Songs That Will Break Your Heart Every Time

What Makes These Songs That Break Your Heart So Powerful?

Some songs that break your heart do it slowly, with a gentle tune that only reveals its sadness after you have been humming along for years.

This countdown follows our episode from #10 to #1. Some of these stories involve real loss, including suicide, and are told here with respect. Chart positions and awards were checked against Billboard records and other reliable sources, and details from the episode that did not hold up were corrected or left out.

The Countdown: 10 Songs That Break Your Heart

#10: Vincent — Don McLean (1972)

In 1970, Don McLean read a biography of Vincent van Gogh. He has said he sat down with a print of The Starry Night and wrote the lyrics on a paper bag.

The gentle melody sounds like a lullaby, yet it is about an artist who suffered greatly and died at 37. In 1972 the song spent two weeks at No. 1 in Britain and reached No. 12 on the Billboard Hot 100. In 2020, McLean's handwritten lyrics were offered for sale at $1.5 million.

#9: Without You — Harry Nilsson (1971)

Badfinger's Pete Ham had a verse without a strong chorus, and his bandmate Tom Evans had a chorus without a verse. They joined the two, and Badfinger recorded the song at Abbey Road in 1970 with Geoff Emerick producing. Paul McCartney later called it "the killer song of all time."

Harry Nilsson's version spent four weeks at No. 1 on the Hot 100 in early 1972 and five weeks at the top in Britain. Mariah Carey took it to No. 3 in America in 1994, and ASCAP counts more than 180 recorded versions.

The writers' own story is one of the saddest in pop. The band was caught in long legal and money troubles, and Ham died by suicide in 1975 at 27, leaving a note that blamed their manager. His daughter was born a month later. Evans died by suicide in 1983, the day after an argument over royalties for this very song.

#8: Alone Again (Naturally) — Gilbert O'Sullivan (1972)

The words describe a man left at the altar who then remembers losing both of his parents, all set to a light, easygoing piano.

O'Sullivan has said it is not autobiographical. His mother was alive when he wrote it, and he was not close to his father, who died when the singer was 11.

The single spent six non-consecutive weeks at No. 1 on the Hot 100 in 1972 and ranked No. 2 for the year. In 1991 it became the center of a landmark court case, when a judge ruled that Biz Markie's unauthorized sample of it was copyright infringement.

#7: I Can't Make You Love Me — Bonnie Raitt (1991)

Nashville songwriters Mike Reid and Allen Shamblin found the idea in a newspaper story about a man and a broken relationship, though accounts differ on the exact story. The writers first wrote it as a fast bluegrass number and reworked it for more than six months.

Slowed down, with Bruce Hornsby on piano, it became something else. Raitt recorded her vocal in one take, and she said the song was so sad that she could not recapture the feeling when they tried again.

It peaked at only No. 18 on the Hot 100, but Mojo later ranked it among the ten greatest songs of all time, and it was voted into the Grammy Hall of Fame.

#6: He Stopped Loving Her Today — George Jones (1980)

Bobby Braddock and Curly Putman wrote this song about a man whose love ends only with his death. Producer Billy Sherrill played it for George Jones in 1978, and Jones found it "too long, too sad, too depressing."

Jones was in poor shape in those years. Sherrill said he kept singing it to the melody of "Help Me Make It Through the Night," and that the spoken recitation was recorded 18 months after the first verse.

Released in April 1980, it went to No. 1 on the country chart, Jones's first solo No. 1 in six years. It won him a Grammy, and it was named the CMA Song of the Year in both 1980 and 1981. George Jones died in 2013 at 81.

#5: Ordinary World — Duran Duran (1992)

Simon Le Bon wrote "Ordinary World" in response to the death of his close friend David Miles, who died of a drug overdose in 1986.

The band worked mostly at guitarist Warren Cuccurullo's home studio in London. When a Tampa radio station played the song before its official debut, it received a cease-and-desist order. Released in the U.S. in December 1992, the single reached No. 3 on the Hot 100 and marked a turning point for the band.

#4: Nothing Compares 2 U — Sinéad O'Connor (1990)

Prince wrote the song and recorded a demo in 1984, then gave it to his side band, the Family, in 1985. His engineer Susan Rogers has said it may have been about his housekeeper, Sandy Scipioni, who left suddenly after her father died.

Sinéad O'Connor's 1990 version topped the charts in the United States, Britain and many other countries. In John Maybury's video, a single tear rolls down her face. She said the tears were real and unplanned, and that she was thinking of her mother, who died in a car accident in 1985.

Prince died in 2016. O'Connor died in July 2023 at 56, and a coroner later found the cause to be natural.

#3: I Will Always Love You — Dolly Parton (1974)

Dolly Parton wrote this song in 1973 as a farewell to Porter Wagoner, her mentor and partner of seven years. It was not a romantic goodbye but a thank-you as she left to go solo.

By her account, she sang it to him, he cried, and he agreed to let her go if he could produce the record. She has said she wrote "Jolene" on the same day, though she later allowed they may have been a few days apart.

The single reached No. 1 on the country chart in 1974, and her new recording for The Best Little Whorehouse in Texas hit No. 1 again in 1982. When Elvis Presley wanted to cut it, Colonel Tom Parker asked for half the publishing rights, and Parton refused. Whitney Houston's 1992 version later spent 14 weeks at No. 1.

#2: The Dance — Garth Brooks (1990)

Tony Arata began the song in the early 1980s and finished it after seeing the 1986 film Peggy Sue Got Married. He told The Tennessean it taught him that you do not get to pick and choose your memories.

A then-unsigned Garth Brooks heard Arata sing it at Nashville's Bluebird Cafe and asked to record it if he ever got a deal. He did. Released in 1990, it spent three weeks at No. 1 on the country chart and won the Academy of Country Music's Song of the Year and Video of the Year.

The video includes footage of John F. Kennedy, Martin Luther King Jr., the Challenger crew, rodeo star Lane Frost and singer Keith Whitley. Brooks once said, "It'll probably always be my favorite song."

#1: Tell Laura I Love Her — Ray Peterson (1960)

Written by Jeff Barry and Ben Raleigh, this story song follows Tommy, who enters a stock car race hoping to win money for a wedding ring, and never comes home. Ray Peterson's version on RCA Victor reached No. 7 on the Hot 100.

In Britain, Decca refused to release it, calling it "too tasteless and vulgar," and destroyed about 25,000 copies that had already been pressed. A cover by Ricky Valance then spent three weeks at No. 1 in the UK. It remains a classic "teenage tragedy song."

Why Sad Songs Stay With Us

Some of these songs hide their sorrow in a cheerful tune. Others grew from losses their writers carried for years. What they share is honesty.

If any of these stories touch something painful in your own life, you are not alone. In the United States, you can call or text 988 to reach the 988 Suicide and Crisis Lifeline at any hour.

Which of these songs that break your heart still catches you off guard, and what memory does it bring back?

Sources and Further Reading

• "Without You" (Badfinger song) — Wikipedia
• "I Can't Make You Love Me" — Wikipedia
• "He Stopped Loving Her Today" — Wikipedia
• "I Will Always Love You" — Wikipedia
• "Tell Laura I Love Her" — Wikipedia