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Rob SheffieldA modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.
Robert Sheffield (b. 1966) is an American music journalist, known best as a frequent contributor to Rolling Stone. Originally from Massachusetts, Sheffield attended Yale University as an undergraduate and then pursued graduate studies at the University of Virginia before eventually settling in Brooklyn, New York. He has published books on a wide variety of artists and genres, including Duran Duran, David Bowie, and the Beatles. His first book, Love is a Mixtape: Life and Loss, One Song at a Time (2007), follows his relationship with his first wife, Renée Crist, who died suddenly, only five years into their marriage, when Sheffield was 31.
Sheffield has been an avid listener to Taylor Swift since 2007, when he happened to hear “Our Song,” the third single from Swift’s self-titled debut album, playing during an advertising break on the CW. He writes that the song’s lyrics were immediately captivating to him, and that he was surprised to learn that they were written and performed by such a young newcomer to the industry. Heartbreak follows the development of his close personal relationship with her music since that moment. Sheffield’s authorial voice throughout the text, therefore, is multifaceted; he speaks both with the authority of a well-established music journalist, and with the personal enthusiasm of a fan.
Taylor Alison Swift (b. 1989), is an American singer-songwriter, widely regarded as one of the most influential musicians of the twenty-first century. Born in Pennsylvania, the daughter of a stockbroker and mutual fund marketing executive, she spent her early childhood on a Christmas tree farm that her father had purchased from a client. Although neither of her parents were professional musicians, Swift was heavily impacted by her maternal grandmother, Marjorie Finlay, who was a successful opera singer and television personality.
Swift fell in love with country music at a young age and was encouraged to pursue her career as a country singer after writing letters to one of her idols, LeAnn Rimes, and learning that Rimes had in fact read them. Her family moved to the Nashville area when Swift was fourteen in order to gain access to better career opportunities for her. Andrea Swift, Taylor’s mother, insisted that her daughter earn her own opportunities, and would drive her around to different record label offices, waiting outside while Taylor went in to hand-deliver her demos to the receptionists. Eventually, Swift began to gain traction as a high-schooler, and released her first album at the age of sixteen. Her first lead single, “Tim McGraw” became a big hit on the charts, and the Recording Academy of America certified it double platinum. Since then, she has had twelve number one songs on the Billboard Hot 100 and has won numerous awards, including fourteen Grammy Awards. Sheffield tracks the explosive trajectory of her career in meticulous detail throughout Heartbreak.
As of 2024, Swift has released eleven original albums: Taylor Swift (2006), Fearless (2008), Speak Now (2010), Red (2012), 1989 (2014), Reputation (2017), Lover (2019), Folklore (2020), Evermore (2020), Midnights (2022), and The Tortured Poets Department (2024). She has also rerecorded Fearless, Red, Speak Now, and 1989, with plans to rerecord Taylor Swift and Reputation. Her “Taylor’s Version” rerecords project is a response to the 2019 acquisition of the masters for her first six albums by Scooter Braun from Big Machine Records, a transaction which Swift asserts she was not informed of ahead of time, despite having spent years attempting to acquire the masters.
In 2005, Taylor Swift became the first signed artist with Big Machine Records, a record label newly founded by Scott Borchetta. A former racecar driver and executive at the Nashville division of DreamWorks Records, Borchetta discovered Swift when she performed in a showcase at Nashville’s hallowed Bluebird Café. Sheffield recounts how vocally thankful Swift was towards Borchetta in the early days of her career. In her Fearless Notes, Swift wrote “Scott Borchetta, thank you for believing in me since I was 14, and still trying to straighten my hair. You’re family” (30). This brief note provides insight into the closeness of Swift and Borchetta’s relationship in its earliest stages, when Swift was very young and needed supportive guidance to navigate the industry.
Swift’s contract with Big Machine ended in 2017 after the release of her sixth album, Reputation. This marked the fulfillment of her 2006 contract with the label, which promised ownership of Swift’s first six albums to Big Machine, without the opportunity for Swift to purchase her masters until all six releases had occurred. Unbeknownst to Swift, Big Machine executives had been in talks to sell the masters to a third party, and Big Machine was ultimately purchased by Scooter Braun’s investment firm, Ithaca Holdings, along with the masters themselves. This deal upset Swift and inspired her to rerecord the six albums in order to regain control of her own music. Amid the controversy, Borchetta claimed that “Taylor had every chance in the world to own not just her master recordings, but every video, photograph, everything associated to her career. She chose to leave” (Scott Borchetta, “So, It’s Time for Some Truth,” Big Machine Label Group, 2019). Swift vehemently denied this claim, and was open about how the sale soured her relationship with Borchetta, writing, “Any time Scott Borchetta has heard the words ‘Scooter Braun’ escape my lips, it was when I was either crying or trying not to. He knew what he was doing; they both did. Controlling a woman who didn’t want to be associated with them. In perpetuity” (Taylor Swift via Tumblr, June 30th, 2019). In a book that addresses the issues of autonomy that Swift and other women in the music industry face, Borchetta’s authority over the trajectory of Swift’s career and control over her profits epitomizes the misogynistic power dynamic that favors male record executives over their female signatories.
Samuel “Scooter” Braun (b. 1981) is an American record executive and talent manager, most famous for his management of big-name artists like Kanye West and Ariana Grande. He is also credited with discovering Justin Bieber in 2008. Braun grew up in Connecticut in a Conservative Jewish household. His management career began while he was attending Emory University, when he began organizing high-profile parties, including afterparties for tours featuring Ludacris, Eminem, and Britney Spears.
In 2019, Braun’s investment firm purchased Big Machine Records, a deal which included the rights to the masters of Taylor Swift’s first six albums. Swift was incensed that she had not been offered the chance to purchase her own masters before the deal occurred. But she was particularly dismayed that the masters were being sold to Braun in light of his association with Kanye West. Braun managed West at the time of the notorious 2016 release of his song, “Famous,” which contains the controversial lines,
I feel like me and Taylor might still have sex
Why? I made that bitch famous
(Goddamn!)
I made that bitch famous.
Adding insult to injury, the song’s music video featured a group of lifelike wax figures depicting celebrities naked in bed together, including one of Swift. Following Braun’s acquisition of Big Machine Records, Swift denounced his involvement with the song and video, writing in a post on Tumblr, “His client, Kanye West, organized a revenge porn music video which strips my body naked. Now Scooter has stripped me of my life’s work, that I wasn’t given an opportunity to buy. Essentially, my musical legacy is about to lie in the hands of someone who tried to dismantle it” (Taylor Swift via Tumblr). Braun thus emerges as one of the primary antagonists in Swift’s career-long mission to achieve total autonomy, though as Sheffield notes, the massive success of her “Taylor’s Version” project has firmly outshined the initial controversy that inspired it.
In Heartbreak, Sheffield identifies many of the figures who have influenced Swift, but the most frequently discussed of these figures is Stevie Nicks (b. 1948), another of the most impactful singer-songwriters of the modern age. Born Stephanie Lynn Nicks, she spent most of her childhood travelling around the American Southwest as her father’s job as an executive with the Greyhound bus company required. Like Swift, she began writing songs as a teenager, and she met her future partner and bandmate, Lindsay Buckingham, as a senior in high school. Buckingham and Nicks would go on to join Fleetwood Mac in 1974 and would prove instrumental to the band’s astronomic success.
Nicks wrote and sang some of Fleetwood Mac’s biggest hits, including “Rhiannon,” “Dreams,” “Landslide,” and “Gold Dust Woman.” She became an icon of second-wave feminist pop culture, carving out an unapologetically feminine niche for herself in the hypermasculine field of 1960s and 70s rock music. Her distinctive aesthetic, which included all-back, flowy outfits, and a love of all-things fairytale and folk culture, earned her a “witchy” reputation, and even inspired widespread rumors that she truly was a witch. When she began receiving threatening mail based on this rumor, Nicks was forced to change her entire mode of dress out of fear. Though Sheffield does not explicitly make this connection in Heartbreak, it is worth noting that Swift’s 2017 song “I Did Something Bad” subtly nods to this period of Nicks’ career with the line “They’re burning all the witches, even if you aren’t one,” tying her own period of controversy to Nicks’s.
Swift’s relationship with Nicks stretches back as far as 2010, when the two performed “Rhiannon” at the Grammys together, a performance that Sheffield deems Swift’s “first big public flop” (9). While the two stayed distant from one another in the public eye for some time afterwards, they have been more openly close in recent years. Sheffield peppers details about this relationship throughout Heartbreak. At a 2022 performance in Atlanta, Nicks publicly thanked Swift for writing the song “You’re On Your Own Kid,” explaining that it helped her through grief following the death of her bandmate and close friend Christine McVie. For her part, Swift has commented on the kinship she feels with Nicks most openly on her 2024 song, “Clara Bow,” where she imagines industry executives telling her,
You look like Stevie Nicks
In ‘75, the hair and lips
Crowd goes wild at her fingertips
Half moonshine, a full eclipse.
Swift’s songwriting has made it clear that she sees her own career as echoing Nicks’, and Sheffield therefore treats Nicks as one of the closest Swift analogues throughout Heartbreak.