| 1999 Kidman/Cruise film? | 24 |
| 1999 Kevin Spacey film | 22 |
| 1999 Keanu Reeves movie with two sequels, with "The" | 62 |
| 1999 Johnny Depp film | 21 |
| 1999 John Travolta thriller, with 'The' | 47 |
| 1999 John Larroquette sitcom | 28 |
| 1999 Jodie Foster title role | 28 |
| 1999 Jodie Foster film set in Siam | 34 |
| 1999 indie romance featuring conjoined brothers | 47 |
| 1999 Iggy Pop album | 19 |
| 1999 hurricane | 14 |
| 1999 horror film set at Hill House | 34 |
| 1999 hit comedy | 15 |
| 1999 hit '-- to Know' | 29 |
| 1999 Heisman winner Dayne | 25 |
| 1999 Heisman Trophy winner Dayne | 32 |
| 1999 Heisman Trophy winner | 26 |
| 1999 headline-grabbing child | 28 |
| 1999 Glenn Gould Prize winner | 29 |
| 1999 Glenn Close film | 21 |
| 1999 George Clooney film in our series | 38 |
| 1999 French Open winner | 23 |
| 1999 French Open runner-up Medvedev | 35 |
| 1999 French Open champ | 22 |
| 1999 Frank McCourt memoir | 25 |
| 1999 Frank McCourt book | 23 |
| 1999 film with the tagline "Fame. Be careful. It's out there" | 75 |
| 1999 film with Albert Brooks and Sharon Stone | 45 |
| 1999 film whose title is a hint to this puzzle's theme | 58 |
| 1999 film that received seven Oscar nominations | 47 |
| 1999 film starring Winona Ryder and Angelina Jolie | 50 |
| 1999 film starring Sarah Michelle Gellar | 40 |
| 1999 film set in the Persian Gulf | 33 |
| 1999 film scripted by Lowell Ganz and Babaloo Mandel | 52 |
| 1999 film satirizing media ruthlessness | 39 |
| 1999 film in which author John Irving plays a stationmaster, with "The" | 81 |
| 1999 Exxon merger partner | 25 |
| 1999 European event said to be the most-watched of its kind in history | 70 |
| 1999 Emmy-winning soap role | 27 |
| 1999 documentary "Pimps Up, ___ Down" | 47 |
| 1999 Devon Sawa/Seth Green horror/comedy | 40 |
| 1999 Denzel Washington role | 27 |
| 1999 David Cronenberg thriller | 30 |
| 1999 David Bowie single | 23 |
| 1999 Crystal/De Niro film | 25 |
| 1999 commando rescue film subtitled "The Lost Patrol" | 63 |
| 1999 comedy featuring aliens called Thermians | 45 |
| 1999 comedy directed by Ron Howard | 34 |
| 1999 combatants | 15 |
| 1999 combatant | 14 |
| 1999 Clorox acquisition | 23 |
| 1999 Claire Danes film, with "The" | 44 |
| 1999 Canadian peace-keeping locale | 34 |
| 1999 Broadway revue | 19 |
| 1999 Broadway hit, with "The" | 39 |
| 1999 British Petroleum acquisition | 34 |
| 1999 Brendan Fraser movie | 25 |
| 1999 Brendan Fraser film based on a Hanna-Barbera toon | 54 |
| 1999 Brendan Fraser film | 24 |
| 1999 Brad Pitt movie | 20 |
| 1999 Brad Pitt film | 19 |
| 1999 Blink-182 smash | 20 |
| 1999 biography starring Jim Carrey | 34 |
| 1999 Bill Pullman movie | 23 |
| 1999 best-selling memoir | 24 |
| 1999 best seller "___ Road" | 37 |
| 1999 Best Director winner | 25 |
| 1999 Best Actor winner | 22 |
| 1999 Backstreet Boys hit | 24 |
| 1999 astronomical event watched by many | 39 |
| 1999 Arnold Schwarzenegger movie | 32 |
| 1999 Anthony Hopkins movie | 26 |
| 1999 and 2015, for short | 24 |
| 1999 album by the punk band Screeching Weasel | 45 |
| 1999 air strike authorizer | 26 |
| 1999 Adam Sandler movie | 23 |
| 1999 Academy Honorary Award recipient | 37 |
| 1999 A.L. Rookie of the Year Carlos | 35 |
| 1999 "Star Wars" release | 34 |
| 1999 #1 hit that introduced the "Cher-bot" vocal recording technique | 78 |
| 1998-2007 Lebanese president Lahoud | 35 |
| 1998-2004 Oldsmobiles | 21 |
| 1998-2004 Olds model | 20 |
| 1998-2001 ABC sitcom | 20 |
| 1998, with "A" | 24 |
| 1998, to the Chinese | 20 |
| 1998, to some | 13 |
| 1998, e.g., in fancy language | 29 |
| 1998's ___ Report | 21 |
| 1998's leading money winner on the PGA tour | 47 |
| 1998's 'Psycho,' e.g. | 33 |
| 1998 World-Series-winning manager | 33 |
| 1998 World Series winning manager | 33 |
| 1998 World Series star Ricky | 28 |
| 1998 World Series player | 24 |
| 1998 World Cup champs: Abbr. | 28 |
| 1998 Winter Olympics skiing star | 32 |
| 1998 Winter Olympics site | 25 |
| 1998 Winter Olympics locale | 27 |
| 1998 Winter Olympics host | 25 |