Top 10 Depressing Holiday Songs

The previous post on Three Depressing Holiday Songs got us started thinking about the best depressing holiday songs.  So, this post features Chimesfreedom’s Top Ten Depressing Holiday Songs.  We selected these top 10 based upon three categories. Points were given for (1) deep depression and sadness; (2) quality of song; and (3) familiarity of the song.

Christmas cheer beer.(1) Fairytale of New York” – The Pogues: Scored high in all three categories.  Discussed in previous post in more detail, but all you really need is the opening line of the song: “It was Christmas Eve, babe,/ In the drunk tank.” Score:  97 points.

(2) “Blue Christmas” – Elvis Presley, etc.: Gets high on the list because very familiar and a good song, but the music is not that sad. For more, we discussed the story behind Elvis Presley’s most famous performance of the song. Score:  93 points.

(3) “The River– Joni Mitchell (and covers): Received most of its points from the deep depression category with both depressing lyrics and music.  Discussed in previous post in more detail.  Score:  91 points.

(4) Pretty Paper” – Roy Orbison:  The lyrics to “Pretty Paper,” which was written by a young songwriter named Willie Nelson in 1963, are a little vague. But a guy is alone on the sidewalk hoping “that you won’t pass him by.” “You’re in a hurry” so you leave him there crying as people laugh in the distance. You suck. Anyway, it has Roy Orbison’s voice, which automatically puts it high on the sounding-sad scale.  If he sang “Jingle Bells” it would make this list. Score:  89 points.

(5) Do They Know It Is Christmas?” – Band Aid: Very famous and depressing: “Where nothing ever grows/ No rain or rivers flow.” And then there is Bono wailing, “Tonight thank God it’s them instead of yooooooooooooo!”  “Do They Know It’s Christmas” would be higher on the list, but by the end we are happily singing “Feed the world” and letting people know it is Christmas Time whether they want to know it or not.   But while it did raise money for a good cause, the song has an extra tinge of sadness because it also reminds us that we did not find a solution to hunger in the 26 years since the song was released.  We mock, but we love the song. Just avoid the two remakes from 1989 and 2004. Score:  88 points. Trivia Question: Who sings the Bono part in the 2004 Band Aid 20 remake?

(5) “Christmas in Prison” – John Prine. We like John Prine and the quality of “Christmas in Prison,” so we are putting it above some other songs even though you may never have heard it. Plus, you got prison: “The search light in the big yard / Swings round with the gun / And spotlights the snowflakes / Like the dust in the sun.” Check out John Prine’s version below (and hear a cover by Arlo McKinley here).  Score:  84 points.

(7) “Christmas Card from a Hooker in Minneapolis” – Tom Waits: Scored high on the depression scale, but not a song for many repeated listenings and not as famous as some of the above songs.  Discussed in previous post in more detail.  Score:  79 points.

(8) I’ll Be Home for Christmas” and “White Christmas” (tie) – Bing Crosby and others: Familiarity got these two into the top ten. The music sounds depressing, but the person is missing one Christmas and seems to still have family they will see again. For “I’ll Be Home For Christmas,” the guy who wrote the lyrics was thinking of a homesick kid in college.  C’mon kid, there are people starving in Africa.  At least “White Christmas” gets bonus sad points from its popularity being connected to WWII soldiers missing home.  These songs are sad, but not hooker-in-prison sad.   Score:  78 points.

(9) “Billy’s Christmas Wish” – Red Sovine: “Billy’s Christmas Wish” may not be as well known as the other songs here, but the song is unbeatable on the depression scale so it makes the list on that alone. Consider: (1) the little boy’s father is in prison for shooting the mother’s boyfriend; (2) the mother works in a bar and lives with an abusive “Mr. Brown;” and (3) then the little boy dies on Santa’s lap at the end. Seriously, that is the song. And then Santa has the nerve to tell us not to be sad because the boy wanted to live with God so “now everything’s alright.” That makes us think that Santa killed Billy.  Score:  72 points.

(10) “The Rebel Jesus” – Jackson Browne. The Top Ten List must have room for a song that gets to the heart of Christmas and how the spirit of it gets corrupted, calling us out for our hypocrisy. Everyone may not know this song, but it is a beautiful song of the season. Score: 68 points.

Well we guard our world with locks and guns,
And we guard our fine possessions.
And once a year when Christmas comes,
We give to our relations.
And perhaps we give a little to the poor,
If the generosity should seize us.
But if any one of us should interfere
In the business of why there are poor,
They get the same as the rebel Jesus

I went shopping today and bought a present for my mom, and then I sang along to “Do They Know It’s Christmas” without doing anything about the poor.  I am a worthless human being.  Thanks Jackson Browne for making me feel like crap.   If you need to feel a little better, you may use the charity of your choice or use these links for CARE, Oxfam, or UNICEF.

Honorable Mention: “Please Daddy Don’t Get Drunk This Christmas” – John Denver: You do not hear this one a lot, and I just discovered Alan Jackson covered the song. The song is sad with the kid worrying whether daddy will be drunk again this Christmas, but it is played as a clap-along song so not as depressing as it could be. Plus, the kid has it good compared to Billy in the Red Sovine song.  Score:  54 points.

Bonus Recent Excellent Sad Holiday Song: Mike Ireland and Holler‘s “Christmas Past.” I found this song last year and really like it, and when you hear it, the melody sounds like a song you have heard many times before. The song features various memories floating by and ends with: “The only company I keep exists in memories / Leaving me alone on Christmas Day.” Sad, but a pretty song.

Bonus Links: In preparing this post, I did some googling and saw that others had compiled similar lists that you may see and compare here, here, here, and here.

What’s your favorite depressing holiday song? Post a comment.

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    3 Depressing Holiday Songs

    Pogues Christmas There are numerous places to go for happy holiday songs about snowmen, toys, and good cheer. But the holidays are often a depressing time of year for many, in part, because the songs and movies create such high expectations of perfection in our lives. So, to counter those expectations, here at Chimesfreedom we revisit three of the best depressing holiday songs, brought to you by Tom Waits, Joni Mitchell, and the Pogues. Because these songs lower one’s expectations, maybe they provide a source of joy for this time of year better than some of the syrupy happy songs.

    Christmas Card from  a Hooker in Minneapolis

    The title of Tom Waits’s song, “Christmas Card from a Hooker in Minneapolis” sums it up. The song starts off with “Silent Night” to give the Christmas setting of the song, and then the “hooker” describes her life to Charley. She spins a tale about a husband and her memories, but at the end she confesses:

    I don’t have a husband
    He don’t play the trombone
    And I need to borrow money
    To pay this lawyer
    And Charley, hey
    I’ll be eligible for parole
    Come Valentines day.

    Then the singer goes back into “Silent Night,” evoking the hidden sadness that underlies that melancholy song, which is about the birth of a savior born into a fate of suffering. If you are not a Tom Waits fan, I realize his voice takes a little getting used to, but his gravely voice highlights the sadness of this tale.

    The River

    From the first notes of the piano introduction to “The River,” on both Joni Mitchell’s original and Sarah McLachlan’s cover, you know you are in for a depressing song even if the initial notes are from the happiest of holiday songs, “Jingle Bells.” Like the two other songs here, “The River” begins by setting the scene for Christmas: “It’s coming on Christmas/ They’re cutting down trees / They’re putting up reindeer / And singing songs of joy and peace.”

    But then, the song centers on memories of a failed relationship. “Now I’ve gone and lost the best baby / That I ever had /Oh I wish I had a river /I could skate away on.”

    I love the Joni Mitchell version of “The River.” Since this post was originally published, Mitchell finally released her first official video for the song in 2022. Check it out below.

    Sarah McLachlan’s version may be even more well known, and it is outstanding too. So here is the McLachlan version of “The River.” But you are warned. It is depressing.

    Fairytale of New York

    The Pogue’s “Fairytale of New York” (1987) is probably my favorite depressing holiday song.  Jem Finer and Shane MacGowan wrote the song, which features MacGowan singing lead and trading vocals with featured British singer Kirsty MacColl.  Interestingly, when the Pogues began recording the song, MacGowan sang the male and female parts.  But record producer Steve Lillywhite suggested his wife Kirsty MacColl create guide vocals for the song, and the band realized she was perfect to use for the parts of the wife in the song.  MacGowan re-recorded his vocals to go with MacColl’s recording, so the two never actually sang together in the studio.

    Despite the depressing lyrics, the joyous Irish tune lifts my spirits, in much the same way we find joy in other sad holiday stories like “Blue Christmas.” You know it is not a typical Christmas song from the first line: “It was Christmas Eve babe/In the drunk tank.” The singer then turns to memories of his “Queen of New York City” as he “can see a better time/When all our dreams come true.”

    Then the band kicks in and the song features an exchange between a couple who are down on their luck.  They reflect on their hope in coming to America (“They got cars big as bars / They got rivers of gold”), tinged with dashed dreams (“But the wind goes right through you/It´s no place for the old”).

    The couple fight and curse each other.   They exchange several barbs, referring to “an old slut on junk” with the holiday wish, “Happy Christmas your arse/ I pray God it’s our last.”  I have read a few different interpretations of what is going on in the song — whether it is a current relationship or a past relationship.  Despite the broken dreams of the song (“You took my dreams from me”), I like to think the song ends with a tiny sparkle of hope, “Can’t make it all alone/ I’ve built my dreams around you.”

    Finally, we’re pulled back to the police station and the drunk tank,

    The boys of the NYPD choir
    Were singing “Galway Bay”
    And the bells were ringing out
    For Christmas day

    Beautiful.

    Bonus Video Information: Recognize the police officer at the beginning of this video? He’s Matt Dillon.

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    Oxford American Southern Music Issue

    Oxford American MagazineThe Oxford American magazine recently released its Twelfth Annual Southern Music Issue, and, as always, the magazine and enclosed CD are outstanding.  Oxford American is billed as “The Southern Magazine of Good Writing,” and once a year, it devotes an issue to southern music, including a CD of the music discussed in the magazine.  I first discovered the annual music issue in 1999, when my friend and co-worker Sid gave me my first copy, and I have been following the magazine ever since.

    The “southern music” of these issues consists of nuggets of a wide variety of the good stuff.  In the CDs I have from past annual music issues, the artists included people I already knew – such as Sonny Burgess, Odetta, and the Del McCoury Band – to new discoveries for me – like the Gosdin Brothers’ 1968 recording of “There Must Be Someone (I Can Turn To)” on this year’s CD.  There are occasional odd gems, like when the 2000 CD included a recording of Robert Mitchum and Lillian Gish singing “Leaning” from Night of the Hunter that made me love the song and his voice outside the context of the haunting scene in the movie.

    Last year, Oxford American started a new approach with its music issue. Instead of covering a broad geography, the magazine began to focus on one state each year.  Last year was Arkansas, and this year’s issue concentrates on Alabama.  I really liked the previous broader approach, but the state-by-state approach is growing on me.  And either way, it is the best magazine-CD out there, and it still covers a wide range of styles and time, with songs from the 1940s through 2010.  Additionally, I like that the magazine’s approach has evolved over the years so now there is a feature story about each track on the CD.

    There are also other articles, like fiction by Greil Marcus and an article about the song-writing team of Felice and Boudleaux Bryant.  Never heard of the Bryants?  The article will tell you the story behind their songs recorded by the Everly Brothers, like “Bye Bye Love” (recorded by the Everlys just to get the $64 session fee).

    Oxford American has struggled through the years to stay in business (like another music magazine I loved, No Depression). From my recollection, and from the missing CD in my collection from one year, the magazine’s troubles peaked in 2004 when they stopped publishing for a period. Do not let that happen again. You may pick up the magazine at most bookstores or order the magazine and back issues from the website, which also has this year’s track listing (under “Further Listening”). FYI, I have no affiliation with the magazine, I just wanted to share.

    A version of this review was also published at NoDepression.com

    John Lennon Anniversary News Roundup

    Today is the thirtieth anniversary of John Lennon’s death.  Below are some of the interesting stories about the anniversary, ranging from Lennon’s life at the Dakota to speculation about a Beatles reunion.  Follow the links of interest.

    — Back in the days before cable news channels, most of us learned about John Lennon’s death while watching Monday Night Football.  The NY Times Blog has the story behind Howard Cosell’s announcement of Lennon’s death, including a link to hear Cosell and Frank Gifford during a commercial break discussing whether or not to say anything.

    –The Behind the Music blog from the UK and MyKawartha.com from Canada both imagine a world where John Lennon was not killed on the streets of New York three decades ago.

    Imagine John Lennon Memorial (jlk)The Los Angeles Times discusses controversies surrounding Lennon’s classic song, “Imagine.”

    The Atlantic Wire questions whether or not John Lennon was a pacifist.

    Huffington Post reviews the new documentary about Lennon’s final days and the murder, Losing Lennon: Countdown to Murder.

    From Australia, the Sydney Morning Herald has information about the doctor who first saw Lennon at the hospital after the shooting.

    — The New York Times discusses life at the Dakota when John and Yoko lived there. John and Yoko brought sushi to the building’s pot luck dinner, and some neighbors were not happy that the couple owned five apartments in the building.

    Rolling Stone has the never-before-published complete interview with Lennon three days before his death as well as other stories.

    Examiner.com presents the television schedule for upcoming Beatles-related shows through December 16. Among the list, Paul McCartney will be on Saturday Night Live this coming Saturday (Dec. 11).

    MusicRadar.com reports the British tabloids are talking about a possible Beatles reunion — with all four Beatles.

    The most important thing today is to play some of John Lennon’s music. You know the songs you like, so I do not need to tell you what to choose. Just listen to whatever you like, and sing along or maybe dance when nobody is looking. That is the best way to remember his gifts to help us and get us through the nights.

    Leave a Comment below to let us know your memories and/or what is your favorite John Lennon song.

    Steve Earle’s “Ellis Unit One” & Justice Stevens

    Not long after he retired, former United States Supreme Court Justice John Paul Stevens was in the news for writing a book review, followed by an appearance on 60 Minutes. The attention on Justice Stevens and his changing views on capital punishment remind me of Steve Earle’s haunting song, “Ellis Unit One.”

    In several appearances after he retired, Justice Stevens described how he changed his mind about the death penalty. Over time, he came to conclude, as the New York Times summarized, that the Supreme Court has “created a system of capital punishment that is shot through with racism, skewed toward conviction, infected with politics and tinged with hysteria.”

    Justice John Paul Stevens
    Justice Stevens was on the Supreme Court in 1976 when the Court, in effect, established the modern death penalty.  In 1972, the Court held that the nation’s death penalty laws violated the constitution, but in 1976 the Court upheld new death penalty laws. In those cases and in cases throughout the decades, Justice Stevens voted to uphold the constitutionality of the death penalty. But in his final few years on the Supreme Court, he came to conclude that the death penalty system was unfair and constituted a pointless taking of life that does not serve society.

    At the time, Justice Stevens joined two other U.S. Supreme Court Justices who voted to uphold the death penalty in 1976 but by the end of their careers had changed their minds: Justices Harry Blackmun and Justice Lewis Powell.  More often than one might guess, over time, some who advocated for and implemented the nation’s death penalty — judges, prosecutors, police officers, wardens, legislators, executioners — eventually conclude that the punishment is unfair, racist, useless, risks executing innocent defendants, and that society would be better off replacing the death penalty with life in prison.

    The news about Justice Stevens reminded me of a song that tells one of these stories, Steve Earle’s “Ellis Unit One,” which appeared on the soundtrack for the 1995 movie Dead Man Walking and is one of the most moving songs ever written about the death penalty.  The song is told from the perspective of a prison guard.  The guard describes getting transferred to death row at Ellis Unit One, the Texas prison unit that housed condemned prisoners at the time the song was written.

    The narrator does not say what he thinks about the death penalty. Steve Earle’s genius here is to understand that the description is enough.

    Well, I’ve seen ‘em fight like lions, boys
    I’ve seen ’em go like lambs
    And I’ve helped to drag ‘em when they could not stand.
    And I’ve heard their mamas cryin’ when they heard that big door slam
    And I’ve seen the victim’s family holdin’ hands.

    Many of the judges who have condemned people to death may have had dreams similar to the one described in “Ellis Unit One”: “Last night I dreamed that I woke up with straps across my chest / And something cold and black pullin’ through my lungs.” Having such a heavy responsibility may haunt one’s dreams, even if the judge is confident in the choice made. Similar dreadful dreams may have led Justices Stevens, Blackmun, and Powell to renounce their earlier decisions.

    When we read about a horrible crime and have the normal initial human reaction to want the perpetrator killed, we often ignore the death penalty system’s toll on the many people it touches, including the guards, the wardens, the judges, the lawyers, the families of the victim, and the families of the condemned.  Whether or not we agree with Justice Stevens, one must acknowledge the costs caused by the continuing use of capital punishment.  While Justice Stevens’s change of heart reveals the legal and practical issues surrounding the death penalty, Steve Earle’s poetic song exposes some of the human toll.

    Bonus Song Information: The reference to “the Walls” in the song is to the nickname for the Huntsville Unit in Huntsville, Texas, about twelve miles away from Ellis Unit.  It is where the Texas inmates are executed.

    Bonus Alternate Versions Information:  In addition to the soundtrack version of the song, Earle has another outstanding version that is a demo with The Fairfield Four providing background singing. The Fairfield Four version appeared on the EP Johnny Too Bad and Earle’s collection of random songs from various side projects, Sidetracks. The latter appears to be available as an import, and the former seems hard to find and overpriced for an EP, but you may hear a clip with the Fairfield Four through the “Johnny Too Bad” link.  This version is worth seeking out.  Finally, a live version of the song is on Steve Earle’s Live At Montreux 2005 album.

    One of Cleveland’s favorite son performers, Michael Stanley, also recorded a version of the song. As a former Clevelander I have the required fondness for MSB, but his version is inferior to Earle’s. As his version progresses, he adds instruments and background singers to the point I thought he was going to break into a full-blown uplifting rock song with a last-minute stay of execution. Still, Stanley has good taste in choosing to cover such a great song, and perhaps it merely suffers by comparison to Steve Earle’s excellent versions. And some may prefer Stanley’s voice and his cover. Leave a comment to let me know what version you like.

    Has anyone ever started talking about a Supreme Court Justice and ended up talking about Michael Stanley?

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