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American singer, songwriter and bassist Esperanza Spalding has forged a reputation as one of the jazz visionaries of the new millennium. Her work has won multiple Grammy Awards and received both critical and mainstream acclaim.

The Portland, Oregon native trained and taught herself on several instruments and was recognized as a prodigious talent from a very early age. Her musical acuity earned her scholarships from Portland State University and Berklee School of Music. Record deals from indie labels soon followed and so her musical career began.

Click on the player above to hear “5 on 5: Esperanza Spalding” and get a feel for Spalding’s genre-pushing career with these five essential tracks:

The Progressive Underground’s 5 on 5: Esperanza Spalding

1. “Ponta De Areia”

Spalding released the heavily Latin-flavored “Junjo” in 2006 and a self-titled album, the jazz fusion-inflected “Esperanza Spalding” in 2008. “Ponta De Areia” from that album is a glorious re-imagining  of the Brant Fernando Rocha/Milton Nascimento classic that was made famous by legendary jazz saxophonist Wayne Shorter and later covered by Earth, Wind & Fire. Sung in Brazilian Portuguese, Spalding’s flute-like voice makes this selection sound as beautiful as ever.

2. “Dorothy Dandridge Eyes”

In 2011, Spalding took home the Grammy Award for best new artist. She was the first jazz artist to ever win the award, and her triumph over pop music darling Justin Bieber sparked controversy and upset his legions of fans and fans of pop music in general.

Undaunted, Spalding dropped two albums which proved to be bookends to each other. “Chamber Music Society”