Was Kenny Rogers’ Ruby (Don’t take your love to town) a hit? Because damn that’s a desparate song if I ever heard one.
How about “I see a Darkness” by Johnny Cash?
“Hurt” Trent Reznor, sung by Johnny made it more desperate.
A great desperate song, but not a hit, would be “New Drink for the Old Drunk” by Crooked Fingers. Lyrics like these make the point:
“Well they kicked you around like a rodeo clown,
and it echoed through town they were beating you down,
and as they spread the word that you liked how it hurt,
all at one you were cause for a pitiful cure.”
[ul]
[li]Bohemian Rhapsody (Queen)[/li][li]Janie’s Got a Gun (Aerosmith)[/li][li]Jeremy and Black (Pearl Jam)[/li][/ul]
One of my favorite songs is “Saturday Night Special” by Conway Twitty. It starts out pretty damn desparate, but has an interesting ending. Not to be confused with the Lynyrd Skynyrd song of the same title, it sounds at first glance like it’s anti-gun or anti-capitalist. But it turns out to be decrying heartlessness towards one’s fellow man.
I’ve placed the lyrics in spoilers because I couldn’t summarize it effectively, but didn’t want to spoil the ending in case you want to hear the record first.
[spoiler]I was there to buy a pistol, she was there to hawk her ring
The broker in that pawn shop deals in almost anything
He’ll pay you for your misery or he’ll sell you someone’s pain
And that twinkle in his greedy eye, means your loss will be his gain
[ REMAINDER OF LYRICS DELETED BY MODERATOR – SEE NOTE BELOW ]
[/spoiler]
His ‘Lucille’ also showcases depseration, but in a third-person perspective.
“There’s a Tear In My Beer” - Hank Williams (the title says it all.)
“Car On a Hill” - Joni Mitchell (Poor two-timed Joni is waiting up all night for a boyfriend who never shows; she keeps waiting to hear a car drive up the hilly street she lives on, and park, rather than just drive by.)
“Eat for Two” - 10,000 Maniacs (Preachy message song told at the POV of a pregnant teenager.)
“Wake Up Little Suzy” - the Everly Brothers (Teenage couple - early 1960s - went out on a date one night, had sex, then fell asleep. They wake up in the morning, and start to panic - "What are we gonna tell your mama? / What are we gonna tell your pop? / What are we gonna tell our friends when they say “ou-la-la?”
And while I can’t recall the name of the song or the band that did it, there was some horrible dirge from the early 1970s describing a car accident victim’s POV as he’s pulled from the wreckage of a car, sees his dead girlfriend’s mangled body, realizes he’s lost an arm, and ultimately dies. The band was a one-(MINOR) hit wonder, and were a shrill Black Sabath ripoff. Does anyone else remember this?
Are you thinking of Last Kiss originally done by J. Frank Wilson and the Cavaliers and popularly covered by Pearl Jam?
If we lived in a just universe, Leslie Jordan would at lease have gotten an Oscar nomination for that movie. (“Shoot her Wardell… shoot her in the hay-ud.”)
Art Vandelay: That sounds like D.O.A by Bloodrock.
That’s it! I recognize both the song & band names. Yeah, boy what a hideous (but memorable) song that was…ick!
Girl - Beatles
She’s the kind of girl who puts you down when friends are there,
You feel a fool.
When you say she’s looking good, she acts as if it’s understood.
She’s cool, cool, cool, cool, Girl! Girl! 
How about the Cardigans’ Lovefool?
Sample lyrics:
“Lately I have desperately pondered,
spent my nights awake and I wonder
what I could have done in another way
to make you stay
Reason will not reach a solution
I will end up lost in confusion
I don’t care if you really care
as long as you don’t go”
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Or **White Flag ** by Dido
“I know you think that I shouldn’t still love you,
Or tell you that.
But if I didn’t say it, well I’d still have felt it
where’s the sense in that?”
[ REMAINDER DELETED BY MODERATOR ]
R. Dean Taylor Gotta See Jane:
How about “She doesn’t dance” in the category of ‘desperate denial?’
As far as ‘white flag’, maybe we’re reading it differently, but the only part of that song I thought was pitiful was that she wasn’t fighting… the ‘I’m promise I’m not trying’ bit and…
The parts about saying what you feel even if the other person thinks it’s wrong, and never falling out of love… maybe I’m still naive enough to think that’s oddly romantic. 
Don’t know how much of a hit it was, but the first thing that occurred to me was Sheryl Crow’s “Strong Enough”, the chorus of which is:
Phil Collins’ “Against All Odds”
I’m reaching a bit deep into the archives here, but:
All for Leyna by Billy Joel
A sample:
I’m failing in school
Losing my friends
Making my family lose their minds
I don’t want to eat
I don’t want to sleep
I only want Leyna one more time
I always thought of this as a sweet, innocent song. Thought they were good kids, went to the drive in, actually tried to watch the movie, but it was so boing they fell asleep. Never thought they actually “did it.”
Wake up little Suzie, wake up, wake up little Suzie, wake up
We both fell sound asleep, wake up little Suzie and weep
The movie’s over, it’s four o’clock and we’re in trouble deep
CHORUS
Wake up little Suzie, wake up little Suzie
Well, what’re we gonna tell your mama, what’re we gonna tell your papa
What’re gonna tell our friends when they say ‘ooh la la’
Wake up little Suzie, wake up little Suzie
Well, I told your mama that you’d be in by ten
Well, Suzie baby, looks like we goofed again
Wake up little Suzie, wake up little Suzie, we gotta go home
Wake up little Suzie, wake up, wake up little Suzie, wake up
The movie wasn’t so hot, it didn’t have much of a plot
We fell asleep, our goose is cooked, our reputation is shotCHORUS
Wake up little Suzie
And I would have to give a mention of Patsy Cline.
I Fall to Pieces
Crazy
Walking After Midnight
She really knew how to do desperate.
How about McArthur Park by Richard Harris. His cake is out in the rain and he’ll never have that recipe again…Ohhhhhh Nooooooo…
Five years from now
She sits at home
Feeding the baby, she’s all alone
Can I make it any more obvious?