| ALFRANKEN | He's done Pat Robertson, Paul Simon, and Paul Tsongas |
| MARION | Birthname of Pat Robertson and John Wayne |
| UMASS | Tsongas Arena is home to one of its hockey teams |
| BROOKE | Tsongas beat him |
| NIKI | Massachusetts Congresswoman Tsongas |
| NEW | Highway where Paul Simon (and Kathy) counted cars in America? (3,6,8) |
| NEWARK | Paul Simon and Whitney Houston were born in which New Jersey city? (6) |
| HOMELESS | Paul Simon and Ladysmith Black Mambazo seek shelter (8) |
| ART | The 2003 Grammy awards heard The Sounds Of Silence performed by Paul Simon and ... Garfunkel |
| JONLOVITZ | He's done Michael Dukakis, Paul Sarbanes, and Caspar Weinberger |
| DANACARVEY | He's done George Bush, Strom Thurmond, and Dan Quayle |
| DANAYKROYD | He's done Jimmy Carter, Richard Nixon, and Bob Dole |
| KEVINNEALON | He's done Joe Biden, Sam Donaldson, and Michael Deaver |
| ELTON | He's done duets with Kiki and Aretha |
| BRYANADAMS | He's done duets with Tina Turner and Barbra Streisand |
| STEPHENSONDHEIM | As songsmith, he's done well. As pensmith, he's done badly |
| SPIRITLEVELS | They're perfect for those looking for an evening out and the barman will be aware of them if he's done a stocktake? (6,6) |
| WAYLAID | In following home, he's done wrongly (7) |
| SHORELINE | Is loner ___ he's done laps here? (9) |
| HOLDUPONESHEAD | After robbery, he's done a runner, appearing to be unashamed |