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Top 10 Best Sad Pop Songs

Songs That Make You Cry

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If you need someone to be sad along with you, or you need a good tearjerker as catharsis, sad pop songs have a treasured spot in pop music memories.  These are 10 of the most powerful sad pop songs. Don't miss the Top 10 Happy Songs as well.

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

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. It 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.

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2. Beatles - "Eleanor Rigby" (1966)

Beatles - "Eleanor Rigby"
Courtesy Parlophone

The Beatles' meditation on loneliness ends with a very stark funeral depiction. Instrumental 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. "Eleanor Rigby" reached #11 on the pop singles chart in the US.

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3. Johnny Cash - "Hurt" (2003)

Johnny Cash - "Hurt"
Courtesy American Recordings

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.

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4. Eric Clapton - "Tears In Heaven" (1992)

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. "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.

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5. Mark Dinning - "Teen Angel" (1960)

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, but it became a #1 hit for Mark Dinning. He had three other minor chart appearances but never returned to the pop top 40.

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6. Carpenters - "Superstar" (1971)

The Carpenters - The Carpenters
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" hit #2 on the pop singles chart, and, although covered by a number of other artists, the Carpenters version is considered by many to be the definitive pop version.

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

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

Recorded in the midst of grief over the death 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." It spent a powerful 11 weeks at #1 on the Billboard Hot 100.

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

Simon and Garfunkel - 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. It was a #3 pop hit on the Billboard Hot 100.

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

Fort Minor - The Rising Tied
© Machine Shop Recordings

Fort Minor's #2 pop hit "Where'd You Go?" could be seen as a sort of polar opposite to Journey's "Faithfully." It details the pain and anger of the partner left behind by someone who is frequently away out of devotion to a career. It could easily match the career of a musician but many others such as soldiers and sports figures as detailed in the video.

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

Carly Simon - Carly Simon
Courtesy Elektra

Carly Simon blasted into mainstream 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.

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