Bob Nastanovich was born in Rochester, New York. When he was in middle school, his family moved to Richmond, Virginia. He attended the University of Virginia, where he met Pavement's Stephen Malkmus and future Silver Jews leader David Berman. The three moved to Jersey City, New Jersey, living and working together at various jobs in art galleries and Nastanovich as a bus driver/bus terminal manager in New York City and Hoboken. It was during this period that Malkmus reunited with longtime friend Scott Kannberg to create the first Pavement album Slanted and Enchanted in drummer Gary Young's makeshift home studio. It is also during this time that the seeds for the future Silver Jews were planted. Nastanovich, upon his introduction to the band in 1990, performed many functions – namely backing vocals, percussion, harmonica, and effects-based keyboard. Initially, his key role was that of assistant time keeper, effectively focusing the efforts of the distracted and eccentric Young. Nastanovich remained a member of the band after Young left, although Steve West became the new drummer. Nastanovich sang lead vocals on live performances of the songs "Debris Slide," "Conduit for Sale," and "Unfair." He's known for his stage presence and his trademark scream. Nastanovich also played on several Silver Jews records. He has tour managed Stephen Malkmus and the Jicks, the Frogs, Huggy Bear, Fila Brazillia and Silver Jews. In addition, he has played on recordings by Palace Brothers, Tall Dwarfs and Pale Horse Riders. Nastanovich is also a sometime member of the improvising post-rock-ish band Misshapen Lodge, formed in Hull on one of his visits to the city. He rejoined Pavement for their worldwide "Reunion" tour in 2010. He currently cohosts The 3 Songs Podcast with Mike Hogan and runs Broker's Tip Records who release 7-inch singles.
Nastanovich married artist Whitney Grey Courtney on February 21, 2009. He is currently employed as a chart caller for Equibase, and works at Prairie Meadows in Altoona, Iowa. He also reports on various racetracks for the Daily Racing Form as a writer and correspondent. By visiting Epsom Race Course on August 27, 2012, Nastanovich, celebrating his 45th birthday, became the first known American citizen to attend horse racing fixtures at all 60 British race courses.