After graduation, Joshua frequented the classroom jam sessions of Bay Area pianist and professor of music (at Laney College in Oakland, California), Ed Kelly.

He continued to work with various quartets, including one with pianist Brad Mehldau until forming a new trio, Elastic, with keyboardist Sam Yahel and drummer Brian Blade.

In 2006, he performed with the New Zealand Symphony orchestra in composer John Psathas' concerto for saxophone and drumkit, Omnifenix, which was released in Rattle Records' album, View from Olympus.

In April 2007, Nonesuch released Redman's first ever piano-less trio record, Back East, featuring Joshua alongside three bass and drum rhythm sections (Larry Grenadier & Ali Jackson, Christian McBride & Brian Blade, Reuben Rogers & Eric Harland) and three guest saxophonists (Chris Cheek, Joe Lovano and Dewey Redman).

Starting in late 2009, Redman began performing with a new collaborative band called James Farm, featuring pianist Aaron Parks, bassist Matt Penman and drummer Eric Harland.

[10][11] In early 2013, it was announced that Redman would release a new collection of vintage and contemporary ballads featuring a jazz quartet and an orchestral ensemble titled Walking Shadows.

Produced by Redman's friend and frequent collaborator Brad Mehldau, the album also features Larry Grenadier (bass) and Brian Blade (drums).

On Sunday, December 8, 2013, Redman joined a group of jazz all-stars onstage at the Kennedy Center Honors in Washington, D.C., to pay tribute to honoree Herbie Hancock in performance.

In addition to his own projects, Redman has recorded and performed with musicians including Joey Alexander, Brian Blade, Ray Brown, Dave Brubeck, Chick Corea, The Dave Matthews Band, Jack DeJohnette, Bill Frisell, Aaron Goldberg, Larry Goldings, Charlie Haden, Herbie Hancock, Roy Hargrove, Roy Haynes, Billie Higgins, Milt Jackson, Elvin Jones, Quincy Jones, Big Daddy Kane, Geoff Keezer, B.B.

King, The Lincoln Center Jazz Orchestra, Letieres Leite & Orkestra Rumpilezz, DJ Logic, Joe Lovano, Yo Yo Ma, Branford Marsalis, Christian McBride, John Medeski, Brad Mehldau, Pat Metheny, Marcus Miller, Paul Motian, Meshell Ndegeocello, Leon Parker, Nicholas Payton, John Psathas, Simon Rattle, Dewey Redman, Dianne Reeves, Melvin Rhyne, The Rolling Stones, The Roots, Kurt Rosenwinkel, John Scofield, Soulive, String Cheese Incident, Clark Terry, Toots Thielemans, The Trondheim Jazz Orchestra, Mark Turner, McCoy Tyner, Umphrey’s McGee, US3, Bugge Wesseltoft, Cedar Walton, Stevie Wonder and Sam Yahel.