Artist - Midland 3

The Best Midland Songs

November 25, 2022 3:55 pm GMT
Last Edited June 21, 2023 10:18 am GMT

email logo
link icon

Link copied

Content Sponsor

One hot summer night in 2017, at around 2am, I was sitting with a friend in a Mexican restaurant in Nashville. We were drinking tequila and bemoaning the fact that Music City was not what it once was.

Just as we’d decided that we would never see their like again, the door to the bar swung open and there stood a most unlikely trio, dressed up beyond the nines in vintage hillbilly formal and swaying slightly in the warm evening air.

It was Midland, and we conceded that we might be wrong about Nashville after all.

Here we picked out 15 of their best moments so far:

Big Machine | 2017

Make A Little

In the follow up to their debut single our intrepid trio are bravely trying to make the whole world a better place just by spreading a little of their love; and if their ardent fans are anything to go by, it’s a plan that might just work. Written by the band with Shane McAnally and Josh Osborne, it gets our fannies fluttering every time it comes on.

Big Machine | 2022

Adios Cowboy

The boys are trying to make a long-distance relationship work, but it’s too late. By the time they get off the phone and get all the way over to Texas, the only thing left of their relationship is a ring by a wine glass and a note telling them it’s all over.

Big Machine | 2019

Roll Away

Midland certainly know how to kick an album off and they know how to close one out too. The last track on their sophomore album, Let It Roll, is a deliciously creamy slice of cosmic country that feels like driving off into the sunset and leaving the worries of the world behind.

Big Machine | 2017

Lonely For You Only

If they wanted to, Midland could have any girl they want, but it’s not just any girl that’s got them going completely lala. It’s not like all the other girls don’t show any interest in them, but sadly for Mark and the boys, “waking up with strangers ain’t no fix at all.” Their just sitting there, waiting for the phone to ring and checking out of the window every time a car drives by. Poor loves, they’ve really got it bad this time.

Big Machine | 2022

The Last Resort

Another day, another leaving note. On the title track to their third studio album, the band were channelling Jimmy Buffett for a kind of countrified Club Tropicana as they hit ever bar on the A1A in search of boozy salvation. “My buzz is high, my expectations low”, they sing, “and I got nowhere else to go”.

Big Machine | 2019

Fourteen Gears

They’re off driving down the highway again on this classic truck song off their second album, pushing their Peterbilt to the limit to get there on time. At least this time they’re going in the right direction, back home before it’s too late. We don’t want to find another bloody break up note.

Big Machine | 2018

The Gator Boys

Midland rewind the clock and set us straight on their origin story, explaining to us all just why it is that everyone calls them “The Gator Boys” and what it is about them that drives the ladies absolutely wild. Apparently it’s all down to their alligator boots and their tight Wrangler pants. Just googling nearest alligator boots stockists now.

Big Machine | 2019

Cheatin’ Songs

Those poor old Gator Boys, they just can’t get a break when it comes to love. This time it’s their wives who are doing all the heart breaking. Slipping their wedding rings into their tight fitting jeans and sneaking around behind their backs. “Maybe I’m jealous”, they sing, “wouldn’t you be? If you saw the way she ain’t looking at me”.

Big Machine | 2017

Check Cashin’ Country

Midland are out on the road 24/7 365 and their Spotify streams sure aren’t paying for their Gant Wrangler jeans. Luckily they’re not in it for the money, they’re just a bunch of dudes out there night after night giving it their all for country music lovers like us. It’s a goddamn impossible way of life.

Big Machine | 2019


Sadly life on the road notches up another casualty and the boys are staring down the barrel of another break up as they had out on tour. Another girlfriend has had enough and regrets ever being foolish enough to think she could change them. Playboys will be playboys after all.

Big Machine | 2017

Burn Out

Sometimes it gets to them. All that heartbreak. Sure, most nights they just get up on that stage and shake their peachy little bums and forget all about it, but there are nights when it all comes back to them and they wonder what life’s all about and if love can ever really last.

Big Machine | 2021

Cowgirl Blues

It’s a foot-stomping handclapping party on this old-timey prairie song off the Sonic Ranch soundtrack. One of Midland’s most infectious and wonderfully simple songs has become a firm fan favourite ever since turning up in their CMT documentary. The only question is, who sings it best? Mark or Jess?

Big Machine | 2022

Longneck Way To Go

D’Artagnan joined forces with the Three Musketeers for this neo-traditionalist country kilonova on The Last Resort: Greetings From. Now who’s who?! Jon Pard is obviously D’Artagnan, the brave and clever romantic hero, driven by love and ruled by chivalry, but occasionally prone to fall into amoral behaviour.

Jess is the oldest, so he’s probably Athos, tortured by a deep melancholy, the source of which no one knows.

Cameron is the quiet and handsome Aramis. Slightly foppish and very stylish, you’re never sure if his mind might be elsewhere. On a mysterious French lover perhaps?

Which means that Mark must be Porthos. Loud, brash, and extremely vain, he enjoys outfitting himself handsomely and has a mistress who is the wife of a wealthy attorney. Probably sounds about right.

Big Machine | 2017

This Old Heart

It’s all got too much for them. Their hearts can’t take any more of this constant suffering! “This old heart’s had all it can take”, they sing, deciding it needs “a little less wrecking and lot more affection” and “some loving and a little less ache”. They’re absolutely right of course. You need to look after yourself, especially when it comes to love. There’s absolutely no point in being with someone who doesn’t appreciate you and love you despite your faults. After all, the key to love is to love back.

Big Machine | 2017

Drinkin’ Problem

Midland’s first is still their finest. Written with McAnally and Osborne, ‘Drinkin’ Problem’ was their debut single. A driving country ballad dripping in double meaning that sounded both like every great country song ever written and as fresh and new as a cold glass of iced lemonade on a sunny day. We knew it was great as soon as we heard it and it still sounds just as great today.


Check out our Holler playlist of the Best Midland Songs below:


For more on Midland, see below:

Written by Mark Hagen
Content Sponsor
Holler Country Music

INTERVIEWIn Conversation: Midland

Brooks & Dunn - Brand New Man Album Cover

Brooks & Dunn - Brand New Man

Holler Country Music

Randall King - Shot Glass

Album – Passage Du Desir – Johnny Blue Skies

'Scooter Blues' by Johnny Blue Skies – Lyrics & Meaning