Apple Podcasts or click play at the top of this page.The 40-Year Test
By Chris Dalla Riva
A few weeks ago, I put out what might end up being the most popular thing I’ve ever written for this newsletter: “Did Frank Sinatra Really Perform at My Grandma's High School?” It’s already surpassed a very popular interview I did with songwriter Billy Steinberg in views. And it looks like it will close in on my most popular piece — a brief history of song titles — before the year is up.
Popularity aside, in that Sinatra piece I wrote a few sentences about the length of the singer’s career that I haven’t really stopped thinking about:
Frank Sinatra is Hoboken’s most famous son. I’d argue that he released genuine musical masterpieces in the 1930s (e.g., “All or Nothing at All”), 1940s (e.g., “I’ll Never Smile Again”, “Saturday Night (Is the Loneliest Night of the Week)”), 1950s (e.g. “I’m a Fool to Want You”, “You Make Me Feel So Young”), 1960s (e.g., “My Way”, “That’s Life”), 1970s (e.g., “I Would Be in Love (Anyway)”), and 1980s (e.g., “Theme from New York, New York”) on his way to becoming one of the best-selling musicians of all-time. That longevity is basically unmatched.
To summarize, Frank Sinatra put out classic records for four decades. That’s a really long time. In fact, it’s so long that it deserves some context. When Sinatra released “All or Nothing at All”, arguably his first classic, President Franklin Delano Roosevelt was still over a year from entering the United States into in WWII. When Sinatra released “Theme from New York, New York”, arguably his last classic, Franklin Delano Roosevelt had been dead for 35 years, eight presidential administrations had passed, and Ronald Reagan was sitting in the Oval Office.
In human years, that’s a long time. In musical years, it’s basically an eternity. Musical trends come and go so fast that you are lucky if you release a single song that garners any attention. This got me wondering: Have any artists other than Frank Sinatra release at least two classic songs at least 40 years apart? Or, more succinctly, have any other artists passed the 40-year test?
I started my investigation by asking people online for their thoughts. Writer and critic
pointed out that Louis Armstrong accomplished the Sinatraian feat. In 1925, he began recording his Hot Five and Hot Seven Sessions, which effectively reinvented not just how the trumpet was played but how jazz was played. 42 years later, he used his raspy voice to record the classic “What a Wonderful World”. That’s a pass in my book.
Most other suggestions I got didn’t cut it, though. Neil Young. Paul McCartney. Joni Mitchell. Sting. While I agree that these artists have released truly great work later in their careers — maybe even matching the quality of the work that made them famous — I don’t think it’s exactly what I’m after. I’m looking for artists releasing at least two songs over at least 40 years apart that receive near-universal praise from listeners or critics.
If, for example, you think Paul McCartney’s first classic was released on The Beatles’ 1963 album Please Please Me, then to pass the 40-year test, he must have at least one classic on Chaos and Creation in the Backyard (2005), Memory Almost Full (2007), Kisses on the Bottom (2012), New (2013), Egypt Station (2018), or McCartney III (2020). I really do love many of those albums and the songs they contain.
“Jenny Wren” from Chaos and Creation in the Backyard is quintessential acoustic Paul.
“Dance Tonight” from Memory Almost Full is some of the most musical fun you’ll have in under three minutes.
“Queenie Eye” from New is a top notch rocker.
Nevertheless, I don’t think any of those songs equal the classic status of something like Please Please Me’s “I Saw Her Standing There”. By contrast, Sinatra’s “Theme from New York, New York” is on par with his work released 40 years earlier.
In order to systematically find other artists who pass the 40-year test, I began looking for lists celebrated songs. Of course, everyone and their mother seems to have a list like this. But I needed lists that had a wider historical scope than those you find in the popular press. The first two collections that I thought had that scope were the recordings preserved in the Library of Congress’s National Recording Registry and those inducted into the Grammy Hall of Fame. These two sources have 1,400+ recordings spanning from 1860 to 2012 across myriad genres.
After I crunched the numbers, there were still only two artists that passed the 40-year test: Frank Sinatra and Louis Armstrong. Duke Ellington came close. His Grammy Hall of Fame-inducted “Black and Tan Fantasy” was released in 1928. 39 years later, he put out the jazz standard “Isfahan” on his concept album Far East Suite, which was also inducted into the Grammy Hall of Fame. After that, there’s no one that passes the 30-year test, let along the 40-year test.
Only using lists from the Library of Congress and the Grammys felt a bit too exclusive, though. Those organizations certainly haven’t gotten around to honoring every classic, especially those from the last few decades. So, I decided to cast my net a bit wider, grabbing eight additional song lists.
After collating the music from all of these sources, I had a list of 2,700+ classic recordings released between 1860 and 2020. If I didn’t find any other artists that passed the 40-year test across all of that music, then maybe Frank Sinatra and Louis Armstrong were the only members of this exclusive club. Let’s take a look.
This is a big long table — and you might have to zoom in to get all of the detail — but here are a few things that jumped out at me. First, we have two more artists who passed the 40-year test. Nat “King” Cole and Johnny Cash. Cash’s inclusion is undisputed. 47 years after releasing his “Folsom Prison Blues”, he put out a haunting cover of “Hurt” by Nine Inch Nails. Those are two classics if there ever were any.
Nat “King” Cole’s passing grade is a bit more questionable, though. I don’t have any issue with his first classic, namely “Straighten Up and Fly Right” from 1944. In fact, there are lots of “King” Cole classics you could pick from the 1940s. His final classic — a 1991 duet with his daughter Natalie on the song “Unforgettable” — is where I take issue. The song is fine. But when it was released, “King” Cole had been dead for decades. Getting the mark from beyond the grave seems suspect at best.
As you peer over the artists that fail the 40-year test but pass the still-difficult 30-year and 20-year tests, you’ll see some familiar faces. Paul Simon. Dionne Warwick. Miles Davis. Frankly, the only things that surprised me while looking at those was that (a) “Not Dark Yet” was considered the Bob Dylan-classic from 1997 and not “Make You Feel My Love” and (b) Neil Young released “Harvest Moon” in 1992. I’d always assumed that song came out in the 1970s.
Beyond those surprises, I’m just happy that I wasn’t lying when I claimed in my recent piece that Sinatra’s longevity was basically unmatched. I’d love if I became more wrong during my lifetime, though. Frank Sinatra, Johnny Cash, Louis Armstrong, and Nat “King” Cole need a few more friends to pass the 40-year test. I’m told they’re getting lonely.
A New One
"Saturday" by julip
2024 - Indie Rock
On September 20, 2024, julip released their third single, “Saturday”. I can’t tell you much about the artist behind the song. Their Spotify biography doesn’t provide much more information than the short write-up that I found on them: “San Francisco based indie rock.”
I can tell you about the song, though. It sounds like it was beamed directly from the mind of rock artist trying to crossover in the early-2000s. And I mean that in the best way possible. I won’t bet that julip will be releasing classics in four decades. (I wouldn’t bet any artist will be doing that.) But I can assure that “Saturday” will be a classic in my apartment for the next few months.
An Old One
"West End Blues" by Louis Armstrong
1928 - Jazz
After college, I led a small band in Massachusetts comprised of guitar, bass, drums, and trumpet. Though I liked to think I was the star, the trumpet was what held it all together. And Pete, the man behind the horn, taught me a lot about jazz during our time as bandmates.
During one conversation about Louis Armstrong, he told me about “West End Blues”. “When Louis played the opening riff on 'West End Blues',” he began, “it was as if you were listening to someone from a different planet. Nobody played anything remotely like that in 1928.” The crazy thing about that description is not just how accurate it is but how it doesn’t even mention the fact that Armstrong also continued to evolve the art of scatting on this recording. 1928 is a long way in the past, but “West End Blues” remains as fresh as ever.
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I would definitely throw in the 46 year gap between 'Space Oddity' (1969) and 'Lazarus' and 'Blackstar' (2015) for David Bowie. I'd also say Radiohead, Nick Cave, and Aphex Twin should be under consideration for a 20+ year gap.
Great write up! Note you may be thinking of Neil Young's album Harvest which was in 1972. https://en.wikipedia.org/wiki/Harvest_(Neil_Young_album)
https://en.wikipedia.org/wiki/Harvest_Moon_(album)