Entertainment Music The Top 10 Sad Christmas Songs Share PINTEREST Email Print Compassionate Eye Foundation / Getty Images Music Rock Music Holiday Music Top Picks Top Artists Pop Music Alternative Music Classical Music Country Music Folk Music Rap & Hip Hop Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Bill Lamb Music Expert M.L.S, Library Science, Indiana University Bill Lamb is a music and arts writer with two decades of experience covering the world of entertainment and culture. our editorial process Bill Lamb Updated December 07, 2018 While most Christmas songs are filled with joy, wonder, and excitement, some are filled with wistfulness and longing. These sad holiday classics include old hits such as "Blue Christmas" and modern ballads such as "Did I Make You Cry On Christmas Day?" 10 of 10 "The Christmas Shoes" WireImage / Getty Images Contemporary Christian group Newsong first released the song "Christmas Shoes" in 2000. It became a crossover hit, reaching #31 on the country chart, #1 on the adult contemporary chart, and #42 on 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 was adapted into a novel and a TV movie starring Rob Lowe and Kimberly Williams. 09 of 10 "Did I Make You Cry On Christmas Day? (Well You Deserved It!)" Kevin Winter / Getty Images In 2006, acclaimed alternative rock performer Sufjan Stevens released "Songs for Christmas," a collection of carols and original Christmas songs he had been singing for years for friends and acquaintances. Stevens' original "Did I Make You Cry on Christmas Day?" depicts simmering anger and sadness during the holidays. 08 of 10 "Christmas (Baby Please Come Home)" Kevin Winter / Getty Images Written by Jeff Barry, Ellie Greenwich, and Phil Spector, 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." U2 recorded a powerful version of the song for the 1987 "A Very Special Christmas" album, featuring backing vocals by Love. In 2010, Rolling Stone named "Christmas (Baby Please Come Home)" the top rock and roll Christmas song of all time. 07 of 10 "Merry Christmas, Darling" Redferns / Getty Images The Carpenters' classic song about spending Christmas apart and dreaming about being together was originally released as a single in 1970. Following the duo's first two smash singles, "Merry Christmas, Darling" reached #1 on the Billboard Christmas songs chart. The song topped that chart again in 1971 and 1973. It did not appear on an album until the Carpenters' 1978 "Christmas Portrait" collection. 06 of 10 "Same Old Lang Syne" Paul Natkin / Getty Images Dan Fogelberg's "Same Old Lang Syne," tells the autobiographical story of meeting a former lover at the grocery store on a snowy Christmas Eve. The pair reminisces and talks about their current lives, and the song ends on a melancholy note as the beautiful snow turns into rain. Dan Fogelberg's recording was released in 1980 and became a top 10 pop hit. The melody of "Same Old Lang Syne" was influenced by Tchaikovsky's "1812 Overture." The recording closes with Michael Brecker playing the melody from "Auld Lang Syne" on the saxophone. Following Dan Fogelberg's death in 2007, the woman Fogelberg met on Christmas Eve in the song came forward and told her version of events, confirming the basic elements of the song's story. 05 of 10 "Please Come Home for Christmas" Redferns / Getty Images "Please Come Home for Christmas" was first recorded by blues singer Charles Brown in 1960. Although it only reached #76 on the Billboard Hot 100, it appeared on the Christmas songs chart for nine years, peaking at #1 in 1972. The song is a plea for a loved one to return and end the Christmas blues. In 1978, the Eagles recorded their own version, which became a top 20 hit on the Billboard Hot 100. Jon Bon Jovi covered "Please Come Home for Christmas" in 1992 on the holiday charity album "A Very Special Christmas 2." An accompanying music video featured supermodel Cindy Crawford. 04 of 10 "Fairytale of New York" Redferns / Getty Images "Fairytale of New York" is considered by many in the U.K. and Ireland to be the best Christmas song of all time. The song is 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 by the band The Pogues and singer Kirsty MacColl was released in 1987. As of 2016, "Fairytale of New York" has reached the top 20 on the U.K. pop singles chart 13 different years. 03 of 10 "I'll Be Home for Christmas" Corbis via Getty Images / Getty Images "I'll Be Home for Christmas" was first recorded by Bing Crosby in 1943 while the U.S. was in the middle of fighting World War II. The record reached #3 on the pop chart upon its release. It soon became a standard song for expressing the feelings of those who must spend the holidays away from home and their loved ones. The BBC briefly banned the song from being played in the U.K. out of concern that it would lower the morale of the troops. 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. 02 of 10 "Blue Christmas" Michael Ochs Archives / Getty Images "Blue Christmas" is the ultimate holiday tune of unrequited love. It first became a country music classic through a 1948 recording by Ernest Tubb, which reached #1 on the country chart. Orchestra leaders Hugo Winterhalter and Russ Morgan also scored hits with their pop versions the same year. The 1957 version by Elvis Presley is now the most famous. It was included on "Elvis' Christmas Album," the bestselling Christmas album of all time in the U.S. 01 of 10 "Have Yourself a Merry Little Christmas" MGM The classic "Have Yourself a Merry Little Christmas" was first sung in the film "Meet Me in St. Louis," starring Judy Garland. The song is intended to comfort a sad five-year-old girl in the film, but the atmosphere remains melancholy and downbeat. The original lyrics were considered too depressing by movie director Vincente Minnelli and he had songwriter Hugh Martin change them to make the song a bit more hopeful. "Have Yourself a Merry Little Christmas" remains one of the most wistful Christmas songs of all time.