In 1968, Radcliff also joined "The Northside Blues Band", alongside Brett Littlehales (harmonica), Guy Dorsey (keyboard), William Bowman (bass), and Van Holmead (drums).

Radcliff was so inspired by Magic Sam that he soon boarded a bus to Chicago, venturing to meet his newfound guitar idol.

Radcliff arrived in Chicago only to learn Magic Sam had suffered a major heart attack and was in Cook County Hospital.

[2] After Sam recovered, he invited Radcliff back to his home at 1513 South Harding Street, in the heart of Chicago's West Side.

They also went to The Key Largo where Otis Rush often performed and The Flash Lounge where Sam introduced Radcliff to Eddie Clearwater.

[3] Some of the other musicians that Sam introduced Radcliff to in Chicago include: Mighty Joe Young (guitar), Ernie Gatewood (who also sometimes played bass for Magic Sam), Otis Rush, Jimmy Dawkins, Mac Thompson (bass), Letha Jones (widow of pianist Johnny Jones), and many other musicians.

Writer Dave Hussong[4] Vintage Guitar Magazine (1990) touches on Radcliff's expansive musical range as a vocalist, instrumentalist, and live performer: "Unencumbered by style restrictions, Radcliff brings a sense of intensity and conviction, both instrumentally and vocally (the latter being an area where many 90's interpreters fall face down) that puts his, and this, live performance into a very special league of its own.

He performed most evenings and was one of the house musicians at the Lone Star Cafe and at Tramps, working with Kinky Friedman, Bernard Purdie, Otis Rush, Lowell Folson, and Big Jay Mc Neeley, amongst many others.

[6] During this time, there were many chance meetings at his shows, including when John Belushi saw Radcliff play at the Lone Star Café with Kinky Friedman in the late 1970s.