With brother Edgar added as a full member of the group, Winter recorded his third album 'Second Winter' in Nashville in 1969, with the two-disc album having just three sides of music, with the fourth side being blank.
Winter's first Columbia album 'Johnny Winter' was recorded and released in 1969, using the same backing musicians who played on 'The Progressive Blues Experiment', plus blues legend Willie Dixon on upright bass and Big Walter Horton on harmonica. King's 'It's My Own Fault' to loud applause, they snapped him up with reportedly the largest advance in the history of the recording industry at that time - $600,000.
Representatives of Columbia Records were at the concert, and after Winter played and sang B.B. His big break came at the end of that year, when Mike Bloomfield, whom he met and jammed with in Chicago, invited him to sing and play a song during a Bloomfield and Al Kooper concert at the Fillmore East in New York City. His recording career began at the age of 15, when his band Johnny and the Jammers released 'School Day Blues' on a Houston record label, and after recording a single with Roy Head And The Traits, he released his first album 'The Progressive Blues Experiment' in 1968. They were encouraged in their musical pursuits by their father John Dawson Winter Jnr, who was also a musician who played saxophone and guitar and sang at churches and weddings, and they appeared on a local children's show with Johnny playing ukulele when he was 10 years old. John Dawson Winter III was born in Beaumont, Texas, on February 23, 1944, two years before his brother Edgar made an apperance in 1946.