A two-time Grammy Award winner and founding member of the original David Grisman Quintet, Phillips has made a career of performing and recording with acoustic music artists.
Since then, Phillips has had the opportunity to work with a virtual "who's who" of acoustic music's finest, including Vassar Clements, Ricky Skaggs, Sam Bush, Stephane Grapelli, Taj Mahal, John Hartford, Jerry Douglas, Alison Brown, Mike Marshall, Stuart Duncan, Tim O'Brien, Bryan Sutton, Chris Thile, Del McCoury, Natalie McMaster, Darrell Scott, and Larry Campbell.
In 1983 Phillips received his first Grammy Award for his work with The New South (Crowe, Skaggs, Rice, and Douglas) in a live concert recording, Bluegrass – The Greatest Show on Earth.
These two CDs are unique in the world of bluegrass or jazz-based instrumental music, successfully featuring only acoustic guitar, bass and mandolin as the complete ensemble.
In November 2006 he appeared on the Late Show with David Letterman with Elvis Costello and Rosanne Cash during a trip to New York to record them both for the Dickens tribute project.