Top Ten Most Inspiring Macklemore Songs

I've become quite the fan this past week, and many of his songs are deeply personal and inspiring. A simple glance at the lyrics really does the trick too. So I hope anyone viewing this list is open to checking out his other work without biases.

To anyone with unwavering opinions, don't worry, I can already feel myself getting sick of these songs (been playing them on loop for days... ) so expect this little obsessive phase to be over within a month or so.

The Top Ten

1 Otherside Otherside

I believe this song will forever be my favorite of Macklemore's. It's just one of those artistic moments when everything just falls into place, and as he personally has felt the grip of drug addiction, he is essentially pouring his heart out into this song. I would know, sometimes there's a drawing that seems to draw itself. When my soul goes into it and it all just... Works. The same is applied here, and it's one of the most powerful songs I've ever heard, especially the remix. - keycha1n

Heart on a plate. This is the soul of Mack through your ears. Enjoy.

No words can truly make you begin to comprehend how deep the lyrics are in this song

2 Same Love Same Love

This song has the most beautiful lyrics I have ever heard anyone sing. When Macklemore sings this song the lyrics and the Melodie literally just fall into place and you know that this is how the world is supposed to be. Some lines of this song have always and will always stay in my memory forever because they are just so strong. I have no words for Macklemore more or this song because it will definitely be my favourite song forever. I don't know any other artist that manages to talk about and express such important topics like these and make it sound so perfect. He puts so much thought and effort into his songs and while other artist let their music define them, Macklemore defines his music and that is why I love and support him.

Never gets old

This song is literally the perfect marriage equality song. I remember I didn't even care about homophobia until after listening to this song because I lived in a very liberal town and didn't even know it existed. But after listening to this, I just broke down and cried. For a pro-LGBT song to go mainstream... That's beautiful. Everything in this song is spot on. - keycha1n

Such good song it should definitely be higher.

3 Starting Over Starting Over

Absolute banger, great tune but also conveys a true message of relapse and hope.

Anyone who was inspired by Otherside, was probably even more inspired by Starting Over. It's songs like these when I really know Macklemore isn't just saying words. There are certain things you can't fake and the emotions expressed in this song is one of them. Just take a listen. The first time listening to it, I sobbed like a wuss and played it over and over... But only after Otherside. Otherwise, you might not understand. - keycha1n

4 Inhale Deep

"it's always the darkest part of the night right before the sun has its break through. The spirit's there to knock you down, but if you make that the end you'll never know the beauty of being able to stand up again."
An older gem of his! - keycha1n

5 Make the Money

"Take away the dot com, name, love, fans, Twitter followers, and the buzz. See, you keep the issues but you take away the drugs and I had to find out who I really was. Who I really wasn't. So sick of who I was becoming. Yeah, tired of running. Time to look at the man in the mirror until I can learn to love him."

Refreshing that this song came out after his mainstream songs. Considering he's spent the last two years making a new album instead of trying to go mainstream with more singles, I sincerely think he hasn't "sold out". I respect that he acknowledges that fame is tempting, but that it can't be why he raps. He seems down to earth, speaking about issues like homophobia, addiction, and racism. I hope he stays that way. It's the reason why I listen to him. - keycha1n

Should be higher.

6 Vipassana

"So I stare into this paper instead of sitting at a cubicle. Take all ugly stuff inside and try to make it beautiful. Use the cement from rock bottom and make it musical. So the people can relate to where I've been,
Where I'm going, what I've seen, what I've heard."

This is why I respect the dude. Plus, I love the jazzy tunes and instrumentals. - keycha1n

7 A Wake

"Celebrate our ignorance whilst these kids keep dying"
Respect dude

Honestly, I couldn't choose one lyric. So here's all of the gems...
"They say thirty is the new twenty, and twenty is the new thirty. Well, I guess makes sense, cause fifteen year olds seem twenty and twenty five year olds seem ten."
"Walk around looking through a fake lens. Apps this good, whose got time to make friends? "
"Don't even tweet, R.I. P Trayvon Martin. Don't wanna be that white dude, million man marchin', fighting for our freedom that my people stole."
"Don't get involved with the causes in mind, white privilege, white guilt, at the same dang time. So we just party like it's nineteen ninety nine. Celebrate the ignorance while these kids keep dying."

Heck, just listen to the song. Its too beautiful. I'm gonna end up reciting the whole thing! - keycha1n

8 Ten Thousand Hours

Thoroughly sorry about putting it so low! This song is so inspiring. Hard work and you will make it. As well as promoting an artistic career. I simply love this song. A wonderful opening track for The Heist. Ten thousand hours drawing... In willing to do it! - keycha1n

9 Jimmy Iovine

Paints the story of a Heist (hence, the album name) to get signed by a label and then being offered a greedy and exploitive deal, and declining. As Macklemore and Ryan Lewis are independent artists, I say its dang amazing they got so far (and mainstream!) without a supporting label. This song definitely takes a couple digs at big record companies saying:

"'No one will give you a better offer than us'
I replied: 'I appreciate the offer', thought that this is what I wanted. Rather be a starving artist than succeed at getting f*****."

Possibly the most hilarious and awesome line this album has to offer. - keycha1n

10 Wings

This song really helps me through hard times and it helps me see the bad in the world, very good song.

Great song about consumerism

This one should be top 10 this is one of his best songs

It is just an amazing song about our consumerism.

The Contenders

11 Drug Dealer

Man! Just listen to this song and you might understand, so real.


Gotta be top 3

I love this song.. it's so eal.. and the truth.. my drug dealer was my doctor for so long...

12 Growing Up

If u have a baby on the way and u are scared and feel unprepared. Listen to this track, it will change you and help you realise the gift u are about to receive.

13 Thin Line

One of my favorite lines in any song:
"The greatest trick the devil ever pulled was convincing women they looked better in their makeup."

This song is so somber and sad. Definitely a change from his previous upbeat party songs. But still sweet. - keycha1n

14 White Privilege II

This song may not be super catchy, but it addresses so many important issues and will forever inspire me to take action.

How is this not on the list?!

Dis be the best

15 Can't Hold Us

I'm officially addicted to this song. - RockFashionista

16 Kevin

This song was amazing, it was about his little brother overdosing.

This isn't on the list >?

17 Glorious

That beautiful song that Macklemore has dedicated to his beloved Grandma.

18 Thrift Shop

I miss when this song foray came out. - TopTensFan

19 Light Tunnels

Dope track No clue why this song wasn't on the list. Its about him going to award show, (winning a much deserved award) and feeling uncomfortable with how the media exploits it to capitalize on the controvesy that they seem to bring every year.

"Wait, hold up, don't play the music, let me finish
This feels so narcissistic, dressed as a celebration to conceal it's a business
Me, me, me, my, my image, my, my songs, my self interest
One big reality show that is scripted
And I can keep trying or get off the competition
I'd rather run out of my fifteen minutes
Than have life past me by and I forget to live it
But that doesn't mean retirement
But I don't like who I am in this environment
I forgot what this art's for
I didn't get through Freshman year to drop out as a Sophomore...
I got the people's attention, don't wanna lose it here
Thinking about my career, miserable here
But wanna make sure I'm invited next year
To the same damn party, ...more

20 Wednesday Morning

Song talks about growing hatred and the world we are building for the future of humanity and how it's terrible.

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List Stats

100 votes
20 listings
4 years, 192 days old

Top Remixes

1. Otherside
2. Starting Over
3. Same Love
1. Otherside
2. Inhale Deep
3. Starting Over


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