the Best in Kerouac & the Beats, Adventure, Politics, Music, Movies, Poetry & other Lifejoys

Brianland header image 2

Taylor Swift, the Grateful Dead and The Beat Generation

November 30th, 2023 · 28 Comments · Grateful Dead, Kerouac and The Beats, Music


Why this Deadhead Beatnik Beatlemaniac loves Pop’s Princess


I’ve been into Taylor Swift since a New York Times profile in 2008 talked about her confessional songwriting and use of social media — at the time, MySpace.  (!)  Her second album Fearless was set to come out (and would go on to win Album of The Year at the Grammys), and she was still a teenager and thought of as a country singer, but I liked how preternaturally self-assured she was (similar to the young Beatles), and how she connected directly with her fans (like the Grateful Dead with their ticket sales and newsletters), and how she wrote so unapologetically autobiographically (like Jack Kerouac & Allen Ginsberg).

Since then she’s gone on to set new standards in live show production and attendance — something the Dead pioneered — and has created the closest thing to global Beatlemania since the originals.

And speaking of the Dead, the Eras Tour shows are clocking in at 3½ hours — longer than even Dead concerts, who are famous for doing the longest shows in music!

And it’s not just the popularity but the quality of the songwriting.  There’s no one alive who’s written more hits and hooks in the last 15 years than her — and she’s only 33 years old!

I love me some Hunter/Garcia and Bob Dylan and Lennon & McCartney, and Taylor just became the first of any of them (or anyone, period) to be Grammy-nominated for Song of The Year seven times!  The Grammys are voted on by the people who make the music we all listen to, and seven times in the past dozen years they thought she wrote one of the five best songs of the year.  The reason both the Dead and the Beatles are still part of culture today is because of their songwriting.  And Taylor Swift is one helluva songwriter.

And another thing about her songs and shows and public persona — she’s all about positivity and happiness and living a life of joy.  All You Need Is Love.  Sometimes some people get bent outta shape when she’s compared to The Beatles — but to my ears, I get the same feeling listening to her as I do from that band that first personified Love.  And it’s probably a big reason both were so popular in turbulent times.  

And then there’s how she treats her band and crew — something that made the news when she gave each of her truck drivers and other crew a life-changing bonus of $100,000 apiece.  The Dead were known to pay their ‘family’ crew significant salaries with benefits and basically include everybody in the profit sharing.  Allen Ginsberg was known for his never-ending philanthropy that often left him with less money at the end of the year than the people who worked for him.

I also love how she’s a dedicated workaholic — something else I admired about The Beatles and both Kerouac and Ginsberg.  Jack died at 47 and has over 50 different books in print;  Allen wrote over 500 poems and never stopped performing and teaching until his body finally wore out at age 70;  and The Beatles’ quality and quantity of output in a condensed time has never been equaled by anybody.

She says in the revealing Miss Americana documentary — “I’m only here because I work hard and am nice to people.”  And for all of us, no matter our age or field of endeavor, that is wise advice and solid motivation.

And then there’s the family aspect.  Taylor’s mom and dad have been supportively involved in every part of her career from the time they up and moved the family to Nashville when she was 14 so she could pursue songwriting.  She calls her mom her best friend.  She’s stayed loyal to her band and dancers, keeping many of them consistent despite changing genres album after album.  Jack and his mother were pretty inseparable his whole life, the Dead were famous for their ‘family’ of friends they stuck with since the ’60s, and the entire Beat Generation was based around a familial sense of camaraderie and support.

And speaking of Jack & Taylor’s closeness with their mothers — they’re also both pretty famous for their lifelong love of their cats.

Jack, his cat, and his mom

And one nice hardcore connection — Aaron Dessner (of The National) — who Taylor’s described as her “collaborator soulmate” and have co-written nearly 30 songs together, is not only a Deadhead but loves him some Jack as well, having scored & performed the music for the best film adaptation of a Kerouac novel, Big Sur.  

And it seems like every person who meets Taylor says how normal she is.  She’s been living in the white-hot media spotlight since she was a teenager, has over-the-top ego reinforcement, and enough money to indulge in every bad habit ever invented — but never once have we seen her make a mess of things — or even insult anyone.

Also like the Dead, as many music reporters have noticed, her fans self-create a giant all-day party in the parking lot around her shows — they call it “Taylor-gating” — and sell trade or ‘miracle’ handmade clothing and jewelry with each other.  Etsy reported that $3 million worth of homemade Taylor friendship bracelets sold in the summer of 2023 alone.  Just as the Dead scene grew organically by the fans creating their own customs and culture, Swifties have created a world by and for themselves.  Even the word ‘Swifties’ was created by fans.  And like ‘Deadheads’ a word was needed to be coined to cover their multitudes.  Their embrace of friendship bracelets that they make and give away to one another echoes how Deadheads would make and gift each other tie-dyed clothing and cassette tapes of live shows. 

And just as a funny–cool sidebar, the Swifties’ friendship bracelets first appeared when she made an Instagram post in 2019 wearing some, but they really kicked off in 2022 with the line on her Midnights album, “So make the friendship bracelets, take the moment and taste it.”  When a new generation of Merry Pranksters gelled in 2014 with the 50th anniversary of the original psychedelic Bus trip across America, these next geners immediately started making and trading bracelets with friendly expressions and lyrics.  So, the Dead’s off-shoot family were already practicing the bracelet love several years before they began filling Swifites’ arms.


When the pandemic hit in 2020, I began an autodidactic Film Studies program and immersed myself in Get Out The Vote operations for Joe Biden, so music wasn’t front of mind.  Having not seen Taylor perform since the Netflix movie of the all-stadium Reputation tour in 2018, I tuned in for her Saturday Night Live appearance in November 2021 and was just jaw-dropped by her mesmerizing 10-minute version of All Too Well.  This was a whole new thing.


How could I not think about Dylan’s 11-minute Sad-Eyed Lady of the LowlandsAfter I recomposed myself, I posted about it to Facebook to let people in other time zones know not to miss it.  The bulk of my friends are Deadheads or Beatle freaks or beatniks so some were surprised I was raving about this pop star — but more fun was the discovery of fellow secret Swifties in my midst.  😄

This jaw-dropping performance really re-sparked my interest.  “Geez — what is this woman up to?!”  I’d heard a few songs from Folklore and Evermore that she created during the pandemic lockdown and could tell she was growing as a songwriter, but I was more into my Film Studies world and unless something was part of a movie it wasn’t gonna be on my front burner.

Then wouldn’t you know it — she wrote and directed a short film based around this All Too Well song!  Now we’re gettin somewhere!  😄


The Toronto International Film Festival (TIFF) even featured the film in 2022, and I discovered that she had actually become a director (!) having helmed all of her own music videos since 2019.  And man, does she know the artform!  Check this out —>


And Variety reported that she’s written a movie script and signed with Searchlight Pictures to make her feature-length directorial debut.  Searchlight is who made the recent Banshees of Inisherin, and Best Picture winners Nomadland, The Shape of Water, Birdman, 12 Years a Slave and Slumdog Millionaire.

And speaking of cinematic masterpieces, Greta Gerwig and Margot Robbie’s Barbie was breaking records in movie theaters at the same time Taylor was rewriting the concert business.  My mother was a feminist before there was a word for it, and she passed it on to me, and in this era of toxic masculinity and women’s rights being taken away it’s so gratifying and empowering to see women (including Beyoncé) dominating two industries that have historically been ruled by men.

This woman has somehow created a fanbase that reflects the collective camaraderie of my favorite band, writes roman à clef songs like my favorite author and poet, and by 2023 at age 33 had manifested the biggest global musical phenomena since The Beatles.  And now she was becoming a filmmaker!

And in late-breaking news — she just became the first artist in any medium that Time Magazine named as their Person of the Year in nearly 100 years of making the distinction!


And she’s 33 years old.  And a solo woman artist.





Bonus Video Round

Here’s Seth Meyers on Howard Stern describing Taylor being the SNL host at age 19 and “what a force of nature she is” writing her own “perfect, fully formed” opening monologue as a song . . .


Then here’s the brilliant funny Monologue Song . . . age 19 . . . 


And then this is one of the most heart-wrenching things I’ve ever seen — documentary footage of her standing up against her own father and managers’ strong pushback about how she’s going to start speaking out politically  . . . 


And here’s a fantastic emotional 7-minute doc on Taylor & her fans made by Time for the Person of The Year award . . .


And here she is giving an inspirational speech for the ages — and for all ages — at my old alma mater NYU . . . 


And just for fun — here’s Dave Grohl telling the story of how Taylor “saved my ass” by playing a song at a party at Paul McCartney’s house . . .


And just cuz it’s funny . . .  this makes me laugh out loud every time — especially Leslie Jones . . .



Bonus Fun-Fact Lightning Round

Taylor Swift is the first living artist in history to have 5 different albums in the Billboard Top 10 at the same time.

She’s the first artist in history to hold all 10 songs in the Billboard Top 10.

She’s had 3 different #1 albums in 2023 alone.

Each album she releases breaks the all-time streaming record on Spotify, iTunes & Apple that she herself set previously, and in 2023 she was the most streamed artist on all three services and the most searched person on Google.

The week that The Beatles’ Now and Then came out and cracked the Top 10 — Taylor was holding the top *21* slots on Spotify the week the Fabs showed up.

And speaking of The Beatles, she did something only they have done, having an album at #1 for six weeks for four consecutive albums.

She writes all her own songs and is the first songwriter in history to be nominated for a Song of The Year Grammy seven times.

She wrote her first song at age 12, and was playing a 12-string guitar by 13!  She has a great story about how her music teacher at the time said she’d never be able to play a 12-string — so she immediately went and learned it and fired his ass.  😄

Ryan Adams recorded a successful track-by-track cover of Taylor’s entire 1989 album.  

With over 4 million concert tickets sold worldwide in 2023 alone, she more than doubles the next closest artist (her good friend Beyoncé) in both tickets and gross.  In fact, in just 8 months this year she surpassed the 5-year-long Elton John Farewell Tour as the biggest grossing tour of all time, bringing in over $1 billion — the first tour in history to cross the “b” line.  And she’s gonna double that by the time it’s over.

The 100-year-old AMC movie chain had their biggest single box office day in history the day her Eras concert movie tickets went on sale, and it’s now the biggest grossing concert film of all time.

She’s a self-made woman billionaire who earned it all by creating art.

And that’s not even getting into her voter registration efforts that led to the biggest single-day record for new registrations in history.

Or that in every city she played in America on the Eras tour she made massive donations to the local food banks.  When she played Levi’s Stadium in San Jose — where I saw the Dead & Company do one of their Fare Thee Well shows in 2015 — the food bank announced she donated “enough to feed 500,000 people every month for a year.”  Swift’s people did not announce the donation — they do it all on the QT — but when Second Harvest announced it they saw a 43% rise in donations because of the awareness she brought to the cause.

Or the $55 million in bonuses she’s given her employees.  Or that she immediately sent another million to the residents in Tennessee hit by the tornados in December 2023 — just as she’d done when one hit in March 2020.  Billboard magazine ran a piece in Dec. 2023 listing some of the other donations she’s quietly made over the years including another million to Louisiana flood relief, books to libraries, money to schools and animal protection & rescue groups and sexual assault services, and paying fans’ medical bills and student loans and back rent.

Or that the U.S. Federal Reserve cited her specifically as being a boost to the economy;  or that Attorney General Merrick Garland quotes her lyrics in conversation;  or that Barbara Walters famously said in her Most Fascinating People ABC special in 2014 — “Taylor Swift IS the music industry.”




Bonus Reading Round 

Here’s my single favorite piece I’ve read about her all year — “Discovering Taylor Swift” — by an obvious storytelling master of the written word, Paul Slansky.

Or here’s another one in Fast Company smartly comparing her to the Grateful Dead.

Or this is a great piece by a New York psychiatrist about how prominent Taylor is among her patients and how the songwriter is therapy for them the rest of the week when they’re not in session.

You may also like The Grateful Dead: Jack Kerouac Manifested as Music.

Or here’s an excerpt from my book The Hitchhiker’s Guide to Jack Kerouac that takes the reader to a show at Red Rocks amphitheater in the summer of 1982.

Or here’s a fun one — The Grateful Dead Played my 30th Birthday.





by Brian Hassett   —

Or here’s my Facebook page if you wanna join in there —



Tags: ···················

28 responses so far ↓

  • 1 Brian Humniski // Dec 1, 2023 at 8:16 AM

    That is why the world is in love with Taylor.

  • 2 Jen Corke Kafer // Dec 1, 2023 at 10:25 AM

    I love this.

  • 3 Becky Musch // Dec 2, 2023 at 10:26 AM

    Nice article, Brian.

  • 4 Dale Topham // Dec 4, 2023 at 12:57 AM

    Just WoW! Looks like you are turning this old beatnik into a ‘Swifty’!

  • 5 Brian Hassett // Dec 4, 2023 at 9:04 AM

    Gubba Dale — I was into Jack when you couldn’t find his books in bookstores, and into the Dead when there was no section for them in the record stores . . .
    and today I find myself loving an artist so many supposedly hip people reject.
    This woman is the giant artist of our time ❤

  • 6 John Allen Cassady // Dec 5, 2023 at 10:56 PM

    She looks familiar. I think I dated her in high school. 🙂

  • 7 Mary Parsons // Dec 6, 2023 at 1:43 AM

    I love this. Very well written!!!

  • 8 Kenneth Morris // Dec 6, 2023 at 8:54 AM

    Appreciate this, Jester. I don’t know her music but know her fans at work & admire her goodness to her crew, fans, & the backlash in Nashville to her left politics. Lots of Dixie Chicks there in retrospect. A great person grounded by family & positivity.

  • 9 Michelle Lynn // Dec 6, 2023 at 9:40 AM

    Fantastic article.

  • 10 Susan Pomerantz // Dec 6, 2023 at 11:47 AM

    Great article, Brian. (My granddaughter is a Swiftie.) Sharing!

  • 11 Scarlett Solomon // Dec 6, 2023 at 12:09 PM

    I shared this article with my step-daughters, too.

  • 12 Lorne Lampert // Dec 6, 2023 at 1:52 PM

    Thanks for this, Brian – All Too Well is my favourite song – maybe a top song ever made – and you just introduced me to the short movie today – MADE MY DAY – thanks BH

  • 13 Wendy Thackway // Dec 6, 2023 at 3:14 PM

    Great article! Love Taylor and all she represents. How can you not???

  • 14 Mark A. Love // Dec 6, 2023 at 4:21 PM


  • 15 Terri Joness // Dec 6, 2023 at 7:50 PM

    Thank you for writing this!

  • 16 Joseph Luna // Dec 6, 2023 at 9:29 PM

    An excellent read! 

  • 17 Ted Lindsay // Dec 6, 2023 at 11:18 PM

    This is great stuff, Brian.

  • 18 Indiana Humniski // Dec 7, 2023 at 6:07 PM

    I love your frequent call-backs to multiple media evidential sources! It’s great how you balance personal opinion and statistical fact. I’m so happy that the love for Taylor is intergenerational! I spoke to my Uncle recently about borrowing a copy of Kerouac.

  • 19 Janice NanaJana // Dec 8, 2023 at 4:13 PM

    This was fantastic. Now I like her even more.

  • 20 Howard Park // Dec 9, 2023 at 4:35 PM

    And like Jerry Garcia and Allen Ginsberg she drives right wing wacks bonkers just by being who she is.

  • 21 Brian Hassett // Dec 9, 2023 at 5:40 PM

    Good one, Howard!

  • 22 Michael Kenneth Smith // Dec 10, 2023 at 8:54 AM

    I couldn’t agree more Brian. Great article! Be magnificent!

  • 23 Megan Reese // Dec 10, 2023 at 8:21 PM

    I LOVE Taylor!!!!!

  • 24 Susan Pomerantz // Dec 11, 2023 at 12:32 PM

    Great article Brian!

  • 25 Jim Parkevich // Dec 13, 2023 at 7:57 PM

    Thanks guy. This 74 yr old dude spent an hour watching these amazing videos!!!

  • 26 Steve Brown // Dec 14, 2023 at 9:05 PM

    I am a Swifty.

  • 27 Jay Matlock // Feb 18, 2024 at 8:53 PM

    LOVE this in-depth article, Brian! Thanks!

  • 28 Sharanam Anandama // Feb 20, 2024 at 5:06 PM

    This would be True..!! I’ve been a Dead fan since 1969 San Francisco till now… age 71 and still going strong … and I LOVE LOVE LOVE being a Swiftie too. She is the BEST to come along in a long time!!!

Leave a Comment

Leave a Reply

Your email address will not be published. Required fields are marked *