The lead vocalist of the rock bands Headstones and Hugh Dillon Redemption Choir, his notable acting roles include Albert Manning in Degrassi: The Next Generation, Mike Sweeney in Durham County, Ed Lane in Flashpoint, Nick in Left 4 Dead 2, Duncan Sinclair in X Company, and Donnie Haskell in Yellowstone.

[2] Dillon grew up living on the same street as future NHL star Doug Gilmour and played hockey with him on the frozen swamp in their neighbourhood.

Formed in 1987, the band's debut album Picture of Health was released in 1993 and featured the singles "When Something Stands For Nothing", "Cemetery", "Tweeter and the Monkey Man" and "Three Angels".

Band members were guitarist J.P. Polsoni, Chris Osti on bass, keyboardist Ben Kobayashi, and percussionist Derek Downham.

[8] The band released an album, The High Co$t of Low Living, in 2005 through The Tragically Hip guitarist Paul Langlois's Ching Music label.

[15][16] Dillon has appeared in a number of feature films, including Lone Hero, Assault on Precinct 13, and Ginger Snaps Back: The Beginning.

Dillon starred as Sergeant Ed Lane in the CTV/CBS police drama series Flashpoint, set in Toronto, which ran for five seasons between 2008 and 2012.

He also played the role of Francis Becker on the third season of the American crime drama series, The Killing[24] opposite Joel Kinnaman, simultaneously appearing on Continuum.