It must have been noisy in the Milchem household while Glenn was growing up. Getting a set of bongos at the age of eight and banging on pots and paint cans for two years proved that Glenn was meant to be a drummer from the start. Finally, seeing the ambition in their son, his parents finally got him a drum set. It, however, sounded terrible; but it was, nonetheless a drum set. At the age of twelve he began to take lessons. The journey to and from Toronto and Oakville and back again proved to be tiresome and the lessons were eventually dropped.

After graduation Glenn put an add in NOW magazine (which proved to be very beneficial for a certain group of people) hoping to start his own band. He got calls from several bands that needed a drummer, and just floated from group to group until he eventually sailed into Andrew Cash's band in 1988. The band toured in the states, which was a new thing to Glenn, and even opened for Melissa Etheridge in Europe.

Glenn was asked by Change of Heart do participate in late ‘91. Their drummer had just left and Glenn was delighted to do his part. But one week after getting a call from Change of Heart, he got a call from someone else. Someone named Jim Cuddy who wanted him to audition his band. The call, however, was quite expected. Andrew cash had told him that Jim had called and asked if he could "steal away his drummer." Glenn recorded Lost Together with Blue Rodeo and went off to tour one last time with Andrew Cash about a month later. Glenn is Blue Rodeo's third drummer; having to replace Mark French who replaced Cleve Anderson, but hopefully his part in Blue Rodeo is a little more stable.