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.
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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 Ted gioia 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. Forty-two years later, he used his raspy voice to record the classic "What a Wonderful World." That's a pass in my book.
[Louis Armstrong, an artist who passes the 40-Year Test. Credit: Library of Congress]
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 Statio-n" (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.
[The Library of Congress’s National Recording Registry is one of the most important resources for musical preservation]
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. Thirty-nine 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.
- Rolling Stone Magazine's Top 500 Songs of All-Time
- ASCAP's Top 100 Songs Between 1914 and 2014
- NPR's Most Important Musical Works of the 20th Century
- Blender Magazine's Top 500 Songs Since You Were Born
- RIAA's Songs of the 20th Century
- Rock and Roll Hall of Fame's Songs that Shaped Rock and Roll
- Time Magazine All-Time 100 Songs
- AcclaimedMusic.com's Top 500 Songs of All-Time
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.
[In 1991, Natalie Cole [left] sold a lot of records through her posthumous collaboration with her father]
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.
This piece was first published on Chris Dalla Riva's Can't get Much Higher.
