Photo credit: CW by Peter Lorré at Parkpop The Hague in 1992; BW unknown
In an interview about Note of Hope. an album that Rob Wasserman produced based on Woody Guthrie writings set to music, Rob briefly discussed Chris’s involvement:
[W]e had just been playing with Bob Weir back in the day. I introduced him to that whole world. So [we] were just jamming and we did a tune [‘On the High Lonesome’] that was a real improv thing, and basically after that we just jammed. It came out very raw and spontaneous.
So it seems that Rob was Chris’s connection to Bob Weir, guitarist and singer with The Grateful Dead. Bob must have liked what he saw in Chris, asking him to open shows and to join him for a song or two on several of Bob’s (sometimes with Rob) not-Grateful Dead shows in the New York area during the early 90’s.
Pete Sears, of Jefferson Starship fame, organized benefit concerts for the Native American Inter-Tribal Bison Co-op that featured, among others, Bob Weir, Jorma Kaukonen, and Chris Whitley. Two excerpts from Unbroken Chain, a Grateful Dead newsletter, provide some info re this benefit:


Chris participated in benefit concerts at The Flood Zone (Richmond, VA 1992-11-21) and TRAX (Charlottesville, VA 1992-11-22). The following playlist contains tracks on which Chris appeared with Bob at the Flood Zone and at an earlier concert at the Meadowlands (1992-07-24 – Listen to full concert)
You can listen to the full Flood Zone set on the Live Music Archive – note that Bob introduces Chris at the end of track 12. Given that the Bob Weir set lists at the Flood Zone and at TRAX contained many of the same songs, it’s possible that Chris also joined Bob for some songs at TRAX. Because no bootleg of Bob’s TRAX concert exists, we’ll never know ….
UPDATE 2022-07-14: Just read an article in the Washington Post about the success of the Intertribal Bison Cooperative in restoring bison to America’s prairies. Reading this paragraph made me think of Chris:
[Bison] “wallows” — huge depressions created by bison’s rolling on the ground — can serve as microhabitats for other animals. After strong rains, those wallows fill with water and welcome insects, frogs and other amphibians, according to McDonald. In one poignant example of a once nearly extinct animal supporting a threatened species, bison’s wallows serve as an ideal habitat for bird’s-foot violets, the preferred food source for the larva of regal fritillary, a rare butterfly.
So … Chris’s lending this talent to support this effort has helped save a butterfly from extinction. Won’t be able to think of/see that lovely creature without thinking of Chris.
Chris also opened for Bob Weir & Rob Wasserman at the Warfield Auditorium, San Francisco, 1993-05-08, where Chris joined Bob and Rob on two tracks – Wang Dang Doodle and Easy Answers – at that show:
You can listen to the full Bob & Rob set on the LMA.
In a separate blog post, I’ve documented all three of these men appearing at the Trios benefit concert at the Beacon Theater in NYC in March 1994. Years later, in Fall 1998, during the Robert Johnson tribute in Cleveland, OH, Chris did a hotel-room recording with Bob Weir, Rob Wasserman, and Jeff Clemens on Robert Johnson’s “Walkin’ Blues”:
If you’re a member of the ATCW Facebook group, you can read our discussions about these joint appearances here.