After a short-lived attempt at launching a career with her sister Lucy (they had a minor hit in the mid-1960s with a version of the children's song "Winken, Blinken, and Nod" as "The Simon Sisters"), and a short spell with eclectic New York rockers Elephant's Memory, Simon launched her solo career in 1971 with the self-titled Carly Simon . The album contained a top-ten hit, "That's the Way I've Always Heard It Should Be", and was followed quickly by a second album, Anticipation , the title cut from which also scored airplay. Simon's major breakthrough, though, was 1972's No Secrets . The album spawned several successful singles, including Simon's biggest hit, "You're So Vain" (see that article for the enduring mystery of who the song is about).
Simon married fellow singer-songwriter James Taylor in 1972 and followed up the success of No Secrets with a series of well-received albums Hotcakes (1974) and Playing Possum (1975). Her sales began moderating, though in the later 1970s she would have hits with "Nobody Does It Better" (from the soundtrack to the James Bond film The Spy Who Loved Me) and "You Belong to Me" (from Boys in the Trees , 1978).
In 1980, Simon collapsed onstage of exhaustion, and largely retired from performing in the 1980s. Torch (1981) was an album of melancholy standards reflecting her mood at the time. "Why" (1982) was a hit in the UK, but few of her singles in the 1980s rose in the pop charts, although some did better among adult contemporary audiences. Moreover, during this time Simon successfully contributed to several film scores, including the songs "In The Wee Small Hours" for Sleepless In Seattle, "Coming Around Again" for Heartburn, and "Let the River Run" for Working Girl (for which she won the Academy Award for Best Song in 1988). The album Coming Around Again (1987) was her strongest during this decade, as exemplified by "Stuff That Dreams Are Made Of", and the title track, which wove in and out of the childrens' song "Itsy Bitsy Spider". These and older songs were featured in a picturesque HBO special set on Martha's Vineyard.
Simon worked on several projects in the 1990s including an opera Romulus Hunt and a cover of "Take Me Out To The Ball Game" for Ken Burns' 1994 film Baseball. In 1995 she put aside years of stage fright long enough to stage an American concert tour in conjunction with Hall and Oates. In 1998, Simon was diagnosed with breast cancer and received chemotherapy. She survived her disease, and in 2000 recorded her first album since her illness, The Bedroom Tapes .