Macy Gray parlayed an utterly unique voice and an outlandish sense of style into pop stardom at the turn of the millennium, appealing to audiences of all colors in search of a fresh alternative to mainstream R&B. After an accidental entry into the music industry, she reached the mainstream in grand style with "I Try," a Top Five pop hit in 1999. A Grammy award for Best Female Pop Vocal Performance, and multiple platinum certifications for the parent album, On How Life Is, followed shortly thereafter. Gray went on to build a sizeable and unpredictable discography that included gutsy original material and bold covers that paid tribute to Stevie Wonder, Nina Simone, and Metallica. By 2016, she was revisiting career highlights with a jazz quartet, as documented on Stripped, but Ruby, issued two years later, affirmed that she wasn't content to live strictly in the past. Gray was born Natalie McIntyre in Canton, Ohio, and grew up a shy youngster frequently teased about her odd-sounding voice. She studied classical piano but also soaked up the music of soul legends like Stevie Wonder, Marvin Gaye, and Aretha Franklin, as well as old-school hip-hop. At boarding school as a teenager, she was exposed to a variety of rock & roll. She moved to Los Angeles to enroll in USC's screenwriting program, where one day she agreed to write lyrics for a friend's original songs. A demo session was scheduled to get the songs on tape, and when the singer failed to show up, Gray -- having adopted the full name of an elderly Canton neighbor as her creative alias -- wound up singing on the recordings, in spite of her distaste for her own voice. One of the songs was never overdubbed with another vocalist, and when the tapes started making the rounds of the local music scene, Gray's raspy growl attracted attention. She sang jazz and pop standards with a band that played in hotels around Los Angeles, continued work as a demo singer, and also performed at an after-hours club she organized. All the buzz led to a recording contract with Atlantic Records. Gray recorded an album, but the label declined to release it. Devastated by this rejection and the breakup of her marriage, Gray retreated to Canton. However, her demo tape continued to make the rounds, and she returned to L.A. to accept a publishing deal with Zomba. This in turn helped lead to a new record contract with Epic. Released in July 1999, On How Life Is won glowing reviews and great word of mouth, but was initially slow to catch on. That changed early the next year, when Gray received Grammy nominations in the categories of Best New Artist and Best Female R&B Vocal. That May, "I Try" peaked at number five on the Billboard Hot 100, and the album went triple platinum by the end of the year. "I Try" prompted three 2001 Grammy nominations: Record of the Year, Song of the Year, and Best Female Pop Vocal, the last of which she won. Gray subsequently recorded with Fatboy Slim, the Black Eyed Peas, and Slick Rick, and made her screen acting debut in the Denzel Washington police drama Training Day. By the time she began work on her second album, Gray was developing a reputation for surreal public appearances and interviews, culminating in an August 2001 incident in which she was booed for apparently stumbling over the lyrics to the national anthem. Released the following month, The Id was a determined effort to play up the crazy side of Gray's image. It entered the Billboard 200 at number 11, quickly went gold on the strength of lead single "Sweet Baby," and featured appearances from Erykah Badu and the Red Hot Chili Peppers' John Frusciante, among others. Between releases, Gray appeared as herself in the blockbuster film Spider-Man and also guested on Santana's Shaman. In April 2003, her third album, The Trouble with Being Myself, arrived on the shelves and peaked at number 44. Gray then moved from Epic to Geffen. With a new production team, including will.i.am and his confederate Ron Fair, Gray returned with a slicker, Tom Joyner-approved version of soul on Big, a March 2007 release that entered the Billboard 200 at number 39. Throughout the following decade, Gray continued to move from label to label with a varied mix of covers and originals in her arsenal. The Sellout, a June 2010 release for Concord, featured some self-composed songs and an appearance from Bobby Brown, and became her fourth Top 40 album. Gray then signed to the 429 label for a pair of full-lengths released in 2012: Covered (March) featured renditions of songs by Metallica, My Chemical Romance, and Kanye West, while Talking Book (October) was a song-for-song tribute to Stevie Wonder's 1972 classic. The Way, a set of original material, was independently released with help from rights management company Kobalt in October 2014. Backed by a jazz quartet featuring trumpeter Wallace Roney, Gray then cut Stripped for the Chesky label. It arrived in September 2016 with new versions of "I Try" and "Sweet Baby" among more covers. Two years later, she moved to Mack Avenue's Artistry subsidiary for Ruby, which featured new material written with the likes of Ryan Tedder and Meghan Trainor. ~ Steve Huey & Andy Kellman
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Pop - Released September 7, 2004 | Epic
In more ways than one, Macy Gray is a bit like the Dan Marino of neo-soul: full of promise and potential but never truly reaching her full blossom. Having only reached the Top Ten promised land once (and Top 40 only three times) in her five-year career on the good ship Epic, it's hard to call this a "very best of" and get excited about the songs held within the packaging. Starting off with the one-two chronological punch of "I Try" and "Do Something," the air starts to leak out of the ball ever so slowly as the compilation progresses, leaving a deflating feeling by the time the new additions are reached. And while "Love Is Gonna Get You" is as delightful as anything she's done in the past few years (the Philly soul strings and Memphis-styled production values make it infectiously delicious), the unforgivable atrocity that is her interpretation of Aerosmith's classic "Walk This Way" cancels that feeling out rather quickly. Nevertheless, if you wanted all of her hits together in one package, this is most definitely the place to start. ~ Rob Theakston
R&B - Released July 3, 1999 | Epic
Macy Gray is such an assured, original vocalist that it's hard to believe On How Life Is is her debut album. She recalls a number of other vocalists, particularly jazz singers like Billie Holiday and Nina Simone, but she is unquestionably from the post-hip-hop generation, which is evident not just from the sound of the record, but the style of her songwriting, which is adventurous and unpredictable. Thankfully, she's worked with a producer (Andrew Slater, who pulled a similar trick with Fiona Apple's debut, Tidal) that lets her run wild and helps her find sounds that match her ideas. That's not to say that On How Life Is is a perfect album -- at times, Gray attempts more than she can achieve -- but it's always captivating, even during its stumbles. And when it works, it soars higher than most contemporary R&B. ~ Stephen Thomas Erlewine
Pop - Released January 1, 2010 | Concord Records, Inc.
Macy Gray began working on The Sellout just after her fourth studio album, Big, and the reasons it took three years to release are evident from the credits: she wrote lyrics plus music for most of the songs. The results of that effort are apparent, and they're not good. Gray wields one of the most naturally talented voices in R&B, but from the evidence here, she's not a songwriter, and her material for The Sellout proves she needn't worry further about selling out if she keeps on composing -- commercial success will easily avoid her. The first single, "Beauty in the World," has a lyric and melody by Gray alone, and despite the positive sentiments in the song, its melody is unmemorable and it includes a few embarrassing lines (e.g., "There is beauty in this world/So much beauty in this world/Always beauty in this world/So much beauty in this world/Shake your booty boys and girls/For the beauty in the world"). Still, there are a parade of collaborators on The Sellout, leading to plenty of solid moments, including the Rodney Jerkins production on "Help Me," the tender "Still Hurts" (written by Teedra Moses and Gray), and a few songs written and produced by Jared Lee Gosselin and Phillip White -- including "Real Love" with Bobby Brown, which succeeds wildly with its updated quiet storm production. Gray's vocals have only gotten better with time, and although she doesn't attempt to stretch at all, she's still one of the best-felt voices in neo-soul. As long as she avoids composing her own material without help from a few professionals, she'll ensure a long career. ~ John Bush
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