A gifted storyteller with enduring appeal, Tracy Chapman's unexpected ascent from the Boston folk scene to mainstream popularity in the late 1980s proved pivotal in helping restore singer/songwriters to the spotlight. Delivered with an earthy grace, her simple melodies and affecting, often socially conscious lyrics resonated with fans around the globe, who helped turn her eponymous 1988 debut into a Grammy-winning multi-platinum success. Seemingly averse to commercial whims, Chapman has managed to avoid the pitfalls of trendiness, building on early hits like "Fast Car" and 1996's bluesy "Give Me One Reason" with a durable catalog that plays to the strength of her craft and convictions. Throughout the 2000s, her fan base remained strong on both sides of the Atlantic with albums like Let It Rain and Where You Live as well as a foray into composing for theater. While her studio output has remained scant since 2008's Grammy-nominated Our Bright Future, Chapman has continued to perform, and in 2015 sang an evocative rendition of Ben E. King's classic "Stand by Me" on one of the final episodes of Late Night with David Letterman that became a viral hit. A Greatest Hits compilation was released that same year.

Raised in a working-class neighborhood in Cleveland, Ohio, Chapman learned how to play guitar as a child, and began to write her own songs shortly afterward. Following high school, she won a minority placement scholarship and decided to attend Tufts University, where she studied anthropology and African studies. While at Tufts, she became fascinated with folk-rock and singer/songwriters, and began performing her own songs at coffeehouses. Eventually, she recorded a set of demos at the college radio station. One of her fellow students, Brian Koppelman, heard Chapman play and recommended her to his father, Charles Koppelman, who ran SBK Publishing. In 1986, she signed with SBK and Koppelman secured a management contract with Elliot Roberts, who had worked with Neil Young and Joni Mitchell. Roberts and Koppelman helped Chapman sign to Elektra in 1987.

Chapman recorded her debut album with David Kershenbaum, and the resulting eponymous record was released in the spring of 1988. Tracy Chapman was greeted with enthusiastic reviews, and she set out on the road supporting 10,000 Maniacs. Within a few months, she played at the internationally televised concert for Nelson Mandela's 70th birthday party, where her performance was greeted with thunderous applause. Soon, the single "Fast Car" began climbing the charts, eventually peaking at number six. The album's sales soared along with the single, and by the end of the year, the record had gone multi-platinum. Early the following year, the album won four Grammys, including Best New Artist.

It was an auspicious beginning to Chapman's career, and it was perhaps inevitable that her second long-player, 1989's darker, more political Crossroads, didn't fare quite as well. Although it was well reviewed, the album wasn't as commercially successful, peaking at number nine and quickly falling down the charts. Following Crossroads, Chapman spent a few years in seclusion, returning in 1992 with Matters of the Heart. The record was greeted with mixed reviews and weak sales, and for a time, it seemed Chapman had begun to fall into obscurity.

Three years later, she rebounded with New Beginning, which featured the bluesy single "Give Me One Reason." Released in 1995, the song slowly climbed the charts, eventually peaking at number three on the Billboard Hot 100 and earning Chapman another Grammy for Best Rock Song in 1997. It was a quiet, successful comeback from an artist most observers had already consigned to languish in cult status. After a four-year break, she delivered her fifth album, Telling Stories, in 2000. The record and its single, "Telling Stories," fared well both in the U.S and in Europe, where Chapman's presence was increasingly in demand.

Throughout the next decade, she would continue to fare well overseas, releasing 2002's Let It Rain and 2005's Where You Live and touring frequently both Stateside and in Europe. Still a socially conscious artist, Chapman was commissioned by the American Conservatory Theater in 2008 to compose the music for their production of Athol Fugard's apartheid-themed play Blood Knot. That same year, she released her eighth album, Our Bright Future, and received another Grammy nomination, this time for Best Contemporary Folk Album. For a number of years following its release, little was heard from Chapman until a 2015 live appearance on The Late Show with David Letterman. Performed during the final week of Letterman's tenure on the show, Chapman's haunting rendition of Ben E. King's "Stand by Me" became a viral hit and was eventually included on her first Greatest Hits compilation, released in November of that year. ~ Stephen Thomas Erlewine & Timothy Monger