How Taylor Swift Turns Heartbreak Into Huge Hits

June 2, 2016, 4:54 PM UTC
LAS VEGAS, NV - MAY 17: Musician Taylor Swift and musician Calvin Harris attend the 2015 Billboard Music Awards at MGM Grand Garden Arena on May 17, 2015 in Las Vegas, Nevada. (Photo by Kevin Winter/BMA2015/Getty Images for dcp)
Kevin Winter — Getty Images

Now that we’ve all had time to recover from the initial shock of the Taylor Swift-Calvin Harris breakup news, it’s time for a reality check: The pop mega-star (and her brand) will be completely fine, if not stronger.

For the past 15 months, Swift had a seemingly perfect relationship with the international DJ. But something bigger happened during that time—Swift transformed from a talented entertainer into a veritable business powerhouse. She took on Apple and forced the tech giant to change the way Apple Music compensates musicians. She was on three Fortune lists for her business savvy, including World’s Greatest Leaders, Most Powerful Women, and 40 Under 40. Most recently, she became the first female artist to win two Grammys for Album of the Year with her album 1989, the fastest-selling album of the past decade.

When reports of the breakup surfaced Wednesday, there was immediate speculation about how her time with Harris might inspire her next song. If history is any indication, then we could expect a powerful new hit in the near future.

Here’s a look at some of Swift’s biggest hits and the ex-boyfriends that are widely believed to have inspired them.


“We Are Never Ever Getting Back Together”

Singer Taylor Swift and actor Jake Gyllenhaal briefly dated back in 2010. Photographs by John Shearer & Vera Anderson/WireImage via Getty Images

Ex-boyfriend: Jake Gyllenhaal, Actor
Billboard ranking: #1
Music video views: 391 million


Celebrity Sightings - Bauer-Griffin - 2012 Taylor Swift and Harry Styles are seen walking around Central Park on December 02, 2012 in New York City.Photography by David Krieger/Bauer-Griffin GC Images

Ex-boyfriend: Harry Styles, Singer/Songwriter
Billboard ranking: #6
Music video views: 420 million

“Back to December”

Columbus Blue Jackets v Los Angeles Kings Taylor Lautner and Taylor Swift attend an NHL game. Photograph by Andrew D. Bernstein/NHLI via Getty Images

Ex-boyfriend: Taylor Lautner, Actor
Billboard ranking: #6
Music video views: 132 million

“Begin Again”

Conor Kennedy and Taylor Swift had a short summer romance in 2012 that lasted 3 months. Photographs by Steven Lovekin/WireImage & Dave J Hogan/Getty Images

Ex-boyfriend: Conor Kennedy, JFK’s Nephew
Billboard ranking: #7
Music video views: 103 million

“Forever & Always”

2008 MTV Video Music Awards - Backstage and Audience Singers Taylor Swift and Joe Jonas at the 2008 MTV Video Music AwardsPhoto by Jeff Kravitz/FilmMagic

Ex-boyfriend: Joe Jonas, Singer/Songwriter
Billboard ranking: #34
Music video views: No official video released

“Dear John”

Z100's Jingle Ball 2009 Presented by H&M - Show John Mayer and Taylor Swift perform onstage during Z100’s Jingle Ball 2009.Photograph by Theo Wargo/WireImage

Ex-boyfriend: John Mayer, Singer/Songwriter
Billboard ranking: #54
Music video views: No official video released