Jack was born to Eugene and Etta Bailey. He began violin lessons at age 6 and started his professional career as a musician at age 16, working with Jack Beasley on KOMA radio. In 1947 he worked at KWKH in Shreveport, La. with "Pop" Echols and the Melody Ranch Boys. In the '50's he went to Gallup, NM with the Benny Martin band which was featured in the motion pictures Ace in the Hole and The Big Carnival. He joined Merle Lindsey and the Oklahoma Night Riders, later known as the Ozark Jubilee Band, with Red Foley. He toured the West coast with Pee Wee King in 1956. He toured with Little Jimmy Dickens, the Wilburn Brothers, Minnie Pearl and others. He backed such greats as Lefty Frizzell, Ernest Tubb and Ray Price. Later Jack joined Frankie McWhorter to form the "Over the Hill Gang." They worked as a team for almost 25 years and performed at Bob Wills Days in Turkey, TX. They were featured at the first two years of the Cowboy Symposium at Ruidosa, NM. Jack worked with Leon Rausch, Curly Lewis, Glen "Blub" Rhees, Benny Garcia, Bob Koefer, Eldon Shamblin, and Bob Wills.
He married Sue Murphy on June 30, 1957 in Goodwell. He graduated from Panhandle State Univ. with a music degree. He taught in the public school system for eleven years and gave private guitar and fiddle lessons. He established the Malachi Recording Studio in Goodwell.
He was in the Army during WW2. As a member of Goodwell Baptist Church he was a deacon and Sunday School teacher. He was a member of the Panhandle Lions Club and the
Musicians Union. He was inducted into the Western Swing Society Hall of Fame in October of 1997.
Survivors include his wife of 41 years; a daughter Rebecca Bailey of Midland, TX; and a son Robert Eugene Bailey of Pampa, TX.