Top 10 Sad Pop Songs

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Mark Dinning - "Teen Angel" (1960)

Mark Dinning Teen Angel
Mark Dinning - "Teen Angel". Courtesy MGM

"Teen Angel" was one of a string of hit songs in the early 1960s that touched on the subject matter of death. This song seems especially morbid as it details returning to a car stalled on railway tracks only to die when hit by a train. Some radio stations refused to play it due to the subject matter. It was also banned by the BBC in the UK. However, it ultimately became a #1 hit for singer Mark Dinning who got his start in country music. Mark Dinning's sister Jean co-wrote "Teen Angel" with her husband Red Surrey. He had three other minor chart appearances but never returned to the pop top 40.

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Beatles - "Eleanor Rigby" (1966)

Beatles Yellow Submarine / Eleanor Rigby
Beatles - "Yellow Submarine" / "Eleanor Rigby". Courtesy Capitol

The Beatles' meditation on loneliness ends with a very stark funeral depiction. Instrumentally the recording uses an ensemble of eight strings to help contribute the feeling of sadness present throughout the song. It is seen as a key song in the Beatles' movement from more mainstream pop into studio experimentation. The grave of a real life Eleanor Rigby stands in the cemetery of the St. Peter's Parish Church in Liverpool, England. She died in 1939. Released as a double A-side single with "Yellow Submarine," "Eleanor Rigby" reached #11 on the pop singles chart in the US.

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Simon and Garfunkel - "I Am a Rock" (1966)

Simon and Garfunkel The Sounds of Silence
Simon and Garfunkel - The Sounds of Silence. Courtesy Columbia

It can be debated whether Paul Simon meant "I Am a Rock" to be taken seriously or it is a gentle mockery of those who disdain others in favor of a personal stoicism. Regardless of his intent, the words do paint a very bleak portrait of isolation and loneliness. "I Am a Rock" was first recorded by Paul Simon solo on his 1965 album The Paul Simon Songbook. Simon and Garfunkel re-recorded it in December 1965 and included it on their Sounds of Silence album. The single was released in May 1966 and became a #3 pop hit on the Billboard Hot 100. It was the third consecutive top 10 pop hit for the duo.

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Carpenters - "Superstar" (1971)

Carpenters Superstar
Carpenters - "Superstar". Courtesy A&M

It might seem unusual that a song about groupies would become one of the biggest hits by adult contemporary stars the Carpenters. However, the emotional nature of the song fits the melancholy voice of Karen Carpenter perfectly. "Superstar" was first written in 1969 by Bonnie Bramlett and Leon Russell. It was recorded by the folk-pop group Delaney and Bonnie and Friends under the name "Groupie (Superstar)." Multiple other artists recorded it until the Carpenters' August 1971 release became known as the definitive version of "Superstar." It hit #2 on the pop singles chart. It earned a Grammy Award nomination for Best Arrangement Accompanying Vocalist.

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Carly Simon - "That's the Way I've Always Heard It Should Be" (1971)

Carly Simon That's the Way I've Always Heard It Should Be
Carly Simon - "That's the Way I've Always Heard It Should Be". Courtesy Elektra

Carly Simon blasted into mainstream pop consciousness with this deeply skeptical depiction of marriage. Her record label worried that the subject matter was too complex for a first single, but it ultimately reached the top 10 on the Billboard Hot 100 and the adult contemporary chart. Carly Simon has said of the song, "When I first wrote it I thought it was an unusual thing for people to break up, and now all my friends are divorced." The song helped Carly Simon win a Best New Artist Grammy Award. "That's the Way I've Always Heard It Should Be" also earned a nomination for Best Female Pop Vocal Performance.

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Sinead O'Connor - "Nothing Compares 2 U" (1990)

Sinead O'Connor Nothing Compares 2 U
Sinead O'Connor - "Nothing Compares 2 U". Courtesy Chrysalis

"Nothing Compares 2 U" first appeared in 1985 in a recording by Prince proteges The Family on their debut album. However, it went relatively unrecognized until Sinead O'Connor recorded and released her version. The song details the pain of a broken relationship. The song hit #1 on the Billboard Hot 100 and in a number of other countries around the world. The release of the song was accompanied by a well-received music video focusing on a close-up of Sinead O'Connor's face experiencing the emotions in the song. Madonna performed the song as part of a tribute to Prince at the 2016 Billboard Music Awards following his death.

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Eric Clapton - "Tears In Heaven" (1992)

Eric Clapton Tears In Heaven
Eric Clapton - "Tears In Heaven". Courtesy Warner Bros.

Eric Clapton and Will Jennings wrote this song about the pain felt when Eric Clapton's four-year-old son Conor fell to his death from the window of a 53rd floor apartment in New York City March 20, 1991. In the aftermath of the tragedy, Eric Clapton has stated that he used his music as a key part of his healing. "Tears In Heaven" reached #2 on the Billboard Hot 100 and won three Grammy Awards including Record of the Year and Song of the Year. It also topped the adult contemporary chart and reached the top 10 at rock radio.

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Puff Daddy and Faith Evans - "I'll Be Missing You" featuring 112 (1997)

Puff Daddy I'll Be Missing You
Puff Daddy and Faith Evans- "I'll Be Missing You" featuring 112. Courtesy Bad Boy

Recorded in the midst of grief over the 1997 murder of rapper the Notorious B.I.G., "I'll Be Seeing You" is built on a sample from the Police's #1 smash "Every Breath You Take." The extended version of the song opens with a spoken word introduction over a choral interpretation of Samuel Barber's "Adagio for Strings." The record spent a powerful 11 weeks at #1 on the Billboard Hot 100 and won a Grammy Award for Best Rap Performance by a Duo or Group. It also reached #1 on pop charts in a number of other countries around the world.

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Johnny Cash - "Hurt" (2003)

Johnny Cash Hurt
Johnny Cash - "Hurt". Courtesy American Recordings

Although originally recorded by the band Nine Inch Nails for their album The Downward Spiral in 1994, it is Johnny Cash's version that truly pulls the pain and emotional intensity from the song. The recording has the distinction of both hitting the modern rock chart and being named the Country Music Association's Single of the Year. "Hurt" was released when Johnny Cash was 71 just six months before his death. Johnny Cash's wife June Carter Cash appears in the music video. She died only three months after it was filmed. The music video earned a Grammy Award for Best Short Form Music Video.

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Fort Minor - "Where'd You Go" (2006)

Fort Minor Where'd You Go
Fort Minor - "Where'd You Go". Courtesy Machine Shop

Fort Minor's #2 pop hit "Where'd You Go?" could be seen as a sort of polar opposite to rock band Journey's ballad "Faithfully." It details the pain and anger of the partner left behind by someone who is frequently away out of devotion to a career. "Where'd You Go" could easily match the career of a musician but also many others including soldiers and sports figures detailed in the video. The song features vocals by Holly Brook who later became better known under the name Skylar Grey. Fort Minor is a side project led by Linkin Park's Mike Shinoda. 

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