Originally from
Anchorage, Kentucky, a suburb of
Louisville, Osborne moved to New York City in the late 1980s to study filmmaking at
New York University, where she had classes with legendary documentarian
George Stoney, among others. Osborne was paying her own way through college and taking time off to earn money for another semester when, by chance, she sang at an open mic night at the Abilene Café. The other musicians encouraged her to return, and she began singing weekly at the Abilene's open mic and at other blues open mics in NYC's East Village. She soon became immersed in NYC's live music scene, forming her own band and playing in nightclubs alongside groups like the Sweetones,
Surreal McCoys,
Spin Doctors,
Blues Traveler, and the
Holmes Brothers, and artists like
Chris Whitley,
Frankie Paris, and
Jeff Buckley. In 1991, she formed her own record label, Womanly Hips, to release her first full-length album,
Soul Show: Live at Delta 88, and she began to tour around the Northeast, building a devoted regional following. She signed a recording contract with Rick Chertoff of
Mercury Records, and released her second (and first major label) album
Relish (1995), which became a hit on the strength of the single "
One of Us". "Right Hand Man" and "
St. Teresa" were minor hits, and "Spider Web" also received radio play. Osborne wrote and directed the second music video for "St. Teresa". Osborne was a co-headliner for the
Lilith Fair in 1997. In 2001, Osborne produced an album for her friends the
Holmes Brothers,
Speaking in Tongues, engineered by Grammy winner
Trina Shoemaker and featuring backing vocals from
Catherine Russell,
Maydie Miles, and Osborne. The album was released by Alligator Records. In 2001, Osborne appeared on
Austin City Limits, singing material mainly from
Righteous Love. In a brief interview segment at the end of the episode, Osborne reflects on her gladness to have gotten out of the limelight of her mid-1990s stardom. She was featured in the 2002 documentary film
Standing in the Shadows of Motown and toured with
Motown sidemen
the Funk Brothers. She and her band accompanied the
Dixie Chicks for a national tour in the summer of 2003, during which time she also joined veteran San Francisco jam-rockers
The Dead as a vocalist, and released her fourth album, titled
How Sweet It Is, a collection of classic
rock and
soul covers. During 2005 and 2006, Osborne performed on numerous occasions with
Phil Lesh and Friends. Her vocals were featured prominently on the album
Live at the Warfield. She continues to make appearances with the band. In February 2007, she appeared on the
Grand Ole Opry. In May 2007, she issued
Breakfast in Bed, produced by
Tor Hyams, a return to the soul music that she had covered on
How Sweet It Is.
Breakfast in Bed also featured the two songs ("
Heatwave" and "
What Becomes of the Brokenhearted") that she had covered for the film
Standing in the Shadows of Motown. The same year, Osborne appeared as a featured guest in the third season of the
Transatlantic Sessions television series, performing "Saint Teresa", "Holy Water", and "Please Don't Tell Me How the Story Ends". Osborne sang lead vocals on the cover of the
Willie Dixon-penned "
Spoonful" on
Vivian Campbell's 2005 solo album,
Two Sides of If. She also provided vocals for "Wayfaring Stranger" on
Spearhead's 1997 album,
Chocolate Supa Highway. She interpreted "
Raglan Road" for
the Chieftains 1999 album,
Tears of Stone, and she covered
Dolly Parton's "Do I Ever Cross Your Mind" on the 2003 tribute album ''
Just Because I'm a Woman: Songs of Dolly Parton. She is featured on the Holmes Brothers 2007 collection State of Grace'' performing "
Those Memories of You", an old Alan O'Bryant
bluegrass tune. Osborne released the studio album
Little Wild One in September 2008. She performed as a guest vocalist on
Sgt. Pepper Live, the 2009 album and DVD by
Cheap Trick. In 2010, she was awarded the Woman of Achievement Award from
Women's Project Theater. She performed with
The Waybacks at
Merlefest, 2011, during the Hillside Album hour, featuring
The Allman Brothers'
Eat a Peach. In 2010, Osborne again produced an album for the
Holmes Brothers on Alligator Records,
Feed My Soul, which featured contributions from keyboard player
Glenn Patscha. Her album
Bring It On Home was released on March 27, 2012. It is a collection of vintage blues and soul covers, and it received a
2013 Grammy Awards nomination for
Best Blues Album. In September 2012, Osborne was featured in a campaign called "30 Songs / 30 Days" to support
Half the Sky: Turning Oppression into Opportunity for Women Worldwide, a multi-platform media project inspired by
Nicholas Kristof and
Sheryl WuDunn's book. Osborne was a member of
Trigger Hippy, along with
Steve Gorman,
Tom Bukovac,
Jackie Greene, and
Nick Govrik. The band released their debut album on September 30, 2014. She announced her departure from the group on her blog in October 2018. On October 31, 2015, Osborne and
Mavis Staples performed in Washington, D.C. at The George Washington University's Lisner Auditorium as part of their Solid Soul Tour. Osborne has a long history of political activism, in particular with
Planned Parenthood Federation of America. She began volunteering as a PPFA clinic escort in NYC in the 1980s, has organized benefit concerts for the group, and was honored as a PPFA "Woman of the Year" in 1997 after she promoted Planned Parenthood from the Lilith Fair stage in Houston, TX, despite being expressly forbidden to do so by the arena's owners, who then blacklisted her from the venue. Osborne released the original album
Love and Hate in 2014 and followed up in 2017 with
Songs of Bob Dylan, another cover album. In 2020, she published
Trouble and Strife, and in 2022, she issued the live compilation
Radio Waves. In 2023, Osborne released the studio album
Nobody Owns You. ==Personal life==