John Mayer and Being Known for What You Want to Be.

By: Jen Shoop

What is it about John Mayer?

I realized, the other day, that his music has accompanied me through two decades of living, and that I handily know his oeuvre better than that of any other music artist’s, and yet my impressions of him are pointillist constructions: small, isolated spots of unexamined information. Interesting to reflect on our contrivances of celebrity, and the provenance of their grist.

Let me start here: I love his music. But my music-snob sister-in-law (she openly owns this title, and has earned it – her taste and encyclopaedic knowledge across so many genres of music is unparalleled) despises it. I can appreciate the dressing-down, because “Your Body Is a Wonderland,” with which his name was for some time (is?) synonymous, is about as bubblegum as it gets. A critic once described Mayer’s music as “pillow-soft songcraft” defined by “dull sentimentality,” and I will admit that even as a starry-eyed high school student, it was difficult not to cringe at “And if you want love / we’ll make it // swim in a deep sea // of blankets.”

Still, he is a widely respected guitarist and a multiple-time Grammy Award winner who has collaborated with many of the greats. Beyond the credentials, though, I straight-up, unapologetically adore his albums — all of them, but especially Continuum. The only songs I skip are “Waiting on the World to Change” (unbearably twee?) and “Daughters,” the latter of which reads patronizing and inauthentic, especially if we are to believe his Lothario persona. Those songs notwithstanding, I listen to him constantly, especially on the weekends. Contrary to the aforementioned critic, I find his lyrics clever and often profound, and his voice and guitar skills simultaneously soothe and stir. He is easy to listen to when I want nothing to disrupt me, but his introspective lyrics can also offer roads into or out of a sudden-onset mood. I can think of dozens of lyrics that have woven their way permanently into my consciousness, given real shape to sentiments I share, including multiple stanzas of “Stop This Train,” which I cried to while we were driving through a terrible storm as we moved our entire world to parts unknown in The Midwest, newlyweds striking out on our own in an infelicitous tempest. The lyrics have pawed at me for well over a decade: the way life can seem to accelerate right out from beneath you, like an ill-footed skateboard.

Stop this train
I want to get off and go home again
I can’t take the speed it’s moving in
I know I can’t
But honestly, won’t someone stop this train?

Don’t know how else to say it
Don’t want to see my parents go

I’m one generation’s length away
From fighting life out on my own

The art of losing, indeed.

His songs reveal a soulful contemplativeness, high EQ, and poetic finesse. I love throwaway lyrics like “I played a quick game of chess with the salt and pepper shakers,” “but you could distinguish Miles from Coltrane,” “So put your faith in a late night show / I bet you didn’t even know / depends on how far out you go / the channel numbers change.” The attentiveness of these lines, the way they condense entire personalities and social awkwardnesses and feelings of isolation into the span of a handful of words, stirs me. I recently learned that he considers his first few albums, “Inside Wants Out” and “Room for Squares,” both of which I listened to compulsively in high school and college, a negotiation with the social anxiety that plagued him in his 20s, before anxiety was a normalized experience. He commented in an interview that “having anxiety in mid ’90s, late ’90s was like, you think you’re going crazy.” (Now, by contrast, it has been widely named and destigmatized.) I’ve re-listened to those albums from that lens and the lyrics glint with new meaning: “Would you want me when I’m not myself? Wait it out while I am someone else?”, he croons in “Not Myself.” The entire songs “Why Georgia?” and “My Stupid Mouth” invite reinterpretation. This must partly explain why I was so deeply drawn to him as a teen: there is a lot in his early work that reminds us of our rich, private interiors, and the way those depths are often at odds with or strangled by the selves we present to the world. Which is more or less the Cliffnotes version of my teenage experience.

Moving away from the ouevre and towards the artist: I’ve seen John Mayer perform live twice, and I’ve virtually studied his guest appearance on NPR’s “Tiny Desk” series. I find him fascinating as a performer in that he permits himself to fall entirely into the musicality of the moment, routinely making what my husband refers to as “stank face.” This, to both of us, seems like the true mark of a musician: he proves himself to be unconcerned with his appearance and instead entirely given over to the music itself.

Still, there are elements of his public persona that give pause. There are deeply uncomfortable interviews he’s given with Playboy and other outlets, and Jessica Simpson had some…choice words about him in her memoir (which is a delight to listen to on audiobook — I truly enjoyed learning more about her). Those recollections of him line up neatly with what Taylor Swift has alluded to in her song “Dear John,” in which she sings:

And I lived in your chess game
But you changed the rules every day
Wondering which version of you I might get on the phone tonight

And, later:

Or maybe it’s you and your sick need
To give love then take it away
And you’ll add my name to your long list of traitors
Who don’t understand
And I’ll look back and regret how I ignored when they said
“Run as fast as you can”

I carry a certain level of circumspection here: these are fellow musicians looking to advance their own careers and personas, and they are, in the end, selling songs and books, and therefore standing to benefit from reported salaciousnesses. But, still. He’s dated a lot of famous women, and the reportage has not been favorable. (What does this mean, as a female listener?)

The other day, spurred on by my recent reflection on how little I know about Mayer, I listened to an interview with him on Call Her Daddy. This was a true blind listen, as I know nothing about the podcast or its host, but I found him in turns rakish, and charming, and self-involved, and music-obsessed in all the ways I had anticipated. But there was one moment that jumped out at me. He’s talking about how he made mistakes in his earlier career, seemingly alluding to the publicity of his womanizing ways, and how he then drew inward, and was able to focus on presenting just the side of him that he believes matters: his musical skills. He says, at this point in his life, there’s no other living artist that won’t at least entertain a musical idea he’s had. (This sounds pompous, but I’m sure it’s true — he’s even covered Beyonce.)

He goes on to say that he is able to live happily because “I’m known for what I do.” He explains that he’s seen fellow celebrities flail when their moments are passing, when they realize they don’t have pegs to hang their hats on. By contrast, he’s always had his love of his music, and his faith that other people will like what he’s playing, to lean on. I thought to myself that this was a good example of someone who has asked: “What do I want to be known for?” and really leaned into the answer.

What are your impressions of Mayer? I’m so curious what my smart Magpies think about his seemingly polarizing music and persona.

And, are there other musicians who you listen to constantly but know little about?


+My reference to our stormy drive to Chicago brought up old memories: “The Chicago that ascends out of Lake Michigan as you approach from the northwest is sprawling, powerful, industrial, towering, and with each passing mile, you are only aware of your impossible smallness alongside it.”

+Holding hands in Chelsea. An ode to my best friend.

+When do you feel most like a mom?

If you want more Magpie, you can subscribe to my Magpie Email Digest for a weekly roundup of top essays, musings, conversations, and finds!

Shopping Break.

+This longline cardigan has been trending among Magpies the past week. J’adore. I especially love this for a new mama — great to layer over leggings/nursing tank during those first few weeks. But also a great option for any of us who aren’t quite into coat territory but run cold.

+All Oribe is 20% off this week! This Royal Blowout spray (a Magpie reader rec!) is absolutely stellar and works great on fine hair (whereas other products have weighed my hair down). I also love their volumizing spray (again, works on fine hair, but use sparingly) and all of their shampoos and conditioners are top-notch. (I have said this elsewhere and will repeat, though, that I think Roz’s slightly less expensive Foundation Shampoo and Conditioner give Oribe a run for their money. The best lather. You can get 15% off with code MAGPIE15.)

+Julia Amory’s new gem-toned caftans are so chic! Love this cranberry one for Thanksgiving. I know a few of you have bought these and RAVE about them. So flattering and feminine.

+Another great, slightly dressier pick for Thanksgiving: this velvet Rhode. Wowza!

+Weezie is running its once-a-year 25% off sale. I absolutely adore their French terry robe. Easily one of my favorite possessions. I wear it every morning while getting the kids ready for school. It’s the perfect weight and length and the sash actually holds the material closed (for some reason, with all my thicker plush robes, the sash just slowly unties). Also love these personalizable cover-ups for kids. My children have worn the last two summers!

+Target is offering 30% off Halloween costumes and accessories, including Squishmallow treat bags! My daughter would flip for one. My children are both going as Mario!

+These rattan pumpkin placemats are so fun for a fall tablescape. Layer on top of one of these $50 tablecloths in a fall print.

+This cute plaid top is en route to me. Love the ric rac trim!

+At this point, I have about four or five different planners/list notebooks/etc, but this productivity/goal-oriented one is so appealing to me.

+This gorgeous ribbed sweater and skirt situation are such a good deal.

+Niche, but a mom on my daughter’s soccer team brings this accordion-style set of folding seats to the games and they are SO handy!

+Seriously pretty gift wrap.

+These high-rise cords are on sale for $31 right now. Love. Very Veronica Beard.

+This velvet gown is on my wishlist.

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40 thoughts on “John Mayer and Being Known for What You Want to Be.

  1. Love that Joyce + Amy brought up the art vs. artist conversation, as I was thinking about it as I read this post! So much food for thought there … especially being a child of the 80s/90s, with increasing mainstream coverage of artists’ opinions and foibles thanks to the internet + social media.

    I can’t say that I’m a John Mayer fan — pretty sure I downloaded his initial EP from Napster (lol) and listened to his first album a bit in high school, but I fall more into the camp that your sister-in-law inhabits 🙂 I have been more into alternative artists/bands since the mid-90s, when I first started buying albums, and accelerated into music snob territory once I hit college thanks to the campus radio station. Consequently, I have very little knowledge of pop, especially between the late 90s and mid-2010s. So weird, I know!

    I am one of those people that will read obsessively about a musician once I fall under their spell, though! Usually not from gossip-type sources, but I like knowing how their lives inform their art.


    1. Yes, lots of angles to this conversation — music snobbery / liking what you like / the relationship between artist and his/her oeuvre / the ethics of listening / etc!

      Tell me more about your favorite singers from the 90s-2010s!! I’m fascinated by your reclusion (is that the right word) from ubiquitous pop. How did you even do it?!


    2. Haha! I definitely did listen to *some* mainstream music during that period — thinking of Aaliyah, Destiny’s Child/Beyonce, certain rappers, etc. — but I didn’t really listen to top 40-type radio after middle school! Instead, I used to spend hours researching artists on the web and then either buying their albums (there was a great independent record store in my town) or downloading mp3s and burning CDs (oh man, I had binders of HUNDREDS of these mixes!) During this period I loved artists like Yo La Tengo, Belle & Sebastian, Rio Kiley, etc. After I left for college in 2002, I pretty much never listened to mainstream radio, which I think has a lot to do with how I avoided a certain block of pop music. I continued my indie leanings in college (with thanks to our excellent indie radio station), and then after college I lived in New York, where I never listened to the radio (didn’t have one at home / rarely drove anywhere). Even now, when we do listen to the radio, it’s usually just local NPR in the car, or WFMU, a beloved freeform station from the NYC area, which we (constantly!) stream on the web (via Sonos or via their app when in the car).

      Also, this isn’t to say I knew nothing about popular music from this period — for example, yesterday I put on this random playlist of songs I had added to Apple Music after the 2020 election (kind of a mix of pump-up-type songs and feel-good favorites) and when Rihanna’s “Umbrella” came on, both of my stepkids were like, “Don’t skip it!” and then we all proceeded to loudly sing it together. lol!!


      1. Ahh! Love the Umbrella moment — so cute! Fun when there are intergenerational appreciations for specific songs. Everyone in my family loves Nirvana, Queen, and Taylor Swift, even my four year old son!


  2. Hi! I had to come to back this post bc I’ve been thinking a lot about goal setting/what motivates people and am curious what aspects of the notebook you linked in the Shopping Break caught your eye? Many thanks!

    1. Hi! I was attracted to all the invitations to designate goals and then to organize weekly/daily activities such that they ladder up to those goals. Recently, I’ve begun to circle items in my to-do lists that are priorities for each day, and then I write two or three big words across the top of each week’s journal page to remind myself of topline goals. Sometimes these are personal (e.g. “RUN 3X,” “MAKE TIME TO READ,” “ZHUSH THE HOUSE”) but sometimes they are writing/blog related. It’s been so helpful for me to glance at the week/day and immediately see what I need to keep top of mind. There are always so many micro tasks to tackle but good to remember the high level, big things first.


  3. Although I’m not really a John Mayer fan, I think the root of this post is an idea I’ve been struggling with lately: do we separate the art from the artist? Can we, and should we?

    For example, I’ve always loved the Harry Potter series, but am very disillusioned with J.K. Rowling nowadays. Perhaps I see the books in a slightly different light now, but so many of the emotional themes still hit the same.

    Or with Taylor Swift dating that controversial musician, or Lizzo’s newest lawsuits…all so disappointing. Yet I still love much of their music! So how to reconcile this? Can you love the art but not the artist? Once art is out in the world, does it become a collective thing, which means it doesn’t belong to the artist anymore? And so it doesn’t really matter who made it?

    1. Completely agree, Amy – just responded to Joyce’s comment below with adjacent thoughts. I’d grappled with this exact issue in earlier drafts of this post but ultimately didn’t feel I’d landed anywhere helpful/interesting/new, and so removed it. I’ve been muddling through these thoughts as I’ve read the interesting comments on this post.

      Thanks for continuing the conversation!


    2. I was going to comment almost exactly what you wrote here. It’s such an interesting topic…the art vs the artist. I also especially struggle with JK Rowling. I love the series she writes now under the pseudonym Robert Galbraith, but have mixed feelings about enjoying her writing. One thing that helped me a lot though, is the excellent podcast The Witch Trials of JK Rowling—so well done, a deep and honest conversation with her and members of the trans community. Highly recommend! I don’t agree with her views but at least I feel I *understand* where she is coming from.

  4. Before my husband and I started dating in 2010, we bonded over “Battle Studies” (!) so Mayer definitely has a place in my heart. Battle Studies and Continuum are my favorites. Stop this Train is a masterpiece. And I saw him live once and was impressed by his guitar playing 🙂

    Zooming out, I feel that I am someone who engages more with the art than the artist. I have never been that obsessed with celebrity personas. I watch less reality TV than almost anyone I know. I am even hesitant to call myself a Swiftie, though I saw Taylor open for Faith & Tim and have been enjoying her albums for forever, I just don’t find myself that interested in her personal life. I consider myself a fan of her work, but not a Swiftie. I wonder if this has to do with getting social media “later” than Gen Z? Or it’s just a personality thing? An interesting topic to ponder 🙂

    1. This is SO interesting, and your note — plus Amy’s — are making me regret some of the edits I made to this musing. Originally, I had a paragraph about what it means to listen to artists (or not listen to artists!) who have troubling personal lives. Philosophically, I believe that once an artist releases something into the world, it ceases to belong to them — it belongs to the reader/viewer/listener, who brings his/her own experiences and contexts to the art, and reconstitutes it. But. It’s difficult to ignore the commercial implications. What does that mean? Another Magpie was writing with similar concerns/thoughts, and she brought up Michael Jackson, Kanye West, etc. So much to think about.


  5. I loved JM until I read Jessica Simpson’s autobiography. OOF. His relationship with her was very mentally abusive, and I can no longer enjoy his music without being reminded of the way he used/mistreated her. He seems to have a track record of this sort of behavior with women, clearly because he is so evidently self-absorbed. Is a masterful lyricist and musician? 100%. But I can no longer in good consciousness support him by streaming his music. RIP.

    1. I totally understand this perspective! That was such a difficult part of the book to read. She seemed in such torment!


  6. I literally listen to John Mayer every single day. Sometimes just in the background, and sometimes I stop and listen to his lyrics almost as a sort of meditation. He is a genius and a poet with elite guitar skills and a gorgeous, soothing voice.

    Surprisingly, I’ve learned some about him recently via Andy Cohen and his most recent book (I guess they are good friends?) and despite Mayer’s questionable ways with women, I believe he can also be a good and loyal friend. I am also rooting for him to find real love because of the longing and pain infused in his lyrics. I’ve actually avoided Jessica Simpson’s book solely because I don’t really want him to be further tarnished for me (willful ignorance, I acknowledge).

    I am happy to know you love him – I don’t really know many others personally who feel how I do about him! Though I know there must be many. I am going to his upcoming show in Baltimore, and the childcare hoops being jumped through to facilitate that are definitely a testament to how much I love his music!

  7. I was a JM superfan in high school- went to several of his concerts in the early aughts- but then promptly abandoned my fandom. So now whenever I hear him I am immediately returned to my 16 year old headspace!

    1. Interesting! Do you feel you outgrew his lyrics or his style? Or maybe just wanted to leave the HS part of you behind?


      1. Both, I think! But I still retain my love for a lot of other artists I listened to in high school, like the Red Hot Chili Peppers and Jack Johnson (which I call my secret shame lol)

        1. HAHA “secret shame.” It’s OK – my secret shame is that I often listen to Celine Dion’s “Falling Into You” album and absolutely LOVE every song. Can’t help it. Sometimes Landon will pop his head in and say “I’m worried about you” as I’m bopping to “All By Myself.” Haha

          Also a fan of RHCP! Still run to them sometimes!


  8. I haven’t posted for a long long time but you got me here. I think he’s the most self-reflective artist of our time. My husband is a die-hard, long-time fan (saw him at an Atlanta Barnes and Noble in the 90s) and then has seen every tour since. In fact one show in Atlanta in front of thousands, we were in the front middle and JM paused to say “Is that you Francois?” It was. I’m a psychoanalyst and I think the progression of his lyrics and vulnerability over time is unparalleled. His narcissism too, but he owns it and I believe has worked on it. Narcissism comes from a place of deep pain and loss. Give “In the Blood” a listen and I think you’ll hear it. Developmentally he has not stalled with stardom as many do. And for the haters, his musical chops are legit, Berklee school of music, Dead and Co, Blues, Pop. Just because he CAN make excellent pop doesn’t mean that’s all there is to him.

    1. I agree with you on the remarkable level of introspection and vulnerability in his lyrics. He really communicates the nuance of emotion, relationships, heartstrings, etc. It’s an interesting to think about that in conjunction with his “lothario” status — it’s like he’s dismantling elements of the stiff-upper-lip, suppress-all-feelings masculine stereotype but then carrying out others.


  9. Add me to the list – I absolutely love John Mayer’s music, especially his first three albums and the live album “Any Given Thursday” (of which I had the DVD!!! in 2003). He had a hilarious limited TV series on VH1 in the early 2000s called “John Mayer Has a TV Show” – my husband and I still quote it to this day. He definitely seems arrogant (and I wouldn’t want my daughter to date him!), but I imagine most people experiencing that level of fame at a young age would be similar.

    1. Had no idea about the show! See, this is what mystifies me — for someone who has listened, compulsively and almost religiously, to his music for decades, I know so little of him and his other pursuits.


  10. One other thing! Highly recommend his recent appearance on Rick Rubin’s podcast, “Tetragrammaton,” which showcases the depth of John’s creative process (and is a bit more nuanced than the “Call Her Daddy” episode — which I also enjoyed!).

      1. On the heels of this post, I did a mini deep dive and ended up listening to John’s appearance on Cory Wong’s podcast, “Wong Notes.” I would recommend that one, too! They spend part of the conversation focusing on the technical aspects of John’s music (and various other popular songs, too), which I found deeply interesting. More fodder for you! Thank you for sparking this little rabbit hole, which I have really enjoyed :).

        1. Thank you so much! I have a whole binge list of Mayer performances and interview now in my queue. Curious how/if these will change my perspectives of him. I already feel like I have more context for him, his music, and his personality thanks to this rich thread of comments! I’ve enjoyed this rabbit hole, too.


  11. Such a John Mayer fan. He is, year after year, my most-played artist. I find very few “skips” on any of his albums. My favorites are Continuum, Born & Raised, and Sob Rock (know that this one had a mixed reception, but people hated B&R at first, too! It’s just such easy listening). People love to dunk on him for the cheesiness of Your Body is a Wonderland, Daughters, etc., but when Eric Clapton calls someone “extremely gifted … a master,” you know they’ve got serious chops!! (Eric went on to say, “I don’t think he even knows how good he is.” !) I highly recommend watching some of his live performances with guitar legends … including Clapton, BB King, and Leon Russell. You can tell that all of them are wowed by John’s talent (and Leon is visibly overcome with emotion). Other fun watches: any of his performances with Keith Urban, his performance with the Rolling Stones from 2012, and his guitar solo at Michael Jackson’s memorial service — where his earpiece went out — so he basically played without knowing how he sounded . I wonder if your SIL would change her mind seeing some of these clips!

    On the personal front: I don’t think any of us ever will ever know what really happened between him and Taylor Swift. I am such a fan of her and her music, too (and loved going to the Eras Tour this summer)! I find some of the general discourse about their relationship to be a bit over the top, bordering on parasocial (with people feeling like they need to defend her online, etc.). I thought it was notable that she said, before the re-release of Speak Now this summer, “I’m 33 years old, I don’t care about anything that happened to me when I was 19… I’m not putting this album out so you can go on the internet and defend me against someone you think I wrote a song about 14 million years ago.”

    I will say that John’s Playboy interview was totally reprehensible. I’d like to think that we give people the room to meaningfully apologize, grow, and change over the span of decades? In John’s case, he basically disappeared for a couple years, and reemerged a markedly more self-aware (and less egomaniacal?) version of himself. But it’s a hard one for me.

    Continue to be a great fan of his music and would highly recommend his Solo Tour (which just started up again in NYC), which really showcases his talent in a stripped down setting (just him and his guitar).

    1. Woohoo! Lots of Mayer fans coming out of the woodwork. It’s so funny, Virginia, because I occasionally mention to Mr. Magpie a piece I’m working on / a theme I’m exploring, and the other day I was chatting with him about the beginning of this musing on John Mayer, and we both agreed it could be controversial. So I’m sort of surprised by the reception!

      Thanks for all the recs for performances! I am going to do a deep dive this weekend.

      I totally agree on the Playboy interview – it turned me off and I still find myself thinking about him through the lens of that article. He later tried to explain and apologize for some of it, even tearfully offering a mea culpa in front of a live audience, but…

      I saw he’s coming to Baltimore and am desperately trying to shuffle around some commitments we’d made to see if I can make it!


  12. John Mayer is the absolute best. He is undeniably talented as a vocalist, songwriter and guitarist (I don’t feel many performers are this way…).
    I don’t typically enjoy listening to live performances when I’m not at the show, but I do love his at the Nokia Theatre. His version of Petty’s “Free Fallin’” is a favorite and “In Your Atmosphere” is special. Chills.
    He had a weird online show for awhile called “Current Mood,” where I feel like you sort of got to know the kind of quirky person he is. I think he seems charming with a dash of a@$hole.

    1. Hi Shauna! I love his version of “Free Fallin!” Actually I like a lot of the acoustic recordings of his music, too — like I am most familiar with one of his early acoustic recordings of “Neon.”

      Your description of his personality captures my perspective too — quirky, creative, charming, full of himself, etc. You might like the podcast I linked for another intimate glimpse into him. Another reader recommended his podcast on “On Being.” Going to listen next.


  13. I LOVE John Mayer. Which is ironic because I am an avid Swiftie. I also find the scrutiny of their relationships ironic because they had one together but they are also mocked relentlessly for being a (wo)man-izer. Both their lyrics are amazing and like you, they have accompanied me over many decades of life, in all different stages of life too. Such a fun thing to look back on – I listen to Room for Squares allllllll the time. My husband is so sick of it – HA!

    1. I also love Taylor Swift’s music, and listen to it *a lot* at home, and agree that it’s interesting that their public personas are often criticized for similar/adjacent things, and yet I have different attitudes toward them and those reputations. I have to think about that for a minute. Why is it?


      1. I have Mayer sweatpants and Taylor merch from Eras and often wear them together on weekends–a secret wish for their union? . I agree–they are so similar and I think now that they’ve had time to grow that they could be perfect for each other. At the very least I am CERTAIN they secretly listen to each others music regularly.

        1. Oh for SURE they listen. What do you make of the theory that “Paper Doll” is about TS? In an interview, he said clearly it is NOT about TS, but then he backtracks and says “Well, I made a promise not to reveal who I’m singing about” (paraphrasing). He did come down hard on TS for writing about him in her songs, saying it was “abusing her talent”? I’m not sure what to make of it all!


  14. John Mayer’s Heavier Things may be my most played album of all time. It was constantly on rotation on my family’s boat in the summer and in the depths of Chicago winter I’ll put it on and imagine myself baking in the hot August sun.

    For me, his best song is always Stop This Train, which I cannot get through without crying and typically will skip on a regular day. “Don’t know how else to say it, don’t wanna see my parents go” is like a knife stabbing you in the heart. Oof.

    He is undoubtedly very talented, but as a person he skeeves me out, particularly in his comments about women. You mentioned Dear John, but for me, the real nail in his coffin as a good man is Taylor’s more recent Would’ve Could’ve Should’ve. “If I was some paint did it splatter on a promising grown man. And if I was a child did it matter if you got to wash your hands” and “God rest my soul, I miss who I used to be. The tomb won’t close. Stained glass windows in my mind. I regret you all the time. I can’t let this go, I fight with you in my sleep. The wound won’t close. I keep on waiting for the sign, I regret you all the time.” And worst of all “Living for the thrill of hitting you where it hurts. Give me back my girlhood, it was mine first.” That buried him personally in an unrecoverable way for me.

    1. Totally agree – love the album, love that song. It will forever remind me of that tempestuous trek to Chicago. Just perfectly marked the transition to my adult life, flying the coop, etc.

      “Would’ve Could’ve Should’ve” was damning and disturbing, too. It’s like an ache!


  15. 100% agree with all of this!! I LOVE John Mayer’s music, and have had similar experiences of relistening to songs at 39 that I loved at 19. I find I still identify with a lot of the music (as we all might, being around a similar age perhaps?) but also appreciate it differently 20 years later. Thanks for this unexpected and relatable post!

    1. So glad I’ve found some fellow Mayerites (?) — I had always thought this might be a shared/common referent point among us because of the themes of his music, the playfulness of his lyrics, his artistry. xx

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