"Time Machines" explores how technology has preserved - and altered - the way we think about the great songs and singers of the past. On a coast-to-coast tour with stops in New York, Palm Springs, Kansas City, upstate New York and even the storied Playboy Mansion in Los Angeles, Michael Feinstein introduces viewers to soundies (the original music videos), the historic building where "jam sessions" were born (and still hosts after-hours gigs) and an eclectic array of performers and collectors who help keep the music alive, including avid collector and music-lover Hugh Hefner, who shares rare footage of cabaret legend Bobby Short, and the British crooner Al Bowlly.