Roy Orbison

For those blasted on acid, hippie ideals such as of peace, love and community seemed self-evident. After the drum circle was over, it turned out that the free love concept was about as sustainable as parties with “free beer.”

Where there is romance there is also eventual heartbreak, and the 60s were no different.

20. Leave Me, by The Hollies

Bitter lyrics and mildly psychedelic sounds don’t often come together, which is exactly what makes this number so glorious. “It’s hard to please” her. Even vocal harmonies don’t work.

19. These Boots Are Made for Walkin’, by Nancy Sinatra

Nancy had very little patience for cheaters as proven by this tune and “Don’t Let Him Waste Your Time.” If walking didn’t work, she’d stampede over them.

18. Delilah, by Tom Jones

Delilah was laughing until Tom Jones pulled a knife on her. Somebody issue this man a restraining order.

17. Release Me, by Engelbert Humperdinck

Engelbert found a new hottie with luscious lips. Still, his last lover couldn’t let go. It must be the sideburns.

16. Hit The Road Jack, by Ray Charles

Ray Charles smiled under the strangest circumstances. It’s no wonder he could also pen whimsical songs after his woman sent him through the meat grinder.

15. Piece of My Heart, by Janis Joplin

If you want to get it on with your ex even after you’ve been burned continually, put this ditty in your playlist. Make sure to guzzle Southern Comfort straight out of the bottle while you’re at it, sadist.

14. The Thrill Is Gone, by B.B. King

Even though B.B. is free from her spell, he sounds as though he’s losing his will to live. The roses don’t smell as vibrant as they used to.

13. Babe I’m Gonna Leave You, by Led Zeppelin

It’s too cold outside for Robert Plant to leave his flame quite yet. “Leave you when the summer comes a rollin’.”

12. I Wanna Be Around, by Tony Bennett

You don’t need to bother getting revenge. Fix yourself a scotch on the rocks and get real comfortable. Some dude will break her heart soon enough as you “sit there applaudin’ from a front-row seat.”

11. She’s Not There, by The Zombies

Should you apologize or shouldn’t you? Don’t waste your time thinking about it. “She’s not there.”

10. You’ve Lost That Loving Feeling, by The Righteous Brothers

The sparkle in her eye has vanished. All she does is nag you about inconsequential things. “That loving feeling” might be gone for good I’m afraid.

9. Hey Jude, by The Beatles

Sir Paul wrote this ballad for John Lennon’s son, Julian. He was having a tough time dealing his parents’ divorce. Paul encouraged Jules to keep his chin up and to let John’s new love, Yoko, into his life.

8. When a Man Loves a Woman, by Percy Sledge

It’s the ultimate love song or breakup song depending on how you process it. Writers Calvin Lewis and Andrew Wright successfully portray the bittersweet nature of love.

7. Paint it Black, by The Rolling Stones

When you’re miserable, sights that would normally bring you “satisfaction” do the opposite.  Bright and beautiful things make you aware of your inner darkness, and that’s scary.

6. The Crying Game, by Dave Berry

“First there are kisses, then there are sighs.” Dealing with heartache was a game Dave Berry couldn’t win.

5. Keep Me Hangin’ On, by The Supremes

If you need more evidence that staying friends with your ex is a bad idea, listen to this cautionary tale. Occasional hookups aren’t worth the ultimate cost.

4. Tracks of My Tears, by Smokey Robinson

Even when you you’ve “moved on,” your last love holds a place in your heart. Smokey’s new girl isn’t a replacement for his “permanent one.”

3. It Ain’t Me, Babe, by Bob Dylan

Perhaps George Costanza didn’t invent the “it’s not you, it’s me” line after all. Bob won’t “open each and every door”, “gather flowers constantly” or “die for you.”

2. Crying, by Roy Orbison

Roy showed the world that a real man doesn’t need to be a stone-faced thug all the time. Guys feel just as deeply as women do.

1. Make It Easy On Yourself, by The Walker Brothers

Words of consolation don’t make rejection sting any less. If you’re the one doing the dumping, “make it easy on yourself.”