That began to change when Helm was 17, and she began listening to her father's music, starting with the Band's debut album, Music from Big Pink. She started soaking up her father's tastes in vintage blues and gospel, and also began striking out in a new direction as a performer. In 1993, Helm made her recording debut: singing backing vocals on Donald Fagen's album Kamakiriad (once again keeping it in the family, as Fagen had married Libby Titus that same year). She also performed in the studio and on tour with the reunited Steely Dan. In 2002, Amy teamed up with a handful of New York roots musicians to form the group Ollabelle, which fused bluegrass and gospel flavors into a sound that earned them a powerful reputation with critics. Ollabelle released their self-titled debut album in 2004, with Levon Helm making a guest appearance as drummer on one track. That year also marked the first of a series of house-party style shows that Levon Helm staged at the recording studio installed in a restored barn on his property; Levon had suffered a serious bout with throat cancer, and the monthly shows, known as "the Midnight Rambles," gave him a chance to return to performing in a comfortable setting as well as play music with friends for fans. Amy was one of the organizers of the Midnight Ramble concerts, and Ollabelle were frequent guests on the bill; as Levon's health improved, he resumed touring, with Amy playing mandolin and singing as part of his road band.
In 2007, Levon Helm released his first album of new material in 25 years, Dirt Farmer, which Amy co-produced with Larry Campbell, and the project was a critical and commercial success that helped jump start Levon's career; it also prompted the release of two more albums with Amy on board, 2009's Electric Dirt and the 2011 live set Ramble at the Ryman. Amy Helm found herself serving double-duty, playing with her father's combo while also recording and touring with Ollabelle, which released two more studio albums (2006's Riverside Battle Songs and 2011's Neon Blue Bird) and a live disc (2008's Before This Time). She also provided guest vocals for a wide range of artists, including the Holmes Brothers, Linda Thompson, Joan Osborne, and Blackie and the Rodeo Kings.
Amy had begun work on a solo album with the Midnight Ramble band when her father died on April 19, 2012; determined to keep the studio open, she continued to host concerts at Levon's barn, and began working with a new band, Amy Helm and the Handsome Strangers. As Amy's new band gained strength from their live work and she became more confident as a bandleader and lead vocalist, she opted to re-record much of the material on her album, though three songs with Levon on drums would make the final cut. In July 2015, Amy Helm released her first solo album, Didn't It Rain, and that same summer, she set out on a joint concert tour with Mavis Staples and Patty Griffin. ~ Mark Deming, Rovi