Top 11 Loser Songs

Top 11 Loser Songs


Without losers, where would the winners be? – Casey Stengel

We’ll hear plenty this month about the new inductees to the Rock and Roll Hall of Fame. Enough already. Let’s celebrate the failures for a change with our Top 11 Songs About Losers.

11. Margaritaville by Jimmy Buffett

When Margaritaville hit the top ten in 1977, it forever cast Jimmy Buffett as the perennial beach bum, drinking the day away. “I was with some friends in a Mexican restaurant on a hot day in Austin, Texas,” Buffett explained in Southern Living.  “We had a couple of margaritas and they really tasted good. The idea starting forming then. Afterwards I was heading back home to Key West. I wrote the song in about six minutes driving down the Overseas Highway. That was a good six minutes.”

Buffett is hardly the slacker he portrays in the song. The entrepreneur has turned what he calls “Drunken Caribbean Rock ‘n’ Roll” into an empire of restaurants, casinos and merchandise that earns $100 million a year. “It’s been a good song to me, very good,” he told Stuff. “It has created a whole world for me and for so many people. I was lucky to write it. And I must point out, I say ‘I wrote it’ but the songs, when they’re done, they belong to the people. This one, well, it’s my hit. Plain and simple.”

10. Beautiful Loser by Bob Seger

The title character of Bob Seger’s Beautiful Loser represents “people who set their goals so high that they’re impossible, so they have comfort in failing,” the singer-songwriter told NPR. But the song is not autobiographical. “A lot of people think I wrote Beautiful Loser about myself,” Seger said in Creem magazine. “I got the idea for that song from a book of Leonard Cohen poetry by the same name. The song was about underachievers in general. I very rarely write about myself that much. I draw on my own experiences like anyone else, but I’m not what you’d call auteuristic. I’m not like my songs at all. I’m a lot more up person than what I write.”

Seger’s career was in the doldrums until the release of Beautiful Loser. The hard rocking Seger told Rolling Stone that Glenn Frey of the Eagles encouraged him to vary his style. “It took over a year to put it together. I wrote five different Beautiful Losers before I settled on one for the record. There was a ballad, a blues, I couldn’t find the right tone. So I played it for Glenn Frey, an old friend, to get some advice. He was the first person to ever hear it. And he loved it, so I stuck with the song until it all got pieced together.”

9. Tobacco Road by the Nashville Teens

John Loudermilk is a prolific songwriter of the ‘60s and ‘70s who wrote hits like Indian Reservation for Paul Revere and the Raiders and Then You Can Tell Me Goodbye for the Casinos. Loudermilk drew from his childhood in Durham, North Carolina to write Tobacco Road, a hit for the Nashville Teens in 1964. The song describes a life of misery in the South: “Grew up in a rusty shack / All I had was hangin’ on my back / Only you know how I loathe / This place called Tobacco Road.”

Loudermilk told American Songwriter that he was inspired by one of his idols, blues and protest singer Josh White. “I think Tobacco Road sounded just like Josh White’s music, bitter and biting. I got the idea for writing that song from a road in our town that was called Tobacco Road because it was where they rolled the hogsheads full of tobacco down to the river to be loaded onto barges. Along that road were a lot of real tough, seedy-type people, and your folks would have just died if they thought you ever went down there.”

8. Poor Poor Pitiful Me by Warren Zevon, Linda Ronstadt and Terri Clark

Talk about a loser… in Warren Zevon’s Poor Poor Pitiful Me, Linda Ronstadt can’t even get suicide right: “Well I lay my head on the railroad track / Waiting on the Double E / But the train don’t run by here no more / Poor poor pitiful me.” Jackson Browne, Zevon’s friend and producer, introduced Ronstadt to the song.

Ronstadt recalled in her autobiography Simple Dreams that Browne demonstrated what would become one of her signature hits. “I recently came across an old cassette tape recorded in my living room in Malibu, sometime around 1976, of Jackson teaching me to sing Zevon’s Poor Poor Pitiful Me, plugging a song for his buddy whose writing he so admired. Listening to the tape, I wonder why Jackson didn’t record it himself, because he sang it better than I did.”

Poor Poor Pitiful Me would become a top ten country hit in 1996 for Terri Clark, who told Billboard how she discovered the tune. “I heard Linda Ronstadt’s version of Poor Poor Pitiful Me one day in the gym when I was working out and I thought, what a cool song. What a great country record that could make. I started doing it live, and it worked. It seems to be the one they really dig. The audience is getting younger, and it’s cool. The kids find it brand-new, and the baby boomers will remember it.”

Poor Poor Pitiful Me by Warren Zevon

Poor Poor Pitiful Me by Linda Ronstadt:

Poor Poor Pitiful Me by Terri Clark:

7. I Fought the Law by the Bobby Fuller Four and the Clash

In July 1966 singer-guitarist Bobby Fuller was found dead in his car, an apparent suicide at age 23. Some have called it murder. In his biggest hit, I Fought the Law, Fuller also comes to a bad end, “breakin’ rocks in the hot sun.” Written by Sonny Curtis of the post-Buddy Holly Crickets, the song became a top ten hit for Fuller and “I fought the law and the law won” entered the country’s lexicon.

Click here to continue to Page 2!

Pages: 1 2

One Response to "Top 11 Loser Songs"

  1. Eric Leo   October 28, 2016 at 9:51 am

    How about “YUMMY YUMMY YUMMY” by The 1910 Fruit Gum Company?


Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.