Although he's retreated from the spotlight in recent years, the diminutive folk singer remains as New York as Woody Allen (Simon appeared in Annie Hall) and Central Park (the site of his most famous concert).
A Newark native, Simon's musical career began when he met Art Garfunkel when they were both 11. An act of kismet, Simon wrote the duo's first song at thirteen, and although he got sidetracked after college writing music for other bands like Tico and the Triumphs, Simon & Garfunkel released their first folksy album in 1964, which initially flopped. However, a few short years later, after increased radio play, Simon & Garfunkel's music was used to score the massively successful and critically beloved film The Graduate, and their album Bridge Over Troubled Water made them folk icons.
Although the pair split in the early 70s for solo projects, they habitually get back together again, such as for their famous 1981 concert in Central Park. In addition to Simon's extensive solo work, he's dabbled in acting, most successfully in Woody Allen's Annie Hall, but has also made many memorable appearances on SNL.
Simon has been married three times, his most famous spouse being Princess Leia herself—Carrie Fisher. [Image via Getty]