Macy Gray

Gray worked on her debut album in 1999 with producer Darryl Swann.[14] Released in the summer of 1999, On How Life Is became a worldwide smash.[15] The first single "Do Something" stalled on the charts, but the second single "I Try" made the album a success.[16] "I Try" (which was originally featured in Love Jones and the Jennifer Aniston-starring romantic-comedy Picture Perfect in 1997)[17] was one of the biggest singles of 1999,[18][19] and subsequent singles "Still" and "Why Didn't You Call Me" ensured the album became triple platinum in the US[20] and quadruple platinum in the UK.[21]

In 2001, Gray won the Grammy Award for Best Female Pop Vocal Performance for "I Try", which was also nominated for "song of the year" and "record of the year".[22] She then collaborated with Fatboy Slim, the Black Eyed Peas, and Slick Rick (on the song "The World Is Yours," from the Rush Hour 2 soundtrack), as well as acting for the first time, in the thriller Training Day.[23] In August 2001, Gray was booed at the Pro Football Hall of Fame exhibition game after forgetting the lyrics to the American national anthem.[24]

Gray visiting the Astrodome as a volunteer, in Houston, Texas, September 3, 2005

Gray's The Id featured appearances by John Frusciante and Erykah Badu on the single "Sweet Baby" (which was co-written with longtime collaborator Joe Solo).[25] The album peaked at number eleven on the Billboard 200.[26] It fared even better in the UK, where it reached number one on the UK Albums Chart and was certified gold by the BPI.[27] The underperformance in the United States, compared to her debut album, may have been due to The Id being released just a week after the September 11, 2001 attacks.[28]

In 2002, she appeared in Spider-Man and contributed a remix of her song "My Nutmeg Phantasy" to its accompanying soundtrack. Gray also worked with Santana on the track "Amoré (Sexo)," for his album Shaman.[29][30]

Also in 2002, she appeared on the Red Hot Organization's compilation CD in tribute to Nigerian Afropop pioneer Fela Kuti, Red Hot and Riot. She appeared on a remake of Kuti's classic track "Water No Get Enemy" alongside prominent neo soul, hip hop and R&B artists, D'Angelo, the Soultronics, Nile Rodgers, Roy Hargrove, and Kuti's son, Femi Kuti.

She recorded a duet with Zucchero called "Like the Sun (From Out of Nowhere)", which featured Jeff Beck on guitar released in 2004 on Zu & Co., a duets collection.[31][32] Her song "Time of My Life" was included in the soundtrack to 8 Mile.[33] A cartoon based on Gray's childhood was being developed, but it never came to fruition.[14][30]

In 2003, Gray released her third studio album, The Trouble with Being Myself, to rave reviews. The lead single, "When I See You," became a radio hit in the US and a top-forty hit in the UK, although the album was not as well received by fans.[34] Nevertheless, it became Gray's third top twenty album in the UK.[35][36] A greatest hits collection and a live album were subsequently released: The Very Best of Macy Gray (2004) and Live in Las Vegas (2005). Additionally, Gray was featured on Marcus Miller's 2005 album Silver Rain, on a cover of Prince's 1986 song "Girls & Boys." She also appeared on the soundtrack to the film Chicago with Queen Latifah and Lil' Kim on "Cell Block Tango/He Had it Comin'."[37]

Gray performing in Toronto, July 23, 2008

Gray began 2007 by being kicked off-stage at a concert in Barbados for profanity (which was part of the show), but she was not aware that it was against the law in that country.[38] She gave a public apology that night to avoid arrest.[39]

In March, Gray released her fourth studio album (sixth overall), Big.[40] Two singles, "Finally Made Me Happy" and "Shoo Be Doo," were released from the album.[39] "What I Gotta Do," another track from the album, is featured on the Shrek the Third soundtrack. It has been considered Gray's comeback album, after a four-year hiatus since her last studio album.[41] The album was critically acclaimed and seen by some as her best work to date.[42] It features collaborations with Natalie Cole, Fergie, Justin Timberlake, and will.i.am, who co-executive produced the album with Gray. It was moderately successful in the US, where it debuted and peaked at number 39 on the Billboard 200, becoming Gray's highest-charting album since The Id.[43] Big reached number 62 on the albums chart in the UK,[44] her lowest-charting UK album, but it achieved some success in several other countries, including Switzerland, the Czech Republic, and Finland, reaching the Top 40 on their album charts.[45]

PBS's Soundstage live concert series premiered a Gray concert on July 5.[46]

Gray performing at the Live Earth Brazil concert at Copacabana Beach, Rio de Janeiro on July 7, 2007

On July 7, 2007, Gray performed at the Brazilian leg of Live Earth at Copacabana Beach in Rio de Janeiro, Brazil.[47] Gray and her band members wore clothes bearing political messages. Gray's dress carried the message "Darfur Red Alert."

In 2008, Gray launched a new campaign under the name "Nemesis Jaxson," with the single "Slap a Bitch."[48]

Early in 2009, Gray recorded the song "Don't Forget Me" for the soundtrack of Confessions of a Shopaholic.[49]

The first single from Gray's fifth studio album The Sellout, "Beauty in the World," is featured in the final sequence of the series finale, "Hello Goodbye," of the ABC television series, Ugly Betty. "Beauty in the World" was also used as the theme in multiple videos created by Microsoft to promote Internet Explorer 9. Both singles released from the album ("Beauty in the World" and "Lately") were top 10 hits on the US Billboard Hot Dance Club Songs Chart.

Upon its release, The Sellout received generally mixed reviews from most music critics. Metacritic gave it an average score of 57, based on 15 reviews;[50] Andy Gill of The Independent gave it three out of five stars; while AllMusic writer John Bush shared a similar sentiment and panned Gray's songwriting.[51]

However, The Boston Globe's James Reed commended its production,[52] and Jeremy Allen of NME gave the album a 7/10 rating.[53]

Gray performs live at the 54th Ljubljana Jazz Festival in Ljubljana, Slovenia, on July 6, 2013

In 2011, Gray signed a deal with 429 Records and started recording a series of covers for her next studio album Covered. The album was officially released on March 26, 2012. The album's first single was "Here Comes the Rain Again" (originally performed by Eurythmics).[54] On February 16, 2012, Gray participated in the Sanremo Festival as a guest, performing alongside Gigi D'Alessio and Loredana Bertè.[55]

For the 40th anniversary of the 1972 Stevie Wonder album Talking Book, Gray covered the entire record and released her Talking Book as a tribute.[56]

In an interview with Oprah Winfrey's Where Are They Now, Gray opened up about her problems with drug abuse, stating that she was ill-prepared for the level of fame she received. The interview coincided with the release of her album The Way, released in October 2014 on Kobalt Records. A world tour was announced shortly after its release.[57]

In 2016, Gray's career continued with an album produced by Chesky Records, the record label founded by Grammy-nominated composer and musician David Chesky. Stripped was released September 9, 2016 and garnered unanimous praise from critics. The album debuted at No. 3 on the Billboard Jazz Chart.[1] Earlier that year, she was featured on Ariana Grande's song "Leave Me Lonely" from her third studio album Dangerous Woman.

Gray appeared in the eighth season of Bravo's Celebrity Poker Showdown, playing for Habitat for Humanity. She finished in third place.[58]

In 2001, she was the voice for Seeiah Owens in the video game SSX Tricky.[59][60]

Gray sang the theme song for the Nickelodeon animated series As Told by Ginger, composed by Jared Faber and Emily Kapnek.[61]

Gray also performed the song on the short-lived UPN romantic comedy Second Time Around starring Boris Kodjoe and Nicole Ari Parker in 2004.

In August 2008, Gray headlined at the 2008 Summer Sundae music festival in Leicester, England, performing cover versions of Rod Stewart's "Do Ya Think I'm Sexy?," Deee-Lite's "Groove Is in the Heart" and Radiohead's "Creep."[62] For the gig, her band wore pink Andy Warhol wigs.[63]

On September 28, 2008, Gray sang the American national anthem as part of the Israeli flag-raising ceremony at the Israeli consulate of Los Angeles.[64][65]

In 2008, Gray collaborated with Australian DJ and singer Kaz James on the song "Can't Hold Back." The single was released in early 2009 in Australia and is credited to Kaz James featuring Macy Gray.[66]

In 2009, Gray briefly competed in season 9 of Dancing with the Stars with professional partner Jonathan Roberts. They were eliminated in a double elimination in week one.

In 2012, she performed the Michael Jackson song "Rock with You" for a special performance of the West End musical Thriller – Live for BBC Children in Need Pop Goes the Musical.

In 2015, Gray was featured on the song "Into the Deep" by Galactic.[67]

In 2016, Gray was featured on the song "Leave Me Lonely" by Ariana Grande.

In 2018, Gray was featured alongside Dolly Parton on a re-recording of "Two Doors Down" for the Dumplin' soundtrack.

In 2020, Gray was featured on the single "Out Of Love" by Canadian band Busty and the Bass. The band also released a notable cover of Gray's "I Try" in 2016.