While playing at The Flamingo, Young met Stephen Stills, whose band the company was playing the same venue, and they became friends. The Squires primarily performed in Winnipeg and rural Manitoba in towns such as Selkirk, Neepawa, Brandon and Giroux (near Steinbach), with a few shows in northern Ontario.
After leaving the Squires, Young worked folk clubs in Winnipeg, where he first met Joni Mitchell. Mitchell recalls Young as having been highly influenced by Bob Dylan at the time. Here he wrote some of his earliest and most enduring folk songs such as "Sugar Mountain", about lost youth. Mitchell wrote "The Circle Game" in response. The Winnipeg band The Guess Who (with Randy Bachman as lead guitarist) had a Canadian Top 40 hit with Young's "Flying on the Ground is Wrong", which was Young's first major success as a songwriter.
In 1965, Young toured Canada as a solo artist. In 1966, while in Toronto, he joined the Rick James-fronted Mynah Birds. The band managed to secure a record deal with the Motown label, but as their first album was being recorded, James was arrested for being AWOL from the Navy Reserve. After the Mynah Birds disbanded, Young and the bass player Bruce Palmer decided to pawn the group's musical equipment and buy a Pontiac hearse, which they used to relocate to Los Angeles. Young admitted in a 2009 interview that he was in the United States illegally until he received a "green card" (permanent residency permit) in 1970.
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