The album, which includes collaborations with Beck, Kid Rock and Ashley Monroe of Pistol Annies, has been one of the most critically acclaimed recordings of Yoakam's career.

In 2005, Yoakam released Blame the Vain on New West, which would establish itself as the premier indie label for the emerging “Americana” movement after the turn of the millennium, cornering the market of this artistry much as Rounder had with folk in earlier decades.

[6] Dwight Sings Buck, Yoakam's second New West release, failed to make the Top 10 country albums chart, and his last significant hit single had been a cover of the Queen song “Crazy Little Thing Called Love” back in 1999.

What had made him singular was his ability to straddle mainstream country and progressive Americana.”[7] After leaving New West amicably, Yoakam came full circle by resigning with Warner Bros. Nashville in 2011.

[11] This return to commercial success and visibility was in part due to Yoakam, who put out quality material for years without having a hit single, taking his place as a country legend in his own right, a maverick and outlaw who, like Buck Owens and Willie Nelson, stuck to his musical guns regardless of trends in the business.

Yoakam liked the Martin Scorsese documentary about George Harrison, Living in the Material World, and 3 Pears takes its title from a scene in which John Lennon plays around with three pairs of glasses.