Cole Swindell learned his first lessons about the music industry by watching other country artists from behind a merch table. From there he moved into writing hit songs for the likes of Luke Bryan and Thomas Rhett before kicking off his own successful recording career.

With his two studio albums and a handful of EP releases, Swindell has seen a long string of popular songs land at the top of the charts. The singer notched his seventh consecutive No. 1 hit with "Flatliner," his duet with Dierks Bentley, in 2017.

With a third studio album in the works, Swindell will likely have more hits in the future -- but for now, these are The Boot's picks for his Top 5 songs.

  • 5

    "Break Up in the End"

    From: 'All of It' (2018)

    "Break Up in the End" is the ninth single of Swindell's career, and it's about being in love but knowing that things just aren't going to work out in the end. "You still think the world of each other," Swindell explains to The Boot. "[This song is] a love story, in a way. Every little line describes a place that I've been at some point. Songs like this are the reason I initially fell in love with country music."

    The first single from Swindell's third studio album, All of It, "Break Up in the End" was written by Jon Nite, Chase McGill and Jessie Jo Dillon.

  • 4

    "Chillin' It"

    From: 'Cole Swindell' (2014)

    "Chillin' It" is one of Swindell's well-received summer anthems. It pairs a laid-back vibe with a catchy chorus: "I got my shades on, top back / Rollin' with the music jacked / One on the wheel, one around you baby / Sunset, I bet there's a chance we can get / Sure enough tangled up, laid back and lazy ..." The platinum-certified single hit No. 1 on the Billboard charts late in 2013. After independently releasing the track, Swindell was signed to Warner Bros. Records, and the song appears on his self-titled debut album, released in 2014.

  • 3

    "Middle of a Memory"

    From: 'You Should Be Here' (2016)

    "Middle of a Memory" was written by Swindell with his good friend and frequent collaborator Ashley Gorley, and Zach Crowell. In it, Swindell sings about a girl leaving too soon, before they could create something special: "Girl, you can't leave someone / In the middle of a dance floor all alone / In the middle of an old-school country song / Right when I was just about to lean on in / Why'd you have to go then?"

    “Songs like ["Middle of a Memory,"] I’m so proud I wrote those, because those are real things that I think we’ve all been through," Swindell tells The Boot. The song became the second single from his sophomore album, You Should Be Here.

  • 2

    "Ain’t Worth the Whiskey"

    From: 'Cole Swindell' (2014)

    "Ain't Worth the Whiskey" is a clever twist on the usual breakup song: "I'll drink to a country song / To another long work week gone / And I'll raise my glass to a long-lost buddy I ain't seen," Swindell sings. "I might stay for one more round / Or I might close this place down / But don't think for a second I'm out to drown your memory / Baby, you ain't worth the whiskey." The song's in a tempo that hints he's ready to party the night away rather than drown his sorrows, too.

    Swindell wrote "Ain't Worth the Whiskey" with Josh Martin and Adam Sanders. It was the third single from his self-titled debut album.

  • 1

    "You Should Be Here"

    From: 'You Should Be Here' (2016)

    It should come as no surprise that the emotional "You Should Be Here" is at the top of the list. Swindell and Ashley Gorley co-wrote the song, about Swindell's heartache over the sudden loss of his father. It became a No. 1, platinum-selling hit, inspiring fans all over the country to share their own stories of loss.

    "I didn’t really [write about my father] until after Ashley said that title. I knew I wanted a song about that, something that would honor him but also help others," Swindell explains to The Boot. "It was an answer to prayer when he said "You Should Be Here." I’ll never forget that title and how it made me feel."

    "You Should Be Here" was the debut single from and title track of Swindell's 2016 sophomore album.