[7] He attended High School of Music & Art in New York City, playing French horn until he flunked and was transferred to the choir, though he spent most of his time on the banjo.

He studied the book Bluegrass Banjo by Pete Wernick and took lessons from Erik Darling, Marc Horowitz, and Tony Trischka.

[8] After graduating from high school, he moved to Boston and became a member of the bluegrass group Tasty Licks, with whom he recorded two albums.

Fleck played banjo on Before These Crowded Streets by the Dave Matthews Band, including the album's debut single "Don't Drink the Water".

[9] In 1989 Fleck was invited to join the supergroup Strength in Numbers, headed by Sam Bush on mandolin, with Jerry Douglas on resonator guitar (dobro), Edgar Meyer on bass, and Mark O'Connor on violin.

Fleck and Meyer composed a double concerto for banjo and bass and performed its debut with the Nashville Symphony Orchestra.

with Jean-Luc Ponty and Stanley Clarke; and recording an album as a member of the Sparrow Quartet with Washburn, Ben Sollee, and Casey Driessen.

[13] In May 2009, the Bluegrass Intelligencer website satirized the upcoming "strategic marriage" of Washburn and Fleck, joking that the couple promised a "male heir" who will be the "Holy Banjo Emperor.

In a New York Times article about the film,[30] Stephen Holden writes: "At every stop on a journey that takes him from Uganda to Tanzania to Gambia and finally to Mali, Mr. Fleck plays and records with gifted local musicians.

He has been nominated in more categories than any other musician,[31][32] namely country, pop, jazz, bluegrass, classical, folk, spoken word, composition, and arranging.