- One of the few artists from his generation to own all the songs he's written.
- Even after their divorce in 1983, he and Carrie Fisher continued to date for eight more years before finally breaking up in 1991.
- Is left-handed, but plays guitar right-handed.
- After his breakup with Carrie Fisher, he was depressed for two years. In 1985, his comeback album "Graceland" included songs about her.
- Attended a recording session in 1974 with Art Garfunkel, former The Beatles John Lennon, and singer Harry Nilsson. Lennon directed the session, and he and Simon reportedly clashed on Simon's cue in the song, leading to Simon's walking out (with Garfunkel close behind, making apologies) before anything was recorded.
- He and Art Garfunkel sang and wrote songs under the name Tom and Jerry in the late 1950s.
- The song, "Scarborough Fair/Canticles," from Simon & Garfunkel's multimillion selling "Parsley, Sage, Rosemary and Thyme" (1966) album, contains a counterpoint melody with antiwar lyrics. The alternate melody and verse were removed when the song was issued as a single in 1967. That is the version that is most heard and performed today, though the original "Canticles " version can still be heard in the soundtrack of The Graduate (1967).
- Has worked several times with friend Chevy Chase. They worked together on Saturday Night Live (1975). Chase has appeared in The Paul Simon Special (1977) and Simon's music videos "You Can Call Me Al" and (alongside Steve Martin) "Proof".
- Opened the first Saturday Night Live (1975) episode after the September 11, 2001, attacks, with his song "The Boxer"; following this was the infamous exchange between Rudy Giuliani and Lorne Michaels, where Michaels asked if it was okay to be funny.
- Asked if there were any songs he'd written that he now regrets recording, he said no. However, he does say he'd hate to be remembered for the song "Feelin' Groovy".
- Once co-hosted Saturday Night Live (1975) with like-named U.S. Senator Paul Simon.
- Elected to the Rock and Roll Hall of Fame (as a member of Simon & Garfunkel) in 1990.
- Honorary member of Saturday Night Live (1975) "five-timers club," for people who have hosted "SNL" five times, even though he has hosted only four times.
- Inducted into the Rock and Roll Hall of Fame in 2001 (as a solo artist).
- Admits he is a highly competitive person, which has colored his relationship with Bob Dylan. He was regularly compared (sometimes unfavorably) to Dylan in the 1960s and responded by disparaging him in the press and even putting out a fairly explicit Dylan put-down song, "A Simple Desultory Philippic (or How I Was Robert McNamara'd into Submission)." He has since been more friendly toward Dylan, even going on tour with him once.
- Is a long-time friend of fellow New Yorker Lorne Michaels, which has led to Simon and/or his songs appearing in numerous Michaels productions, including Saturday Night Live (1975) (several appearances as both host and musical guest); The Rutles: All You Need Is Cash (1978) (brief appearance); and Coneheads (1993) (song "Kodachrome"). Michaels has also produced several of Simon's specials, including: The Paul Simon Special (1977); The Concert in Central Park (1982)_; and Paul Simon: Born at the Right Time (1993).
- He and Peter Gabriel were recognized by critics for their efforts in the 1980s to use their popularity to bring "world music" to a much bigger audience in the West. Simon covered Gabriel's song "Biko"--about a murdered black activist from South Africa--for Gabriel's tribute album "And I'll Scratch Yours," released in 2013.
- Generally considers his solo work, especially the albums "Graceland" (1986) and "The Rhythm of the Saints" (1990), to be superior to his work with Simon & Garfunkel.
- The "sleepy boy" he sings about in his song "St. Judy's Comet" (from the album "There Goes Rhymin' Simon") is his son Harper Simon. The lines "My traveling companion is nine years old / He is the child of my first marriage" in another song, "Graceland" (from the album of the same name), also refer to Harper.
- Before finding fame as a singer/songwriter under his real name, he had a handful of minor hit singles under two pseudonyms. The best known is Jerry Landis, a name he initially used as a member of the duo Tom and Jerry; he also issued some solo material under this name. When the hits as Landis stopped coming, he changed his stage name to Tico and made some very minor chart entries as a member of Tico & The Triumphs.
- Former son-in-law of Eddie Fisher and Debbie Reynolds. Former brother-in-law of Todd Fisher. Former half-brother-in-law of Joely Fisher and Tricia Leigh Fisher.
- Didn't want to return to the US from England, where he was enjoying success with his solo album there, but Columbia Records invoked the letter of his and Art Garfunkel's recording contract, forcing him to come back. His UK album went out of print, and was only reissued in 2004.
- Inducted into the Songwriters Hall of Fame in 1982.
- Has four children: son Harper Simon (b. September 7, 1972), with ex-wife Peggy Harper, and son Adrian Edward Simon (b. December 1992), daughter Lulu Simon (b. April 1995), and son Gabriel Elijah Simon (b. May 1998) with wife, Edie Brickell.
- Released non-charting singles using the names True Taylor (in 1958) and Paul Kane (in 1963). Also wrote songs for other artists under the name Jerry Landis, and released a few singles using that name. He later used the name Tico and had some minor hit singles as Tico & The Triumphs.
- Designated a Kennedy Center Honors recipient for 2002 to replace Paul McCartney. McCartney had originally accepted the award, but later withdrew because of a "personal scheduling conflict"--the wedding of his niece.
- Simon & Garfunkel were voted the 40th Greatest Artists in Rock 'n' Roll by "Rolling Stone" magazine.
- Is a Life member of Alpha Epsilon Pi fraternity
- Was in the fraternity Alpha Epsilon Pi in college with Art Garfunkel.
- Was slated to play Dunbar in Catch-22 (1970) before the character was dropped.
- Awarded the first Gershwin Prize for Popular Music in 2007 by the Library of Congress.
- Graduated from Queens College of the City University of New York (CUNY).
- Graduated in 1958 from Forest Hills High School in Forest Hills, Queens, New York.
- Like Steve Martin, Loren Michaels and Mike Nichols, he has had his portrait painted by artist Eric Fischl.
- Mentioned in the song "Haiti" by Caetano Veloso and Gilberto Gil.
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