Julie Roberts, "Rain on a Tin Roof"
Julie Roberts (2004)
Roberts' "Rain on a Tin Roof" offered early proof that Stapleton had a great gift for heart-wrenching songs. It's a sparely constructed so that every instrument has plenty of room to drip with misery and longing. Sitting firmly at the intersection of country and adult contemporary, this should have been as big a hit as Bonnie Raitt's "I Can't Make You Love Me."
Kenny Chesney, "Never Wanted Nothing More"
Just Who I Am: Poets And Pirates (2007)
Satisfaction and comfort has been Chesney's calling card – at least since 2002's No Shirt, No Shoes, No Problems-- and this Stapleton track fits him like a glove. As the title suggests, Chesney "never wanted nothing more" than what he has already; luckily for him, the events described in the song just keep getting better and better. The guitar here is reminiscent of the Grateful Dead's classic "Sugar Magnolia," another buoyant song about total contentment.
Lee Ann Womack, "Either Way"
Call Me Crazy (2008)
Few genres describe tragedy better than country, but Womack's "Either Way" pushes past sadness into post-melancholy, an even more devastating state where the singer is completely numb to the world around her. The song's first line -- "we pass in the hall, on our way to separate rooms/ the only time we ever talk is when our monthly bills are due" -- is enough to turn anyone off matrimony for life. You can hear Stapleton add his other-worldly holler behind Womack on the hook: "you can go or you can stay, I won't love you either way."
Blake Shelton, "100 Miles"
Startin' Fires (2008)
7 years can be an eternity in pop music; if you go back to Shelton's early music, it's a world away from his current country-rap-pop crossover hits like "Boys 'Round Here." This tune is old-school to the core, opening with a gentle lead guitar, an aching line of pedal steel, and a touch of organ. Shelton sings the hook in a jumbled, breathless rush, pleading with his ex to forgive him and take him back. Stapleton's backing vocals add toughness and grit to Shelton's croon.
Steeldrivers, "Where Rainbows Lie"
Stapleton served as the frontman for the Steeldrivers on two albums. "Where Rainbows Lie" remains one of their most powerful songs, with an easy guitar riff -- doubled on the banjo -- that could play equally well in a small room or a large stadium (if we lived in a world where a band like the Steeldrivers got to play in stadiums). Stapleton applies a little Willie Nelson-like quaver to his singing in the song's opening portion; he's biding his time and gathering his strength so he can rip into the hook. It's a tune about aging, and there's plenty of sadness here, but also the promise of freedom.
Adele, "If It Hadn't Been for Love"
21 (Deluxe Edition) (2011)
On the deluxe edition of her blockbuster second album, Adele included a straightforward cover of a song from The Steeldrivers' self-titled debut, released in 2008. Adele has recorded several covers in her career, mostly of tunes from famous artists -- Sam Cooke, Bob Dylan and the Cure. Add Chris Stapleton to the list.
Luke Bryan, "Drink a Beer"
Crash My Party (2013)
This song gave Stapleton a lot of exposure when he helped Bryan perform it at the 2013 CMAs. At the 2014 CMT "Artists of the Year" event, Stapleton accompanied Lady Antebellum in a touching tribute rendition after the death of Bryan's brother-in-law.
Kellie Pickler, "Ring for Sale"
The Woman I Am (2013)
Stapleton plays both sides of the fence: he'll make you weep, but his tracks are also some of the hardest you'll find in Nashville. Pickler's "Ring for Sale" is ringing southern rock. Pickler's been cheated on, but she doesn't give a damn -- the guitars are too jaunty for any melancholy. "I'd love to hit him," Pickler sings, "so I'm gonna hit him, hit him right where it hurts." Stapleton adds a well-timed backing vocal just as Pickler sings "hit him," a clever sonic evocation of that imagined blow.
Jason Aldean, "Too Fast"
Old Boots, New Dirt (2014)
Stapleton landed a cut on Aldean's most recent album, like Shelton's "100 Miles," from years earlier, this is a declaration of love after mistakes were made: "Wanna be the man that you thought I was, wanna be the man that made you fall in love," sings Aldean. "Can't undo everything I've done, let me tell you right now, baby you're the only one." Stapleton is a rock on the chorus (as per usual), which nods to Dobie Gray's classic "Drift Away."