The son of writer and radio program director Bob Mackowycz, Sr., he first became prominent as a rock musician with the band Glueleg.
Mackowycz also served as a regular contributor to Radio 2's The Strombo Show.
He earned a 2008 National Screen Institute Drama Prize for the script to the film short The Way It Used to Be.
He graduated from the Canadian Film Centre's Prime Time Television program.
On July 18, 2011, Mackowycz announced that he would be leaving the CBC following the July 25 edition of Radio 2 Morning and was succeeded as host of Radio 2 Morning by Tom Power.