His vocal talent was appreciated at an early age when the eight-year-old Jeffrey was appointed head chorister at St. John's Cathedral in Winnipeg.
[2][3] While studying at the conservatory, Jeffrey took the tenor role in the Canadian premiere of Michael Tippett's "A Child of Our Time", under Mazzoleni's direction, at the University of Toronto's Convocation Hall.
He also undertook classical repertoire with choirs throughout Ontario, including the tenor roles in Handel's "Messiah" and Mendelssohn's "Elija", in Sudbury.
Jeffrey's last appearance on the concert stage was in a 1994 production of "Amahl and the Night Visitors" for music director Lloyd Bradshaw at St. Anne's Anglican Church in Toronto.
[2] While in the British capital, Robert Jeffrey was offered the role of Tony in H. M. Tennent's Scandinavian tour of "West Side Story".
Returning to Toronto in 1964, he appeared as Mr. Ringo in one of the early productions of Susan Douglas Rubeš' Young People's Theatre, "The Dandy Lion".
In 1968 Jeffrey joined a roster of Canadian musical comedy stars (including Jack Creley and Rita Howell) in the annual touring revue "Spring Thaw," established him as a stage presence across the country for the next three years (1968, 69, 70).
In November he was back on that stage as one of the quartet of performers for the Canadian premiere of "Jacques Brel is Alive and Well and Living in Paris"[2] (with Stan Porter, Arlene Meadows and Loro Farrell).
The successful run of this production led to an invitation to open in the show in Boston with Arlene Meadows, Robert Guillaume and Judy Lander, at the Charles Playhouse.
Jeffrey remained in Boston for two years, joined in the Brel show by such artists as Denise LeBrun, Sally Cooke, George Ball and Shawn Elliott.
"Of Moon & June & Honeymoon," a song revue which Jeffrey co-devised with director Ron Ror, set to music by Doug Randle, opened at Old Angelo’s cabaret[2] on Elm Street with a cast of Christine Chandler, Brian McKay and Barbara Barsky.
At the end of the Toronto run, artistic director Michael Ayoub saw the show and invited the production to open his Muskoka Festival (re-staged by Bernard Hiatt), based in Gravenhurst, Ontario, that summer.
In 1972 he played Sancho Panza in Heinar Piller's Grand Theatre (London, Ontario) production of "Man of La Mancha"(with Michael Fletcher and Denise Ferguson).
After "Moon & June" in Toronto, he was invited to be part of Roderick Cook "One More Time"(1974) with Connie Martin and David Brown at the Colonial Tavern.
Lui's Vancouver production of Ben Bagley's "The Decline and Fall of the Entire World as Seen through the Eyes of Cole Porter" with Ross Petty and Roma Hearn.
[7] Back in Toronto in 1977 he directed and appeared in another revival of "Jacques Brel," with Barbara Collier, Nora McClellan and Rudy Webb, at the Bayview Playhouse.
In 1980 he directed "To Eternity through Noise & Smoke" for Magda Zalan's Podium Productions, which featured Nancy Palk, Sean Hewitt, Marcia Tratt and Joe Zeigler, at Toronto's St. Lawrence Centre for the Arts.
In 1979 Tony Lloyd, artistic director of Theatre Sudbury invited Jeffrey to direct Peter Mews, Marylu Moyer and Pam Hyatt in "Anne of Green Gables: The Musical"(1980).
Besides Jeffrey, PFG was made up of Daniel Hill, Robert Crossman, Drew Mullin, David Greene, Aaron Woodley and Paul G. Russell.