This glam-rocker-and-much-more-besides can certainly do some {{Tear Jerker}}s. In chronological order:

* "Space Oddity". The tale of a routine space mission, accompanied by sad music and Major Tom philosophizing -- and then "Can you hear me, Major Tom? Can you hear me, Major Tom? Can you" "heeeeeeeeeeeeeeeere... am I floating 'round my tin can..."
** The true tragedy of this is that the song is two-layered: one is the implied suicide by Major Tom. The other is that the song was released at the very end of TheSixties: depending on interpretation, its either about drugs or technology, the two great hopes of the Space Age that never delivered on their Utopian promises. "And I think my spaceship knows which way to go..."
** Music/PeterSchilling's "Major Tom", a sequel of sorts to this song, can be even more of a TearJerker...
** If you take the interpretation that Major Tom's capsule malfunctioned completely, enjoy imagining his slow, asphyxiating death... alone.
** There's a [[ Masters of Song Fu]] challenge that deals with reinterpreting this song, and both have an undertone of loneliness. From Jeff [=MacDougall=]'s take: "I'm high!/ Can you see me?/ I'm the blink in the night sky./ I'm not afraid./ Everything's clear./ Tell my wife no need for tears."
** [[ Now in children's book form!]] And yes, it is somehow ''more'' heartbreaking.
* "God Knows I'm Good", from the Space Oddity album. There is something very sad about the tale of a hungry old lady, forced to compromise her values just so she can eat.
* The imagery in the first verse of "Life on Mars?" (''Hunky Dory'') is decidedly heartbreaking. It doesn't help that the song is used in some of the more emotionally charged moments of the [[Series/LifeOnMars2006 TV series of the same name]].
** If one wasn't affected by "Life on Mars?" before, the [[SuicideIsPainless certain associations]] it acquired in the series finale of the eponymous TV show can add a profound sense of sadness to the song.
** As if the original version wasn't sad enough, the one Bowie performed on the Tonight Show with Johnny Carson is simply [[ devastating.]]
*** And topped even that performance when he sang at a [[ hurricane Katrina benefit concert]] in 2005. Only a year after his heart attack, a worn-out looking Bowie sang alone on stage with just a piano accompaniment. Ever the showman, his hand was bandaged and his eye was made up like it was bruised- to reflect the pain and loss of the victims. This particular troper was in tears!
* The final song of ''Ziggy Stardust'', "Rock 'n' Roll Suicide". The chorus of "Give me your hands!" before the LastNoteNightmare...
** The first song, "Five Years", can be pretty depressing too. (The take of Bowie used for the closing repetitions of the chorus sounds the way it does because he was in tears as he sang.)
** "Ziggy Stardust" itself is sad too; after all, it's about his decline and demise. Made even worse by the ''Stage'' live version, which sounds like something fit for a funeral owing to the synthesizers.
* The entire second half of ''Low''. Four slow, quiet, somber, mostly instrumental, intensely saddening songs. Especially "Subterraneans".
* ""Heroes"" is more poignant than gloomy, but still a tearjerker.
** Music/PeterGabriel's cover more so.
** Played at the end of ''Film/LoneSurvivor'' to a montage of real-life deceased soldiers even ''more'' so.
* "Ashes to Ashes" (''Scary Monsters'') -- there's something about its understated melancholy that gets to some people.
-->"I never done good things\\
I never done bad things\\
I never did anything out of the blue..."
** Some more depressing lines -- which reference "Space Oddity" -- include:
-->"I heard a rumor from Ground Control\\
Oh no, don't say it's true\\
(Later in song) Ashes to ashes, funk to funky\\
We know Major Tom's a junkie\\
Strung out in heaven's high\\
Hitting an all-time low"
* Here's Bowie's take on Creator/BertoltBrecht's "[[ The Drowned Girl]]" -- a cruelly detailed recounting of a demise.
* "Strangers When We Meet" is a rather strange example. While it works as a TearJerker at the end of ''1. Outside'' '''musically''', its '''text''' adds even more to the creepiness of this album if you consider that it's supposed to be sung by the Minotaur character.
* Many songs from ''Hours...'', especially this [[ live version of "Seven."]]
** "Thursday's Child", particularly the [[ video]], is another sad song -- but is, at least, hopeful.
* Many songs from ''Heathen'' are tearjerkers, especially the title track.
** [[ The live version of "Slip Away"]] is particularly heartbreaking, considering it opens with a clip from ''TheUncleFloydShow'', the song's subject matter, which is - in a weird way - a mediation on death.
--> Did you ever stop and think if there wasn't an Uncle Floyd show, what everyone else would be doing?
* ''Reality'' runs headlong into this.
** "The Loneliest Guy." Even the ''title'' is depressing.
** If we're talking about ''Reality,'' we can't forget "Days". "Do I need a friend? Well, I need one now..."
** As it became clear that nothing would bring him out of his retirement in TheNewTens, the final track, "Bring Me the Disco King" went down as his bittersweet, introspective swan song...and then, nearly ten years later, ''The Next Day'' said otherwise.
* The sudden relaunch of the official website, the announcement of ''The Next Day'', and release of its first video on January 8, 2013 jerked a lot of tears worldwide. That "Where Are We Now?" turned out to be such a poignant song/video -- specifically the full-body reveal of a melancholy-looking Bowie on the "As long as there's ''me''" [troper's emphasis] line -- only made it worse.