From the Desk of CLASSICKONG
Welcome back, music lovers, to another edition of This Day in Music History!
It’s Friday, October 23, 2026, and we’ve got quite a collection of stories today!
We’re celebrating unforgettable music from Chicago, Meat Loaf, Bob Dylan, Jimi Hendrix, and Culture Club. We’ve got some remarkable birthdays, a few heartfelt remembrances, and a little piece of technology that changed the way we listen to music.
And since Halloween is right around the corner, we’ve got classic monsters, horror movies, and some Boston Cream Pie waiting for us at Honey’s Diner!
So grab your coffee, turn up the volume, and let’s see what happened on October 23!
National Days – Boston Cream Pie and Horror Movies!
National Boston Cream Pie Day
Oh boy!
October 23 is National Boston Cream Pie Day!
And despite the name, Boston Cream Pie is actually a cake, featuring layers of sponge cake, creamy custard, and chocolate glaze.
Now THAT sounds like something worth celebrating!
I can already picture Honey bringing a big slice over to CLASSICKONG at the diner.
And knowing that gorilla, one slice probably isn’t going to be enough!
National Horror Movie Day
And with Halloween just around the corner, we’ve got another reason to celebrate.
National Horror Movie Day!
Now folks, I grew up loving the classic Universal monsters.
Dracula, Frankenstein, the Wolf Man, and the Mummy!
Those old black-and-white horror films had something special. The atmosphere, the castles, the fog, the dramatic lighting, and those wonderful vintage movie posters.
I even used to get my parents to buy me Fangoria magazine whenever I could.
Then along came movies like The Exorcist.
Let me tell you something, folks. After seeing that one, I didn’t sleep particularly well for a while!
ROFLMAO!
And of course, the 1980s brought us Michael Myers, Freddy Krueger, Jason Voorhees, and a whole new generation of horror icons.
But I’ve always had a soft spot for those classic vampire movies.
The spooky castles, the mysterious atmosphere, and, well, let’s just say some of those beautiful vampire ladies could make a fellow forget all about the danger!
Of course, Honey might have something to say about that!
ROFLMAO!
And while we’re discussing unusual National Days, apparently somebody thought National Slap Your Irritating Co-Worker Day was a good idea.
Folks, I strongly recommend skipping that one.
Unless you enjoy unemployment, court appearances, and explaining yourself to a judge!
Let’s stick with the Boston Cream Pie.
1976 – Chicago Takes “If You Leave Me Now” to No. 1
On October 23, 1976, Chicago reached the top of the Billboard Hot 100 with “If You Leave Me Now,” beginning a two-week stay at No. 1.
Written and sung by Peter Cetera, the song appeared on Chicago X (1976, Columbia Records).
What a beautiful recording!
From Cetera’s unmistakable vocals to those gorgeous harmonies, acoustic guitars, and lush orchestration, everything fits together perfectly.
Chicago had already established itself as one of America’s finest bands, blending rock, jazz, and a tremendous horn section. But this song introduced another side of their musical personality to an even wider audience.
And let’s give credit where it’s due. The musicianship in Chicago was extraordinary. These guys could play!
“If You Leave Me Now” became the band’s first No. 1 single in the United States and went on to win two Grammy Awards.
Sometimes a song doesn’t need to knock down the walls to make an impression. Sometimes all it takes is a beautiful melody, a heartfelt vocal, and musicians who understand exactly what the song needs.
And Chicago certainly delivered.
1993 – Meat Loaf Rules the Charts with “I’d Do Anything for Love”
On October 23, 1993, Meat Loaf was enjoying his reign at No. 1 on the UK Singles Chart with “I’d Do Anything for Love (But I Won’t Do That).”
The song came from Bat Out of Hell II: Back into Hell (1993, MCA Records), his long-awaited reunion with songwriter Jim Steinman.
Now, folks, we’ve talked about Meat Loaf and this song before. But some performances are worth revisiting!
I’ve never made any secret of my admiration for Meat Loaf. He’s one of my all-time favorite singers.
And this recording demonstrates exactly why.
The power, the emotion, the theatrical delivery, and that incredible voice!
Jim Steinman didn’t write ordinary little three-minute rock songs. He created musical epics. And Meat Loaf was one of the few singers who could bring those enormous compositions to life.
After the extraordinary success of the original Bat Out of Hell in 1977, nobody could have guaranteed that the magic would happen again sixteen years later.
But it did.
The song spent seven weeks at No. 1 in Britain and also topped the American charts.
And as for what Meat Loaf wouldn’t do for love?
Well, buddy, the answer is in the song itself!
What a voice. What a performer.
Rest in peace, Meat Loaf. Your music continues to ROCK!
1963 – Bob Dylan and “The Times They Are A-Changin’”
October 23 brings us to the recording sessions for one of the most important songs in American popular music.
Bob Dylan’s “The Times They Are A-Changin’.”
The song’s recording sessions took place on October 23 and 24, 1963, with the familiar album master recorded on October 24. It became the title track of The Times They Are A-Changin’ (1964, Columbia Records).
Dylan was only 22 years old.
Think about that for a moment.
America was experiencing enormous social change. The civil rights movement was challenging segregation and discrimination. Young people were questioning long-established traditions. The country was struggling with deep political and cultural divisions.
And here was this young songwriter with an acoustic guitar, writing words that would resonate for generations.
Years later, Dylan explained his intentions in a 1985 interview with Cameron Crowe:
“This was definitely a song with a purpose.”
And what a purpose it served.
The song became closely associated with the civil rights movement, protest gatherings, and the changing attitudes of the 1960s.
Over the years, it has been performed by countless artists and used to express the hopes, frustrations, and aspirations of people living through periods of change.
But here’s what makes it extraordinary.
Dylan didn’t write a song that belonged exclusively to 1963.
He wrote something that could speak to people living decades later.
The world continues to change. Technology changes. Music changes. Society changes. Sometimes those changes bring progress, and sometimes they bring new challenges.
And sometimes, as we grow older, we find ourselves wondering what happened to the world we once knew.
I think that’s something every generation experiences.
But there’s an important distinction between recognizing change and blindly accepting everything that comes along.
We can embrace progress while still appreciating the lessons, traditions, and values that helped shape us.
And we can disagree about those changes without treating one another like enemies.
That’s a message worth remembering.
More than sixty years after Dylan recorded this extraordinary song, the times are still changing.
And something tells me they always will.
1966 – The Jimi Hendrix Experience Records “Hey Joe”
On October 23, 1966, The Jimi Hendrix Experience recorded “Hey Joe” at De Lane Lea Studios in London.
The single was released in December 1966 on Polydor Records.
Now here’s something that might surprise a few people.
Jimi Hendrix didn’t write “Hey Joe.”
The song is generally credited to Billy Roberts and had already been performed by other artists before Hendrix recorded his version.
But what Jimi did with it was remarkable.
Former Animals bassist Chas Chandler recognized the song’s potential and helped bring Hendrix to London, where the Experience came together with Noel Redding on bass and Mitch Mitchell on drums.
And speaking of Mitchell, what a tremendous drummer!
His jazz-influenced approach gave the Experience a rhythmic personality that was unlike most rock bands of the era.
Hendrix transformed “Hey Joe” into a slow, blues-driven performance filled with tension and emotion.
And here’s another interesting detail.
Jimi wasn’t particularly confident about his singing voice. Chandler encouraged him to bring the vocals forward rather than hide them in the mix.
Imagine that!
One of rock music’s most recognizable performers wasn’t entirely comfortable with his own voice.
“Hey Joe” became the Experience’s debut single and reached No. 6 on the UK Singles Chart.
The song’s story is dark, but its importance to rock history is undeniable.
It introduced a guitarist whose imagination and creativity would change the instrument forever.
1982 – Culture Club Tops the UK Charts
On October 23, 1982, Culture Club reached No. 1 in Britain with “Do You Really Want to Hurt Me.”
The song appeared on Kissing to Be Clever (1982, Virgin Records).
What a terrific record!
Boy George’s soulful voice, the gentle reggae-inspired rhythm, and that unforgettable melody made this one of the defining songs of the early 1980s.
And let’s not forget the band’s musicianship. The arrangement is beautifully restrained, allowing the vocal and melody to do the work.
Of course, the song also found a hilarious second life in the 1998 comedy The Wedding Singer, starring Adam Sandler and Drew Barrymore.
Remember the Boy George impersonator who keeps singing it at wedding receptions?
That character was played by Alexis Arquette, a talented actor and performer from the well-known Arquette acting family.
Sadly, Alexis passed away on September 11, 2016, at just 47 years old.
Alexis was remembered with affection by friends, fellow performers, and fans, including Boy George himself.
And that little role in The Wedding Singer continues to make audiences smile.
Sometimes a great song becomes so closely associated with an era that all it takes is hearing the opening notes to bring back a flood of memories.
And “Do You Really Want to Hurt Me” certainly does that.
Rest in peace, Alexis.
2001 – Apple Introduces the iPod
On October 23, 2001, Apple introduced the original iPod, a portable digital music player that helped revolutionize how people carried and listened to their music.
Now folks, before anybody gets confused, the iPod wasn’t some bean-shaped enclosure you crawled into to escape your wife, your kids, or that never-ending list of household chores!
ROFLMAO!
No sir!
It was a little device that could hold approximately 1,000 songs in your pocket.
The original model featured a 5 GB hard drive and sold for $399.
At the time, that was pretty impressive technology.
Of course, as the years passed, smartphones eventually took over most of the jobs that dedicated music players once performed.
And look where we are now.
We’ve got a telephone that plays music, takes pictures, gives directions, pays bills, searches the internet, and occasionally even makes a phone call!
Ain’t technology wonderful?
The iPod was an important chapter in the history of recorded music, even if some of us still enjoy putting a physical record on the turntable.
Musical Birthdays – October 23
Dwight Yoakam – Born 1956
Happy 70th birthday to Dwight Yoakam, one of country music’s most distinctive singers and songwriters.
With songs like “Guitars, Cadillacs,” “Honky Tonk Man,” and “A Thousand Miles from Nowhere,” Dwight helped bring a traditional country sound to a new generation.
But he’s also a talented actor.
Remember his performance as Doyle Hargraves in Billy Bob Thornton’s 1996 film Sling Blade?
Buddy, what a character!
Dwight made Doyle so unpleasant and believable that you wanted to reach through the screen and throw the guy out of the house yourself!
That’s some serious acting.
“Weird Al” Yankovic – Born 1959
Happy 67th birthday to “Weird Al” Yankovic!
Now here’s a guy who has made millions of people laugh for decades.
And one of my favorites has always been “Eat It,” his hilarious parody of Michael Jackson’s “Beat It.”
The song appeared on “Weird Al” Yankovic in 3-D (1984, Scotti Brothers Records).
And that music video!
The dancing, the costumes, the gang confrontation, and Weird Al turning a serious pop hit into a comedy about eating your dinner!
ROFLMAO!
You have to admire somebody who can take music seriously enough to make it sound great while having that much fun with it.
Robert Trujillo – Born 1964
Happy 62nd birthday to bassist Robert Trujillo, known for his work with Suicidal Tendencies, Ozzy Osbourne, Infectious Grooves, and Metallica.
Trujillo is a powerful, energetic player who brings tremendous presence to the stage.
And after all the discussions we’ve had about Metallica’s bass sound over the years, it’s nice to celebrate a musician who makes absolutely certain everybody knows there’s a bass player in the band!
Ellie Greenwich – Born 1940
Remembering songwriter Ellie Greenwich, born October 23, 1940.
What a remarkable collection of songs she helped create!
“Be My Baby,” “Da Doo Ron Ron,” “Then He Kissed Me,” and “Leader of the Pack” are just a few examples of her extraordinary songwriting legacy.
Working with Jeff Barry and other collaborators, Greenwich helped shape the sound of American pop music during the 1960s.
These weren’t simply hit records. They became part of the soundtrack of an entire generation.
Ellie Greenwich passed away on August 26, 2009, at the age of 68.
Greg Ridley – Born 1943
Remembering Greg Ridley, bassist for Spooky Tooth and Humble Pie.
And with Halloween right around the corner, how appropriate is a band named Spooky Tooth?
ROFLMAO!
But seriously, Ridley was a fine musician whose bass playing helped anchor some terrific British rock recordings.
His work with Humble Pie remains an important part of that band’s sound, providing the foundation for some powerful rock performances.
Ridley passed away on November 19, 2003, at the age of 60.
Ernie Watts – Born 1945
Happy 81st birthday to saxophonist Ernie Watts.
A highly respected musician whose work crosses jazz, pop, and rock, Watts has performed and recorded with an extraordinary range of artists.
His career is a reminder of just how much great musicianship exists beyond the spotlight.
Remembering Mother Maybelle Carter – 1978
On October 23, 1978, country music lost one of its most important pioneers, Mother Maybelle Carter, at the age of 69.
As a member of the original Carter Family, Maybelle helped establish the sound of early country music.
Her innovative guitar technique, often called the Carter Scratch, allowed her to play melody and rhythm together, influencing countless guitarists who followed.
And yes, folks, she was the mother of June Carter Cash, making her Johnny Cash’s mother-in-law!
Talk about a musical family!
Mother Maybelle’s contributions extended far beyond her own recordings. Her influence can still be heard in country, folk, bluegrass, and acoustic guitar playing today.
A genuine American music pioneer.
Rest in peace, Mother Maybelle.
Remembering Jerry Jeff Walker – 2020
On October 23, 2020, singer-songwriter Jerry Jeff Walker passed away at the age of 78.
Walker wrote one of the most beautiful and enduring songs in American popular music.
“Mr. Bojangles.”
Originally appearing on his 1968 album Mr. Bojangles (Atco Records), the song tells the story of an aging performer whose life is filled with both joy and sadness.
It went on to be recorded by numerous artists, including the Nitty Gritty Dirt Band and John Denver.
But this song has always meant something very personal to me.
I used to ask my dad to perform “Mr. Bojangles” for me whenever I could.
And I never got tired of hearing him sing it.
It’s funny how music works.
Sometimes a song reminds you of a certain year, a particular place, or something you were doing when you first heard it.
But other songs bring back the people you love.
For me, “Mr. Bojangles” will always be one of those songs.
Thanks for the music, Jerry Jeff.
And thanks for the memories, Dad.
Final Spin – What Time Cannot Take Away
Back in 1963, a young Bob Dylan reminded the world that the times were changing.
And boy, was he right.
We’ve watched the world change in ways we never could have imagined. The way we communicate, the way we listen to music, even the way we treat one another.
Some of those changes have been wonderful. Others? Well, I’m not so sure.
But here’s something I’ve come to appreciate as I’ve gotten older.
Just because the world changes doesn’t mean everything that came before it loses its value.
Look at the music we’ve celebrated today.
Chicago gave us a beautiful song about love. Meat Loaf reminded us how powerful a voice and a great song can be. And Jerry Jeff Walker gave us “Mr. Bojangles,” a song that will always remind me of my dad.
My father isn’t here to sing that song for me anymore. But every time I hear it, a little piece of those wonderful memories comes back.
And no amount of technology or changing times can take that away.
Maybe that’s one of life’s most important lessons.
We can’t stop time. We can’t hold on to every moment. And we certainly can’t keep the world from changing.
But we can decide what we carry forward.
The love we give our families. The kindness we show a stranger. The respect we give someone who sees the world differently. And the memories we create for the people who will one day remember us.
Because someday, long after we’re gone, a song might come on the radio and remind somebody of us.
And wouldn’t it be wonderful if that memory brought a smile to their face?
The times will always be changing, my friends. Let’s make sure the things worth remembering never go out of style.
And that’s gonna do it for today, friends. Hopefully I’ve maybe put a smile on your face, and a song in your heart.
Take care of yourselves, help others when you can, and always, always, keep the music playing.
Listen to Today’s Broadcast/Podcast
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References
- Billboard – Music Charts and Chart History
- Official Charts – UK Singles Chart History
- Bob Dylan – Official Website
- The Official Jimi Hendrix Website
- Chicago – Official Website
- Apple Newsroom – Apple Introduces iPod
- Country Music Hall of Fame and Museum
- Songwriters Hall of Fame
- Encyclopaedia Britannica
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