Two of his works, Sounds of Silence (1966) as part of Simon & Garfunkel and the solo Graceland, were inducted into the National Recording Registry for their cultural significance, and in 2007, the Library of Congress voted him the inaugural winner of the Gershwin Prize for Popular Song.

[3][4][5] His father, Louis (1916–1995), a professor of education at the City College of New York,[6] was a double-bass player and dance bandleader who performed under the name Lee Sims.

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.

By 1962, working as Jerry Landis, he was a frequent writer/producer for several Amy Records artists, overseeing material released by Dotty Daniels, the Vels and Ritchie Cordell.

Simon enjoyed moderate success with singles as part of the group Tico and the Triumphs, including "Motorcycle", which reached number 99 on the Billboard charts in 1962.

[18] He produced Jackson C. Frank's first and only album and 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".

[21] The success of the single drew Simon back to the US to reunite with Garfunkel, and they recorded the albums Sounds of Silence (1966), Parsley, Sage, Rosemary and Thyme (1966) and Bookends (1968).

[22] Simon & Garfunkel also contributed to the soundtrack of the Mike Nichols film The Graduate (1967), starring Dustin Hoffman and Anne Bancroft.

[39] Simon faced accusations that he had broken the cultural boycott imposed by the rest of the world against the apartheid regime in South Africa[40] by organizations such as Artists United Against Apartheid,[41] anti-apartheid musicians (including Billy Bragg, Paul Weller and Jerry Dammers),[42] and James Victor Gbeho (then Ghanaian Ambassador to the United Nations).

Sessions for the album began in December 1989 in Rio de Janeiro and New York and featured guitarist J.J. Cale, and Brazilian and African musicians.

The lead single, "The Obvious Child", featuring the Grupo Cultural Olodum, became Simon's last Top 20 hit in the UK and appeared near the bottom of the Billboard Hot 100.

Simon embarked on the Born at the Right Time Tour and promoted the album with further singles, including "Proof", which was accompanied by a humorous video that featured Chevy Chase and Steve Martin.

"[51] The musical told the story of a real-life Puerto Rican youth, Salvador Agron, who wore a cape while committing two murders in New York in 1959.

Some critics praised the combination of doo-wop, rockabilly and Caribbean music that the album contained, but Songs from The Capeman was a failure, and for the first time in Simon's career he did not reach the Top 40 of the Billboard charts.

In March 2004, Walter Yetnikoff published a book called Howling at the Moon, in which he criticized Simon and his previous business partnership with Columbia Records.

[54] In 2007, Simon was the inaugural recipient of the Gershwin Prize for Popular Song, awarded by the Library of Congress, and he later performed as part of a gala of his work.

In May 2009, Simon toured with Garfunkel in Australia, New Zealand and Japan; and in October 2009 they appeared together at the 25th anniversary of the Rock and Roll Hall of Fame concert at Madison Square Garden in New York City.

On February 26, 2012, Simon paid tribute to fellow musicians Chuck Berry and Leonard Cohen, who had received the first annual PEN Awards for songwriting excellence at the JFK Presidential Library in Boston, Massachusetts.

[69] On December 19, 2012, Simon performed at the funeral of Victoria Leigh Soto, a teacher killed in the Sandy Hook Elementary School shooting.

[82] On February 5, 2018, Simon announced his intention to retire from touring, citing time away from his family and the death of longtime guitarist Vincent Nguini.

[84] In 2018, Simon released his fourteenth solo studio album, In the Blue Light, which consisted of re-recordings of lesser-known songs from his catalog, some with altered arrangements, harmonic structures and lyrics.

[89] The album was described as 33 minutes of uninterrupted musical meditation, consisting of seven pieces performed on acoustic guitar, linked by a motif derived from "Anji", with elements of folk, blues and jazz, and with lyrics that reflected on life, death and faith.

"[17] For the next few months, isolated by the pandemic on a ranch in Texas, Simon worked on a series of guitar pieces, and added sounds like distant church bells produced by amplified upside-down wine glasses.

He played music producer Tony Lacey, a supporting character in the 1977 Woody Allen feature film Annie Hall, and made a cameo appearance in the movie The Rutles: All You Need Is Cash the following year.

Simon appeared alongside George Harrison on the Thanksgiving Day episode of SNL on November 20, 1976, and they performed "Here Comes the Sun" and "Homeward Bound" together.

He amazed his friend by remembering intricate details about prior meetings with passers-by, but drew a complete blank when he was approached by Art Garfunkel.

His songwriting catalog had earned 39 BMI Awards, including numerous citations for "Bridge over Troubled Water", "Mrs. Robinson", "Scarborough Fair" and "The Sound of Silence".

Named in honor of George and Ira Gershwin, this award recognized the profound and positive effect of popular music on the world's culture.

Among the performers who paid tribute to Simon were Stevie Wonder, Alison Krauss, Jerry Douglas, Lyle Lovett, James Taylor, Dianne Reeves, Marc Anthony, Yolanda Adams and Ladysmith Black Mambazo.

In 1970, after recording "Bridge Over Troubled Water", he held auditions for a young songwriters' workshop at the invitation of the NYU's Tisch School of the Arts.