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Top 10 Sad Christmas Songs

Songs That May Make You Cry

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Most classic Christmas songs are filled with the joy, wonder, and excitement of the season. However, there are sad Christmas songs as well. They may make you cry or simply be an emotional alternative to the happiness of most Christmas songs. These are 10 of the very best sad Christmas songs.

1. "Have Yourself a Merry Little Christmas"

Meet Me in St. Louis
Courtesy MGM

The classic Christmas song "Have Yourself a Merry Little Christmas" was first sung in the film Meet Me in St. Louis by Judy Garland at a point when the family at the center of the movie is upset about an impending move to New York away from their life in St. Louis. The song is intended to comfort a sad five year old girl in the film, but it maintains a strong sense of melancholy and sadness. The original words to the song were considered too depressing by movie director Vincente Minnelli and he had songwriter Hugh Martin change words to make "Have Yourself a Merry Little Christmas" a bit more hopeful. It remains one of the top sad and wistful Christmas songs of all time.

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2. "Blue Christmas"

Elvis Presley - Elvis' Christmas
Courtesy RCA

"Blue Christmas" is the ultimate holiday tune of unrequited love. It first became a country music classic through a 1948 recording by Ernest Tubb. However, a 1957 version by Elvis Presley has become known as the standard. Moaning backup singers add to the overall classic feel of gloom while Elvis Presley sings of having a "blue blue blue" Christmas.

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3. "I'll Be Home for Christmas"

Josh Groban - "I'll Be Home for Christmas"
Courtesy Reprise Records

"I'll Be Home for Christmas" was first recorded by Bing Crosby in 1943 while the US was in the middle of fighting World War II. It soon became a standard song for expressing the feelings of those who must spend the holidays away from home and loved ones. In 1965 when astronauts Frank Borman and James Lovell were away from earth during the holiday season they requested that NASA play the song for them. Josh Groban's 2007 version was picked up to help comfort families whose loved ones were away fighting wars in Iraq and Afghanistan.

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4. "Fairytale of New York"

Pogues - "Fairytale of New York"
Courtesy the Pogues

"Fairytale of New York" is considered by many in the UK and Ireland to be the best Christmas song of all time. The basics of the song are about a drunken man thinking back to past Christmas celebrations while incarcerated in a New York City jail. The man remembers a failed relationship and much of the song involves words of bickering and crushed dreams. The recording of the song by the band the Pogues and singer Kirsty MacColl was released in 1987 and has since been embraced in the UK and Ireland as one of the top Christmas songs of all time returning to the pop singles chart every year.

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5. "Please Come Home for Christmas"

Eagles - "Please Come Home for Christmas"
Courtesy Elektra

"Please Come Home for Christmas" was first recorded and released by blues singer Charles Brown in 1960. It reached #1 on the Billboard Christmas songs chart in 1972. In 1978 the band the Eagles recorded their own version which became a top 20 hit on the Billboard Hot 100. The song is a lament about spending Christmas alone and a plea for a lover to no longer roam and end all sorrow, grief and pain.

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6. "Same Old Lang Syne"

Dan Fogelberg - Very Best of Dan Fogelberg
Courtesy Epic

Dan Fogelberg's song "Same Old Lang Syne" tells the autobiographical story of meeting a former love on a snowy Christmas Eve. The pair reminisce, talk about imperfections in their current lives, and the song ends on a melancholy note as the beautiful snow changes into rain. Dan Fogelberg's recording was released in 1981 and became a top 10 pop hit.

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7. "Merry Christmas Darling"

Carpenters - "Merry Christmas Darling"
Courtesy A&M Records

The Carpenters classic song about spending Christmas apart and dreaming about being together was originally released as a single in 1970. Following in the wake of the duo's first two smash singles, "Merry Christmas Darling" reached #1 on the Billboard Christmas songs chart. It did not appear on an album until the Carpenters' 1978 Christmas Portrait collection. With the melancholy notes in the singing of Karen Carpenter it is a classic of sadness that can accompany holiday celebrations spent apart.

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8. "Christmas (Baby Please Come Home)"

Various Artists - A Christmas Gift for You from Phil Spector
Courtesy Sony

This Christmas classic depicts the sadness of watching everyone else celebrate happily while missing an absent lover. "Christmas (Baby Please Come Home)" was first recorded by singer Darlene Love for the classic Phil Spector Christmas collection A Christmas Gift for You from Phil Spector. It did not receive strong acclaim at first when released in 1963, but its reputation has built strongly since. Darlene Love began singing the song annually on the Late Show with David Letterman in 1986 and continues more than 20 years later. U2 recorded a powerful version of the song for the 1987 A Very Special Christmas album. Darlene Love provided backing vocals.

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9. "Did I Make You Cry on Christmas Day? (Well, You Deserved It!)"

Sufjan Stevens - "Did I Make You Cry on Christmas Day? (Well, You Deserved It)"
Courtesy Asthmatic Kitty

Acclaimed alt rock performer Sufjan Stevens released a collection of Christmas carols and original Christmas songs he had been singing for years for friends and acquaintances as the album Songs for Christmas in 2006. This original song depicts simmering anger and sadness during the holidays.

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10. "Christmas Shoes"

Newsong - "Christmas Shoes"
Courtesy Reunion Records

Contemporary Christian group Newsong first released the song "Christmas Shoes" in 2000. It landed on the country chart and the Billboard Hot 100. The song's story about a little boy wanting to buy his dying mother the perfect gift touched a chord with many listeners. In 2002 the song's story was adapted into a novel and a TV movie.

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