Henry thought he sounded like Elvis Presley around age 5, then he sang in the choir in grade 7 and 8. By age 11 Henry had self-learned guitar and harmonica when his grade 9 teacher, Ms. Osbourne, introduced him to the Trombone. Henry's natural affinity for the Trombone won him Kiwanis lessons with Murray Ginsberg the 2nd trombone player with the Toronto Symphony Orchestra. That same year, Henry played his first gig on lead guitar and by age 16 started playing trombone at the Balmy Beach Club with the Western Technical School Big Band led by Red Heron. During his last year at Bloor Collegiate Henry was voted president of the Senior Band and then went on to play full time thanks to his all time favourite Trombonist Russ Little who had just left the Woody Herman Big Band. As a test Henry recalls asking Russ to play Flight of the Bumble Bee and to everyone's amazement he did it one Octave up.
By age 20 Henry ended up playing with Crowbar who had a major hit on the charts in Canada called “Oh What a Feeling”. Crowbar ended up in England where they were backed up by Fleetwood Mac, Status Quo, the Average White Ban and they played on the same bill with Gladys Knight and the Pips on BBC TV’s “Old Grey Whistle”. During a subsequent performance of "Turn on Your Lovelight” at Maple Leaf Garden’s in Toronto for Prime Minister Pierre Elliot Trudeau, Henry played a 2 minute up-front solo to a crowd of 22 thousand screaming fans and supporters. Henry has recorded with Crowbar, Stampeders, Endangered Species Big Band, the Blue Willow Blues Band, and most recently with TomCattt. Henry's complimentary horn parts and solo on Tomcattt's song "Oooooutcha" is a creative, driving and towering force.