The band started at an Electronic Frontier Foundation (EFF) benefit at The Fillmore Auditorium in 1997. At this time the band included Roger McNamee, a venture capitalist; Giles McNamee, investment banker, board member of EFF and Roger's brother; guitarist Bert Keely of Microsoft; Bill Bennett, a marketing and communications strategist; and Tony Bove (rechristened "TBone"), author of books about computers and the Internet. The band had its roots in acoustic performances Roger and Giles McNamee gave as the Other Brothers in lounges around New England during the early 1980s.[citation needed]
The band backed Grateful Dead members Bob Weir and Mickey Hart in a series of fund-raisers[3] for Al Gore and Bill Clinton (Tipper Gore played congas during one Silicon Valley soiree[4]).
The band spent three consecutive summers (2000–2002) taking a special course developed specifically for them by Jefferson Airplane guitarist Jorma Kaukonen, who assembled a faculty that included guitarist G.E. Smith, bassist Jack Casady (Kaukonen's partner in the Airplane and Hot Tuna), and pianist Pete Sears of Jefferson Starship and Hot Tuna who joined the band after these camps. Casady also produced the band's CD 52 Week High.[5]
The band toured from 2001–2006 sharing concert bills with artists and bands such as Little Feat, Leftover Salmon, Country Joe McDonald, Bob Weir, Ratdog, Mickey Hart, Steve Kimock Band, Particle, and The String Cheese Incident, and have appeared on stages ranging from the Alaska State Fair to B.B. King's club in Times Square, New York City. In June 1998, the band played The Troubadour (London), and again in June 2001; on the latter trip, the band recorded tracks at Abbey Road Studios.[citation needed]
The Flying Other Brothers performed benefit concerts for groups as diverse as Seva Foundation, Camp Winnarainbow, the Lucile Packard Children's Hospital, and the Rex Foundation. The band also played as the backing band for all-star benefit concerts including one for Jefferson Airplane drummer Spencer Dryden on May 22, 2004 at Boz Scaggs's club Slim's, featuring Bob Weir, Warren Haynes, Peter Rowan, and David Nelson. The concert was put together by Pete Sears.
The band also played as the backing band for a benefit memorial concert on July 29, 2005, for concert promoter Chet Helms at the Great American Music Hall. The music was put together by Pete Sears and featured T Bone Burnett, Bob Weir, Mickey Hart, David Nelson, Country Joe McDonald, Terry Haggerty, Leigh Stephens, Bobby Vega and Joli Valenti & Friends. The $50 admission price also included a package of limited edition posters designed by such artists as Stanley Mouse, Wes Wilson, Chris Shaw, and Alton Kelley.[7][8]
On May 23, 2006, the band backed Bob Weir and Mickey Hart and jammed with New Riders of the Purple Sage in a benefit for Vermont Senator Patrick Leahy at Washington, DC's Renaissance Hotel.[9] The band's last tour in 2006 included several dates with Particle in the Pacific Northwest, a tour of Alaska, and the Hardly Strictly Bluegrass Festival in Golden Gate Park, S.F., in which T Bone Burnett joined the band for a song.
The band recorded tracks in Village Recorders, Santa Monica, CA with T Bone Burnett as producer (August 5–7, 2006), but these have not been released except "Take a Drive", plus two tracks "Another Summer of Love" and "Road to Here" released as part of the retrospective box set Circle Back"