Winter's first Columbia album, Johnny Winter, was recorded and released in 1969. It featured the same backing musicians with whom he had recorded The Progressive Blues Experiment, bassist Tommy Shannon and drummer Uncle John Turner, plus Edgar Winter on keyboards and saxophone, and (for his "Mean Mistreater") Willie Dixon on upright bass and Big Walter Horton on harmonica. The album featured a few selections that became Winter signature songs, including his composition "Dallas" (an acoustic blues, on which Winter played a steel-bodied, resonator guitar), John Lee "Sonny Boy" Williamson's "Good Morning Little School Girl", and B.B. King's "Be Careful with a Fool".
The album's success coincided with Imperial Records picking up The Progressive Blues Experiment for wider release. The same year, the Winter trio toured and performed at several rock festivals, including Woodstock. With brother Edgar added as a full member of the group, Winter also recorded his second album, Second Winter, in Nashville in 1969. The two-disc album only had three recorded sides (the fourth was blank). It introduced more staples of Winter's concerts, including Chuck Berry's "Johnny B. Goode" and Bob Dylan's "Highway 61 Revisited". Johnny entered into a short-lived affair with Janis Joplin, which culminated at a concert at New York's Madison Square Garden, where Johnny joined her on stage to sing and perform.
Beginning in 1969, the first of numerous Johnny Winter albums was released which were cobbled together from approximately fifteen singles (about 30 "sides") he recorded before signing with Columbia in 1969. Many were produced by Roy Ames, owner of Home Cooking Records/Clarity Music Publishing, who had briefly managed Winter. According to an article from the Houston Press, Winter left town for the express purpose of getting away from him. Ames died on August 14, 2003, of natural causes at age 66. As Ames left no obvious heirs, the ownership rights of the Ames master recordings remains unclear. As Winter stated in an interview when the subject of Roy Ames came up, "This guy has screwed so many people it makes me mad to even talk about him."