Simon was born on October 13, 1941, in
Newark, New Jersey, to
 His father, Louis (1916–1995), was a college professor,
double bass player, and dance bandleader who performed under the name "Lee Sims". His mother, Belle (1910–2007), was an elementary school teacher. In 1945, his family moved to the
Kew Gardens Hills section of
Flushing, Queens, in New York City. The musician
Donald Fagen has described Simon's childhood as that of "a certain kind of New York Jew, almost a stereotype, really, to whom music and baseball are very important. I think it has to do with the parents. The parents are either immigrants or first-generation Americans who felt like outsiders, and assimilation was the key thought—they gravitated to black music and baseball looking for an alternative culture."
 Simon, upon hearing Fagen's description, said it "isn't far from the truth."
 Simon says about his childhood, "I was a ballplayer. I'd go on my bike, and I'd hustle kids in
stickball." He adds that his father was a
New York Yankees fan:
I used to listen to games with my father. He was a nice guy. Fun. Funny. Smart. He didn't play with me as much as I played with my kids. He was at work until late at night. ... Sometimes [until] two in the morning."
Simon's musical career began after meeting
Art Garfunkel when they were both 11. They performed in a production of
Alice in Wonderland for their sixth-grade graduation, and began singing together when they were 13,
 occasionally performing at school dances. Their idols were
the Everly Brothers, whom they imitated in their use of close two-part harmony. Simon also developed an interest in jazz, folk, and blues, especially in the music of
Woody Guthrie and
Simon's first song written for himself and Garfunkel, when Simon was 12 or 13, was called "The Girl for Me," and according to Simon became the "neighborhood hit." His father wrote the words and chords on paper for the boys to use. That paper became the first officially copyrighted Paul Simon and Art Garfunkel song, and is now in the
Library of Congress. In 1957, in their mid-teens, they recorded the song "Hey, Schoolgirl" under the name Tom & Jerry, given to them by their label Big Records. The single reached No. 49 on the pop charts.
After graduating from
Forest Hills High School, Simon majored in English at
Queens College, while Garfunkel studied mathematics at
Columbia University in
 Simon was a brother in the
Alpha Epsilon Pi fraternity,
 earned a degree in English literature, and briefly attended
Brooklyn Law School after graduation, but his real passion was
rock and roll.
Between 1957 and 1964, Simon wrote, recorded, and released more than 30 songs, occasionally reuniting with Garfunkel as Tom & Jerry for some singles, including "Our Song" and "That's My Story". Most of the songs Simon recorded during that time were performed alone or with musicians other than Garfunkel. They were released on several minor record labels, such as Amy, Big, Hunt, King, Tribute, and Madison. He used several pseudonyms for these recordings, including Jerry Landis, Paul Kane, and True Taylor. Simon enjoyed some moderate success in recording a few singles as part of a group called Tico and the Triumphs, including a song called "Motorcycle" that reached No. 97 on the
Billboard charts in 1962. Tico and the Triumphs released four 45s. Marty Cooper, known as Tico, sang lead on several of these releases. A childhood friend,
Bobby Susser, children's songwriter, record producer, and performer, co-produced the Tico 45s with Simon. That year, Simon reached No. 99 on the pop charts as Jerry Landis with the
novelty song "The Lone Teen Ranger." Both chart singles were released on
Simon & Garfunkel
In early 1964, Simon and Garfunkel got an audition with
Columbia Records, whose executive
Clive Davis was impressed enough to sign the duo to a contract to produce an album. Columbia decided that the two would be called simply "Simon & Garfunkel," abandoning the group's previous name "Tom and Jerry." Simon said in 2003 that this renaming as "Simon & Garfunkel" marked the first time artists' surnames had been used in pop music.
 Simon and Garfunkel's first LP,
Wednesday Morning, 3 A.M., was released on October 19, 1964; it consisted of 12 songs in the folk vein, five written by Simon. The album initially flopped.
Simon moved to the UK to pursue a solo career, touring
folk clubs and
coffee houses. At the first club he played, the Railway Inn Folk Club in
Brentwood, Essex, he met Kathy Chitty who became his girlfriend and inspiration for "Kathy's Song," "
America," and others. He performed at
Les Cousins in London and toured provincial folk clubs that exposed him to a wide range of musical influences. In 1965, he recorded a solo LP
The Paul Simon Songbook in Britain.
While in the UK, Simon co-wrote several songs with
Bruce Woodley of the Australian pop group
the Seekers, including "I Wish You Could Be Here," "Cloudy," and "
Red Rubber Ball." Woodley's co-author credit was omitted from "Cloudy" on the
Parsley, Sage, Rosemary and Thyme album. The American group
the Cyrkle recorded a cover of "Red Rubber Ball" that reached No. 2 in the U.S. Simon also contributed to
the Seekers catalogue with "Someday One Day," which was released in March 1966, charting around the same time as Simon and Garfunkel's "
Back on the American East Coast, radio stations began receiving requests for one of the Wednesday Morning tracks, Simon's "
The Sound of Silence." Their producer,
Tom Wilson, overdubbed the track with
bass guitar and
drums, releasing it as a single that eventually went to No. 1 on the U.S. pop charts.
The song's success drew Simon back to the United States to reunite with Garfunkel. Together they recorded four more albums:
Sounds of Silence;
Parsley, Sage, Rosemary and Thyme;
Bookends; and the hugely successful
Bridge over Troubled Water. Simon and Garfunkel also contributed extensively to the soundtrack of the
Mike Nichols film
The Graduate (1967), starring
Dustin Hoffman and
Anne Bancroft. While writing "
Mrs. Robinson," Simon originally toyed with the title "Mrs. Roosevelt". When Garfunkel reported this indecision over the song's name to the director, Nichols replied, "Don't be ridiculous! We're making a movie here! It's Mrs. Robinson!"
Simon and Garfunkel returned to the UK in the fall of 1968 and did a church concert appearance at Kraft Hall, which was broadcast on the BBC, and also featured Paul's brother Ed on a performance of the instrumental "Anji."
Simon pursued solo projects after Bridge over Troubled Water, reuniting occasionally with Garfunkel for various projects, such as their 1975 Top Ten single "
My Little Town." Simon wrote it for Garfunkel, whose solo output Simon judged as lacking "bite." The song was included on their respective solo albums—Paul Simon's
Still Crazy After All These Years and Garfunkel's
Breakaway. Contrary to popular belief, the song is not autobiographical of Simon's early life in New York City.
 In 1981, they reunited again for the famous
concert in Central Park, followed by a world tour and an aborted reunion album, to have been entitled Think Too Much, which was eventually released (without Garfunkel) as
Hearts and Bones. Together, they were inducted into the
Rock and Roll Hall of Fame in 1990.
In 2003, Simon and Garfunkel reunited once again when they received a
Grammy Lifetime Achievement Award. This reunion led to a US tour—the acclaimed "Old Friends" concert series—followed by a 2004 international encore that culminated in a free concert at the
Rome that drew 600,000 people.
 In 2005, the pair sang "Mrs. Robinson" and "Homeward Bound," plus "Bridge Over Troubled Water" with
Aaron Neville, in the benefit concert From the Big Apple to The Big Easy – The Concert for New Orleans (eventually released as a DVD) for
Hurricane Katrina victims.
The pair reunited in April 2010 in New Orleans at the
New Orleans Jazz & Heritage Festival.
After Simon and Garfunkel split in 1970, Simon began writing and recording solo material again. His album
Paul Simon was released in January 1972, preceded by his first experiment with world music, the Jamaican-inspired "
Mother and Child Reunion," considered one of the first examples of
reggae by a white musician. The single was a hit, reaching both the American and British Top 5. The album received universal acclaim, with critics praising the variety of styles and the confessional lyrics, reaching No. 4 in the U.S. and No. 1 in the UK and Japan. It later spawned another Top 30 hit with "
Me and Julio Down by the Schoolyard".
Simon's next project was the pop-folk album,
There Goes Rhymin' Simon, released in May 1973. It contained some of his most popular and polished recordings. The lead single, "
Kodachrome," was a No. 2 hit in America, and the follow-up, the gospel-flavored "
Loves Me Like a Rock" was even bigger, topping the
Cashbox charts. Other songs like the weary "
American Tune" or the melancholic "Something So Right" — a tribute to Simon's first wife, Peggy, which received a Grammy Award nomination for Best Song of the Year — became standards in the musician's catalog. Critical and commercial reception for this second album was even stronger than for his debut. At the time, reviewers noted how the songs were fresh and unworried on the surface, while still exploring socially and politically conscious themes on a deeper level. The album reached No. 1 on the Cashbox album charts. As a souvenir for the tour that came next, in 1974 it was released as a live album,
Live Rhymin', which was moderately successful and displayed some changes in Simon's music style, adopting world and religious music.
Still Crazy After All These Years was his next album. Released in October 1975 and produced by Simon and
Phil Ramone, it marked another departure. The mood of the album was darker, as he wrote and recorded it in the wake of his divorce. Preceded by the feel-good duet with
Phoebe Snow, "Gone at Last" (a Top 25 hit) and the Simon & Garfunkel reunion track "My Little Town" (a No. 9 on Billboard), the album was his only No. 1 on the Billboard charts to date. The
18th Grammy Awards named it the
Album of the Year and Simon's performance the year's
Best Male Pop Vocal. With Simon in the forefront of popular music, the third single from the album, "
50 Ways to Leave Your Lover" reached the top spot of the Billboard charts, his only single to reach No. 1 on this list. Also, on May 3, 1976, Simon put together a benefit show at
Madison Square Garden to raise money for the
New York Public Library. Phoebe Snow,
Jimmy Cliff and the Brecker Brothers also performed. The concert produced over $30,000 for the Library.
After three successful studio albums, Simon became less productive during the second half of the 1970s. He dabbled in various projects, including writing music for the film
Shampoo, which became the music for the song "Silent Eyes" on the "Still Crazy" album, and acting (he was cast as Tony Lacey in
Woody Allen's film
Annie Hall). He achieved another hit in this decade, with the lead single of his 1977 compilation,
Greatest Hits, Etc., "
Slip Slidin' Away," reaching No. 5 in the United States.
In 1980 he released
One-Trick Pony, his debut album with
Warner Bros. Records and his first in almost five years. It was paired with the
motion picture of the same name, which Simon wrote and starred in. Although it produced his last Top 10 hit with the upbeat "Late in the Evening" (also a No. 1 hit on the
Radio & Records American charts), the album did not sell well, in a music market dominated by
Hearts and Bones in 1983. This was a polished and confessional album that was eventually viewed as one of his best works, but the album did not sell well when it was released. This marked a low point in Simon's commercial popularity; both the album and the lead single, "Allergies," missed the American Top 40. Hearts and Bones included "
The Late Great Johnny Ace," a song partly about
Johnny Ace, an American
R&B singer, and partly about slain
John Lennon. A successful U.S. solo tour featured Simon and his guitar, with a recording of the rhythm track and horns for "Late In The Evening." In January 1985, Simon lent his talent to
USA for Africa and performed on the
relief fundraising single "
We Are the World."
As he commented years later, after the disappointing commercial performance of Hearts and Bones, Simon felt he had lost his inspiration to a point of no return, and that his commercial fortunes were unlikely to change. While driving his car in late 1984 in this state of frustration, Simon listened to a cassette of the Boyoyo Boys' instrumental "Gumboots: Accordion Jive Volume II" which had been lent to him by Heidi Berg, a singer songwriter he was working with at the time. Lorne Michaels had introduced Paul to Heidi when Heidi was working as the bandleader for Lorne's "The New Show". Interested by the unusual sound, he wrote lyrics to the number, which he sang over a re-recording of the song. It was the first composition of a new musical project that became the Grammy-award winning album
Graceland, a mixture of musical styles including
Simon travelled to South Africa to embark on further recording the album. Sessions with African musicians took place in
Johannesburg in February 1985. Overdubbing and additional recording was done in April 1986, in New York. The sessions featured many South African musicians and groups, particularly
Ladysmith Black Mambazo. Simon also collaborated with several American artists, singing a memorable duet with
Linda Ronstadt in "Under African Skies," and playing with
Los Lobos in "All Around the World or The Myth of the Fingerprints." Simon was briefly listed on the U.N. Boycott list but removed after he had indicated he had not violated the cultural boycott.
Warner Bros. Records had serious doubts about releasing such an eclectic album to the mainstream, but did so in August 1986. Graceland was praised by critics and the public, and became Simon's most successful solo album. Slowly climbing the worldwide charts, it reached #1 in many countries, including the UK, Canada, Australia, and New Zealand—and peaked at #3 in the U.S. It was the second-best-selling album of 1987 in the US, selling five million copies and eventually reaching 5x Platinum certification. Another seven million copies sold internationally, making it his best-selling album. Much of the success of the album was due to the lead single, the upbeat "
You Can Call Me Al," whose lyrics describe a man experiencing an identity crisis. The track featured many memorable elements—a catchy
synthesizer riff (played by
Adrian Belew of
King Crimson], an easy
whistle solo, and an unusual bass run, in which the second half was a reversed recording of the first half. "You Can Call Me Al" was accompanied by a humorous video featuring actor
Chevy Chase, which introduced Simon to a new audience through
MTV. In the end, the track reached UK Top 5 and the U.S. Top 25. Further singles, including the title track, "The Boy in the Bubble" and "Diamonds on the Soles of Her Shoes," were not commercial hits but became radio standards and were highly praised.
At age 45, Simon found himself back at the forefront of popular music. He received the
Grammy Award for
Album of the Year in 1987 and also
Grammy Award for Record of the Year for the title track one year later. He also embarked on the very successful Graceland Tour, which was documented on music video. Simon found himself embracing new sounds, which some critics viewed negatively—however, Simon reportedly felt it was a natural artistic experiment, considering that
world music was already present on much of his early work, including such Simon & Garfunkel hits as "
El Condor Pasa" and his early solo recording "
Mother and Child Reunion," which was recorded in
Kingston, Jamaica. One way or another, Warner Bros. Records (who by this time controlled and reissued all his previous Columbia albums) re-established Simon as one of their most successful artists. In an attempt to capitalize on his renewed success, WB Records released the album
Negotiations and Love Songs in November 1988, a mixture of popular hits and personal favorites that covered Simon's entire career and became an enduring seller in his catalog.
After Graceland, Simon decided to extend his roots with the
The Rhythm of the Saints. Sessions for the album began in December 1989, and took place in
Rio de Janeiro and New York, featuring guitarist
J. J. Cale and many Brazilian and African musicians. The tone of the album was more introspective and relatively low-key compared to the mostly upbeat numbers of Graceland. Released in October 1990, the album received excellent critical reviews and achieved very respectable sales, peaking at #4 in the U.S. and No. 1 in the UK. The lead single, "The Obvious Child," featuring the Grupo Cultural Olodum, became his last Top 20 hit in the UK and appeared near the bottom of the
Billboard Hot 100. Although not as successful as Graceland, The Rhythm of the Saints was received as a competent successor and consistent complement on Simon's attempts to explore (and popularize) world music, and also received a Grammy nomination for Album of the Year.
Carrie Fisher said in her autobiography
Wishful Drinking that the song "She Moves On" is about her. It's one of several she claimed, followed by the line, "If you can get Paul Simon to write a song about you, do it. Because he is so brilliant at it."
The success of both albums allowed Simon to stage another New York concert. On August 15, 1991, almost a decade after his concert with Garfunkel, Simon staged a second concert in Central Park with African and South American bands. The success of the concert surpassed all expectations, and reportedly over 750,000 people attended—one of the largest concert audiences in history. He later remembered the concert as, "...the most memorable moment in my career." The success of the show led to both a live album and an
Emmy-winning TV special. In the middle, Simon embarked on the successful Born at the Right Time Tour, and promoted the album with further singles, including "Proof"—accompanied with a humorous video that again featured Chevy Chase, and added Steve Martin. On March 4, 1992, he appeared on his own episode of
MTV Unplugged, offering renditions of many of his most famous compositions. Broadcast in June, the show was a success, though it did not receive an album release.
After Unplugged, Simon's place in the forefront of popular music dropped notably. A Simon & Garfunkel reunion took place in September 1993, and in another attempt to capitalize on the occasion, Columbia released
Paul Simon 1964/1993 in September, a three-disc compilation that received a reduced version on the two-disc album
The Paul Simon Anthology one month later. In 1995 he made news for appearing on
The Oprah Winfrey Show, where he performed the song "Ten Years," which he composed specially for the tenth anniversary of the show. Also that year, he was featured on the
Annie Lennox version of his 1973 song "Something So Right," which appeared briefly on the UK Top 50 once it was released as a single in November.
Since the early stages of the nineties, Simon was fully involved on
The Capeman, a musical that finally opened on January 29, 1998. Simon worked enthusiastically on the project for many years and described it as "a New York Puerto Rican story based on events that happened in 1959—events that I remembered."
 The musical tells the story of real-life Puerto Rican youth
Salvador Agron, who wore a cape while committing two murders in 1959 New York, and went on to become a writer in prison. Featuring
Marc Anthony as the young Agron and
Rubén Blades as the older Agron, the play received terrible reviews and very poor box office receipts from the very beginning, and closed on March 28 after just 68 performances—a failure that reportedly cost Simon 11 million dollars.
Simon recorded an album of songs from the show, which was released in November 1997. It was received with very mixed reviews, though many critics praised the combination of
Caribbean music that the album reflected. In commercial terms,
Songs from The Capeman was a failure—it found Simon missing the Top 40 of the Billboard charts for the first time in his career. The cast album was never released on CD but eventually became available online.
After the disaster of The Capeman, Simon's career was again in an unexpected crisis. However, entering the new millennium, he maintained a respectable reputation, offering critically acclaimed new material and receiving commercial attention. In 1999, Simon embarked on a North American tour with
Bob Dylan, where each alternated as headline act with a "middle" section where they performed together, starting on the first of June and ending September 18. The collaboration was generally well-received, with just one critic, Seth Rogovoy, from the Berkshire Eagle, questioning the collaboration.
In an attempt to return successfully to the music market, Simon wrote and recorded a new album very quickly, with
You're the One arriving in October 2000. The album consisted mostly of folk-pop writing combined with foreign musical sounds, particularly grooves from North Africa. While not reaching the commercial heights of previous albums, it managed at least to reach both the British and American Top 20. It received favorable reviews and received a Grammy nomination for
Album of the Year. He toured extensively for the album, and one performance in Paris was released to home video.
In the aftermath of the
September 11 attacks, Simon sang "Bridge Over Troubled Water" on
America: A Tribute to Heroes, a multinetwork broadcast to benefit the September 11 Telethon Fund. In 2002, he wrote and recorded "
Father and Daughter," the theme song for the animated family film
The Wild Thornberrys Movie. The track was nominated for an
Academy Award for Best Song. In 2003, he participated on another Simon & Garfunkel reunion. One year later, Simon's studio albums were re-released both individually and together in a limited-edition nine-CD boxed set, Paul Simon: The Studio Recordings 1972–2000.
At the time, Simon was already working on a new album with
Brian Eno called
Surprise, which was released in May 2006. Most of the album was inspired by the
September 11 terrorist attacks, the
Iraq invasion, and the war that followed. In personal terms, Simon was also inspired by the fact of having turned 60 in 2001, which he humorously referred to on "Old" from You're the One.
Surprise was a commercial hit, reaching #14 in the
Billboard 200 and #4 in the UK. Most critics also praised the album, and many of them called it a "comeback".
Stephen Thomas Erlewine from
AllMusic wrote that "Simon doesn't achieve his comeback by reconnecting with the sound and spirit of his classic work; he has achieved it by being as restless and ambitious as he was at his popular and creative peak, which makes Surprise all the more remarkable." The album was supported with the successful
Surprise Tour from May-November 2006.
In March 2004, Walter Yetnikoff published a book called 'Howling at the Moon', in which he criticized Simon personally and for his tenuous business partnership with
Columbia Records in the past.
Simon performing live in
, Germany, July 25, 2008
In 2007 Simon was the inaugural recipient of the
Gershwin Prize for Popular Song, awarded by the
Library of Congress, and later performed as part of a gala of his work.
After living in
Montauk, New York, for many years, Simon relocated to
Simon is one of a small number of performers who are named as the
copyright owner on their recordings (most records have the recording company as the named owner of the recording). This noteworthy development was spearheaded by the
Bee Gees after their successful $200 million lawsuit against
RSO Records, which remains the largest successful lawsuit against a record company by an artist or group. All of Simon's solo recordings, including those originally issued by
Columbia Records, are currently distributed by
Legacy Recordings unit. His albums were issued by
Warner Music Group until mid-2010.
 In mid-2010, Simon moved his catalog of solo work from
Warner Bros. Records to
 where Simon and Garfunkel's catalog is. Simon's back catalog of solo recordings would be marketed by Sony Music's
Legacy Recordings unit.
In February 2009, Simon performed back-to-back shows in New York City at the
Beacon Theatre, which had recently been renovated. Simon was reunited with Art Garfunkel at the first show as well as with the cast of The Capeman; also playing in the band was Graceland bassist
Bakithi Kumalo. In May 2009, Simon toured with Garfunkel in Australia, New Zealand, and Japan. In October 2009, they appeared together at the 25th Anniversary of The Rock & Roll Hall of Fame concert at
Madison Square Garden in New York City. The pair performed four of their most popular songs, "
The Sound of Silence," "
The Boxer," "
Cecilia," and "
Bridge Over Troubled Water."
So Beautiful or So What
 was released on the
Concord Music Group label on April 12, 2011.
 The album received high marks from the artist, "It's the best work I've done in 20 years."
 It was reported that Simon attempted to have
Bob Dylan guest on the album.
On November 10, 2010, Simon released a new song called "Getting Ready for Christmas Day". It premiered on
National Public Radio,
 and was included on the album
So Beautiful or So What. The song samples a 1941 sermon by
the Rev. J.M. Gates, also entitled "Getting Ready for Christmas Day".
 Simon performed the song live on
The Colbert Report on December 16, 2010.
 The first video featured J.M. Gates' giving the sermon and his church in 2010 with its display board showing many of Simon's lyrics; the second video illustrates the song with cartoon images.
In the premiere show of the final season of
The Oprah Winfrey Show on September 10, 2010, Simon surprised
Oprah and the audience with a song dedicated to Oprah and her show lasting 25 years (an update of a song he did for her show's 10th anniversary).
Rounding off his 2011 World Tour, which included United States, England, the Netherlands, Switzerland and Germany, Simon appeared at
Ramat Gan Stadium in
Israel in July 2011, making his first concert appearance in Israel since 1983.
 On September 11, 2011, Paul Simon performed "
The Sound of Silence" at the
National September 11 Memorial & Museum, site of the
World Trade Center, on the 10th anniversary of the
September 11 attacks.
On February 26, 2012, Simon paid tribute to fellow musicians
Chuck Berry and
Leonard Cohen who were the recipients of the first annual PEN Awards for songwriting excellence at the
JFK Presidential Library in Boston, Massachusetts.
 In 1986 Simon was awarded an Honorary Doctor of Music degree from
Berklee College of Music where he currently serves on the Board of Trustees.
On June 5, 2012, Simon released a 25th anniversary box set of Graceland, which included a remastered edition of the original album, the 2012
documentary film Under African Skies, the original 1987 "African Concert" from
Zimbabwe, an audio narrative "The Story of 'Graceland'" as told by Paul Simon, and other interviews and paraphernalia.
 He played a few concerts in Europe with the original musicians to commemorate the anniversary.
On December 19, 2012, Simon performed at the funeral of
Victoria Leigh Soto, a teacher killed in the
Sandy Hook Elementary School shooting.
On June 14, 2013, at
Back to Bass Tour, Simon performed his song "
The Boxer" and Sting's "
Fields of Gold" with Sting.
In September 2013, Simon delivered the Richard Ellmann Lectures in Modern Literature at
In February 2014, Simon embarked on a joint concert tour titled
On Stage Together with English musician
Sting, playing 21 concerts in North America.
 The tour continued in early 2015, with ten shows in Australia and New Zealand,
 and 23 concerts in Europe,
 ending on 18 April 2015.
On August 4, 2015, Simon performed "
Me and Julio Down by the Schoolyard", "
Homeward Bound", and "
Late in the Evening" alongside
Billy Joel at the final concert of
Nassau Coliseum on
 On September 11, 2015, Simon appeared during the premiere week of
The Late Show with Stephen Colbert. Simon, who performed “
Me and Julio Down by the Schoolyard” with Colbert for his surprise appearance, had been promoted prior to the show as "Simon and Garfunkel tribute band Troubled Waters."
 Simon's additional performance of "An American Tune" was posted as a bonus on the show's YouTube channel.
Simon also wrote and performed the theme song for the comedian Louis C.K.'s show Horace and Pete, which debuted January 30, 2016. The song, which can be heard during the show's opening, intermission, and closing credits, is sparse, featuring only Simon's voice and an acoustic guitar. Simon made a cameo appearance onscreen in the tenth and final episode of the series.
On June 3, 2016 Simon released his thirteenth solo studio album,
Stranger to Stranger via Concord Records.
 He began writing new material shortly after releasing his twelfth studio album,
So Beautiful or So What, in April 2011. Simon collaborated with the Italian
electronic dance music artist
Clap! Clap! on three songs—"The Werewolf", "Street Angel", and "Wristband". Simon was introduced to him by his son, Adrian, who was a fan of his work. The two met up in July 2011 when Simon was touring behind So Beautiful or So What in
Italy. He and
Clap! Clap! worked together via email over the course of making the album. Simon also worked with longtime friend
Roy Halee, who is listed as co-producer on the album. "I always liked working with him more than anyone else," Simon noted.
 Following the release of the album, Simon noted that “showbiz doesn’t hold any interest for me” and discussed future retirement as "I am going to see what happens if I let go".
On July 25, 2016, he performed "
Bridge over Troubled Water" at the
2016 Democratic National Convention.
 On May 24, 2017, he debuted "Questions for the Angels" with jazz guitarist
Bill Frisell on
The Late Show with Stephen Colbert.