| 1 | Introduction Paul Simon & Bob Costas | - |
| 2 | 50 Ways to Leave Your Lover Paul Simon & Lyle Lovett | - |
| 3 | The Boxer Paul Simon, Alison Krauss, Shawn Colvin & Jerry Douglas | - |
| 4 | Mother and Child Reunion Paul Simon & Stephen Marley | - |
| 5 | Under African Skies Paul Simon & Miriam Makeba | - |
| 6 | Clip From Paul Simon Graceland: The African Concert (Zimbabwe, 1987) | - |
| 7 | Homeless Paul Simon & Ladysmith Black Mambazo | - |
| 8 | Mrs. Robinson | - |
| 9 | Clip From Yankee Stadium Tribute to Joe DiMaggio (April 25, 1999) | - |
| 10 | Slip Slidin’ Away Paul Simon, James Taylor & The Dixie Hummingbirds | - |
| 11 | Sunday Morning With the Sensational Nightingales (poem) Paul Simon, Phil Collins & The Dixie Hummingbirds | - |
| 12 | That Was Your Mother Paul Simon, Buckwheat Zydeco & Lyle Lovett | - |
| 13 | Homeward Bound (clip from Saturday Night Live, November 20, 1976) Paul Simon & George Harrison | - |
| 14 | Still Crazy After All These Years Paul Simon & James Taylor | - |
| 15 | El Condor Pasa Paul Simon & Marc Anthony | - |
| 16 | Late in the Evening Paul Simon & Marc Anthony | - |
| 17 | Gone at Last Paul Simon, Yolanda Adams & Jessy Dixon | - |
| 18 | Something So Right Paul Simon & Dianne Reeves | - |
| 19 | The 59th Street Bridge Song (Feelin’ Groovy) -The Muppets (Grover and Elmo) | - |
| 20 | Graceland Paul Simon, Alison Krauss & Jerry Douglas | - |
| 21 | Diamonds on the Soles of Her Shoes Paul Simon & Ladysmith Black Mambazo | - |
| 22 | Bridge Over Troubled Water Paul Simon & Art Garfunkel | - |
| 23 | Father and Daughter | - |
| 24 | Me and Julio Down by the Schoolyard Paul Simon & Stevie Wonder | - |
| 25 | Loves Me Like a Rock Paul Simon, Stevie Wonder & The Dixie Hummingbirds | - |
| 26 | Sounds of Silence Paul Simon & Philip Glass | - |
