Cassette tapes of varying colors

Mixtapes & Music Playlists

If you aren’t creating and sharing music playlists with your friends and family, all I can tell you is that you are missing out on one of life’s most understated paths for rapport and immediacy.

I just put together my 2022 playlist. The rule this year was to limit it to just 11 songs. This was after the 19 for 2019, 20 for 2020, etcetera overwhelmed everyone. We decided that 20+ songs distributed among us were 400+ songs of too much sharing.

Music playlists are the modern version of the mixtape, which some of us spent a good part of our lives making and sharing. Those who weren’t around in the 1970s can’t imagine the breakthrough that cassette tapes represented. Prior to that, the only long-form listening experiences were ad-supported radio or albums. Cassettes allowed custom creative combinations and newfound portability. Technology has since vastly expanded the distribution possibilities.

Cassette deck from the 1970s

While I mixed many a cassette over the years, I still remember the first one I ever heard. My older brother returned home during a college break with a mixtape that blew my little elementary school mind wide open. By the time I flipped over to its B side, which launched with Mott the Hoople’s live version of David Bowie’s “All the Young Dudes”, I was fully transported out of my life and into whatever I imagined living on my own might become. That life definitely had great music echoing across the quad from distant speakers, and it for sure included older girls who weren’t my sisters.

If you aren’t creating and sharing music playlists with your friends and family, all I can tell you is that you are missing out on one of life’s most understated paths for rapport and immediacy.

My 2022 playlist is a tribute to the most memorable or influential live performances in my musical lifetime. The late great Taylor Hawkins, drummer for the Foo Fighters, said that when you are learning you just have to get out and perform. These tunes inspire my performance ambitions as I learn to play guitar and drums: 2022 Roger That Live

The individual songs:

Mary Had a Little Lamb – Live at Montreux Casino by Stevie Ray Vaughan

What better way to kick things off than revisiting the first song I ever played live in concert? Fourth grade band, right-hand side, first chair in the back row, rocking the trombone.

Mama – Live Busking by Cam Cole

A truly talented musician with an amazing combination of guitar and foot drums. You might recognize him from his great cameo with this very song on Ted Lasso as “the undiscovered mega talent”:

Another master of this setup is my friend Andy Braun—follow him here and stay tuned for his new original compositions. Watching Andy play inspired me to learn the foot drums while I’m moving from beginner to intermediate on guitar. So far, I and everyone else in hearing distance have learned this is ridiculously hard to do, which is making this one of the craziest things I’ve ever attempted.

Foot drums

Chicago – Live by Crosby, Still, Nash & Young

CSNY’s 4 Way Street album surged to #1 in the summer of 1971, marking both the first live rock album I ever heard and my gradual awakening to the tumult around me as a freshly tuned in seven-year-old. As a Chicagoan, these lyrics felt like a call to arms:

Somehow people must be free
I hope the day comes soon
Won't you please come to Chicago
Show your face

From the bottom of the ocean
To the mountains on the moon
Won't you please come to Chicago
No one else can take your place

We can change the world
Re-arrange the world
It’s dying … to get better

This performance, with its mis-struck piano chords and an indignant Graham Nash simultaneously cajoling allies and berating injustices, was one of my first realizations about how intensely grown-ups disagreed about the paths forward as they sought to change the world.

I’m not a very political person, but I do feel strongly about change and its many avenues. There is a great Paul Graham quote from his interview with Robert Greene:

I asked Zuckerburg what question could be put on the Y Combinator application that would detect people like him. And he said, “When was the first time you realized things were broken and you wanted to fix them?”

This song was mine. When was yours?

The Tracks of My Tears – Live At The Carter Barron Amphitheatre by Smokey Robinson & The Miracles

This audible book / performance from Smokey Robinson brilliantly combines autobiography, his co-founding of Motown Records, and the creative process behind the most memorable of his dozens of Top 40 hits. Smokey wrote over 4,000 songs, but it is his telling of the friendships and their exceptional moments that bring this home. The Miracles’ first disastrous rehearsal at the Apollo Theater being rescued by the great Ray Charles is such a time capsule.

Learn to Fly – Live by Rockin’1000

I don’t need to become a brilliant musician. I just want to play well enough that I blend in with 999 other musicians. Guaranteed goose bumps when you watch the video version:

83 Medley – Live at the Oak Mountain Amphitheatre by John Mayer

And most my memories have escaped me
Or confused themselves with dreams
If heaven's all we want it to be
Send your prayers to me
Care of 1983

You pick your year. John Mayer chose 1983. I pick 1974—the year my older brother and I played through the entire 162 game Cubs season with Statis Pro Baseball and my little sister turned one years old.  

It’s Too Late – The Carnegie Hall Concert by Carole King

If you haven’t seen the musical “Beautiful”, spoiler alert—you will absolutely get your heart torn apart during this song. Ripped out, thrown on the ground, stomped on and then run over and flattened by the nearby M42 bus. Still, you don’t have to know the background story to feel this version’s raw declarative honesty. Of course, why wouldn’t it feel that way? This was Carole King’s very first concert performance in front of an audience.

It used to be so easy, livin' here with you
You were light and breezy, and I knew just what to do
Now you look so unhappy and I feel like a fool

There'll be good times again for me and you
But we just can't stay together, don't you feel it, too?
Still I'm glad for what we had and how I once loved you

But it's too late, baby, now it's too late
Though we really did try to make it (we can't make it)

Carole King strode aside the Cambrian explosion of singer-songwriters as a true giant. She wrote or co-wrote 118 hits on the Billboard Top 100 before launching her own extraordinary solo career. Listening to this feels like riding a time machine to one of the greatest moments in musical history.

Don’t Let Me Down – Rooftop Performance / Take 1 by The Beatles

Clearly forgetting the lyrics, John Lennon sings a string of nonsense syllables to launch the third verse of Don’t Let Me Down. While John improvises, George turns back from adjusting his amp and smiles. Ringo drums on, cracking up, and the band repeats the four bar sequence as Paul and John seamlessly sync with each other to restart the verse.

Seeing George Harrison’s reaction, both on the rooftop and again during replay in the sound booth, brought to mind that it had been ten years since the then 14-year-old George joined the band via an audition for John on the upper deck of a bus. There were only four people who knew what it was like to be a Beatle, and George’s appreciative smile seems to bridge the entirety of that decade.

It is a rare clip as the official 414 million view video edits out the improvisation and you don’t know why George is laughing. There is also a fun rehearsal clip that shows the impact that Billy Preston’s keyboards bring to the track and the band’s spirits. If you are a Disney+ subscriber you can see the greater context beginning at the 1:37:45 mark in The Beatles: Get Back; Part 3: Days 17-22:

This was the Beatles’ last public performance on January 30, 1969. There are so many significant moments in this three-part documentary from Peter Jackson. I regularly play it on a nearby monitor, the volume muted, as a reminder of what a room feels like as the creative process unfolds.

Live And Let Die – Live by Paul McCartney

Waiting with my wife and friends for Paul to perform on the south lawn in Grant Park during Lollapalooza 2015, I notice the stage is standing in the same location where I used to launch myself sideways onto the hard packed dirt as part of penalty kick goalie drills during high school. Our soccer team shared this field with all sorts of animal events and we’d wonder how much of that hot and dusty goal area was disintegrated horse droppings.

Grant Park, Chicago view from the South Field looking North

Several dozen summers later and two hours into that night’s 32 song set, the anthemic chords of Live and Let Die explode as pillars of flames shoot out from the stage and fireworks light up the southern sky. I turn 180 degrees to take in the Chicago skyline and the floodlit hundred thousand fans, knowing this is home.

Raise Your Hand – Live at the Roxy Theatre by Bruce Springsteen & The E Street Band

The last encore of my first rock concert—and as it turned out, nearly the Uptown Theatre’s last rock concert (ten weeks later it closed for what has now been forty-one years). Springsteen wanted to play one last smaller venue (4,381 seats) before The River was released. Near the end of the concert, the balconies were undulating like that old newsreel footage of the Tacoma Narrows bridge collapse that they show you in physics class.

Angela / Someone to Watch Over Me – Live at Milliken Auditorium by Bob James

When the house lights come up and the jazz or oldies begin to play softly over the speakers, you know the show is over. When I DJ’d I’d do the same with Earl Klugh’s classical guitar masterpiece Wishful Thinking.

My three favorite jazz songs of all time are Wishful Thinking, Chuck Mangione’s Feels So Good, and Bob James’s Angela (Theme from ‘Taxi’)—all released when I was a teenager. I didn’t want this playlist to end, so this is the longest live version of these that I could find.

Thanks to Jim Coughlan, Monika Ek, Glenn McWhinney, and Mike Whealan for reading drafts of this.

Bonus Content & Community Update:

We've received feedback from dozens of friends who provided their favorite live performances. There are two additional playlists that will continued to be updated and modified to reflect these all-time great shows:

This first playlist presents close to 100 video greats. This is a favorite to put on the screen while working out or simply when wanting to hang out with musical legends. A useful YouTube keyboard shortcut: hit Shift-N to skip to the next video.

This second playlist begins with perhaps the greatest introduction of band members ever recorded. Listen closely to who is playing the organ. Yes, it is Billy Preston once again!

Finally, if you are reading this here for the first time, I want to share what was included in the emailed version to subscribers:

The Always Invert newsletter and community continues in an exciting new direction. Going forward we will be following up our topics with tools and tricks to help make you a power user of today’s software innovations.

You are invited to join us in the community portal where we share our no code and low code strategies, discoveries and development processes. We will also be providing resources that will put you on the path to create your own custom solutions.

Of course, if you simply want to join in the fun I’ve had putting together and sharing my 2022 playlist, read on! You too are welcome in the community to follow along, provide feedback, and generate inspiration as we continue this exploration.

Please share your favorite playlists in the community comments or contact me directly in the usual spots on social or via email.

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