Born and raised in the Bronx's Riverdale neighborhood, Simon's father was the successful book publisher Richard L. Simon, co-founder of Simon & Schuster. In an attempt to overcome a childhood stuttering problem, she turned to singing at a young age and soon began to write her own songs. She and her elder sister Lucy formed a short-lived folk duo, the Simon Sisters, in the mid-'60s, releasing a handful of albums for the independent Kapp label before parting ways in 1969. Within a year Simon had secured a major-label deal with Elektra which issued her eponymous 1971 solo debut. Not unlike her peers Carole King and Joni Mitchell, Simon wrote in an introspective, confessional style and earned her first taste of success with the Grammy-nominated "That's the Way I've Always Heard It Should Be," a Top Ten hit that questioned the merits of marriage. She followed it in November of that year with Anticipation, a similarly successful record whose title track -- supposedly written before going on a date with Cat Stevens and later used in a series of popular Heinz ketchup commercials -- also became a significant hit.
After winning the Grammy Award for Best New Artist in March 1972, Simon became a household name with the November release of "You're So Vain" from her third album, No Secrets. A canny take-down of an arrogant male lover, the song became a massive chart-topping hit around the world, sparking decades of speculation about the identity of its subject. Simon has hinted that it was written about three different men, only one of which, actor Warren Beatty, was revealed. The album, too, was a big success, reaching number one in numerous countries and going platinum in the U.S. Around this time, Simon married fellow singer/songwriter James Taylor, who duetted with her on 1974's "Mockingbird," another Top Ten hit from her fourth album Hotcakes. That album's sense of joy and domestic tranquility resonated with fans and helped it reach the number three spot, just behind Simon's labelmates Bob Dylan and Joni Mitchell. Released a year later, Playing Possum represented more of a shift toward rock and adult contemporary pop, with strong material like "Waterfall" and "Attitude Dancing," and a rather controversial cover photo of a lingerie-clad Simon that earned yet her another Grammy nomination, this time for album packaging. She kept on cruising through the second half of the '70s, taking on even more of a soft pop glow on 1976's crafty Another Passenger, an album which featured backing by members of the Doobie Brothers and Little Feat, and yielded the Michael McDonald-penned hit "It Keeps You Runnin'." A year later Simon was asked to write the theme song to the James Bond film The Spy Who Loved Me. Her contribution, "Nobody Does It Better," was an instant classic, becoming another international chart-topper and one of the Bond franchise's best-loved themes. 1978's Boys in the Trees put her back in the Top Ten after Another Passenger's somewhat disappointing sales. It was also a creative triumph with a more varied array of moods and styles including the jazzy hit "You Belong to Me." Simon ended the decade with 1979's Spy, a commercial disappointment, that nonetheless produced a handful of standout cuts including the fan favorite "Never Been Gone."
Having completed her contract for Elektra, Simon signed with Warner Bros. for 1980's Come Upstairs. Its hit single "Jesse" helped it perform better than Spy, but overall she had begun a commercial slide toward the middle of the pop charts that lasted for much of the '80s. She and Taylor, who divorced in 1983, appeared in the protest film No Nukes and she also contributed songs to In Harmony and In Harmony 2, a pair of Grammy-winning Sesame Street albums produced by her sister Lucy Simon. Simon's 1981 LP, Torch, saw her taking on a set of jazz standards long before singing the great American songbook became trendy among rock musicians. Over the next few years, she became something of a musical journeywoman, guesting on other artist's releases and contributing to various soundtracks including the Chic-produced "Why" from 1982's Soup for One, which became a hit in the U.K. She also found success in Britain appearing on Lynn Goldsmith's quirky 1983 Will Powers track "Kissing with Confidence." While her own albums Hello Big Boy (1983) and Spoiled Girl (1985) were commercial disappointments, she continued to write quality material and landed songs in films like Swing Shift, Nothing in Common, and The Karate Kid II, as well as guesting on albums by Jesse Colin Young and Nils Lofgren. After joining the Arista label, Simon rebounded with 1987's Coming Around Again and its hit title track which she'd written for the Mike Nichols film Heartburn. Two years later, another Mike Nichols film sparked a revival in Simon's career. Written, produced, and performed by Simon for 1988's Working Girl, "Let the River Run" won an Oscar, a Grammy, and a Golden Globe, making her the first single artist to win all three major awards for the same song.
Simon's career in the '90 followed in a similarly diverse fashion beginning with 1990's My Romance, her second standards album, and Have You Seen Me Lately, a set of new originals. Over the next few years she continued composing soundtrack music for directors like Nichols and Nora Ephron. She also began a concurrent career as an author of children's books and was commissioned by the Met and the Kennedy Center to write the "family opera" Romulus Hunt. Her well-received 1994 album, Letters Never Sent, was literally composed from a box of unsent letters she uncovered in her home. Following the 1995 retrospective box set, Clouds in My Coffee, and subsequent concert film, Live at Grand Central, Simon issued Film Noir (1997), the third album in her jazz standards series. At the end of 1997, a breast cancer diagnosis and subsequent surgery and chemotherapy treatment temporarily sidelined her music career. This eventually led to the recording of The Bedroom Tapes, a stripped-down collection of new material she wrote and recorded in the late '90s while recovering from her illness.
Released in 2000, the album was considered by critics to be a highlight of her post-'70s career. After issuing her first holiday album, 2002's Christmas Is Almost Here, she wrote a set of songs for the soundtrack to Disney's 1993 animated feature Piglet's Big Movie; several of the songs featured her two children, Ben and Sally Taylor. 2005's Moonlight Serenade, her fourth collection of jazz standards, became a surprise hit, peaking at number seven on the Billboard 200 and returning Simon to the Top Ten for the first time since the mid-'70s. 2007's Into White, another collection of covers and standards, performed similarly well, hitting number 13 upon its release. A year later, This Kind of Love marked Simon's return to original music. Featuring more sparse acoustic arrangements, it was another critical and commercial hit despite the fact that its label, the Starbucks-owned Hear Music, folded just days before the album's release. She later sued the label for its failure to promote the release. Continuing with the back-to-basics approach of this period, Simon recorded acoustic versions of her older songs, along with a couple of new tracks, and released them on the 2009 album Never Been Gone.
A period of relative quiet followed over the next decade. She made a handful of live appearances, joining Taylor Swift for a 2013 performance of Simon's classic "You're So Vain," and accepting a Founders award from the publishing rights organization ASCAP. In November 2015, Simon published her first memoir, Boys in the Trees: A Memoir, along with an accompanying two-disc compilation called Songs from the Trees: A Musical Memoir Collection. Among her few studio dates of this era was an unlikely appearance on U.K. group Gorillaz's 2017 album, Humanz. In late 2019, Simon published a second memoir devoted to her friendship with the late Jacqueline Kennedy Onassis titled Touched by the Sun: My Friendship with Jackie. ~ Timothy Monger, Rovi
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