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In 1964, James fled to Toronto. Soon after his arrival three drunk white men tried to attack him outside a club; a trio of other men came to his aid. One of those men was Levon Helm, who at the time was an undiscovered member of Ronnie Hawkins' backing band. He invited James to their show later that night and he ended up performing onstage with them. In Toronto James made friends with local musicians Neil Young and Joni Mitchell. To avoid being caught by military authorities, James went under the assumed name, "Ricky James Matthews". That same year, James formed the Mynah Birds, a band that produced a fusion of soul, folk and rock music. In 1965, the band briefly recorded for the Canadian division of Columbia Records, releasing the single, "Mynah Bird Hop"/"Mynah Bird Song". At one point, Nick St. Nicholas of later Steppenwolf fame was a member; eventually bassist Bruce Palmer replaced him by the time "Mynah Bird Hop" was recorded. James and Palmer recruited guitarists Tom Morgan and Xavier Taylor and drummer Rick Mason to form a new Mynah Birds lineup, and soon traveled to Detroit to record with Motown. Before the group began recording their first songs for the label, Morgan left, unhappy about the label's attitude towards the musicians. Neil Young eventually took his place. It was while in Detroit that James met his musical heroes, Marvin Gaye and Stevie Wonder. After meeting Wonder and telling him his name, Wonder felt the name "Ricky James Matthews" was "too long", and instead told James to shorten it to "Ricky James".

In 1966, a financial dispute in Toronto between James and the Mynah Birds' handler, Morley Shelman led to Motown's learning of James's fugitive status with the Navy. Hoping to prevent any scrutiny, Motown execs told Rick they would not be releasing any more of his material and convinced him to come back and work with them after straightening out his legal issues. James surrendered himself to the FBI, and, in May 1966, was sentenced by the Navy to five months' hard labor for unauthorized absence. He was not yet 19 years old. James escaped from the Brooklyn Naval Brig after only six weeks' confinement, but following another six months as a fugitive, surrendered himself a second time. With help from his mother, James found legal assistance from his cousin, future Congressman Louis Stokes and an attorney, former Marine Captain John Bracken, who pled James' second court-martial down from a potential five years' hard labor to five months. After his release from Portsmouth Naval Prison in August 1967, James returned to Toronto and endured another detention, initially derailing resumption of his career with Mynah Bird bandmate Neil Merryweather, with whom he would later collaborate, first at Motown and then in Los Angeles.

In 1968, again working under the pseudonym Ricky Matthews, James produced and wrote songs at Motown for acts such as The Miracles, Bobby Taylor & the Vancouvers, and The Spinners. According to James, he briefly got involved in pimp activity during this time, but stopped because he felt he was not qualified for it due to the harsh activity and the abuse of women there. It was during this third stint at Motown that James met musician Greg Reeves. Reeves, hoping to find a better situation than the US$38 a week (US$625 in 2019 dollars) he was earning as a session bassist for Berry Gordy, joined James, looking to "hitch a lift from Neil Young's rising star," and relocated to Los Angeles.

On one of his first nights in Los Angeles, James was crashing on musician Stephen Stills' couch. When he awoke he saw a stoned young man sitting on the floor in the lotus position. The man's wrists were bleeding so a scared James sought help. James was later formally introduced to the man who was Jim Morrison, lead singer of the Doors. After the Doors opened for Buffalo Springfield at the Whisky a Go Go, Morrison tricked James into taking acid.

In California, James initially worked as a duo with Greg Reeves, but soon after James introduced Reeves to Neil Young, it was Reeves, not James, who was hired as bassist for the newly formed rock supergroup, Crosby, Stills, Nash & Young. Around this time James formed several versions of the rock band Salt'N'Pepper and got involved with hair stylist Jay Sebring, who agreed to invest in his music. In 1969, James claimed that Sebring invited him to attend a party at actress Sharon Tate’s house, but he was too hungover to get out of bed. The next morning he discovered that Sebring had been murdered when he saw the Los Angeles Times headline "Sharon Tate, Four Others Murdered."

In 1970, James and Salt'N'Pepper member Ed Roth later were included in Bruce Palmer's solo album The Cycle Is Complete. The duo also recorded as part of the group Heaven and Earth in Toronto. Heaven and Earth eventually changed their name to Great White Cane and recorded a self-titled album for the Los Angeles label Lion Records, released in 1972. James formed another band, Hot Lips, afterwards. He also briefly replaced Joe Mendelson in the Toronto blues band McKenna Mendelson Mainline. During this period James and Mainline guitarist Mike McKenna co-wrote the song "You Make the Magic" which would later be released by The Chambers Brothers as a B-side to their single "Boogie Children."