| 1999 Jodie Foster title role | 28 |
| 1999 John Larroquette sitcom | 28 |
| 1999 Kevin Spacey film | 22 |
| 1999 Kidman/Cruise film? | 24 |
| 1999 Lenny Kravitz hit | 22 |
| 1999 Limp Bizkit single | 23 |
| 1999 Matthew McConaughey film | 29 |
| 1999 Melissa Joan Hart movie | 28 |
| 1999 Meryl Streep movie | 23 |
| 1999 N.C.A.A. hoops champs | 26 |
| 1999 National League MVP | 24 |
| 1999 Nissan Open winner | 23 |
| 1999 Nobelist in literature | 27 |
| 1999 peacekeeping mission | 25 |
| 1999 Plummer movie The _____ | 28 |
| 1999 reality-show satire | 24 |
| 1999 Reese Witherspoon movie | 28 |
| 1999 Ron Howard comedy | 22 |
| 1999 Ron Howard satire | 22 |
| 1999 Russell Crowe movie | 24 |
| 1999 satire of reality shows | 28 |
| 1999 Sean Connery movie | 23 |
| 1999 Seattle protest subj. | 26 |
| 1999 Stanley Cup champions | 26 |
| 1999 Stanley Cup winner | 23 |
| 1999 subject of a tug-of-war | 28 |
| 1999 title role for Julia | 25 |
| 1999 Tony-winning musical | 25 |
| 1999 U.S. Open champ Andre | 26 |
| 1999 U.S. Open winner Andre | 27 |
| 1999 U.S. Open winner Stewart | 29 |
| 1999 Winona Ryder movie | 23 |
| 1999 World Series MVP Rivera | 28 |
| 1999, on Chinese calendars | 26 |
| 1999-2000 name in the news | 26 |
| 1999-2004 Oldsmobile model | 26 |
| 19th Amendment beneficiaries | 28 |
| 19th Amendment beneficiary | 26 |
| 19th Amendment champion | 23 |
| 19th Amendment proponent | 24 |
| 19th Amendment subject | 22 |
| 19th book of the Bible | 22 |
| 19th C. American painter | 24 |
| 19th C. engine engineer | 23 |
| 19th c. French landscapist | 26 |
| 19th C. German physicist | 24 |
| 19th century canal name | 23 |
| 19th century cartoonist | 23 |
| 19th Century folk song | 22 |
| 19th century French composer | 28 |
| 19th century inventor Howe | 26 |
| 19th Century socialite Peggy | 28 |
| 19th century soprano __ Patti | 29 |
| 19th century South Seas novel | 29 |
| 19th dynasty Egyptian king | 26 |
| 19th dynasty's founder | 26 |
| 19th in a Greek series | 22 |
| 19th of 24 Greek letters | 24 |
| 19th pres.'s monogram | 25 |
| 19th ___ (golf clubhouse) | 25 |
| 19th-c. French landscapist | 26 |
| 19th-century abolitionist | 25 |
| 19th-century actor ___ Booth | 28 |
| 19th-century Arctic explorer | 28 |
| 19th-century Boer republic | 26 |
| 19th-century botanist Gray | 26 |
| 19th-century bric-a-brac | 24 |
| 19th-century British novelist | 29 |
| 19th-century card game | 22 |
| 19th-century cartoonist | 23 |
| 19th-century chief justice | 26 |
| 19th-century distiller | 22 |
| 19th-century educator Horace | 28 |
| 19th-century educator Willard | 29 |
| 19th-century expansion policy | 29 |
| 19th-century globetrotter | 25 |
| 19th-century humorist Bill | 26 |
| 19th-century humorist Ward | 26 |
| 19th-century Italian patriot | 28 |
| 19th-century literary family | 28 |
| 19th-century literary inits. | 28 |
| 19th-century literary sisters | 29 |
| 19th-century literary trio | 26 |
| 19th-century mail transport | 27 |
| 19th-century military family | 28 |
| 19th-century samurai home | 25 |
| 19th-century sea novelist | 25 |
| 19th-century social reformer | 28 |
| 19th-century South Seas tale | 28 |
| 19th-century trade route | 24 |
| 19th-century trail terminus | 27 |
| 19th-century U.S. money | 23 |
| 19th-century violin virtuoso | 28 |
| 1:15 P.M.: Taking cover | 23 |
| 1:51, 2:51 or 3:51, e.g. | 24 |
| 1A and 1B, on many airplanes | 28 |
| 1st Earl of Beaconsfield | 24 |
| 1st, 2nd and 3rd, e.g.: Abbr. | 29 |
| 1st, 2nd and 3rd, perhaps | 25 |
| 1st, 2nd, 3rd, etc.: Abbr. | 26 |