In 1992, Randall won a Grammy award under the winner name 'Emmylou Harris & Nash Ramblers (Larry Altamanuik, Sam Bush, Roy Huskey, Jr., Al Perkins, Jon Randall Stewart), artists.' for Best Country Performance By A Duo Or Group With Vocal.
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In 1999 he earned a Grammy Nomination for best bluegrass album of the year for his work on the album Bluegrass Mandolin Extravaganza on which he played with fellow mandolin greats Sam Bush, David Grisman, Ronnie McCoury, Jesse McReynolds, Bobby Osborne, Ricky Skaggs and Buck White.
Co-produced by Willis, Alison Rogers and Jamie Oldaker, guest musicians include Oldaker (drums, percussion); Sam Bush & Tim O'Brien (mandolin, vocals); Viktor Krauss, Roscoe Beck & Freebo (bass); Bruce Bouton (steel guitar); Mickey Raphael (harmonica); Walt Richmond (piano, organ); Joel Guzman (accordion); Marcia Ball, Tommy Malone, Abra Moore & Alison Rogers (vocals).