500 Greatest Albums: Taylor Swift Looks Back on Her ‘Only True Breakup Album’ ‘Red’

As part of our newly updated survey of the 500 Greatest Albums of All Time, we’re publishing a series of pieces on the making and impact of key records from the list. Taylor Swift’s Red came in at number 99. Hear Swift reflect on the album in the second episode of our 500 Greatest Albums podcast.

The creation of Taylor Swift’s transformational album Red began at a rehearsal for the singer-songwriter’s tour supporting her 2010 album Speak Now. Hurting after a recent breakup, Swift began ad-libbing heartsick lyrics over a four-chord riff as her touring band spontaneously joined in behind her. “I think they could tell I was really going through it,” Swift says. The rehearsal jam would end up serving as a rough 10-minute sketch for “All Too Well,” Red’s emotional centerpiece.

After writing all of Speak Now alone as a way to show her critics that she didn’t need to use co-writers, Swift was ready for a new creative challenge when it came time to craft her fourth album. “I’ve always been aware of what my detractors say, because I use it as a springboard for what to do next,” she says. “With Red, I had a different thing I wanted to prove: a thirst for learning.” 

A half-dozen years into her career, Swift was already fearful of being seen as a has-been, and was worried about remaining creatively static. She wanted to reach outside of Nashville for the first time, working with her favorite pop songwriters, from Max Martin and Jeff Bhasker to Dan Wilson and Butch Walker. “It actually was an interesting wrestling match with my own fears of remaining stagnant that made Red the kind of joy ride that it ended up being,” she says. 

Swift’s fourth album also marked a country-pop crossroads for the singer, the fleeting stage of her career when she was introducing herself fully to the world of Top 40 while still successfully servicing her more rootsy singles to country radio. “I was standing on a state line,” the singer says, “and I had a foot on either side of the border line.”

She began writing the record in her comfort zone, working with Nathan Chapman and Liz Rose for her left-field Nashville originals like “Red,” “State of Grace,” and “All Too Well” before she headed to L.A.

When she began writing with producers like Martin, Swift was eager to welcome in outside inspiration. “I wanted to go in as a student,” she says. Swift wanted to add a dubstep drop to the ballad she had written called “Trouble,” but it wasn’t until the producer Shellback suggested adding a frantic drum beat to the song’s verse that it morphed into “I Knew You Were Trouble.” On “We Are Never Ever Getting Back Together,” Martin and Shellback proposed drawing out the first word of the chorus (“we-eeeeeee”’), “like little kids on a playground.” 

Swift was overflowing with material during the writing of Red, coming up with ideas for tracks like “Treacherous” on the way to the studio. When it came time to actually record, she had written 30 songs. 

Swift trimmed those 30 down to 16, and the end result was her most sprawling, uninhibited work, an album whose messy sonic contradictions anchored the emotionally chaotic story Swift was trying to tell. “It was sort of a metaphor for how messy a real breakup is, and this is my only true breakup album,” says Swift. “I love Jackson Pollock, and I see this album as my splatter-paint album, using all the colors and throwing it at the wall and seeing what sticks.”

In hindsight, Red was a second career beginning of sorts for the pop star, the moment when she amassed the fresh songwriting tools and pop sensibilities that she’d spend the following decade deploying in full. “It was sort of like my college years of going out and trying stuff,” she says. “This was me being, ‘What do I want from a songwriting session?’ And picking up little bits as you go. … It was really sort of the beginning of everything that I’m doing now.”

Additional reporting by Brittany Spanos