Photo Credit: Beth Garrabrant

Taylor Swift wrote her third album entirely on her own. This was partly a result of Swift getting her “best ideas at 3 am in Arkansas,” as she would tell Songwriter Universe, but it also served as a rebuttal to critics and other commentators who had previously doubted teenage Swift’s creative contributions towards her own music. Like the preceding LP, Fearless, Speak Now is an album centered on coming-of-age, but of the two, it is Speak Now that speaks most precisely to the growing pains of this stage of life. The album’s greatest songwriting feat remains its ability to capture the duel pull of yearning for adulthood autonomy (“Someday, I’ll be big enough so you can’t hit me”) and the lost innocence of childhood (“Wish I’d never grown up”).

Though Speak Now would ultimately prove to be one of Swift’s least commercially successful albums, it remains a vital addition to the superstar’s discography; containing the most affecting songwriting of Swift’s career up until that point and hinting at the heights she would reach on Red with standout “All Too Well” two years later. “Back To December” expertly curates intimate memories to form a tapestry of longing and regret – “tan skin”, a “sweet smile”, “how you held me in your arms” – while “The Story of Us” captures the displacement that comes from suffering an intense breakup at such a tender age (“I used to know my place was the spot next to you // Now I’m searching the room for an empty seat”). 

Speak Now also happens to represent the last time that Swift appeared in the public consciousness as the lovesick, teenage underdog, and not the global pop superstar who would become vilified in the press for her every move. This plays into the coming-of-age narrative that shapes Speak Now – of an emerging adult daunted by the dueling forces of fame and heartbreak. “Mean” with its cries of “Someday, I’ll be big enough so you can’t hit me,” against a harsh critic, is one of a number of songs that emphasize Swift’s young age while writing this album. Listening to that line, it’s hard not to also relate it back to her relationship with John Mayer (who is the focus of the preceding song “Dear John”) who was 32 when he met a 19-year-old Swift. 

“Dear John” is Speak Now’s greatest songwriting feat – and still remains a highlight of Swift’s catalog thus far. Across seven minutes, Swift speaks of heartbreak so overwhelming it consumes one wholly – where one person can turn somewhere vibrant into a “sad, empty town.” The song – a continually building, cathartic epic tinged with classic alt-country, pedal steel guitar-amplified sorrow – served to solidify Swift’s status as a great, rather than merely good songwriter; one who went on to be widely considered among the greatest living musicians. 

The re-recording of “Dear John” remains a triumph after all these years, but some of Speak Now’s other iconic cuts don’t fare so well. No longer an adolescent underdog, Swift struggles to sell the revenge tales of “Better Than Revenge” and the title track, which now read as more petty than triumphant. Elsewhere, her voice – which is richer but more understated than in 2010 – struggles to sell the youthful urgency of a song like “Sparks Fly” (“Drop everything now, meet me in the pouring rain,” cries Swift, without the requisite enthusiasm) or the immediacy required to sell the album’s pop-punk cuts. The re-recording further suffers because the ‘From The Vault’ tracks are the weakest we have gotten thus far – lacking highlights like “Nothing New,” “Mr. Perfectly Fine,” “You All Over Me,” or the 10 minute version of “All Too Well.”

Speak Now (Taylor’s Version) fares best when Swift’s songwriting is at its most ambitious – dense, descriptive, vibrant, and evocative. “Dear John” is obviously a prime example of this, but so is “Enchanted.” The latter number, which previously enjoyed a spike in popularity thanks to TikTok, captures momentary bliss like lightning in a bottle – speaking to those moments where love illuminates everything around it and drowns out all sorrow (“This night is sparkling, don’t you let it go // I’m wonderstruck, blushing all the way home”). Pairing such sentiments with euphoric pop arrangements, “Enchanted” set the stage for some of Swift’s greatest pop hits to-be, including “Style” and “Cruel Summer.” The best moments on Speak Now – both the original and Taylor’s Version – are every bit as enchanting as whoever Swift is singing about on this mid-album highlight.

Written by: Tom Williams