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His first album performance was on the record Live at the Paramount, recorded in Seattle, Washington. McDougall sang "Glace Bay Blues" on that album. On the following studio album Artificial Paradise, McDougall took the lead vocals on two tracks, "Samantha's Living Room" and "Lost and Found Town". The album was a rare departure from Burton Cummings' exclusive vocals, and although it was a critical success, McDougall did not sing lead on any further recordings during the Cummings era.
McDougall left the band in June 1974 after the album Road Food was released, but he showed up as the lead singer of a reformed Guess Who (minus Burton Cummings) in 1977-1980. Around 1996, while Jim Kale was touring with his version of the Guess Who in the United States, MacDougall created his own version of the Guess Who called The Best of the Guess Who, which included Guess Who/Brother alumni Bill Wallace and Winnipeg musicians James Creasey and Scott Brown. This band performed many shows around Canada as well as the United States. Although he was not a part of the 1983 Guess Who reunion that toured Canada, he was a part of the post-2000 reunion band that has done two cross-country tours (with Cummings, Randy Bachman, Garry Peterson and Bill Wallace). Since the breakup of this lineup, McDougall has been performing at local venues around the Winnipeg area with the Donnie McDougall Band.