In October 2011, he self-released his second solo album titled "Piety & Desire" — featuring the Felice Brothers, Brandi Carlile, Jolie Holland, Ketch Secor, and Samantha Parton (of the Be Good Tanyas) — where he "creates a whole film and stereo hi-fi noir milieu" by realizing "a dozen rootsy, ambient and mostly catchy hardscrabble southwestern tinged originals." His third, self-titled album was released by ATO Records on 3 March 2015. Leaving the "relative security of the popular roots band Old Crow Medicine Show" and suffering a "tough breakup with a one-time fiancée," forced a reevaluation of Landry's life helping to generate the "introspective, generally dark songs that pour out of him' on this album. Landry says of his "map out of the darkness":  "Love Rides a Dark Horse" was released by ATO Records & Loose in October 2017. Landry says of the impetus for the album: The album includes contributions from Ross Holmes on fiddle (Mumford & Sons, Bruce Hornsby), Skylar Wilson on keyboard (Andrew Combs, Rayland Baxter), and Logan Matheny on drums (Roman Candle, The Rosebuds). American Songwriter notes "Landry’s looming yet subtle baritone — somewhere between Leonard Cohen, Kris Kristofferson and Dave Alvin — unspool (sic) stories of broken hearts." Landry shared stage at Americana Music Festival in September 2015 with acts such as Loretta Lynn, Steve Earle, Pokey Lafarge, and Gillian Welch. He opened for Warren Haynes and The Wood Brothers on tour in Fall of 2015. After touring Sweden in 2016, Landry performed at Twisterella (2016) and both the Latitude Festival in Suffolk, England and Longitude Festival in Ireland in 2017. Landry contributed music for the "Run Away Dog" (2017) soundtrack. He appeared in "Austin to Boston" (2014), which chronicled four bands riding in five Volkswagen buses across three thousand miles, and featured: Ben Howard, The Staves, Nathaniel Rateliff, and Bear's Den. Landry appeared in "Big Easy Express" (2012) with his former band, Old Crow Medicine Show. He also appeared at the end of Be Good Tanyas video "The Littlest Birds".