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The Top 5 Songs About Debt & Financial Struggle

The best musicians of each generation make songs that capture the feelings of the moment. That is to say, true cultural icons sing songs about what most people in their day and age are going through. With debt as a major part of most American households (almost 87 percent of families are in debt according to, it only makes sense that many brilliant artists of our generation (and generations past) have written some incredible songs about personal financial heartache and struggle.

These are songs that self-reflect on the pain of working to scrape by, in spite of that burning desire inside all of us to pursue our dreams and passions. This desire to follow our passions is something that the 18th century poet, Gerard Manley Hopkins, so eloquently described as a person’s “instress”. The "instress" is that drive inside all of us that pushes us to be what we are truly supposed to be, what we have been put on this earth to do.

Too many people work a job they hate, to get money they need, to barely pay off the debts they owe. It’s a bleak existence. We all know that there has to be more to life. The songs that have been compiled for the following list are songs that capture this ageless struggle of what it’s like to be broke with dreams of something better.

5. “Scenes from an Italian Restaurant” – Billy Joel

Billy Joel’s 1977 hit song “Scenes from an Italian Restaurant” is a narrative opus that captures the heartbreaking tale of ne’er do-well high school sweethearts Brenda and Eddie, who dreamed of a perfect life together built on their love. However, instead of happily ever after, what they found was a life of financial ruin brought on by ignorance, laziness, and naiveté. The song’s heart-wrenching tale finds its financial pulse within the following lyrics:

Brenda and Eddie were still going

Steady in the summer of ‘75

When they decided the marriage would

Be at the end of July

Everyone said they were crazy

Brenda you know you’re much too lazy

Eddie could never afford to live that

Kind of life

But there we were wavin’ Brenda and

Eddie goodbye

They got an apartment

With deep pile carpet

And a couple of paintings from Sears

A big waterbed that they bought

With the bread

They had saved for a couple of years

They started to fight

When the money got tight

And they just didn’t count

On the tears

Brenda and Eddie got swept away by their high school romance and couldn’t see past the fairy tale. They got married and started their life together, in spite of the warnings given by those close to them. They refused to understand that despite what the Beatles had always taught them, love is NOT all you need. What they really needed was more education. They probably should have gone to college after high school instead of rushing to settle down together. Ironically, they did get their education. That is, they learned their lesson the hard way and it really cost them.

4. Juicy -- The Notorious B.I.G

“Juicy” is one of the late great rapper Biggie Smalls’s most recognizable hits (if not the most recognizable) and for good reason. It is a lyrical masterpiece that is to rap music what A Tale of Two Cities is to English Literature. However, instead of Dickens’s comparison of the cities of Paris and London – “It was the best of times, it was the worst of times” -- Biggie compares his life before rap -- where he and his mother struggled to get by -- to his life after rap -- where he was living a life of complete luxury. The following verse highlights Biggie’s Dickensian technique, which he uses to compare the ups and downs of his financial journey:

Super Nintendo, Sega Genesis

When I was dead broke, man, I couldn’t picture this

50-inch screen, money green leather sofa

Got two rides, a limousine with a chauffeur

Phone bill about two G’s flat

No need to worry, my accountant handles that

And my whole crew is loungin’

Celebratin’ everyday, no more public housin’

Thinkin’ back on my one-room shack

Now my mom pimps an Ac’ with minks on her back

And she loves to show me off of course

Smiles every time my face is up in The Source

We used to fuss when the landlord dissed us

No heat, wonder why Christmas missed us

Birthdays were the worst days

Now we sip champagne when we thirsty

It’s not hard to see why this song made the list; the financial struggle that Biggie overcame is front and center in this compelling work. The palpable pain of having so little and the subsequent relief of finally getting everything he could ever want, has an alluring effect on the listener, and one cannot help but be pulled into the song’s story and feel sympathy for this man’s struggle, and likewise, want to celebrate his triumphant victory. He does what we all want to do, what we are all here to do: achieve our dreams by following our “instress” in spite of our financial circumstances. Unfortunately, however, not everyone achieves glory by chasing their dreams and throwing financial concern to the wind. The next song on the list is a perfect example of this hard truth.

3. Against the Wind – Bob Seger

“Against the Wind” is a song that harkens back to an earlier time and reflects on the point in a man’s life where nothing is as it seems. For some this might be a controversial choice for the list. The reason I say that is because unlike the other songs on the list, the financial struggle of this song is only addressed directly in one line of one stanza:

Guess I lost my way

There were oh so many roads

I was livin’ to run and runnin’ to live

Never worried about payin’ or even how much I owe

The speaker in this song’s narrative highlights the struggle of being a young, fool-hearty man trapped in a world that seems to stand in his way at every turn. The whole song is a paradox; he is a man reflecting back on a better time that wasn’t actually better. In other words, the good ol’ days weren’t so good after all. Nonetheless, the song has an awareness of this, and that awareness is its saving grace.

"Against the Wind" shows us that ignorance is in fact bliss. This sentiment is captured perfectly in the lyrics, “I wish I didn’t know now, what I didn’t know then.” It is a chill-inducing line to say the least, because I think we can all relate to looking back on our lives at one point or another, and wondering how we could have thought the way we did and been so naive. “Against the Wind” is a representation of the heartache that often comes with growing up. True wisdom, financial or otherwise, is often acquired through making mistakes as we learn and grow. As we saw earlier, with Brenda and Eddie in Billy Joel’s song, when we are young we make bold, foolish decisions that can end up hurting us in the end. In other words, because of our youthful ignorance and unrelenting dream chasing, we oftentimes end up doing things that lead us to financial ruin. Some might say that the experience and the journey pay for themselves in the lessons that they teach. Perhaps. Or maybe it is just like the old adage goes, “Youth is wasted on the young.”

Nevertheless, “Against the Wind” is more than a song with one line about the cause and effect of not having money or making good on one’s debts, it encapsulates the feeling of the struggle itself, as we all try to make it in this world. At one time or another in our financial journey, we travel “Against the Wind” as it were, and we discover whether or not we truly have what it takes to get by (and perhaps even thrive) in a world that too often says "no."

2. “Mockingbird” – Eminem

“Mockingbird” is just one of many Eminem songs that is written directly to his daughter. Nonetheless, it prominently stands out amongst the others in the category. It is a new-age rap lullaby that is the epitome of what this blog post is trying to express. “Mockingbird” could have just as easily have been number one on the list. Debt and financial struggle are not only on display in this song, they are the point on which the whole narrative of the tune resides. The gut-wrenching heartache brought on by lack of funds is palpable in the following verse:

It’s funny

I remember back one year when Daddy had no money

Mommy wrapped the Christmas presents up

And stuck them under the tree

And some of them were from me

‘Cause daddy couldn’t buy ‘em

I’ll never forget that Christmas

I sat up the whole night cryin’

‘Cause daddy felt like a bum

See daddy had a job

But his job was to keep the food on the table for

You and mom

And at the time, every house that we lived in

Either kept getting broken into or robbed

Or shot up on the block

And your mom, was saving money

For you in a jar trying to start a piggy bank for you

So you can go to college

Almost had a thousand dollars

‘Till someone broke in and stole it

And I know it hurt so bad it broke your mama’s heart

And it seemed like everything was just starting

To fall apart

Mom and dad were arguing a lot

So mama moved back on the Chalmers in the flat

One bedroom apartment

And dad moved back to the other side of 8 mile and Novarra

And that’s when daddy went to California with his CD

And met Dr. Dre and flew you and mama out to see me

But daddy had to work

And you and mama had to leave me

Then you started seeing daddy on the TV

Much like “Juicy”, Eminem puts Christmas directly in the spotlight of his song about financial heartache and struggle. There is something about that holiday that seems to amplify one’s state of financial being. If you are happy and abundant, then that’s what Christmas will feel like. However, if you are not (like Biggie and Em) then expect an amplification of the feelings of lack and insufficiency. No one could ever find all the right words to speak of Eminem’s lyrical brilliance; luckily, that is not what this blog post is here to do. What this post is trying to clarify is that when it comes to providing the listener with a visceral feeling of what its like to have nothing and struggle financially, one would be hard pressed to find anything better than “Mockingbird.”

Yet, nevertheless…

1. “Maggie’s Farm” – Bob Dylan

“Maggie’s Farm” is the ultimate anthem of struggling to get by and breaking your back to make end’s meet. It is sung from the point of view of a laborer who has finally had enough, and is now "going to work on Maggie’s Farm no more."

Verse after verse he lists all of the people in Maggie’s family and the specific reason why he’s had enough of working on her farm. The speaker may be far from financially well off, but this song represents his decision: that even being completely broke is better than putting up with these terrible working conditions any longer. Take verse two as an example. In this verse the speaker calls out Maggie’s brother, and the petty, belittling treatment he exerts over him constantly, and that he has finally had enough of it:

Well, he hands you a nickel

And he hands you a dime

And he asks you with a grin

If you are having a good time

Then he fines you every time you slam the door

I ain’t gonna work for Maggie’s brother no more

The reason that this song is number one on the list is because it fully encapsulates everything this blog post has been about, and it does so throughout the song's entirety. It does this not only lyrically through the direct and simple words it chooses to use, but it does so quite literally, by using a poetic technique that keeps repeating the same rhyme pattern over and over, verse after verse, simply changing out a different family member of Maggie’s and a different reason why the speaker can no longer work on the farm. This repetition recreates the repetitive, routine and mundane pattern often associated with any laborious activity. In other words, the song is literally mimicking the pattern and effect of work itself. The song is so laborious that we should probably get paid just for listening to it. (I say that sarcastically of course) Moreover, like the previous four songs on the list, this song highlights the drive within us (our “instress”) to pursue something better:

Well, I wake up in the morning,

Fold my hands and pray for rain

I got a head full of ideas

That are drivin’ me insane

It’s a shame the way she makes me scrub the floor

I ain’t gonna work on Maggie’s Farm no more

The speaker calls on God to save him from having to work on the farm, praying for rain so he can stay inside and think. He has these important ideas in his head -- perhaps these are ideas to be something better than a simple laborer. Nonetheless, his dreams are soon dashed, because even if it does rain, and he can stay inside, there’s always more work to do. That is, Maggie makes him scrub the floor instead. He realizes that the work will only stop if he stops working. So that’s why “he ain’t gonna work on Maggie’s Farm no more."

Conclusion: The Right Balance

Whether it’s high school sweethearts who let love blind them, aspiring rappers trying to get by while pursuing their dreams, or young men and women who throw financial care to the wind in pursuit of something better, debt and financial struggle come in many forms. Nonetheless, it’s in finding the right balance between the opposing forces of work and joy, where one finds the path to financial freedom and happiness. Fortunately, we have been blessed with these stories of others, so that we can learn from their example and act in a way that is in our own financial interest.


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