| 19th c. French landscapist | 26 |
| 19th C. engine engineer | 23 |
| 19th C. art style emphasizing nature | 36 |
| 19th C. American painter | 24 |
| 19th c. actor Booth | 19 |
| 19th book of the Bible | 22 |
| 19th Amendment subject | 22 |
| 19th Amendment proponent | 24 |
| 19th Amendment champion | 23 |
| 19th Amendment beneficiary | 26 |
| 19th Amendment beneficiaries | 28 |
| 19th Amendment backer | 21 |
| 1999-2007 House speaker Dennis | 30 |
| 1999-2006 NBC series | 20 |
| 1999-2004 Oldsmobile model | 26 |
| 1999-2004 Oldsmobile | 20 |
| 1999-2004 Olds | 14 |
| 1999-2001 Broadway musical revue | 32 |
| 1999-2000 NBA MVP | 17 |
| 1999-2000 name in the news | 26 |
| 1999-2000 "Dame" on Broadway | 38 |
| 1999, on Chinese calendars | 26 |
| 1999, e.g. | 10 |
| 1999, 2000 and 2001 Best Actor nominee (he won once) | 52 |
| 1999 Yankee pitcher | 19 |
| 1999 Yankee | 11 |
| 1999 World Series runner-up: Abbr. | 34 |
| 1999 World Series MVP Rivera | 28 |
| 1999 Women's World Cup host | 31 |
| 1999 Winona Ryder movie | 23 |
| 1999 Will Smith movie | 21 |
| 1999 war site | 13 |
| 1999 war combatant | 18 |
| 1999 US Open champ | 18 |
| 1999 U.S. Ryder Cup team captain | 32 |
| 1999 U.S. Open winner Stewart | 29 |
| 1999 U.S. Open winner Andre | 27 |
| 1999 U.S. Open winner | 21 |
| 1999 U.S. Open champ Andre | 26 |
| 1999 U.S. Open champ | 20 |
| 1999 Top 10 hit for Sixpence None the Richer | 44 |
| 1999 Tony-winning musical | 25 |
| 1999 Tom Hanks film, with "The" | 41 |
| 1999 Tom Cruise movie | 21 |
| 1999 title role for Julia | 25 |
| 1999 Tim Allen/Sigourney Weaver cult comedy | 43 |
| 1999 teammate of Brandi, Briana, et al. | 39 |
| 1999 teammate of Brandi, Briana et al. | 38 |
| 1999 Sutherland movie | 21 |
| 1999 subject of a tug-of-war | 28 |
| 1999 Steven Soderbergh movie, with "The" | 50 |
| 1999 Stanley Cup winner | 23 |
| 1999 Stanley Cup finals competitor | 34 |
| 1999 Stanley Cup champions | 26 |
| 1999 sitcom about a hockey player-turned-social worker | 54 |
| 1999 Seattle protest subj. | 26 |
| 1999 Sean Connery movie | 23 |
| 1999 sci-fi thriller (with "The") | 43 |
| 1999 sci-fi film | 16 |
| 1999 satire of reality shows | 28 |
| 1999 Russell Crowe movie | 24 |
| 1999 Ron Howard satire | 22 |
| 1999 Ron Howard film | 20 |
| 1999 Ron Howard comedy | 22 |
| 1999 Ron Howard bomb | 20 |
| 1999 romantic comedy based on "Pygmalion" | 51 |
| 1999 Ricky Martin song calling for movement | 43 |
| 1999 Richard Belzer book, "___, JFK, and Elvis" | 57 |
| 1999 Reese Witherspoon movie | 28 |
| 1999 recipient of the Mark Twain Prize for American Humor | 57 |
| 1999 reality-show satire | 24 |
| 1999 rap hit featuring Snoop Dogg | 33 |
| 1999 Pulitzer-winning play by Margaret Edson | 44 |
| 1999 Pulitzer Prize-winning play | 32 |
| 1999 Pulitzer Prize-winning Margaret Edson play | 47 |
| 1999 Pulitzer Prize-winning drama | 33 |
| 1999 Plummer movie The _____ | 28 |
| 1999 peacekeeping mission | 25 |
| 1999 Pacino film directed by Oliver Stone | 41 |
| 1999 Oscar winner for "Shakespeare in Love" | 53 |
| 1999 Oscar nominee for both direction and screenwriting | 55 |
| 1999 Nobelist in literature | 27 |
| 1999 Nissan Open winner | 23 |
| 1999 NFL Defensive Player of the Year Warren | 44 |
| 1999 NBA champs | 15 |
| 1999 National League MVP | 24 |
| 1999 N.F.L. Defensive Player of the Year | 40 |
| 1999 N.C.A.A. hoops champs | 26 |
| 1999 movie directed by Ron Howard | 33 |
| 1999 movie about a reality show | 31 |
| 1999 Motorcycle Hall of Fame inductee | 37 |
| 1999 Meryl Streep movie | 23 |
| 1999 memoir that was a bestseller | 33 |
| 1999 Melissa Joan Hart movie | 28 |
| 1999 McConaughey film | 21 |
| 1999 Matthew McConaughey movie | 30 |
| 1999 Matthew McConaughey film | 29 |
| 1999 Limp Bizkit single | 23 |
| 1999 Lenny Kravitz hit | 22 |
| 1999 Kubrick film | 17 |