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.

In 2017, Stapleton returned with his second and third studio albums: From A Room: Volume 1 and From A Room: Volume 2The two discs take their name from Nashville's historic RCA Studio A, where he recorded both projects. Volume 1 came out on May 5, 2017, with Volume 2 following on Dec. 1 of that year. After releasing "Either Way" -- a track previously recorded by Lee Ann Womack -- as Volume 1's first single, Stapleton dropped "Broken Halos" as its second single that July. That song became his first chart-topper on the Billboard Country Airplay chart in March of 2018.

Meanwhile, Stapleton maintains his reputation for memorable duets, cameos and collaborations. He co-wrote three of the songs that appear on pop star Justin Timberlake's 2018 studio album, Man of the Woods, and lent vocals to that album's song "Say Something." The two artists have performed the song on many notable occasions, such as a post-Superbowl set on The Tonight Show Starring Jimmy Fallon in February of 2018.

Stapleton also recorded a cover of Elton John's "I Want Love" for a 2018 set of tribute albums to the pop icon, alongside a slew of other prominent artists within the country genre and beyond. To round out his diverse set of interests, the singer made a brief, easy-to-miss cameo in an episode of Game of Thrones in April of 2019.

When it comes to a wide range of musical contributions and cross-genre collaborations, Stapleton has showed no signs of slowing down. He and pop star Pink shared a new duet, "Love Me Anyway," in April of 2019. Just a few months later, in July, Stapleton teamed with Ed Sheeran and Bruno Mars to release a '70s rock-inspired track called "Blow."

Stapleton's industry accolades also continue to pile up, too. He won Male Vocalist of the Year for a whopping fourth consecutive year at the 2018 CMA Awards. That year, he also brought home trophies in the categories of Single and Song of the Year, both for "Broken Halos."

Long 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 10 best songs. Tunes from his records, covers and those recorded by other artists were all fair game for this list.

  • 10

    "Say Something"

    From Justin Timberlake's 'Man of the Woods' (2018)

    Even though Stapleton and Timberlake might seem at first glance like they don't have much in common, the pair realized that they actually had a whole lot of the same influence when they first began performing together at the CMA Awards in 2015. Three years later, their hit duet "Say Something" didn't just inspire a streak of surprise show in Nashville and beyond in the middle of 2018 -- it showcased the pair's mutual love of soul, R&B and powerful songwriting.

    "We just have fun. It looks like the odd couple to most people, but we have a lot of the same musical influences," Stapleton explained at the time. "Old R&B and soul music and things like that. We just enjoy hanging out."

  • 9

    "Nobody to Blame"

    From 'Traveller' (2015)

    What happens when you play a country song backwards? You get your truck back, and then you get your dog back, and then you get your wife back, of course. Country heartbreak may be predictable enough to be a punchline, but when it's done right, there's nothing better.

    "Nobody to Blame," off Stapleton's first studio album, tells the classic country tale of losing it all -- and having no one to blame but himself. The song became Stapleton's first Top 10 single on the Billboard Country Airplay chart after its release in late 2015, and it also earned him a trophy in the category of Song of the Year at the 2016 ACM Awards.

  • 8

    "Millionaire"

    From 'From A Room, Vol. 2' (2017)

    As Stapleton's songs go, "Millionaire" is pretty dang uplifting. Released in 2017 off of his third studio album, From A Room, Vol. 2, the song's chorus features harmonies from the artist's wife, Morgane, who often sings alongside him onstage.

    One potential explanation for the song's (relatively) sunny outlook on love and life, however is that Stapleton didn't write it. In fact, he wasn't even the first artist to record "Millionaire": Both distinctions belongs to singer-songwriter Kevin Welch, who penned the track in 2002. Four years later, soul giant Solomon Burke also cut the track for his 2006 album, Nashville.

  • 7

    "When the Stars Come Out"

    From 'Traveller' (2015)

    Stapleton may never have released "When the Stars Come Out" as a single, but this dreamy deep cut off of his studio debut, Traveler, paints the singer's typically raspy vocals in a whole new light.

    Surrounding the album's release, Stapleton told the L.A. Times that "When the Stars Come Out" was inspired by an evening walk down an L.A. city street. "As I walked, I noticed that everybody looked like 'somebody.' They all looked famous. They all looked like stars" he recalled. "I began to toy with the notion that maybe all of the L.A. stars are walking around. And perhaps, some nights, they shine brighter than the city lights."

  • 6

    "Crash and Burn"

    From Thomas Rhett's 'Tangled Up' (2015)

    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. The song's success also helped cement Stapleton's position as a multifaceted writer who could lend his pen to any style of country music, not just the traditional country that he gravitated toward as a performer.

  • 5

    "Parachute"

    From 'Traveller' (2015)

    Few songs showcase Stapleton's sheer vocal prowess better than "Parachute," the third single off of his debut studio album. Fast-paced and full-throttle, the single may not have climbed as high on the charts as some of his later releases, but "Parachute" made for a captivating live performance, adding to what was, in 2015, a rapidly expanding, voracious fanbase.

  • 4

    "Drink a Beer"

    From Luke Bryan's 'Crash My Party' (2013)

    "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 tragic losses of his brother and sister at an early age. "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.

  • 3

    "Tennessee Whiskey"

    From 'Traveller' (2015)

    Stapleton's recording of "Tennessee Whiskey" is a highlight of his first 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. Two years later, 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.

  • 2

    "Traveller"

    From 'Traveller' (2015)

    Stapleton's eponymous -- and first -- track on his debut album ultimately got a bit overlooked amid the success of "Tennessee Whiskey," but "Traveller" is worth revisiting for another listen. Early on, the song expertly represented Stapleton's blend of influences, lyrical prowess and extraordinary vocal chops. The song won Stapleton a Grammy for Best Country Solo Performance in 2016.

  • 1

    "Broken Halos"

    From 'From A Room, Vol. 1' (2017)

    "Broken Halos" is among Stapleton's saddest -- and most personal -- songs: He recorded the track on the day that a childhood friend, who was exactly the same age as he was, died of pancreatic cancer. Co-written by Stapleton and his frequent collaborator Mike Henderson, the song became the second single off of From A Room, Vol. 1 in 2017. It became the singer's first No. 1 on the Country Airplay chart, as well as entering the Top 10 on the Hot Country Songs chart.

    As Stapleton continued to perform "Broken Halos" throughout 2017, the song's message seemed to become more apropos than ever.  Following the devastating Oct. 1 mass shooting at the 2017 Route 91 Harvest Festival, Stapleton dedicated a performance of the song to those close to the tragedy. The song offers solidarity for those grieving or in pain, but also provides a message of hope. "Angels come down from the heavens / Just to help us on our way," Stapleton sings. "Come to teach us, then they leave us / And they find some other soul to save."