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Kurt Rosenwinkel has been one of the most important jazz guitarists in the game for the last quarter-century.

In addition to the acclaim he’s enjoyed from the jazz universe for his impressive work as a band leader, the Philadelphia-born guitarist has also established himself not only in the world of jazz (working with the likes of Gary Burton, Joe Henderson and Paul Motian) but hip-hop as well.

On a string of incredibly underrated solo albums released by Q-Tip of A Tribe Called Quest—2008’s The Renaissance, 2009’s Kamaal The Abstract and the still-unreleased “lost” LP OpenRosenwinkel has made himself known as one of the most in-demand session players around today.

This month, Rosenwinkel—now a resident of East Berlin, Germany, and an esteemed professor at the Jazz Institute—turns a new page in his career, stepping out from his role as an instrumentalist extraordinaire to debut his first album as a singer-songwriter, Caipi.

The first title released on the guitarist’s new label Heartcore Records (named after his landmark 2003 LP for Verve), Caipi is a work 10 years in the making that intersects Rosenwinkel’s love for Brazilian pop and classic rock with a wide array of guests that speak directly to his creative intentions for this collection.

As a singer, the 46-year-old father of two has a fine set of pipes that nod to the likes of Kenny Rankin and Paul Simon, and showcases his range justly on tracks like the Radiohead-esque “Hold On’ and the touching “Ezra,” a ballad dedicated to his youngest son. Additional vocals were provided by singer Amanda Brecker, the daughter of jazz royalty Eliane Elias and Randy Brecker, who sings in Portuguese on the song “Kama,” as well as multidimensional Brazilian singer Pedro Martins, whose own debut is being produced by Rosenwinkel as we speak in London.

Longtime associate Mark Turner joins the fold on tenor sax throughout the course of Caipi as well. Yet the biggest get for this record was the recruitment of Eric Clapton. An avowed Rosenwinkel fan who first jammed with him at the 2013 Crossroads Festival, Clapton joins Rosenwinkel for the Caipi highlight “Little Dream,” a song that ties together everything that makes this album one of the year’s best jazz releases so far.

Rosenwinkel will be returning to the States for a brief tour to debut the amazing live band he’s assembled to bring Caipi to life, including a five-night stand at Birdland on March 15.

The Observer recently caught up with the guitarist to discuss this intriguing new direction in an already well-established career as one of modern jazz’s most versatile string men.

The Best in Jazz: Kurt Rosenwinkel’s New Album ‘Caipi’ Is a Must-Listen