It played quite a bit on the country stations I listen to.
Every time I heard it I thought, that’s not country, that’s pop/rock. It’s new country, which is a cross between soft rock and 70s pop. I don’t like it. The song, I mean, not the music in general.
Leonard Cohen’s “Dress Rehersal Rag”. Agh! It somehow got onto my iPod in my gym session mix. Itls not a song you want to hear 3/4 th the way through a 5K run!
mm
Some of the songs in the book I didn’t mind, but never fully understand the background. And now that the faults are pointed out- cringe.
Maybe, but isn’t that preferable to hearing the song while doing your morning shave?
Here are selected ones from my sad songs directory. Maybe country and goth-ish music is cheating though! 
Dixie Chicks - Cold Day In July
Dixie Chicks - You Were Mine
Eagles - Lyin’ Eyes
Eagles - After The Thrill Is Gone
Eagles - Tequila Sunrise
Elvis Presley - Are You Lonesome Tonight
Evanescence - My Immortal
Fleetwood Mac - Landslide
Loretta Lynn - If Teardrops Were Pennies
Martina McBride - Where Would You Be
Nine Inch Nails - Something I Can Never Have
Patsy Cline - Crazy
Patsy Cline - I Fall To Pieces
Patsy Cline - Sweet Dreams (Of You)
Patty Loveless - Don’t Toss Us Away
Patty Loveless - Love Builds The Bridges
Patty Loveless - I Know You’re Married (But I Love You Still)
Poison - Every Rose Has Its Thorn
Country Death Song - Violent Femmes.
Two that are in the book- and would get my vote every time:
Honey (Bobby Goldsborough)
Seasons in the Sun (Terry Jacks)
They are bad on every level.
Crucifixion Lane by Procol Harum
Here’s the last verse:
“You’d better listen anybody, 'cos it’s me and you --that’s it
and in case you find your maker perhaps you’ll plead for us a bit
All my sick is in my stomach, all my sweat is clearly fear
and if you could see inside me I don’t think you’d have me here
Tell the helmsman veer to starboard, bring this ship around to port
and if the sea was not so salty I could sink instead of walk
And in case of passing strangers who are standing where I fell
tell the truth: you never knew me, and in truth it’s just as well”
They play it on the pop and the country stations here, both with the bleep. I always think, isn’t whiskey addictive and destructive too, people???
Marianne Faithfull’s *Ballad of Lucy Jordan * is depressing, but also brilliant so I guess it may not fit the bill.
When I was at a bookstore this weekend, I scanned through the book and, even taking the author’s distinction into account, I still think depressing is not the right term to use for most of these songs. I think maudlin is the best way to describe them.
It’s usually the happier songs that get me down. The ones that remind me of what I don’t have, no matter how hard I’ve tried to get it. Lazlo Bane’s “I’m No Superman” is a good example. It’s a song about friendship, and the guy singing it sounds like he knows all too well that he wouldn’t be where he is without his buds.
Well I’ve never had a gang, or a posse, or a group of chums. Most of the people I click with intellectually are online friends. And as self motivated as I am, as much I workout for myself at 3am under the influence of no one at all, or how much I write for the sake of experience, or how much I read so I can entertain myself with thoughts, I know I could do it all better if only I had a few people I could live for. That might sound desperate, but you can only live comfortably for yourself to an extent. That’s what it comes down to.
I’ll find my crowd someday, but for now “I’m No Superman” is just depressing as hell.
Alternatively, “Creep” by Radiohead makes me feel wonderful. Someone out there can relate to me. I like that.
Any folk songs? I’m a folkie fan, but it does seem like a lot of folk songs are “Severely Depressing Songs to Commit Sucide By” 
For depressing, you want Johnny Cash’s cover of Hurt.
For bad, there’s always the collected works of Boyz II Men or N’Sync.
Really?
Sorta changes the meaning of it, doesn’t it? Now the song is really sad as opposed to weepily sentimental. Poor doggie. 
I think “End of the Road” might fit the bill.
I’ve never thought the song made any sense.
Her lyric:
I called you last night in the hotel
Everyone knows but they won’t tell
But their half-hearted smiles tell me somethin’ just ain’t right
I’ve been waitin’ on you for a long time
Fuelin’ up on heartaches and cheap wine
I ain’t heard from you in three damn nights
I put your picture away
I wonder where you been
I can’t look at you while I’m lyin’ next to him
If she’s lying next to “him” why is she calling the dude at the hotel? Why is she whining about not hearing from the dude for three nights when she’s lying next to someone else?
It doesn’t help that I hate both of the singers.
If you can’t be with the one you love, love the one you’re with.
I always found that Ode To Billy Joe was hardly uplifting, but it never got a mention