[1] Members of the Grateful Dead themselves, including rhythm guitarist/singer Bob Weir, bassist Phil Lesh, drummer Bill Kreutzmann, vocalist Donna Jean Godchaux and keyboardists Vince Welnick and Tom Constanten, have all appeared on stage and performed with Dark Star Orchestra.

When a 70s show is being performed, vocalist Lisa Mackey provides Donna Godchaux's female harmonies and now too, since 2012, plays Harmonica on the Ron "Pigpen" McKernan tunes.

In November 1998, on the eve of their first anniversary, Mike Gordon and Jon Fishman of Phish joined DSO at Martyrs' after their own show.

Their popularity has grown continually, playing at larger venues and theaters, collaborating with guests including Grateful Dead alumni Bob Weir, Phil Lesh, Bill Kreutzmann, Donna Jean Godchaux-Mackay, Vince Welnick and Tom Constanten.

The band reeled for a while, featuring the talents of guest keyboardists, including Dan Klepinger and Tom Ryan, until selecting Rob Barraco as a permanent replacement in 2007.

In 2009 John Kadlecik joined a new band with original Grateful Dead members Phil Lesh and Bob Weir called Furthur.

For DSO's 2009–10 winter shows, he was replaced by guitarist Jeff Mattson of the Zen Tricksters and the Donna Jean Godchaux Band.