While attending the
University of Southern California, she agreed to write songs for a friend. Together, they wrote a collection of songs and recorded them in Solo's studio. The demo tape gave Gray the opportunity to sing at jazz cafés in Los Angeles. Although Gray did not consider her unusual voice desirable for singing, Macy returned to Ohio but in 1997
Los Angeles based
Zomba Label Group Senior VP A&R man
Jeff Blue, convinced her to return to music and signed her to a development deal, recording new songs based on her life experiences, with a new sound, and began shopping her to record labels. In 1998, she landed a record deal with
Epic Records. She performed on "Love Won't Wait", a song on the
Black Eyed Peas' debut album
Behind the Front.
1999–2001: On How Life Is Gray worked on her debut album in 1999 with producer
Darryl Swann. Released in the summer of 1999,
On How Life Is became a worldwide smash. The first single, "
Do Something", stalled on the charts, but the second single, "
I Try", made the album a success. "I Try" (which was originally featured in
Love Jones and the
Jennifer Aniston-starring romantic-comedy
Picture Perfect in 1997) was one of the biggest singles of 1999, and subsequent singles ("
Still" and "
Why Didn't You Call Me") ensured the album became triple platinum in the U.S. and quadruple platinum in the UK. In
2001, Gray won the
Grammy Award for Best Female Pop Vocal Performance for "I Try", which was also nominated for the
Song of the Year and
Record of the Year Grammys. 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. In August 2001, Gray was booed at the
Pro Football Hall of Fame exhibition game after forgetting the lyrics to the
American national anthem.
2001–2005: The Id and The Trouble with Being Myself 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). The album peaked at number eleven on the
Billboard 200. It fared even better in the UK, where it reached number one on the
UK Albums Chart and was certified gold by the
BPI. 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. 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 duet collection. Her song "Time of My Life" was included in the
soundtrack to 8 Mile. A cartoon based on Gray's childhood was being developed, but it never came to fruition. Nevertheless, it became Gray's third top twenty album in the UK. 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'".
2007–2010: Return to music and Big 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. She gave a public apology that night to avoid arrest. In March, Gray released her fourth studio album (sixth overall),
Big. Two singles, "
Finally Made Me Happy" and "
Shoo Be Doo", were released from the album. The album was critically acclaimed and seen by some as her best work to date. 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 U.S., where it debuted and peaked at number 39 on the
Billboard 200, becoming Gray's highest-charting album since
The Id.
Big reached number 62 on the albums chart in the UK, 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.
PBS's
Soundstage live concert series premiered a Gray concert on July 5. On July 7, 2007, Gray performed at the
Brazilian leg of
Live Earth at
Copacabana Beach in
Rio de Janeiro, Brazil. 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". Early in 2009, Gray recorded the song "Don't Forget Me" for the soundtrack of
Confessions of a Shopaholic.
2010–2011: The Sellout 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; 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. However,
The Boston Globes James Reed commended its production, and Jeremy Allen of
NME gave the album a 7/10 rating.
2011–2015: Covered, Talking Book, and The Way 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). On February 16, 2012, Gray participated in the
Sanremo Festival as a guest, performing alongside
Gigi D'Alessio and
Loredana Bertè. 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. 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.
2016–present: Stripped and Ruby 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 almost unanimous praise from critics. The album debuted at No. 3 on the
Billboard Jazz Chart. Earlier that year, she was featured on
Ariana Grande's song "Leave Me Lonely" from her third studio album,
Dangerous Woman. Gray released her tenth studio album,
Ruby, in September 2018. ==Other work==