Born in Peterborough, Ontario in 1938, Jack Bailey was entering talent contests with his own material by the time he was 12. As a teen he was already showing up on TV on Cliff McKay's Holiday Ranch, Pick The Stars, Carl Smith's Country Music Hall, and Country Hoedown.
"The Bad Apple" b/w "What's The Matter With Me" with the Dan Penny Orchestra was released on Roulette Records in '59. One of Canada's earliest rockabilly records, it was a precursor to his next group, The Naturals. Recorded in Halifax and released on Mala Records, "Life's Like The River" b/w "Memories of You" was on the airwaves in '61, and before the end of the year came "Oh What Love Is" b/w "Beneath The Moonlight."
He signed a deal with NY based Ford Records for American distribution, and three more singles appeared up to '63, after they'd adopted more of a pop/doo-wop persona. All recorded in the Big Apple, "Tiger Lil" b/w "Your Magic Touch," "I Cried" b/w "I Was A Fool To Care," and "Let's Live A Little" b/w "With This Ring I Thee Wed" all kept Bailey on the airwaves, but nothing broke ground on the charts.
Dominion released his first full album in '67. First time producers Dallas Harms and Robert Spooner were on hand for JACK BAILEY BREAKS OUT. Bailey wrote all the songs himself, now shifting over to a more folk/country sound with tracks like the lead-off "This Old Road Of Love," "30 Miles Ahead," and "Where Lord From Here," which also showed his strong gospel roots.
His second solo record in '71 was self-titled. He'd signed with GRT, and "The Whole World's Down On You" and "On Your Way Out" both got decent airplay in pockets around the country. Other noteable cuts included "Molly Brown" about a man off to war and the love he was leaving, and "Don't Waste Your Love On Me."
HERE'S TO LOVIN' YOU followed a year later. it marked the first time Ray Griff produced him, and this time the only tracks Bailey wrote were "That Time" and "On Your Way Out." The covers were diverse - from Conway Twitty's "I Can't See Me Without You" to The Beatles' "I'm Looking Through You." The quasi-orchestral title track, "Darlin'," (one of two written by Griff) and the cover of Marty Robbins' "My Woman, My Woman, "My Wife" b/w the previously unreleased "Charlie's Picture" kept Bailey on the charts for the next year and a half.
His final album with GRT came in the summer of '73, KEEP ME. "I Can't Look Sunday In The Eye" and "Aaron Brown" were the singles, and , and "The Key To My Happiness."
By the time THEN AND NOW was released in '77, he'd all but stopped touring. The album spanned his entire career and the evolution of his music. It was followed in '81 by the obviously-themed THE GREATEST HITS OF HANK WILLIAMS, recorded at Starburst Studios in Toronto with himself and Cyril Rawani producing.
His last album was TEARS OF A MAN in 1983, with his daughter Kim providing the cover portrait. No singles were released and it was recorded at Grange Studios in Ajax, Ontario. Predominantly traditional country covers, the only track Bailey wrote was "The Place Where I Used To Live," along with co-producer/violinist Cecil Bank's "Pow Wow" and "Give Me A Chance." His last single came a year later - "Westward Home" - the story of Mormon pioneers heading west by wagon train to escape persecution.
He died of heart failure in 1987 at the age of 49. Bailey always preferred not to stray too far from family and home, so the majority of his larger scaled live events were in and around Ontario. One exception was when he rented a motorhome for the band, and made a trip to Oklahoma for a week-long private gig at someone's farm. His limited tour schedule also always included time to play the lodges and other functions up north in the Lake Kawasha region. He was also one of the go-to Canadian stars others turned to when they came up from Nashville. During his career, Bailey opened for the likes of Hank Snow, Faron Young, and Charley Pride, among many others.
His songs occasionally have popped up on compilation discs over the years, and his memory was immortalized when he was posthumously inducted into the Pathway of Fame in his hometown of Peterborough. Then in 2010 a celebration of his life was held - basically a 35 minute slideshow with his music as backdrop, entitled "Walk With Me."