Best Country Music Songs of May 2021: “What We’re Listening To” Picks

Country Swag’s “What We’re Listening To” playlist highlights the wide range of our team’s favorite songs and artists when it comes to the country music genre.  At the end of the day, we are all fans first with a passion for country music and are eager to share with you all what we’ve got on repeat each month.

Find below each of our team member’s favorite songs and why in our May 2021 picks of the current best country music songs. Then be sure to give our Spotify account a follow and listen to our favorite tracks!





Stephanie Wagner, Founder

Pick: “When the Party’s Over” – Donovan Woods
Songwriters: Donovan Woods, Tom Douglas, Travis Wood

This month I have been hooked on Donovan Woods’ “When the Party’s Over”. This song randomly came on one day and immediately caught my attention. I love the picture it paints of the best part of the night not being the actual party, but when the party is over and you just have that alone time with that special someone. You can almost feel the magic described in the lyrics and I think it’s a moment of the night that everyone can relate to.

“‘Cause when the party’s over // I get to pull you in closer // We dance a little bit slower // Vinyl still spinning // Night’s just beginning // Girl, were gonna keep on rocking // Come on kiss me like no one’s watching // Your black dress gets to dropping // And the fireworks start // Yeah the night’s been so good, so far // But the best part, is when thе party’s over”


Dylan Bestler, Contributing Writer

Pick: “Momma Didn’t Raise No” – Garrett Biggs
Songwriters: Ethan Willis, Garrett Biggs, Joseph Maliszewski, Matthew McSwain

I found this song by accident after the playlist I made on YouTube ended. I left it on, because the title intrigued me, and it’s a good thing that I did. Not only is it very catchy, but the story is also inspiring. Biggs praises the way his mother raised him and credits her for shaping him into the strong man he is today, even though he wasn’t the most well-behaved child.

“Oh I might be a little rough around the edges // And from the outside looking in I might seem helpless // But I’ve been blessed with a strong backbone // I never could’ve made it on my own // And it’ll be written on my headstone // ‘Cause momma didn’t raise no”

I’ve written this before; my favorite songs are ones that are personal to the artist yet can relate to others as well. I feel most people don’t appreciate just how much their parents do for them until they move out or go away to college—at least that’s when I realized. Biggs captures that feeling well in this song and it hit me hard, especially right after Mother’s Day. I suggest checking out some other songs from Biggs’ catalog too!


Kristina Callahan, Contributing Writer

Pick: “More Time Fishin'” – Thomas Rhett
Songwriters: Josh Thompson, Rhett Akins, Thomas Rhett, Will Bundy

I love just about every song Thomas Rhett puts out, but this song really hits home for me. After a crazy and difficult year and a half, Rhett gives us some sound advice everyone should take to heart in his new song “More Time Fishin’.”

“You can spend your whole life // Tryin’ to make a killin’ // But what’s it all worth without a little livin’? // Don’t wanna look back at all the things I’m missin’ // And wake up wishin’ I spent more time fishin’, yeah // More time fishin’, yeah”

The song is about not wasting time and doing things you love now because you never know when it’ll be too late. It’s so easy to get caught up with work, errands, house chores and forget about the important things in life. Whenever I need a reminder of that, this is my go-to song.


Erin Crosby, Contributing Writer

Pick: “Figured Out” – Lacy Cavalier
Songwriters: Brian Phillips, Kyle Schlienger, Lacy Cavalier, Nick Luebke

This month, I’ve been listening to Lacy Cavalier’s vibey new song, “Figured Out”. If you’re looking for a new song that’s fun to sing along to and just chill out, this is it.

“You got it figured out // Imma sit back and watch cuz // You know your way around // Like I swear nobody else does // Using fingertips like a paintbrush // I’m your work of art that’ll never be done // You got it figured out”


Caleigh DeCaprio, Contributing Writer

Pick: “Days Go By” – Keith Urban
Songwriters: Andrew Powell, Keith Urban

I had an early morning road trip earlier this morning and needed to switch up what I’ve been listening to so I scrolled through my old playlists and played my summer playlist from 2016 (I had just gotten my truck and graduated from high school). The first song to play was “Days Go By” by Keith Urban (much older than 2016 I know) but it put me in such a good mood as I watched the sunrise in the rearview mirror. It was such a vibe and put me in the perfect ‘summer’s coming’ mood for the rest of my drive of singing and dancing ahead. I highly recommend diving into your old playlists if you need to switch things up, if you want to bring back memories, or if you’re getting super antsy about summer.

“Days go by / I can feel them flyin’ / Like a hand out the window in the wind / Cars go by / Yeah, it’s all we’ve been given / So you better start livin’ right now / ‘Cause days go by”


Erica Zisman, Contributing Writer

Pick: “when was it over?” – Sasha Sloan ft. Sam Hunt
Songwriters: Henry Agincourt Allen, Emi Dragoi, Sam Hunt, Sasha Sloan, Shane McAnally

My song pick for May is actually a collaboration. When I heard that Sasha Sloan was going to join forces with Sam Hunt, I was immediately intrigued. I have been loving cross-genre collaborations and I especially love the whole genre-bending trend. Their song “when was it over?” is an instant bop.

“I didn’t ask if you were okay // After a fight with your mom // The last time I stayed over at your place // And you woke up alone // Was it the first time you pulled away // Second time that we drove to Texas // Third time we ran into one of my random exes // So was it ever real? // Or was it all pretend // The way you act has good me wonderin’ // When was it over for you?”

The push-pull nature of the song feels effortless, but it’s the lyrics and the simple production that gets me every time. This song could easily fit in with any genre because of how simply gorgeous it is. When I heard that Shane McAnally had a hand in writing it with Hunt and Sloan, I knew exactly why I had fallen in love with it so easily. I encourage everyone to give it a listen!


Listen to our picks on our “What We’re Listening To” playlist on Spotify and be sure to give it a follow, so you can catch our monthly updates.