| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| After a short stint on "Melrose Place", Ashlee Simpson-Wentz was Broadway bound as Roxie Hart in this musical | Chicago | $1,600 | DJ | POP CULTURE | 2010-02-01 | #5846 | |
| The Harlem Globetrotters were founded in this city famous for its blues & its fire | Chicago | $200 | J | POP CULTURE AMERICA | 2004-09-13 | #4601 | |
| In December 1987, Alderman Eugene Sawyer was selected as mayor of this U.S. city | Chicago | $500 | J | CURRENT EVENTS | 1988-05-23 | #871 |