In May, I described the momentum of the Eras Tour and the career milestone accolades gathering in its wake as something that would be folded into Taylor’s approach for award season campaigning. True to my forecast, that velocity is now translating into awards-show recognition and, perhaps more notably, into a sustained conversation about the substance of her career and the legacy it has already established.
Earlier this year, Taylor spoke to New York Times Magazine as one of the publication’s 30 Greatest Living Songwriters and appeared in a nearly 30 minute interview with culture reporter Joe Coscarelli. In June, she was entered into the Songwriters Hall of Fame (a first of two-part HOF inductions as she also enters Nashville’s Hall this coming autumn) and delivered a 20 minute acceptance speech. Last week, at the Clive Davis Theatre in Los Angeles, Taylor sat down with the Recording Academy’s Songwriters & Composers Wing for their Icon Sessions for a “20-Year Retrospective” on her career. That conversation tipped just past the 40 minute mark.
📝 ICYMI: My Liner Notes on the above milestones are each worth a deep dive!
These conversations on music, the industry, and songwriting are studded with the hard-won wisdom and charming anecdotes of a career that has, rather inconveniently for anyone still trying to define it, already become historic. The in-progress voice memos of workshopping songs she previously tucked into the deluxe versions of her albums feel positively quaint in retrospect. Now, they function as brief previews of the expansive fascination that Taylor continues to maintain about her own process two decades into a career that is likely still just in its first phase. The younger version of me who could recite those behind-the-scenes interludes by heart (“So over the years, a lot of people have asked me to describe my songwriting process from beginning to end …”) could only dream of having hours of transcribed discussion of Taylor talking about songwriting. Swoon!
These milestones have packed her resumé and the award season nominations have begun to stack up accordingly. So far: an Emmy-nominated Eras Tour film, nine MTV Video Music Award nominations, and a warm reception for Toy Story 5’s “I Knew It, I Knew You” among country audiences that seems to have primed the song for a potential Country Music Association Award nomination — alongside the genuine Oscar conversation being had around the track.
Appearances like this are the underpinning of a successful awards campaign. Offering exclusives, being in rooms, and giving access to the people who decide these awards are the building blocks of a strategic award operation. At this juncture in her career, it demonstrates Taylor’s work ethic and ambition that she is actively vying for these trophies. It’s inspiring to see her continue to dive in head-first.
When we first heard word of Taylor’s participation with the Grammy Museum, I was instantly giddy and hopeful we would get to see coverage. As a lover of the live acoustic format, her original session with the museum back in 2015 remains an all-time favorite of mine. It, and its accompanying talk, is a set that’s absolutely worth watching (or revisiting)! “Wildest Dreams” on electric guitar, in particular, will knock the socks off anyone who loves Taylor’s vocal register /raises hand.
Naturally, I had plenty of liner notes on Taylor’s Grammy Museum conversation this year. From the stories she shared about her career and craft to the reflections that offered a glimpse at where she is now. Scroll ahead for my top takeaways!
And in case you missed Taylor’s interview and performance, you can catch it in full on YouTube here.
What did you think of Taylor’s Icon Session? I’d love to hear your liner notes on it all so please click below to discuss it in the comments — I look forward to joining you there!
A few notes before diving in:
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Liner Notes on Taylor Swift’s Icon Sessions with the Recording Academy

A Vintage Dress That Gives Her Dignity
“I’m not a moodboard artist. I’m a mood artist.” - Taylor Swift






