Paul Simon Rates His Songs and Performs on 'Colbert' Ahead of New Documentary

Ahead of the release of the three-and-a-half hour, two-part docuseries (March 17 & 24), In Restless Dreams: The Music of Paul Simon, the man himself sat down for the entirety of The Late Show With Stephen Colbert to talk about, what else, music.

Simon shared early memories of hearing songs that inspired him, and also took some shots at a song that he loathes. The latter is the 1966 tune "The 59th Street Bridge Song (Feelin' Groovy)." Colbert emphasized that "it's a youthful song," but Simon shot that down.

"Sometimes in shows, if I made an error in some other song, I would sing that song as punishment," he explained to laughter from Colbert and the audience. However, when asked what five songs he would play for himself, without hesitation he first named the title song from his 1986 Grammy-winning album Graceland.

Simon continued his setlist with "Me and Julio Down By The Schoolyard" and "Mother and Child Reunion" (from 1972's Paul Simon) and 1980's "Late In The Evening." For ballads: two songs he recorded with Art Garfunkel ""The Sound of Silence" and "The Boxer") and his solo hit from 1975 "Still Crazy After All These Years." Simon also recalled a hilarious anecdote about Frank Sinatra covering "Mrs. Robinson" in his trademark Rat Pack 'ring-a-ding-ding' delivery that Simon nearly put a stop to. But he let it go and now plays the record at the conclusion of his live shows.

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The two-part docuseries (directed by Emmy and Oscar-winning filmmaker Alex Gibney) brings the viewer on a journey through Simon's 2023 release Seven Psalms and his nearly 65-year musical legacy. Streaming service MGM+ said in a previous press release: "The docuseries juxtaposes Simon’s process of making a new album during the COVID-19 pandemic against archival material tracing Simon's career and creative journey, including revelatory, previously unseen footage from such historic moments as the recording of Bridge Over Troubled Water and Graceland, Simon & Garfunkel's unforgettable reunion concert in Central Park, and ten years later, Simon's solo concert there, where he performed before 750,000 people."

It's easy to see why Graceland holds a special place with Simon. After a downward turn in the early '80s, both personally and professionally, he happened upon a bootleg cassette of mbaqanga, South African street music. Intrigued by this sound, he and engineer Roy Halee spent time in Johannesburg in 1984 recording South African musicians.

Simon, however, caught backlash from anti-apartheid organizations who saw this as a break in the cultural embargo with the segregated nation. The pendulum swung wildly from praise for recognizing the significance of that music, to accusations of exploiting the heritage of indigenous music. Yet, Simon persevered with a cross-cultural tour and was rewarded with his most successful album to date: in 2006, Graceland was inducted into the U.S. National Recording Registry as "culturally, historically, or aesthetically important."

With a career encompassing early success with partner Garfunkel and a solo career that stretches from the 1970s to the present day, Simon recently sold publishing rights to his compositions to Sony Music for a reported $250 million dollars. Nine of his albums have charted on the Billboard 200, with four reaching No. 1, including the soundtrack to The Graduate. He has won 16 Grammy Awards, including three Album of the Year honors and three for Record of the Year. He was inducted into the Rock and Roll Hall of Fame twice: as a member of Simon & Garfunkel in 1990 and in 2001 as a solo artist.