OK, I’m capable of being melodramatic.  I’ll admit that.  In high school and college, I would make mix tapes (and yes they were cassette tapes) that I titled Eclectic Mellow that I’d put on when I wanted to sit in the dark and contemplate the injustice of life.  This almost always coincided with periods where I didn’t have a girlfriend.

Such reveries have gotten less common as I’ve mellowed somewhat with age.  My adult life just doesn’t have the same unstructured blocks of time that allow for a good old-fashioned marathon pity party.  But I still enjoy a solid dark, sad or just flat out mopey song all the same.

So, here are 25 songs from my Ipod that, besides being great songs, are also perfect for the next time you just need to get in touch with your melancholy side:

1. Overkill - Colin Hay - Yes, I’m leading off with the Men at Work song.  But don’t listen to that version.  Pick up lead singer Colin Hay’s haunting acoustic version.  Stripped of the 80s cheese, this is a wonderful meditation on doubt.
Key lyric: I can’t get to sleep/I worry about the implications.

2. Time After Time - Cyndi Lauper - Another 80s classic, but this one works in any of its iterations (and is pretty much foolproof as a cover by other artists too).  My current favorite version is a duet with Sarah McLachlan (who shows up in her own right later on this list).
Key lyric:  After my picture fades and darkness has turned to grey.

3. Midnight Train to Georgia - Gladys Knight - OK, so I first have to admit that while I have the Gladys Knight version on my Ipod, it is really the live version by the Indigo Girls that kills me.  Seriously, I tear up every time I hear it.  The struggle of the singer trying to support someone they love who has failed spectacularly — that’s pretty damn sad.  In a good poignant way.
Key lyric:  But he sure found out the hard way that dreams don’t always come true.

4. Only You - Yaz - This song shouldn’t work on any level.  Simplistic cheesy 80s synthesizers and what sounds like a drum machine is the recipe for a crappy song.  Instead you get a classic.  It all rides on Alison Moyet’s voice, which will break your heart.
Key lyric: This is going to take a long time and I wonder what’s mine.

5.  Brick - Ben Folds Five - OK, time to get out of the 80s.  It took me awhile before I understood what this song was actually about.  It’s sad enough without knowing that it is a guy taking his pregnant girlfriend for an abortion.  One of the best songs about loss ever.
Key lyric:  Now she’s feeling more alone than she ever has before.

6. Piece of my Heart - Big Brother and the Holding Company - Janis Joplin has one of the best rock and roll voices of all time.  When she sings about hurt, you feel it.
Key lyric:  Never never never never never never hear me when I cry at night.

7. Can’t Fight It - Bob Mould
Key lyric: And it’s strange to see the friends you had all fade away.

8. I Don’t Like Mondays - Boomtown Rats - This is one of the first rock songs that I remember thinking about the lyrics.  The story of a girl on a shooting rampage in her school scared the hell out of me.  No key lyrics for this one — the whole song still just gives me a visceral reaction that humanity is going down the tubes.

9.  Better Be Home Soon - Crowded House - Desperation personified.
Key lyric: Stripping back the coats of lies and deception/Back to nothingness like  a week in the desert.

10. Five Years - David Bowie - Another story song.  This one makes me want to write a book about the slow burn lead up to an inevitable apocaplyse.  Now all I need are characters and a plot.
Key lyric:  We’ve got five years, that’s all we’ve got.

11.  Funny How Love Is - Fine Young Cannibals - In college, a guy on my floor was making a mix for his long-distance girlfriend.  All the songs had the word “love” in the title.  He was not happy when he realized it was a break-up song.
Key lyric:  I don’t want your magazines.  I don’t want your clothes.  Take them from my house, let me be alone.

12. Change - Fishbone - Not the usual loud raucous angry Fishbone. This is quiet melancholy and sort of angry Fishbone.

13. Landslide - Smashing Pumpkins - Yeah, I know it is Fleetwood Mac, but I like this verison. Deal with it.
Key lyric: Well, I’ve been afraid of changing ’cause I built my life around you.

14. Walking After You - Foo Fighters - Sad and creepy.
Key lyric: If you accept surrender, I’ll give up some more.

15. On Your Porch - The Format - Story song about a kid trying to do what’s right be a sick parent. Brutal.
Key lyric: What’s left to lose, you’ve done enough, and if you fail well then you fail but not to us.

16. Bizarre Love Triangle - Frente - Love the New Order original too, but this is another one that needed to be stripped down to understand the depth of despair in the lyrics.
Key lyrics: Everytime I see you falling, I get down on my knees and pray.

17. Shadow of the Day - Linkin Park
Key lyric: And the shadow of the day will embrace the world in grey and the sun will set for you.

18. Patience - Guns ‘n’ Roses - Not sure why this song gets me. But it does. Every time.

19. Black - Pearl Jam - I confess I don’t own Ten. In fact, I had been hearing this song for years before I even realized it was on their first album. And I didn’t know the title for another couple of years. None of that changes the fact that it is a brilliant song.
Key lyric: The pictures have all been washed in black.

20. Don’t Give Up - Peter Gabriel - How can a song about not giving up be so utterly depressing. Exhibit A.
Key lyric: I am a man whose dreams have all deserted.

21. I Will Remember You - Sarah McLachlan
Key lyrics: Weep not for the memories.

22. You’re Wondering Now - The Specials
Key lyric: Curtain has fallen, now you’re on your own, I won’t return, forever you will wait.

23. Don’t Grow - Stuart Matthewman - This was on the soundtrack of Twin Falls, Idaho, a micromini-movie about conjoined twins. You can’t fully feel the lyrics without realizing the plot hinges on the twins’ surgical separation where only one of them can survive.

24. Good Feeling - Violent Femmes - This band always felt like damaged goods. Rarely more so than in this song.
Key lyric: Good feeling, won’t you stay with me just a little longer.

25. Keep Me In Your Heart - Warren Zevon - Zevon knew he was dying when he recorded this. A deeply moving love song to living. Good to end this list with a reminder that melancholy can be uplifting in its own way, right?