Sheryl's playing is unquestionably "sizzling". She has groomed incredible chops and impeccable taste with which she applies them. It's said (by Lee Metcalf, The Villager) that she can "go from zero to blazing in two beats", but she is continually praised for never sacrificing melody and lyricism for technique.
"She balances superior technical skills with a strong lyrical sense and swinging touch..." continues Metcalf, and Joe Taylor of Soundstage says "Bailey combines an astonishing command of the fingerboard with a seemingly endless flow of melodic invention."
As for the guitar, she's hardly had it out of her hands since the age of 13. That was when her mother finally relented to Sheryl's begging for a Harmony Strat from the J.C. Penney catalogue.
Though Sheryl was a rock-star wannabe, the influence of her pianist mother got her obsessed with learning harmony, and her first teacher in Pittsburgh, John Maione, introduced her to the guitar tradition-Wes, Jimmy Raney, George Van Eps, Joe Pass and others.
She eventually attended Berklee College of Music. Her years of dedication and focus won her 3rd place in the Thelonius Monk International Jazz Guitar competition in 1995, and she was chosen as a Jazz Ambassador for the U.S. State Department in 2000 for a South American tour.
She is now said to be "One of the top players in an emerging generation of jazz guitarists" (John Heidt, Vintage Guitar).