The Beatles, Kinks and Jimi Hendrix were among his early bookings with Stringfellow later recalling how he rang Brian Epstein from a phone box and negotiated an £85.00 fee for the then little-known Fab Four to play Sheffield's Azena Ballroom. Soon after agreeing the booking, Beatlemania erupted, landing the flamboyant entrepreneur the first of many successful business deals.
"Brian (Epstein) gave me his word and he stuck to it. I picked the Beatles up in a Ford Anglia," Stringfellow told
The Yorkshire Post in 2014. "It was just pandemonium when the Beatles came on stage. It was the most exciting night of my life," he remembered some fifty years later.
The mid to late 1960s also saw Howlin' Wolf, Wilson Pickett, The Small Faces, Stevie Wonder, The Searchers, Elton John, The Who, Rod Stewart, Tina Turner, Pink Floyd and The Rolling Stones perform at Stringfellow's various Sheffield venues, The Black Cat Club, The Blue Moon and King Mojo Club.