Sheryl Bailey was born on May 20, 1966, and grew up on a farm outside Pittsburgh in a family where music was assumed rather than chosen. Her grandmother, Dr. Sally Tobin Dietrich, held a doctorate from Columbia and taught music, as had her own mother before her; Bailey's mother Sally played piano well enough to be asked to fill in on church organ, and raised four children alone. All of them took piano lessons, and all four went into the arts. Bailey took up trumpet in grade school after a second-grade aptitude test told her she was not band material, an insult she answered by making first chair and holding it into high school. She got her first guitar at thirteen, a Harmony bought from the J.C. Penney catalogue after a sustained campaign against her mother's better judgement, and spent the next several years on hard rock, working out Peter Frampton, Robin Trower and Van Halen solos by ear and slowing records down by weighting the turntable with a rock.

Jazz arrived from two directions at once: her older brother John came home announcing that he was into fusion, and Pittsburgh's public station WYEP gave her a music she found exotic and immediately meaningful. Her mother's response to a daughter who was skipping school to practice was to telephone Duquesne University and find her a teacher. That teacher, John Maione, ran her through the guitar tradition from the beginning, Charlie Christian and Eddie Lang and Carl Kress through Django Reinhardt and Joe Pass, and on to Wes Montgomery, Jimmy Raney, George Van Eps and Kenny Burrell. By fifteen she was practising six hours a day on a written schedule that split the time evenly between heavy metal and jazz. Maione brought her into Duquesne's summer jazz programs, where she first saw Tal Farlow play, and later Joe Pass, and where the Pittsburgh guitar institution Joe Negri taught. She spent a year at Duquesne, playing in the big band and in an ensemble led by the saxophonist Eric Kloss, before a fellow student talked her into leaving for Berklee College of Music.

Berklee gave her the harmony she had gone looking for. She studied with Ed Tommasi, Bruce Arnold, Bret Willmott, Jon Damian and Hal Crook, practised and transcribed for ten hours a day, and took her Bachelor of Music in 1988. In her last stretch there she played in the house band at Wally's Café, where Antonio Hart was in the band the summer before she left, and led her first billed jazz gig, a weekend at the Willow Jazz Club with the saxophonist Matt Otto and drummer Matt Wilson. Friends starting an Afro-pop group took her to Baltimore, and she stayed roughly from 1990 to 1995, booking her own gigs, working the house band at the Haven, playing in the trumpeter Allen Houser's band at Bertha's and in the organist Greg Hatza's trio, and meeting the pianist George Colligan and the trumpeter Alex Norris. She began teaching at Towson University around 1992, and in the same period toured Japan and the East Coast with the saxophonist Gary Thomas, taking the guitar chair Paul Bollenback had held. Her first album, Little Misunderstood, came out of that Baltimore circle, with Colligan on keyboards, Vince Loving on electric bass and Adrian Green on drums.

In 1995 she took third place in the Thelonious Monk International Jazz Guitar Competition at the Kennedy Center in Washington, behind Jesse van Ruller and Paul Pieper, in front of a panel of Jim Hall, Pat Martino, Pat Metheny, John Scofield and Mark Whitfield. She was the competition's first female instrumentalist finalist. By her own account she moved to New York officially in 1996 after a year of commuting from Baltimore; her own current biography dates her standing on the New York scene from 1998. Either way the pattern was the same: she rented a rehearsal room and ran sessions almost daily, played the Zinc Bar and Smalls nightly, and worked in the bassist Dwayne Burno's band alongside Myron Walden, with Jeff Ballard and Joe Farnsworth among the drummers. In 2000 the U.S. State Department made her a Jazz Ambassador for a South American tour built on Duke Ellington's repertoire, and a later program on Louis Armstrong sent her back into music she had never played.

The band that became her signature is the Sheryl Bailey 3, an organ trio she has kept running since 2001 and which holds a residency of more than fifteen years at New York's 55 Bar. Gary Versace on Hammond B-3 and Ian Froman on drums made The Power of 3 (2002), Bull's Eye (2003) and Live @ The Fat Cat, cut over two nights at the Christopher Street club in November 2005. Brian Charette took the organ chair for the Mel Bay concert film and disc Live in NYC (2008), and Ron Oswanski for A Meeting of Minds (Cellar Live, 2013), a program of twelve Bailey originals. Around the trio she has run a quartet in two forms, the Sheryl Bailey 4 of For All Those Living (2010), with Jim Ridl, Gary Wang and Shingo Okudaira and twenty percent of its sales given to the Ronald McDonald House of New York, and the current SBQ with Harvie S, Neal Smith and a rotating piano chair.

Her sideman work has always run wider than the organ trio suggests. She held the guitar chair in David Krakauer's Klezmer Madness and its successor Ancestral Groove for two decades, on Live in Krakow (Label Bleu, 2003), Bubbemeises: Lies My Gramma Told Me (2005), the John Zorn Book of Angels volume Pruflas (Tzadik, 2012) and Checkpoint (2014); Krakauer's funk-klezmer band Abraham Inc., co-led with Fred Wesley and Socalled, put her on lead guitar for eight of the nine tracks of Tweet Tweet (2009) and throughout Together We Stand (2019). She played the live "Liberty City" that closes the Japanese edition of Richard Bona's Munia: The Tale, recorded at the Jazz Standard in August 2002, and toured with Bona's Afro-pop band. She shared the guitar chair with Dida Pelled in Sherrie Maricle's DIVA Jazz Orchestra for the Johnny Mandel songbook The Man and His Music, recorded live at Dizzy's Club in May 2010 with Sharel Cassity on lead alto. Since 2016 she has held the guitar chair in the Anat Cohen Tentet, on Happy Song (recorded at Avatar Studios in August 2016) and Triple Helix (recorded at Sear Sound in January 2019), the second of which was nominated for the Grammy for Best Large Jazz Ensemble Album. In Boston she has become a regular in the tenor saxophonist Jerry Bergonzi's circle, on Bergonzi's Extra Extra (Savant, 2023), the co-billed Beantown Ballads (2024) and the bassist Bob Nieske's 8 Pieces for Sextet (2022).

Two of her records are acts of advocacy. A New Promise (MCG Jazz, 2009) is a tribute to Emily Remler, the guitarist who died in 1990 at thirty-two, produced by Marty Ashby and scored by Mike Tomaro for the sixteen-piece Three Rivers Jazz Orchestra with Bailey as the solo voice; it takes in three Remler compositions and a Bailey title tune written in her memory. Bailey later wrote the liner notes for Remler's posthumous Cookin' at the Queens: Live in Las Vegas 1984 and 1988 (2024). Homage (PureMusic, 2023), her twelfth album as a leader, is a quartet record for Pat Martino, opening with "The Velvet Hammer," written for him, and it followed her appearance on the Alternative Guitar Summit's Honoring Pat Martino, Volume 1 (HighNote, 2022), where she and Ed Cherry share "Willow." She has been on the Berklee faculty as a professor of guitar since 2000, moved from New York to Boston in 2020 to become Assistant Chair of the college's Guitar Department, and taught at the Collective School of Music in New York from 2005 to 2019. Her Mel Bay book Moveable Shapes: Concepts for Re-Harmonizing II-V-I's appeared in 2009, and her Bebop Dojo curriculum is published through TrueFire.

Bailey is a bebop player who arrived at bebop through heavy metal, and both halves of that are audible. The technique is rock-bred, fast and even and unbothered by tempo, which is what people mean when they quote Lee Metcalf on her going from zero to blazing in two beats; the content underneath is Charlie Parker, worked out on the electric guitar with the phrasing intact rather than translated into guitar idiom. She has said that in Baltimore in the early 1990s other players kept asking what she was doing over fusion vamps with distortion and a wah pedal, and that the answer was simply the Omnibook. Her early models were the Berklee generation of Mike Stern, John Abercrombie and John Scofield; New York sent her backwards, to Grant Green, Wes Montgomery, Tal Farlow and Pat Martino, and it is Martino's long unbroken eighth-note line and Green's groove that the Sheryl Bailey 3 is built on. As a writer she names Horace Silver for his blues sense and comping, Thelonious Monk for the tunes, and the middle and late 1960s Blue Note records of Hank Mobley and Kenny Dorham for their feeling, with early Chick Corea close behind. Adam Levy in Guitar Player credited her with one of the most compelling tones of her generation, DownBeat's Phillip Booth called her one of the new greats of the instrument, and Berklee's own record lists her as a DownBeat Critics Poll Rising Star in each year from 2014 through 2019.