Taylor Swift Saddest Songs (Ranked) by Davis Hughes on Apple Music (2024)

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Taylor Swift Saddest Songs (Ranked) by Davis Hughes on Apple Music? ›

“In my mind, the saddest song I've ever written is 'Last Kiss. ' My most scathing is 'Dear John' and my most wistfully romantic is 'Enchanted,'” she writes. “Dear John” has long been said to be about singer John Mayer, who was rumored to have dated Swift when she was 19 and he was 32.

“In my mind, the saddest song I've ever written is 'Last Kiss. ' My most scathing is 'Dear John' and my most wistfully romantic is 'Enchanted,'” she writes. “Dear John” has long been said to be about singer John Mayer, who was rumored to have dated Swift when she was 19 and he was 32.

The letters H, E, Y, B, E and R were randomly capitalized throughout the lyrics of “Glitch.” Unscramble those letters, and the first word from the message is revealed: Hereby. Take part in Swift's The Tortured Poets Department word search on Apple Music today through April 18 to get her full message.

"It's Nice to Have a Friend" is one of the most divisive songs in Taylor's discography — you either love it or skip it.

“I hereby conduct an investigation of the conduct of…” one fan spitballed on X. The words “hereby” and “conduct” also reminded fans of the handwritten note Swift shared on Instagram when she announced the upcoming release of “The Tortured Poets Department” in February.

Experts say it is normal and often helpful to connect with heartbreaking music, and Swift even shared her own philosophy in an Instagram post about the album.

The number 13 has had a special significance in Swift's career through the years. As she previously explained to MTV News, "I was born on the 13th. I turned 13 on Friday the 13th. My first album went gold in 13 weeks.

In an open letter to Apple , Swift said she was withholding the record as she was unhappy with the three-month free trial offered to subscribers. Now Apple says it will pay artists for music streamed during trial periods. "We hear you @taylorswift13 and indie artists. Love, Apple ," tweeted executive Eddy @Cue .

By midnight Sunday, Apple — one of the most powerful companies in the world — had capitulated to the 25-year-old pop star, saying it would pay royalties on all music for the three-month trials. One of its senior executives, Eddy Cue, even said he called Ms. Swift personally to give her the news.

What is Taylor Swift's least streamed song ever? ›

Taylor Swift's "All Too Well (10 Minute Version)" is the longest song in history to reach No. 1. The song, which clocks in at just over 10 minutes long, beat out longtime record holder Don McLean, whose eight-minute track "American Pie" held the top position for four weeks in 1972.

You'd think being part of Taylor Swift's “squad” of A-list pals is something you'd want to shout about, but the singer's long-term bestie Ash Avignone has tended to keep their friendship low key and out of the spotlight over the years.

To listen to explicit songs, turn restrictions off on any of your devices. If restrictions are turned off on all of your devices, but you still can't play explicit songs, you might need to turn restrictions for music on then off again. Learn more about using restrictions on your iOS device or in iTunes on a Mac or PC.

The red 'E' means that it contains explicit content - you can prevent/allow buying explicit songs via Settings > General > Restrictions > Music & Podcasts > Explicit 'on' (allow) and 'off' (prevent).

"Taylor Swift" is widely regarded as Swift's worst album, but that's only because all her albums are good. Something has to be the "worst" — that's how rankings work — and "Taylor Swift" is often overlooked, being the singer's first and most rudimentary work.