His songs have been recorded by The Civil Wars, Buddy Miller, Alison Krauss, Toby Keith, Ricky Skaggs, Bruce Hornsby, Keb' Mo', Garth Brooks, The Nitty Gritty Dirt Band, Cindy Morgan, Shawn Mullins, The North Mississippi Allstars.

His co-writing partners include: Will Kimbrough, Matraca Berg, Chuck Cannon, Cindy Morgan, Wayne Kirkpatrick, Gordon Kennedy, Keb' Mo', and Emmylou Harris.

Later in 2013, Madeira and occasional production partner Lynn Nichols produced the major-label debut of Pawnshop Kings, a brother duo from Southern California.

The year 2014 marked the release of Humming People's "City of Lost Men", produced in Norway by Madeira, leading to a long-standing relationship with the band.

Madeira produced Treasure of the Broken Land: The Songs of Mark Heard featuring Red Dirt Boys, Rodney Crowell, Buddy Miller, The North Mississippi Allstars, Amy Speace, Willie Sugarcapps, and others.

[11] The single received critical acclaim from Rolling Stone who called the piece a poignant yet optimistic New Orleans jazz-inspired tribute to Madeira's late partner.

[12] Madeira appeared as a member of The Ascendants on their 2023 Kickstarter album along with Jimmy Abegg, Steve Hindalong, Matt Slocum and Ben Pearson.