He is an Honours Graduate in Contemporary History and a qualified teacher. Cutler's O.U degree was gained at the end of the 1980s. Cutler worked for Blackhill Enterprises as stage manager and master of ceremonies on a series of 1960s gigs in the U.K. and Europe with different artists, including Pink Floyd, Eric Clapton, The Rolling Stones, Alexis Korner, et al. In 1969, he acted as master of ceremonies at The Rolling Stones concert in Hyde ParkLondon. Following the Hyde Park show, Cutler was asked to be the personal road manager to The Rolling Stones during their 1969 Tour of America, which culminated in the infamous Altamont Free Concert where Afro-American arts student Meredith Curly Hunter, Jr. was killed in front of the stage. Cutler is commonly credited with first uttering The Rolling Stones' famous intro line, “Ladies and Gentlemen, the Greatest Rock and Roll Band in the World…The Rolling Stones!” Cutler can be seen in many scenes in the documentary filmGimme Shelter which covers the events of the 1969 American tour, and can be heard on The Rolling Stones live albumGet Yer Ya-Ya's Out! introducing the band. He can also be seen in the film Festival Express and Stones in the Park. Throughout his rock and roll career, Cutler was around and was agent for some of the largest rock and roll shows in history outside of Woodstock including The Rolling Stones in Hyde Park, the Grateful Dead's Europe '72 tour and the Dead's participation in the Festival Express train tour across Canada. However, the Festival Express was a huge loss for the promoters and Europe ‘72 wasn’t as profitable as promised.
Following the events at Altamont, Cutler stayed in the U.S. to deal with the aftermath, was befriended by Jerry Garcia, and subsequently hired by the Grateful Dead as their tour manager. He went on to become a co-manager of the band and eventually became their agent and tour manager. Cutler organized the Dead's appearances at a number of memorable events including: the 1970 Festival Express Tour of Canada, The Summer Jam at Watkins Glen, and the 1972 European Tour of the Grateful Dead, the musical results of which can be heard on the Dead's triple live album Europe '72. Through his company, Out of Town Tours, Cutler coordinated the appearances of many artists including: Grateful Dead, The Band, The Allman Brothers, The New Riders of the Purple Sage, The Sons of Champlin, Mike Bloomfield, Ramblin' Jack Elliott and others. In 2006, Sam collaborated with Melbourne indie-rock group Black Cabon the track "Valiant" which appeared on the band's 2006 release Jesus East. In the track, Sam reminisces on his days with the Grateful Dead and preaches advice for the kids of today. Sam toured around Australia and Asia promoting his book.
