[citation needed] Henry's next two recordings, Short Man's Room (1992) and Kindness of the World (1993), featured members of the country-rock band the Jayhawks.

The album was called an "atmospheric marvel" by one reviewer[5] and Ann Powers of The New York Times wrote: Henry has "found the sound that completes his verbal approach.

"[6] Scar, released in 2001, featured jazz musicians Marc Ribot, Brian Blade, Brad Mehldau and saxophonist Ornette Coleman on "Richard Pryor Addresses a Tearful Nation."

According to AllMusic's Thom Jurek, the album is a "triumph not only for Henry—who has set a new watermark for himself—but for American popular music, which so desperately needed something else to make it sing again.

AllMusic's Jurek described this album as "the sound of....electric guitars in an abandoned yet fully furnished Tiki bar in Raymond Chandler's Los Angeles.

Henry and his sister-in-law recorded a duet, "Guilty by Association," on the charity album Sweet Relief II: Gravity of the Situation, and collaborated on the songs "Jump" on Confessions on a Dance Floor, "Devil Wouldn't Recognize You" on Hard Candy, and "Falling Free" on MDNA.

[9] After producing the Grammy-award-winning album Don't Give Up on Me by Solomon Burke,[10] Henry produced additional records and in 2006 opened up a home studio where he often collaborates with recording engineer Ryan Freeland and Los Angeles-based musicians such as Jay Bellerose, Greg Leisz, David Piltch, Patrick Warren and Keefus Ciancia.

The album focuses on facets of blues with a sprinkling of jazz, rock and pop and traces the rugged history of American storytelling.

It was recorded at his LA home studio, The Garfield House, in 2013 with his regular band of musicians (Jay Bellerose, Jennifer Condos, Levon Henry, Greg Leisz, John Smith, and David Piltch).

[18][19][20][21] Henry has been described as "a modest-selling 'critic's darling' with a reputation for pushing the envelope"[22] and who writes "songs [that] don't fit into an easily defined box"[23] and instead is influenced by folk, blues, jazz, rock and country.