In the last couple months of 2015, Chris Stapleton became the year's breakout country star: After earning critical acclaim for his debut solo album, Traveller, he nabbed New Artist of the Year, Male Vocalist of the Year and Album of the Year at the 2015 CMA Awards. The attention he received following the event earned Stapleton his first-ever No. 1 album on the all-genre Billboard 200.

Before earning success as an artist in his own right, though, Stapleton was a well-known name in Nashville: His songs have been cut by numerous other country stars ... and Adele! The singer-songwriter was the guy everyone in Music City loved.

The following are The Boot's picks for Stapleton's five best songs. Tunes from his record, covers and those recorded by other artists were all fair game for this list.

  • 5

    "Tennessee Whiskey"

    Stapleton's recording of "Tennessee Whiskey" is a highlight of his solo record, but he's not the song's writer. The tune was written by Dean Dillon and Linda Hargrove and originally recorded by David Allan Coe in 1981; George Jones' version of the track reached No. 2 in 1983. Stapleton's performance of the song, with Justin Timberlake, at the 2015 CMA Awards propelled "Tennessee Whiskey" to No. 1 on Billboard's Hot Country Songs chart.

  • 4

    "Crash and Burn"

    (Sung by Thomas Rhett)

    Written by Stapleton and Jesse Frasure, "Crash and Burn" became Rhett's fourth consecutive No. 1 song. As Rhett describes, it's a "feel-good song with a sad melody." "Crash and Burn" was Rhett's lead single from his sophomore album, Tangled Up, and its throwback vibe helped the singer to continue setting himself apart from other male country artists.

  • 3


    "Traveller," the debut single from Stapleton's debut solo album, was nominated for two Grammy Awards, Best Country Solo Performance and Best Country Song, at the 2016 ceremony. Not bad for a solo debut, huh? Stapleton's commitment to both his country and bluegrass roots is apparent in the song, both lyrically and sonically, and the down-to-Earth lyrics, such as, "I’m just a traveller on this Earth / Sure as my heart’s behind the pocket of my shirt / I’ll just keep rolling 'til I’m in the dirt / ‘Cause I’m a traveller, oh, I’m a traveller" are part of the singer's greatness.

  • 2

    "Never Wanted Nothing More"

    (Sung by Kenny Chesney)

    "Never Wanted Nothing More" was written by Stapleton and Ronnie Bowman, and released by Chesney on his Just Who I Am: Poets & Pirates record. It dropped in 2007 and became Chesney's fastest-climbing No. 1 single, hitting the top slot on the Billboard Hot Country Songs chart in just eight chart weeks. The smash hit recalls important moments in the narrator's life: buying his first car, getting married, finding God and more. As Chesney wryly notes, “... only in a country music song can you get laid and saved in three minutes."

  • 1

    "Drink a Beer"

    (Sung by Luke Bryan)

    "Drink a Beer," written by Stapleton and Jim Beavers, wasn't written specifically for Bryan -- but it's literally a perfect fit.

    "... Luke took it, and it really brought weight to it when Luke did it because of his family situation," Stapleton recalls, referring to Bryan's late brother and sister. "So, once again, it was one of those things where the right artist and the right song turned into something special."

    "Drink a Beer" will strike a chord with anyone who's experienced loss or heartbreak. Bryan performed a heart-wrenching rendition of the song at the 2013 CMA Awards.