Madeira recorded three solo albums. He received the Nashville Music Award (Nammy) for Best Keyboardist in 2000.[citation needed]
In 1986, he received a Humanitarian Award from ASCAP for his effort in raising consciousness and money for the Ethiopian hunger crisis.[citation needed]
From 1976 to 1978, Madeira was a member of the Phil Keaggy Band, with Lynn Nichols, Terry Andersen and Dan Cunningham.[3] The Ithaca, New York-based band released one album together, entitled Emerging. The band broke up in 1978 and Madeira relocated to Nashville in 1983 where he worked as a sideman and a songwriter, making solo records independently.[4]
In 2008, Madeira joined Emmylou Harris's band "The Red Dirt Boys".[5]
In 2013, Madeira released "PM", his first solo album in 15 years.[8] Madeira released his first book, God on the Rocks: Distilling Religion, Savoring Faith in June 2013, published by Jericho Books. Later in 2013, Madeira and occasional production partner Lynn Nichols produced the major-label debut of Pawnshop Kings, a brother duo from Southern California. Madeira appeared with Neil Young, Sheryl Crow, Leon Russell, and Jack White on CMT's Willie Nelson's 80th Birthday Party, hosted by CMT network.
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's song "From This Valley" (co-written and recorded by The Civil Wars) won the Grammy for Best Country Performance by a Duo in 2014.[9]
Madeira commenced work on a follow-up to his "Mercyland" project in the summer of 2014. "Mercyland: Hymns For The Rest Of Us, Vol II" was released on Mercyland Records in 2016. And in 2015, Madeira finished two solo projects, "Motorcycle" and "Soul Of A Man".
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. It was released in 2017.
In 2016, Madeira wrote the liner notes for John Scofield's Grammy winning "Country For Old Men". In 2017, Madeira produced several records for indie artists including Sammy Horner and The Sweet Sorrows, and The Mosleys. Madeira and the other members of The Red Dirt Boys joined Emmylou Harris again for a tour with John Mellencamp.
In April 2018, Madeira release the album "Providence" featuring Madeira on piano and vocals, Chris Donohue on upright bass, and Bryan Owings on drums. Recorded at Nashville's Sound Emporium, the jazz/blues/Americana outing included guest guitarists Will Kimbrough, James Hollihan, and John Scofield.[10]
In 2019, Phil Madeira released the Open Heart album, along with a single "Remember Me".[11]It was a poignant yet optimistic New Orleans jazz-inspired tribute to his late partner.[12]
1995: Off Kilter (self-released, UK and Europe only) critically acclaimed for its dark, moody vibe, Madeira played all instruments except drums (Charlie Morgan) on this recording of songs devoted to matters of the heart.