Bob Montgomery is an internationally recognized performing artist who has appeared throughout Europe, Australia, Canada, Mexico, Japan, China, Great Britain, New Zealand and the United States. He has performed in back-up orchestras for such artists as Sammy Davis Jr., Diana Ross, Tony Bennett, Quincy Jones, Nancy Wilson, and many more. Bob toured Europe with Clark Terry's "Big Bad Band", served as artist-in-residence in Adelaide, South Australia, appeared as featured soloist with the Albuquerque Jazz Orchestra for the International Trumpet Guild, and appeared at Town Hall in New York City with Clark Terry for the New York JVC Jazz Festival's tribute to Clark Terry. Clark mentions Bob several times in his Autobiography “Clark” and Bob appears in Clarks movie “Keep On Keepin’ On”.
Bob's reputation as an educator has earned him many awards, including "Teacher of the Year", "Jazz Educator and Performer of the Year", and "Colorado Jazz Educator Of The Year". In 2004 Bob was awarded the Bethany College Alumni of Merit Award for distinguished service in the Arts and in 2007 was inducted into the Garden City, KS (his home town) Hall of Fame. In 2012 the Five Points Jazz Festival honored Bob for lifetime contributions to the development and appreciation of Jazz. Bob has served both Kansas and Colorado as State IAJE (International Association for Jazz Education) President, and has directed All-State Jazz Ensembles in Colorado, Kansas, Arizona, Iowa, and Oklahoma. Bob was founder and director of Clark Terry's All American Jazz Camp and Rich Matteson's Mile High Jazz Camp. He is Executive Director of Colorado Jazz Workshops, Inc., Founding board member of the "Colorado Gift of Jazz", advisory board member of the Telluride Jazz Celebration, and a member of the board of trustees for the International Foundation for Jazz. Bob is founder and director of the “Telluride Jazz All-Star” program held each year at the Telluride Jazz Celebration. This program has helped hundreds of young jazz musicians enter the world of jazz as professional performers. (2016 is the 23rd year of the program).