The Grammy Awards are awarded annually by The Recording Academy of the United States for outstanding achievements in the music industry. Often considered the highest music honour, the awards were established in 1958. Simon has received fourteen nominations and won two awards, as well as one honorary.

Simon’s career began with a short-lived music group with her sister Lucy, as the Simon Sisters. They were signed to Kapp Records in 1964, and released two albums for the label that year, beginning with their debut album, Meet The Simon Sisters. They had a minor hit with the lead single, “Winkin’, Blinkin’ and Nod”, a children’s poem by Eugene Field that Lucy had put to music. Their second album, Cuddlebug, quickly followed. The duo made one more album together, 1969’s The Simon Sisters Sing the Lobster Quadrille and Other Songs for Children, before Lucy left to get married and start a family. Later, Simon collaborated with eclectic New York rockers Elephant’s Memory for about six months. She also appeared in the 1971 Miloš Forman film Taking Off, playing an auditioning singer, and sang “Long Term physical Effects”, which was included in the 1971 soundtrack for the film.

Simon was signed by Jac Holzman to Elektra Records in 1970. She released her self-titled debut album, Carly Simon, in March 1971. The album contained her breakthrough top-ten hit “That’s the Way I’ve Always Heard It Should Be”, which peaked at No. 10 on the Billboard charts, and earned Simon a nomination for Best Female Pop Vocal Performance at the 14th Annual Grammy Awards. The album itself peaked at No. 30, and Simon won Best New Artist at the same ceremony.

From 1972 to 1979, Simon sang backup vocals on the following James Taylor songs and albums (not counting compilations): “One Man Parade” from 1972’s One Man Dog, “Rock ‘n’ Roll Is Music Now”, “Let It All Fall Down”, “Me and My Guitar”, “Daddy’s Baby” and “Ain’t No Song” from 1974’s Walking Man, “How Sweet It Is” from 1975’s Gorilla, “Shower the People”, “A Junkie’s Lament”, “Slow Burning Love” and “Family Man” from 1976’s In the Pocket, and “B.S.U.R.” from 1979’s Flag. She also co-wrote with Taylor the song “Terra Nova” on his 1977 album JT.

Simon married fellow singer-songwriter James Taylor on November 3, 1972. They had two children, Sarah “Sally” Maria Taylor (born January 7, 1974) and Benjamin “Ben” Simon Taylor (born January 22, 1977), both of whom are musicians and political activists. Simon and Taylor divorced in 1983. In June 2004, Simon said that she no longer speaks to her ex-husband. “I would say our relationship is non-existent. It’s not the way I want it.”

The follow-up single, “The Right Thing to Do”, was another sizable hit later in 1973, reaching No. 4 on the Adult Contemporary chart and No. 17 on the Pop chart. That same year, Simon performed on Lee Clayton’s album Lee Clayton and co-sang on the song “New York Suite 409” and on Livingston Taylor’s album Over the Rainbow and sang with both Livingston and his famous brother, James Taylor (who was, by then, her husband) on the songs “Loving Be My New Horizon” and “Pretty Woman”.

In 1974, Simon followed the smash No Secrets album with Hotcakes, which became an instant hit, reaching No. 3 on Billboard’s Album Chart and was certified Gold. Hotcakes included two top ten singles, “Mockingbird”, a duet with James Taylor that peaked at No. 5 on Billboard’s Pop Singles chart, and “Haven’t Got Time for the Pain”, which hit No. 2 on Billboard’s Adult Contemporary chart. The same year, Simon provided vocals on Tom Rush’s album Ladies Love Outlaws and co-sang with Rush on “No Regrets” and as backup on “Claim on Me”. In 1975, Elektra released her first greatest-hits album, The Best of Carly Simon; this became Simon’s all-time best-selling disc, and eventually reached Triple-Platinum status in the United States.

Simon is one of the various artists mentioned in the 1974 Reunion song “Life Is a Rock (But the Radio Rolled Me).”

In 1977, Simon had an international hit with the million-selling gold single “Nobody Does It Better”, the theme to the James Bond film The Spy Who Loved Me. The song, her second-biggest U.S. hit after “You’re So Vain”, was 1977’s biggest Adult Contemporary hit, where it held No. 1 for seven straight weeks. The single peaked one step behind Debby Boone’s mega-hit “You Light Up My Life” on Billboard’s Pop Singles chart from October 22 to November 5, 1977, and received Grammy nominations for Song of the Year and Best Pop Vocal Performance, Female. In 2012, Rolling Stone ranked it the third-greatest James Bond theme song. Billboard ranked it No. 2 on its list that same year. Also in 1977, Simon co-produced Libby Titus’s album Libby Titus and sang backup on two songs: “Can This Be Our Love Affair?” and “Darkness ‘Til Dawn”, the later which comes from Simon’s Another Passenger.

Simon’s career took another upward swing in 1978 with the hit album Boys in the Trees. The album produced two Top 40 singles; the jazzy and sensual “You Belong to Me”, which hit the Top 10 on both the Pop and Adult Contemporary charts, and “Devoted to You”, a duet with James Taylor. Boys in the Trees was a major success, and returned Simon to Platinum album status in the U.S. “You Belong to Me” later earned Simon yet another Grammy nomination for Best Pop Vocal Performance, Female. She was featured on the front covers of People and Rolling Stone magazines that spring. Also in 1978, Simon and Taylor sang backing vocals on two songs for Taylor’s sister Kate’s album Kate Taylor: “Happy Birthday Sweet Darling” and “Jason & Ida”. They sang backup on three songs on John Hall’s debut solo album John Hall, “The Fault”, “Good Enough” and “Voyagers”. They also sing backup on one song, “Power”, from Hall’s next album, also titled Power (1979).

On November 2, 1978, Simon guested on the song “I Live in the Woods” at a live, four-hour concert by Burt Bacharach and the Houston Symphony Orchestra at Jones Hall in Houston, Texas. All the songs at that concert became Bacharach’s album Woman, which was released in 1979. That year, shortly after the Three Mile Island nuclear accident, from September 19 to 22, a series of concerts were held at New York City’s Madison Square Garden and sponsored by Musicians United for Safe Energy (MUSE), a group of musicians against nuclear power, co-founded by John Hall. Always politically active, Simon and James Taylor were part of the concerts which later became a documentary and concert film, No Nukes (1980), as well as a live album of the same name (1979).

In 1979, Simon released her last album for Elektra, entitled Spy. The albums sales were a disappointment, peaking at only No. 45 on the Pop albums chart, although a hard-edged single from the album, “Vengeance”, became a modest hit and received airplay on U.S. album rock stations, and peaked at No. 48 on the Pop singles chart. “Vengeance” earned Simon a Grammy nomination for Best Rock Vocal Performance, Female in early 1980—the first year to feature the new category. The album also features a track entitled “Never Been Gone”, which became a fan favorite, as well as one of her personal favorites. In 2009, she released Never Been Gone, a newly recorded greatest hits album entitled after the track.

In 1980, Simon signed with Elektra’s sibling label Warner Bros. Records and released her ninth studio album, Come Upstairs. In Pittsburgh, Pennsylvania, during a show to promote the album, Simon collapsed onstage from exhaustion. She subsequently performed considerably less throughout the 1980s. From that album, Simon scored another million-selling U.S. Gold single with the hit “Jesse”, which peaked at No. 11 and remained on the charts for nearly six months. After the major chart success of “Jesse”, Simon’s singles became generally less successful in the mid 1980s, although most of them did well on Adult Contemporary radio formats. Simon also contributed the song “Be With Me” to the 1980 album In Harmony: A Sesame Street Record, which was produced by her sister Lucy and Lucy’s husband, David Levine. Simon can also be heard on the song “In Harmony”, along with other members of the Simon/Taylor families. Carly and Lucy contributed a “Simon Sisters” song—which was called “Maryanne”—to the 1982 follow-up album In Harmony 2, which was also produced by Lucy and her husband. Both albums won Grammy Awards for Best Album for Children.

Torch (1981) was an album of melancholy jazz standards, recorded long before it became fashionable for rock artists to delve into the “great American songbook”. It peaked outside the top 40 on album charts (at No. 50) but remained on the charts for nearly six months and subsequently became one of her best-selling catalogue albums. The album was well-received critically, and featured one original song by Simon, “From The Heart”, as well as a cover of Stephen Sondheim’s “Not a Day Goes By” from his musical Merrily We Roll Along. Also in 1981, Carly Simon was the second female solo artist to be featured on MTV’s first day of the air in her video for “Vengeance” (Pat Benatar was the first female solo artist to appear on MTV, and Juice Newton was the third).

In 1982, she sang the Nile Rodgers & Bernard Edwards-produced single “Why”, from the soundtrack to the film Soup for One. It was a top ten hit in the U.K., and successful throughout Europe. Although “Why” stalled at No. 74 in the U.S., the song became a mellow classic in the aftermath of its being picked up to be covered and sampled by different artists from around 1989 onward. She had another UK success with the single “Kissing with Confidence”, a song from the 1983 album Dancing For Mental Health by Will Powers (a pseudonym for photographer Lynn Goldsmith). Simon was the uncredited singer of the song co-written and mixed by Todd Rundgren.

In 1983, she made her last album for Warner, Hello Big Man, but this also suffered from disappointing sales; it did receive positive critical recognition. The lead single from the album, “You Know What to Do”, peaked at No. 83 on the Pop singles chart, and Simon filmed a music video for it at her home on Martha’s Vineyard, MA. That same year, Simon performed on two albums, The Perfect Stranger by Jesse Colin Young (singing on the track “Fight For It” with Young) and Wonderland by Nils Lofgren (singing on the track “Lonesome Ranger” with Lofgren). By this time, her contract with Warner Bros. had ended. In 1985, she signed with Epic Records and made one album for them, Spoiled Girl. The album yielded two singles, “Tired of Being Blonde” and “My New Boyfriend”, with only the former charting. The album was commercially unsuccessful and her contract with Epic was cancelled.

In 1986, Simon signed with Arista Records and soon rebounded from her career slump. Her first album for Arista, Coming Around Again (1987), gave Simon another international hit with the title track (which was featured in the film Heartburn), returning her to the Billboard Pop Top 20 and the UK Top 10 (it also garnered her a Grammy nomination for Best Female Pop Vocal Performance).

As a tribute to Christa McAuliffe, who was slated to be the first teacher in space and who died in the 1986 Space Shuttle Challenger disaster, Simon wrote and recorded a song entitled “You’re Where I Go”. McAuliffe was a Simon fan and had taken a cassette of her music on board the shuttle. In 1987, Simon also sang the theme for the 1988 Democratic National Convention, “The Turn of the Tide”, for a Marlo Thomas television special Free to Be… a Family. The song was later included on the 1988 soundtrack album of the same name on A&M Records.

Simon married James Hart, a writer, poet and businessman, on December 23, 1987. The couple divorced in 2007.

The Boston Music Awards are a set of music awards given annually that showcase talent in the Boston, Massachusetts area. Founded in 1987, Simon has received two nominations, and won one award, as well as one honorary award.

The Coming Around Again album also featured the Top 10 Adult Contemporary hits “Give Me All Night”, “The Stuff That Dreams Are Made Of”, “All I Want Is You” (which featured Roberta Flack on backing vocals), and a cover of “As Time Goes By” (featuring Stevie Wonder on harmonica). The album itself was her first Gold release in nine years, and went Platinum in 1988. In October 2017, Hot Shot Records released a two-disc 30th Anniversary deluxe edition of the album. These and older songs were featured in a picturesque HBO concert special entitled Live from Martha’s Vineyard, where Simon and her band performed live on a pier. Most of these songs were compiled for her 1988 album, Greatest Hits Live. The album continued her mounting comeback, quickly going Gold, and was later certified Platinum by the RIAA in 1996. From Live a recording of Simon’s evergreen “You’re So Vain” was released as a single in the UK.

Simon is the first artist to win all three major awards (Oscar, Golden Globe and Grammy) for a song that is composed and written, as well as performed, entirely by a single artist (the only other such artist being Bruce Springsteen for “Streets of Philadelphia”, from the 1993 film Philadelphia). The Working Girl soundtrack album was released in August 1989, and featured more music from Simon. That same year, Simon released her first children’s book, Amy the Dancing Bear.

On television, she appeared (also as herself) in a 1989 episode of Thirtysomething, and was a guest-caller named Marie on a 1995 episode of Frasier entitled “Roz in the Doghouse”. She also appeared in a 2013 episode of Family Guy entitled Total Recall, and on a 2014 episode of Bob’s Burgers entitled “Work Hard or Die Trying, Girl”. Simon sang the outro song.

In 1990, Simon released two albums: her second standards album My Romance, and an album of original material Have You Seen Me Lately, featuring a title track that was supposed to have been the main theme for Postcards from the Edge; the entire title sequence – including the song – was deleted by producers, although a great deal of Simon’s underscore compositions and thematic interludes remain in the film, eventually earning her a BAFTA nomination for Best Film Score. In addition to the title track, the album also featured a major (No. 4) Adult Contemporary chart hit with “Better Not Tell Her”—Simon’s biggest hit of the 1990s.

Her second children’s book, The Boy of the Bells was also published in 1990. In 1991, Simon wrote her third children’s book, The Fisherman’s Song, which was based on the song of the same name from her 1990 album Have You Seen Me Lately. The same year, she performed a duet with Plácido Domingo on the song “The Last Night of the World” (from the Miss Saigon musical) on Domingo’s album The Broadway I Love.

Simon’s Playing Possum (1975) and Another Passenger (1976) continued her run of high-profile and generally well-received album releases. Playing Possum was a Top Ten album, and garnered a successful Top 40 single “Attitude Dancing” and two other charting singles, but its racy album cover, which depicts Simon wearing only a black negligee and knee-high black boots, generated controversy. In 1991, Rolling Stone ranked it No. 20 on their list of the 100 greatest album covers. Another Passenger produced only one charting single on the Billboard Pop singles chart, “It Keeps You Runnin'”, written by Michael McDonald of the Doobie Brothers, which peaked just outside the Top 40, at No. 46, and the second single, “Half A Chance”, only charted on the Adult Contemporary chart. Despite the lukewarm commercial reception, the album was, and remains, one of Simon’s best reviewed works, with Rolling Stone calling it “Carly Simon’s best record”. The album became a favorite among many of Simon’s fans. 1976 also saw Simon contributing backup vocals on the song “Peter” on Peter Ivers’s album Peter Ivers. She also made her only appearance on Saturday Night Live. It was a pre-taped performance—a rare occurrence on that show—because Simon suffered terrible bouts of stage fright. In the appearance, she sang two songs: “Half A Chance” and her signature song, “You’re So Vain”.

In 1992, Simon wrote the music for the Nora Ephron film This Is My Life, which included the song “Love of My Life”, a No. 16 Adult Contemporary hit. In 1993, she contributed the song “In the Wee Small Hours of the Morning” to the film Sleepless in Seattle and recorded the same song in combination with “Guess I’ll Hang My Tears Out to Dry” with Frank Sinatra for his album Duets. By this point, Sinatra’s health was too poor for him to record, so the feat was accomplished by producers lifting an isolated prerecorded vocal track from an earlier performance and laying a new background – and Simon – behind it.

In 1993, Simon was commissioned by the Metropolitan Opera Association and the Kennedy Center to record a contemporary opera that would appeal to younger people. The result was Romulus Hunt (named after its 12-year-old protagonist), released in November of that year. In December 2014, the Nashville Opera Association premiered a new performance edition of the opera. She also published her fourth children’s book, The Nighttime Chauffeur. Simon also contributed to Andreas Vollenweider’s album Eolian Minstrel, she co-wrote the song “Private Fires” with Vollenweider and was featured vocalist on the song.

In 1994, she covered the song “Take Me Out to the Ball Game” for Ken Burns’ film Baseball, as well as a recording of “I’ve Got a Crush on You” for Larry Adler’s covers album The Glory of Gershwin. That same year, Simon recorded and released another album of original songs, Letters Never Sent. The album originated from Simon finding an old box of letters that she’d written, but never mailed, and she set a handful of them to music. “The Night Before Christmas”, from the soundtrack to This Is My Life, was also used in the film Mixed Nuts.

In April 1995, Simon surprised thousands of commuters at New York’s Grand Central Terminal with an unannounced performance which was filmed for a Lifetime Television Special, entitled Live at Grand Central. It was also released on home video in December of that year. Also in 1995, she performed on an American concert tour in conjunction with Hall & Oates. On August 30, 1995, Simon made a rare joint appearance with her ex-husband, James Taylor, for a concert on Martha’s Vineyard. Dubbed “Livestock ’95”, it was a benefit for the Martha’s Vineyard Agricultural Society, with over 10,000 people in attendance.

Simon performed a duet with Mindy Jostyn on the song “Time, Be on My Side”, which featured on Jostyn’s 1995 album Five Miles from Hope about her recent battle with colon cancer. Ten years later, Jostyn died from the disease at the age of 43. 1995 also saw the release of Simon’s Clouds in My Coffee, a three-disc boxed set of highlights from her 30-year career from 1965 to 1995.

Simon scored the biggest success of her career in 1972–73, with “You’re So Vain”. It hit No. 1 on the U.S. Pop and Adult Contemporary charts, and sold over a million copies in the United States alone. It was one of the decade’s biggest hits and propelled Simon’s breakthrough album No Secrets to No. 1 on the U.S. album charts, where it stayed for five consecutive weeks. The album achieved Gold status that year, and by its 25th anniversary in 1997 it had been certified Platinum. “You’re So Vain” received Grammy Award nominations for Record of the Year, Song of the Year, and Best Pop Vocal Performance, Female. Additionally, in 2008, it was listed at No. 72 on the Billboard Hot 100’s list of the top 100 songs from the chart’s first 50 years, August 1958 through July 2008. On August 23, 2014, the UK Official Charts Company gave it the accolade of ‘ultimate song of the 1970s’.

Simon continued to write and record music for films, and wrote the theme songs to several more movies; these included “Two Little Sisters” from 1996’s Marvin’s Room, and “In Two Straight Lines” from 1998’s Madeline. 1997 saw the release of Simon’s third standards album, Film Noir, recorded in collaboration with Jimmy Webb, for which she was nominated for the Grammy Award for Best Traditional Pop Vocal Performance. John Travolta dueted with Simon on the track Two Sleepy People, and film director Martin Scorsese wrote the booklet’s liner notes. She also released her fifth children’s book, Midnight Farm. She was diagnosed with breast cancer in 1997, and underwent surgery that year, as well as chemotherapy. The Very Best of Carly Simon: Nobody Does It Better, a UK-only greatest hits album, was released in 1999. Also that year, Simon worked again with the Swiss musician Andreas Vollenweider, and was the featured vocalist for the song “Your Silver Key” on Vollenweider’s album Cosmopoly.

Groovie Ghoulies recorded a song simply titled “Carly Simon”, which was released on their 1999 album Fun in the Dark.

On May 16, 2000, Simon released the album The Bedroom Tapes, largely written and recorded at home in her bedroom while she was recuperating from her health problems of the previous couple of years. The Bedroom Tapes was Simon’s first album of original songs in almost six years; despite this, it was a commercial disappointment, peaking at No. 90 on the Billboard 200. The album was acclaimed by critics, with AllMusic writing “She is as a raw as she was on 1975’s Playing Possum and just as sweet as 1987’s Coming Around Again, but Simon is fresh. Although in her mid-fifties, she is still a charmer.” Billboard called the album “A feast for fans of intelligent, richly crafted pop music” and People wrote that the album “unfolds like a one-woman show,” calling it a “Boffo performance.” The album’s opening track, “Our Affair”, was remixed by Richard Perry and featured on the soundtrack of the Gwyneth Paltrow/Ben Affleck film Bounce (2000).

In 2001, Simon performed on “Son of a Gun” with Janet Jackson on Jackson’s album All for You; the song was released as a single and peaked at No. 28 on the Billboard Hot 100. She also contributed back-up vocals on two songs, “Don’t Turn Away” and “East of Eden”, for Mindy Jostyn’s 2001 album Blue Stories. In November 2001, Simon’s Oscar-winning song “Let the River Run” was used in a public service ad for the United States Postal Service. Entitled “Pride”, it was produced to boost public confidence and postal worker morale in the wake of the September 11, 2001, attacks and the 2001 anthrax attacks.

During the 1990s, the American press reported an incident between Simon and the Pretenders’ vocalist Chrissie Hynde at a Joni Mitchell concert at New York’s Fez Club. Some reports stated that a drunk and disorderly Hynde grabbed Simon around the neck and punched her, although Simon attempted to put these rumors to rest on her official website in 2002.

In 2002, Simon recorded a Christmas album, Christmas Is Almost Here, for Rhino Records, while she was in Los Angeles to lend support to her son Ben Taylor and his band. That same year, Simon personally chose all of the songs for a new two-disc anthology album, simply titled Anthology. This release represented every one her studio albums (up until that point) with at least one song, digitally remastered, and also released on Rhino Records. The following year saw a re-release of her Christmas album with two extra tracks, “White Christmas” (with Burt Bacharach) and “Forgive” (with Andreas Vollenweider). These two tracks were also released as a CD single. She also performed several concerts during the 2004 holiday season at Harlem’s Apollo Theater, along with BeBe Winans, son Ben and daughter Sally, Rob Thomas, Livingston Taylor, Mindy Jostyn and Kate Taylor, along with other members of the Taylor and Simon family.

The subject of the “You’re So Vain” song itself became one of the biggest mysteries in popular music, with the famous lyric “You’re so vain/I bet you think this song is about you”. For more than 40 years, Simon has not publicly revealed the name of the subject. She hinted that it could be a composite of several people, with most press speculation considering Mick Jagger, who sings backup vocals on the recording, and Warren Beatty. Simon hinted the identity to a variety of talk shows and publications over the years, and, on August 5, 2003, auctioned off the information to the winner of a charity function for US$50,000, with the condition that the winner, television executive Dick Ebersol, not reveal it. Finally, in November 2015, Simon, promoting her about-to-be-published memoir, said, “I have confirmed that the second verse is Warren” and added that while “Warren thinks the whole thing is about him”, he is the subject only of that verse, with the remainder of the song referring to two other, still unnamed men.

Simon wrote and recorded songs for the Disney Winnie the Pooh films Piglet’s Big Movie in 2003 and Pooh’s Heffalump Movie in 2005, as well as the direct-to-video A Very Merry Pooh Year in 2002. Several of her songs were also featured in the 2004 film Little Black Book which starred Brittany Murphy and Holly Hunter, with Simon appearing as herself in a cameo role at the end of the film. In spring of 2004, Simon released her fourth greatest hits album, the single disc Reflections: Carly Simon’s Greatest Hits. The album was a great commercial success, peaking at No. 22 on the Billboard charts (No. 25 in the UK), and remaining on the chart for 19 weeks. On March 2, 2007, the album was certified Gold by the RIAA.

“Anticipation” was covered by Mandy Moore on her 2003 album Coverage. Fred Astaire covered “Attitude Dancing” on his 1975 album of the same name. Anita Baker covered “You Belong to Me” for the 1990 album Rubáiyát: Elektra’s 40th Anniversary, and latter included it on her album Rhythm of Love, released in 1994. Jennifer Lopez also covered the song, on her 2002 album This Is Me… Then. Amy Grant covered “The Night Before Christmas” on her 1992 holiday album Home For Christmas. In 2013, Walled City Records in association with Iris Records and Derry City Council released a cover of “Let the River Run”, performed by Máiréad Carlin and Damian McGinty. Morrissey covered “When You Close Your Eyes”, the closing track from Simon’s 1972 album No Secrets, on his 2019 album California Son.

In 2005, she released her fourth album of standards, titled Moonlight Serenade. A surprise hit, it reached No. 7 on the Billboard Album charts, her highest-charting album since Boys in the Trees, and she was nominated for the Grammy Award for Best Traditional Pop Vocal Album. To promote Moonlight Serenade, Simon performed two concerts on board the RMS Queen Mary 2 which were recorded and released on DVD in 2005 as A Moonlight Serenade on the Queen Mary 2. Accompanied by her children, Sally and Ben, Simon embarked on a concert tour across the United States—her first tour in 10 years, entitled The Serenade Tour. She also sang a duet, “Angel of the Darkest Night”, with Mindy Jostyn on Jostyn’s 2005 album Coming Home. The album was released several months after Jostyn’s death on March 10, 2005. One of Simon’s closest friends, Jostyn was married to Jacob Brackman, Simon’s long-time friend and musical collaborator. In 2005, Simon became involved in the legal defense of musician and family friend John Forté with his struggle against a federal incarceration.

Simon again teamed up with Swiss musician Andreas Vollenweider for his 2006 holiday album, Midnight Clear. She performed vocals on the tracks “Midnight Clear”, “Suspended Note”, “Hymn to the Secret Heart” and “Forgive” (which was a song Simon wrote for her own 2003 holiday album Christmas Is Almost Here Again). Also in 2006, Simon performed with Livingston Taylor on his album There You Are Again, singing on the opening track “Best of Friends”, which became a Top 40 Adult Contemporary hit.

Simon has been close friends with James Taylor’s younger brother Livingston Taylor for over 40 years. Livingston said, “I love Carly and Carly loves me. She’s a ferocious advocate and supporter of my music.” They have worked as a musical duo for some songs such as “Best of Friends”, released in Livingston’s 2006 album There You Are Again, and others earlier in their careers.

In 2007, Simon released her fifth album of covers, a collection of “soothing songs and lullabies” called Into White for Columbia Records. The collection featured covers of songs by Cat Stevens, the title track, recordings by Judy Garland, the Beatles and the Everly Brothers, as well as two new original songs, “Quiet Evening” and “I’ll Just Remember You”, and a re-recording of Simon’s own “Love of My Life”. It also featured vocal collaborations with her musician children, Ben and Sally. The album continued Simon’s recently rejuvenated high chart profile and became Billboard′s Hot Shot Debut, entering the chart at No. 13.

In March 2008, it was announced that Simon had signed to the Starbucks label, Hear Music. She released a new album entitled This Kind of Love with them in the spring of 2008. The album was her first collection of original songs since 2000’s The Bedroom Tapes. However, in October 2009, it was reported that Simon was suing Starbucks, saying they did not adequately promote the album—even though it made the US Top 20 (No. 15) and sold nearly 150,000 copies. Simon’s lawsuit stated that Starbucks publicly announced it was backing out of participation in Hear Music just days before the album came out—a decision that she claimed doomed the record before it was even released.

On June 19, 2008, Simon and her son Ben performed “You’re So Vain” together on The Howard Stern Show on Sirius Satellite radio.

In an interview published on May 1, 2008, with the Bay Area Reporter, an LGBT news service, Simon was asked about the possibility of a performance in the True Colors Tour. She responded, “The part that I could be involved in is the gay and lesbian part. The part that would be hard for me is to commit to a tour, because I’m not very comfortable being onstage. But the part that would be easiest for me would be singing on behalf of all of us. I don’t consider myself to be not gay… I’ve enlarged all of my possibilities. I have a lot of extremely personal stories to tell about that, but we won’t go into that right now. Let’s just say that it just depends upon who I’m with.”

In 2008, Simon was reportedly dating Richard Koehler, a surgeon specializing in minimally invasive laparoscopy. Koehler, who is ten years younger than Simon, was said to have been dating her as early as 2006. In 2015 the two were reported living together in Martha’s Vineyard.

“You’re So Vain” has been covered and sampled by artists as diverse as Liza Minnelli, Faster Pussycat, and Marilyn Manson (featuring Johnny Depp). Foo Fighters covered the song at the “Grammy Nominations Concert Live!!” in 2008. The song “Starfuckers, Inc.” by Nine Inch Nails references “You’re So Vain” by quoting the chorus. Queens of the Stone Age sampled the song as “You’re So Vague” on the deluxe edition of their album Rated R. Janet Jackson sampled the song in “Son of a Gun (I Betcha Think This Song Is About You)”, with Simon providing featured vocals. Trey Songz directly samples the song in the chorus of his single “About You”, featured on his 2015 album Trigga Reloaded.

Adam Sandler covered “Nobody Does It Better” before receiving the MTV Generation Award on the 2008 MTV Movie Awards (the words were modified to reflect Sandler). Celine Dion also performed the song as part of her self-titled show in Las Vegas. Radiohead used to perform the song as part of their set during the mid-90s. Bobby Brown covered the song with Whitney Houston on his 1997 album Forever.

In October 2009, Simon released Never Been Gone, an album of acoustic reworkings of some of her classic songs. The album was released via Iris Records. On November 26, 2009, Simon appeared on the Care Bears float of the 83rd Annual Macy’s Thanksgiving Day Parade, where she sang “Let the River Run”.

On March 2, 2010, BBC Radio 2 broadcast An Evening With Carly Simon where Simon performed live for the first time in the UK with her son Ben to a small audience of approximately 100 people. This coincided with the UK release of the Never Been Gone album, which was released for the Mother’s Day season and peaked at No. 45, Simon’s first studio album to reach the UK Top 100 since 1987’s Coming Around Again. Simon also appeared on various UK television shows to promote the album, including The One Show and BBC Breakfast.

In May 2010, Simon revealed she had been one of the several celebrities who fell victim to financial advisor Kenneth I. Starr, whose Ponzi scheme lured her into “investing” millions of dollars with him, which she lost.

On July 27, 2013, in Foxborough, Massachusetts, Simon performed “You’re So Vain” with Taylor Swift on her Red Tour. Swift had previously cited Simon as a musical influence and “You’re So Vain” as one of her favorite songs.

On November 24, 2015, Simon published Boys in the Trees: A Memoir, an autobiographical book focusing on her childhood and her early life, from age five until thirty-five. The two-disc compilation album Songs From The Trees (A Musical Memoir Collection) was simultaneously released along with the book.

In 2016, Simon confirmed during a book signing that she and her son Ben Taylor were working to release EDM remixes of her signature songs. She also said she wanted to record an album with her two children.

In April 2017 Simon featured on the Gorillaz album Humanz on the track “Ticker Tape”.

In 2018, Simon, at 72, came to terms with the Universal Music Publishing Group to administer her song portfolio.

In October 2019, Simon released a second memoir entitled Touched by the Sun: My Friendship with Jackie, which recounts her friendship with former First Lady Jacqueline Kennedy Onassis. As a tie-in to its release, Simon also released a newly mixed live version of “Touched by the Sun”, taken from her Live at Grand Central concert, as a single.