| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| Title that completes the line "I'd like to help you in your struggle to be free, there must be..." | "50 Ways to Leave Your Lover" DD | $2,000 | DJ | MUSICAL NUMBERS | 2002-10-01 | #4157 | |
| According to Paul Simon, 2 of them are "Slip out the back, Jack" & "Make a new plan, Stan" | "50 Ways To Leave Your Lover" | $100 | J | SONGS BY THE NUMBER | 1998-11-09 | #3261 | |
| Paul Simon hit that begins by saying, "The problem is all inside your head" | "50 Ways To Leave Your Lover" | $400 | J | NUMBERS IN SONG | 1988-01-04 | #771 |