- Took up piano at age 6.
- Became a fan of opera while a teenager; he also discovered the music of Edith Piaf, Al Jolson and Judy Garland at that time.
- Began his musical career at age 13 with the McGarrigle Sisters and Family, which included his mother Kate, aunt Anna and sister Martha.
- His song "I'm a-Runnin'," which was featured in the 1988 Canadian film Tommy Tricker and the Stamp Traveller, earned him Juno and Genie nominations.
- Appeared in high-school productions of Cabaret and Godspell.
- Scored a record deal after his dad, impressed by a demo tape he'd made, passed it on to singer-songwriter and record producer Van Dyke Parks, who in turn gave it to record executive Lenny Waronker, who'd just joined DreamWorks.
- Recreated Judy Garland's famed 1961 show at New York's Carnegie Hall in 2006, releasing it a year later as Rufus Does Judy at Carnegie Hall.
- Wrote the opera Prima Donna for New York's Metropolitan Opera. The Met refused to stage it, however, when he insisted the libretto be sung in French, not English. It eventually premiered at the 2009 Manchester International Festival in Manchester, England.
- Had a child in 2011 with longtime friend Lorca Cohen, the daughter of singer-songwriter icon Leonard Cohen.