5 Inspirational Macklemore Songs You Probably Haven’t Heard

What works of pop-media (books, TV, music, movies, art) have had the most profound impact on your life?

For over two years, I would yammer to anyone that was even remotely interested in hip-hop about Macklemore. ”He’s a white guy from Seattle who raps about real issues and his life, not just 40s, bitches, and blunts, man,” or so my elevator pitch would go.

Recently, Ben (Macklemore) has experienced worldwide success thanks to the insanely popular “Thrift Shop”. I recently expressed my dislike for the song, which instantly brought accusations that my antipathy was only because an artist I had liked for a while suddenly became popular. This is a half truth, sure.

While I am subject to the phenomenon of snobbery that anyone who was a fan of an artist before they got big is, what actually ’bothers’ me is that of all his work, the song people now associate Macklemore with is the one with the least important message.

It’d be the equivalent of the most moving, dramatic, and soul-enriching film you’ve ever seen only being remembered by the masses for a scene that was merely comic relief.

And that’s exactly what I fear– that Mack will fade into one-hit wonder oblivion (yes, you could make arguments about “Same Love” also being a hit- I just wish it was as popular as “Thrift Shop”) and be remembered only as the goofy white guy that rapped about poppin’ tags and zebra jammies, when his lyrics have so much more to offer the world.

Ultimately, it’s not his success that bothers me at all, considering I used to tell anyone that would listen about his music.  It’s just that I wish it was almost any other song of his that people got to experience first. 

The source of this contradiction and, sure- selfishness- is that, more than any other musician, Ben has had a lasting and extremely positive impact on my life and creative pursuits, one that I can only begin to describe in this post. Thus, I have a strong emotional connection with his music, which doesn’t make me a bigger or ‘better’ fan of his compared to anyone else, it just makes me feel a certain away when I hear “oh yeah Macklemore, I know him, the Thrift Shop guy, right?”

But that’s the amazing thing about music, is it not? One song can mean a thousand different things to a thousand different people.

That, and as my brother put it so eloquently, I am going to miss paying less than a small fortune to see him live again.

In my small effort to share the so-much-more Macklemore has to offer, here are five songs of his that inspired me to be more:

1. Inhale Deep

Cause it’s easier to spend your life drunk and high on drugs
Than to put everything in a recording, put it out, and then get judged

I really paid attention to the lyrics and message in “Inhale Deep” when I was beginning the ascent out of what I consider to be the lowest point of my life. I devolved from leading an active social life and being on my college’s rowing team to falling into the 420 24/7 lifestyle, and my social circle consisting of whoever was out of their mind next to me on the couch staring at the TV.

For nearly two years, I had been in denial that marijuana had any kind of effect on my social skills, grades, relationship with my family. . .anything. After catching mono the winter of my junior year, reducing what semblance of fitness I had left to skin and bones, and giving me plenty of time in social isolation to evaluate where my life was headed, I started to see how much my lifestyle had been holding me back from reaching my potential.

“Inhale Deep” spoke to me at just the right time, in the way a song can come on the radio that perfectly describes your life and emotions in that instant. It was refreshing and a relief to hear that somebody else recognized the drug’s subtle power in stifling creative productivity and causing life to revolve around fear and anxiety, when everyone I had surrounded myself with at college was telling me the opposite, still in denial.

2. Vipassana

So I stare into this paper instead of sitting at a cubicle
Take all the ugly shit inside and try to make it beautiful
Use the cement from rock bottom and make it musical

A hip-hop song about meditation? It’s exactly as amazing as it sounds. The track peaked my interest in the practice, and now that it’s a daily habit of mine I can relate to many of the realizations and ideas mentioned in the lyrics.

The song touches on mindfulness, permanence, and other spiritual concepts that I was just starting to comprehend a little over a year ago. Around that time, going on a Vipassana (a 10-day retreat where you don’t say a single word the entire time) retreat also made its way onto my Bucket List.

3. Starting Over

But I’d rather live tellin’ the truth and be judged for my mistakes
Than falsely held up, given props, loved and praised

To me, much of Ben’s appeal, more than any other artist I’ve ever listened to, is the pure unadulterated honesty about his life. A recovering alcoholic and drug addict, he recounts in detail the pain that falling off the wagon after three years of sobriety caused him, his family, and potentially his relationship with his fans. In a chill-inducing verse, Mack discusses having a fan come up to him just 48 hours after his relapse, confessing that she wouldn’t be standing there today if not for his music.

While the addictions I fought were undoubtedly very minor in comparison to what Ben went through, the song made me realize that this is one of the secrets to producing great art- telling the truth about life in the simplest and most relatable manner possible. For too long my writing endeavors were spent trying to please an audience that didn’t exist. This ultimately lead to frustration and little improvement in the craft. As soon as I started just writing whatever was on my heart and mind, several things happened- I started having fun again, my motivation to write everyday couldn’t be contained, and perhaps most rewarding, people began to reach out to me and tell me that they enjoyed my writing and that they could relate to my message.

4. Hold Your Head Up

Freedom is acknowledging the mask you have on
And possessing the strength to take it off

The ultimate pick-me up/pep-talk track. “Hold Your Head Up”, with it’s mellow, rainy day kind-of-vibe, touches on all the truisms and cliches you become desensitized to from hearing so many times in your youth. Be true to yourself, accept the things you cannot change, choose your friends and job wisely, and so on. While such a song concept could easily come off as try-hard and cliche, Ben pulled it off in such a way that makes the song really hit home to absolutely anyone across all walks of life.

5. The End

I strayed, you brought me back in
Trying to sneak a flask outside of that gym
She said “You don’t need that, look within.”

At first listen, “The End” sounds like a charming recollection and romanticization of a high school prom or homecoming dance. When you examine the lyrics further and take into account Ben’s past, though, you start to realize that something bigger is being referred to. In my mind, he is using “Winter Ball 2012″ as a metaphor for his relationship with music, how he was scared of the places it would take him at first, how it makes him feel alive, and ultimately how it would save his life and take him to the heights he is today.

The dance could also be a metaphor for life in general, and his date reality, but however you interpret it, it’s one of the most touching, beautiful, and well-crafted hip-hop songs you will ever hear.

Honorable mentions (like I could stop at five): “White Privilege”“The Town”“I Said Hey”“The Magic”“Contradiction”“Tommy Chong”


  1. Kayla Reply

    One of the most inspirational of his works to me is Fallin. I know so many people that cut, and do drugs&alcohol that it reminds me of their lives and how they feel with depression. It’s on the Unplanned Mixtape 🙂

    • Thanks for the comment, Kayla! I love “Fallin”, too–Mack’s pain from the breakup with his girlfriend comes through so strongly in both the lyrics and the beat.

  2. Raven Reply

    I’m actually kind of surprised there are other people out there that appreciate macklemore like I do=) pleasantly surprised, I’m a new fan and like most people I first got into him and heard about him through “thrift shop” but since listening to his other music I too am now annoyed by the song. Like most singles, it’s such a shallow representation of his music and talent and true depth as a person, it will be a shame if that’s all he’s known for but the fact that you have this blog and are interested in the true him shows that there’s hope for the rest of the world. I came on here because of your mention of his song “the end”, I wanted to know what it really meant, if it was speaking about a high school dance and special experience he had with a girl. If that was all that it was about it’s still impressive because the way he does it is so intimate and beautiful and soulful; but after looking around and reading some other takes on it I’ve realized that there’s an even deeper meaning to it. I’ve listened to it multiple times and it never occurred to me that when he says “Winter Ball 2012 The End”, that he was probably referring to the Mayan calendar ending and thus the end of the worldO.O(as some people believed). So I thank you for being a fellow lover of Ben/macklemore and partially reigniting my faith in humanity=D (p.s. sorry for leaving such a long comment, I don’t make an effort to speak my mind online or in public often, unless I’m inspired to do so and you and macklemore inspire me so thanks again).

    • Thanks so much for the long comment, Raven!

      “The End” is still one of my favorites–partly because it’s one of those songs you can interpret one way, then listen to again a few months later and interpret completely different. Mack truly gets better the deeper into his stuff you go–if you haven’t, check out his first EP from 2000, Open Your Eyes, on YouTube.

      Thanks again for reading and taking the time to write!

  3. jessie Reply

    love this, I’m newly sober and these tunes keep me coming back, reminds me how easy my brain makes it to forget where i was and how low i got… thank you

    • Thanks for the comment, Jessie, and congrats on your sobriety. Stay strong!

  4. Collin Reply

    As someone who was introduced to Macklemore by Thrift Shop, I totally agree that most of his songs are unfairly overlooked. But me being a fan of Macklemore goes to show how Thrift Shop was a good thing; without it, me and countless others would never have been exposed to him. So while it’s a shallow song, it was good for him to get his name out there.

  5. Danny Chaney Reply

    Love the article I know it’s late but I just happened to find Macklemore right before going into rehab for … the stuff that has taken 4 of his friends lives according to the track that saved me “Otherside” I brought him up to the facilitator and let him know it wasn’t typical “money,hoes, and clothes” rap and hopefully turned a few more people on to him I actually lived in his neighborhood Capitol Hill way back anyhow just wanted to say Thanks for the article

    • Thanks for the comment Danny and I’m glad his music had such a positive impact on you, too!

  6. Angelica Reply

    Hi, I love everything about this.
    I read from Colombia, and i really love music of Macklemore,and fortunately never gone through a situation where you think this is the end but the lyrics of macklemore are very inspiring.

  7. Jared Reply

    I was introduced first through the popular hits on Heist. For some reason I listened to the rest of his album and stumbled upon the treasure that is Macklemore. Naturally, I needed (and still need) more. Thank you Andrew for this website, the honorable mentions, and the bucket list (which I can’t click on until I finish posting this). And thanks to the commenters who also made recommendations.

    • Glad you enjoyed the post, Jared! His stuff truly gets better the deeper and deeper you dig!

  8. This article is pretty old but probably around the time I got into macklemore. I pretty much did the same thing you did… Pitched a socially aware white rapper from Seattle and was mortified when it was thrift shop he was becoming known for. I found this article while googling to see if “the end” touched anyone else the way it did me. I recently just got out of a 7 year relationship and ‘the end’ was one of “our” songs. Months later I find myself revisiting that song in reminiscence. Hell, I wrote some poetry to that song for her, poetry that she still keeps folded up in a small pocket in her purse. Macklemore really made songs that made me “feel,” interestingly modern songs seem to gravitate to escaping emotions with sex and drugs. Just my two cents.

    • Hi Zed–I am touched by your story and I am glad that you can relate to my little post. “The End” is indeed an extremely powerful song (and obviously I imagine probably even moreso in your circumstance). Here’s hoping that his new album has some tracks of that caliber on it.

  9. Benjamin Reply

    Beautiful music, beautiful musician

  10. Ashley Taylor Reply

    This man is pure genius!! He sends such strong and powerful messages with the majority of his songs. I would have loved to have seen his rise to fame and notoriaty come from work that in my opinion is so much greater than “Thrift shop” as well. Even though it still sends a positive message about not buying into the hype of material things and just being you he definitely has more than that to offer. I honestly don’t think I’ve listened to a track that I’ve not appreciated in one way or another just from the words laid down. Being able to write the more mainstream music and go on about zebra jammies and mopeds all while speaking real truth is, like I said to start, pure genius.

  11. Brianna Cooper Reply

    This explains exactly my thoughts on The End. However, one question; what does Macklemore mean by “At the end of this night, yeah I’ll be set free” and everything about this girl that seemingly loses her life?

    • Meghan Reply

      I was wondering the same thing. While the metaphor idea works for some of the song, the ending doesn’t add uo. Like the line you quoted, and “seconds away from god” and “I will never see you again”
      It almost hints towards the death of the ‘main character’ or the girl.

  12. Cassandra Reply

    Great article Andrew! I am a huge fan of Macklemore and one of my absolute favorite songs is “Starting Over”.

    • andrewelsass Reply

      It still gets me after all these years!

  13. David Dennis Reply

    Awesome article Andrew – I struggle with song interpretations and was just introduced to Mac through leadership training at my office where we are learning to think better (meditate), write more and be truth tellers (ask curious questions and have uncomfortable conversations in the spirit of getting better) rather than taking the easy path – I am a 51 year old executive and have come to love Mac and now understand why my 19 year old son is such a fan (although we favor different songs😀). I love his new Gemini album that is filled with so many personally meaningful lyrics that it has become one of my favorite albums of all time – “Intentions”, “Excavate”, “10 Million” and “Good Ole Days” just to name a few. I am sure you are aware but just thought I would share my thoughts – the songs are so meaningful that they often bring me to tears – I cannot wait to listen to the songs mentioned in your article. DD

    • andrewelsass Reply

      Hi David,

      Thanks for sharing how you found Mac’s music–it seems like everyone has a unique story about how and when they discovered it, and I’m glad it’s something you and your son can share together. Also, that sounds like much more exciting office training than I ever had. Thanks again for taking the time to write!

  14. Thanks man. Really well written. The perfect balance of you and him. I’m an old fan of Ben’s too, and his music helped me through some tough times too. Keep on.

  15. I have never relaly relpied to articles. Sometimes i start but then just leave it and go to another site. I just wanna say, that one of the first songs of Mack i heard was Thrift shop and I wasnt much of a fan of it. This one song made me think Mack was just another rapper. But last month i accidently came upon the song The Town and my mind was blown. Im originally from Vancouver and moved when I was 3 years old so i dont have mich memory of thr city. When i listened to The Town, my eyes watered up because I never visited Vancity in my life after I left and i just had the urge to go bavk and visit. And since Seattle and Vancouver basically siblings I had a love for Seattle that I never knew.

    Hell even writing all this is making me a little emotionally lol.

    I wait for the days I can visit home as well as Seattle. Two beautiful cities.


    The Bearded Child

    • andrewelsass Reply

      Thanks for the comment and I can relate to how you feel–I had never even been to Seattle when I first heard the “The Town” but it still made me feel emotional toward a place I had never even been!

  16. chris Reply

    I love Macklemore so much…
    i was actually fairly surprised that Wing$ wasn’t in here

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