| 2000 Best New Artist Grammy winner | 34 |
| 2000 Best New Artist Grammy winner ___ Lynne | 44 |
| 2000 Best Original Screenplay nominee | 37 |
| 2000 Best Picture nominee | 25 |
| 2000 best seller on social epidemics | 36 |
| 2000 Best Song Oscar winner | 27 |
| 2000 Best Supporting Actress for "Pollock" | 52 |
| 2000 biopic about James Joyce's love | 40 |
| 2000 Britney Spears hit | 23 |
| 2000 Broadway hit | 17 |
| 2000 Broadway show featuring music by Elton John | 48 |
| 2000 Bruce Willis film | 22 |
| 2000 Cadbury Schweppes acquisition | 34 |
| 2000 Cameron Crowe movie | 24 |
| 2000 Camp David summit attendee | 31 |
| 2000 Camp David visitor | 23 |
| 2000 candidate | 14 |
| 2000 CBS premiere | 17 |
| 2000 comedy "Me, Myself & ___" | 44 |
| 2000 custody-fight kid | 22 |
| 2000 De Niro/Stiller comedy | 27 |
| 2000 Democratic campaign slogan? | 32 |
| 2000 Disney movie starring Bruce Willis | 39 |
| 2000 election concern | 21 |
| 2000 election debacle? | 22 |
| 2000 election scrap | 19 |
| 2000 election's point of contention | 39 |
| 2000 Elton John/Tim Rice musical | 32 |
| 2000 Eminem hit | 15 |
| 2000 Eminem single | 18 |
| 2000 erupter | 12 |
| 2000 essay collection by David Sedaris | 38 |
| 2000 Eugene Levy film with the tagline "Some pets deserve a little more respect than others" | 102 |
| 2000 film "Billy ___" | 31 |
| 2000 film about a mission to Mars | 33 |
| 2000 film featuring the voice of Mel Gibson | 43 |
| 2000 film set in a confectionery | 32 |
| 2000 film told largely in reverse chronological order | 53 |
| 2000 film with an unseen Mel Gibson | 35 |
| 2000 flash-in-the-pan band from Nassau | 38 |
| 2000 Flushes alternative | 24 |
| 2000 Gere title role | 20 |
| 2000 Green Party candidate | 26 |
| 2000 gynecologist title role for Richard Gere | 45 |
| 2000 Hanks movie | 16 |
| 2000 Heisman Trophy winner ___ Dayne | 36 |
| 2000 hit album by Britney Spears | 32 |
| 2000 hit for Creed | 18 |
| 2000 Home Run Derby winner | 26 |
| 2000 Hugh Jackman film | 22 |
| 2000 Hugh Jackman movie | 23 |
| 2000 in-flight movie? | 21 |
| 2000 Italian film starring Monica Bellucci | 42 |
| 2000 Jackie Chan movie | 22 |
| 2000 Jason Biggs comedy-romance | 31 |
| 2000 Jennifer Lopez thriller | 28 |
| 2000 Jim Carrey movie "Me, Myself & ___" | 54 |
| 2000 JT LeRoy novel | 19 |
| 2000 Kyocera acquisition | 24 |
| 2000 Leading Actor nominee Penn | 31 |
| 2000 Liev Schreiber film | 24 |
| 2000 Martin Lawrence movie | 26 |
| 2000 Martin Lawrence/Nia Long comedy | 36 |
| 2000 Mel Gibson film | 20 |
| 2000 Mel Gibson flick | 21 |
| 2000 Mel Gibson movie | 21 |
| 2000 memoir by Stephen King | 27 |
| 2000 movie based on Marvel Comics characters | 44 |
| 2000 movie from Aardman Animation featuring product placement | 61 |
| 2000 musical that won four Tonys | 32 |
| 2000 musical with the song "Every Story Is a Love Story" | 66 |
| 2000 musical with the song "Fortune Favors the Brave" | 63 |
| 2000 N.B.A. championship star | 29 |
| 2000 N.B.A. M.V.P. | 18 |
| 2000 N.B.A. scoring leader for the Lakers | 41 |
| 2000 N.L M.V.P. who played for the Giants | 41 |
| 2000 N.L. home run champ | 24 |
| 2000 N.L. MVP Kent | 18 |
| 2000 Natalie Portman/Ashley Judd film | 37 |
| 2000 National League MVP Jeff | 29 |
| 2000 NBA Championship runner-up | 31 |
| 2000 NBA Finals MVP | 19 |
| 2000 NBA MVP | 12 |
| 2000 newsmaker Gonzalez | 23 |
| 2000 Nicolas Cage movie, with "The" | 45 |
| 2000 Nobel Peace Prize winner Kim ___-jung | 42 |
| 2000 Olympic gymnast ___ Ray | 28 |
| 2000 Olympic hurdles gold medalist ___ Shishigina | 49 |
| 2000 Olympics baseball gold medal winner | 40 |
| 2000 Olympics city | 18 |
| 2000 Olympics greeting | 22 |
| 2000 Olympics host | 18 |
| 2000 Olympics locale | 20 |
| 2000 Olympics platypus mascot | 29 |
| 2000 Olympics site | 18 |
| 2000 or 2004 | 12 |
| 2000 Oscar nominee Lee | 22 |
| 2000 Peace Nobelist Kim ___ Jung | 32 |
| 2000 Peace Prize recipient Kim __-jung | 38 |
| 2000 Peter Gabriel album | 24 |