| 2000 polling place litter | 25 |
| 2000 pounds | 11 |
| 2000 presidential also-ran | 26 |
| 2000 presidential candidate | 27 |
| 2000 presidential candidate Alan | 32 |
| 2000 presidential candidate Keyes | 33 |
| 2000 presidential hopeful | 25 |
| 2000 Radiohead album | 20 |
| 2000 recount figure | 19 |
| 2000 Renée Zellweger title role | 34 |
| 2000 Richard Gere "late show"? | 40 |
| 2000 Richard Gere role | 22 |
| 2000 Richard Gere role opposite Farrah Fawcett | 46 |
| 2000 Richard Gere title role | 28 |
| 2000 Richard Gere/Winona Ryder movie | 36 |
| 2000 Ricky Martin hit | 21 |
| 2000 role for Julia | 19 |
| 2000 runner | 11 |
| 2000 runner-up | 14 |
| 2000 Santana hit | 16 |
| 2000 sci-fi film | 16 |
| 2000 Sean Penn film, with "The" | 41 |
| 2000 Series losers | 18 |
| 2000 site | 9 |
| 2000 Stanley Cup champions | 26 |
| 2000 Sting duet with Cheb Mami | 30 |
| 2000 Subway Series losers | 25 |
| 2000 Subway Series stadium | 26 |
| 2000 Summer Olympics city | 25 |
| 2000 Summer Olympics mascot | 27 |
| 2000 Super Bowl champs | 22 |
| 2000 Super Bowl player | 22 |
| 2000 Super Bowl winner | 22 |
| 2000 Supreme Court case | 23 |
| 2000 Supreme Court case hinging on the 14th Amendment | 53 |
| 2000 Sutherland movie | 21 |
| 2000 terrorist target | 21 |
| 2000 title role for Gere | 24 |
| 2000 title role for Julia | 25 |
| 2000 title role for Renée | 28 |
| 2000 title role for Richard Gere | 32 |
| 2000 Tom Green comedy | 21 |
| 2000 Tom Hanks movie | 20 |
| 2000 Tony role for Heather Headley | 34 |
| 2000 U.S. Open champ | 20 |
| 2000 U.S. Open champ Marat | 26 |
| 2000 U.S. Open champ Safin | 26 |
| 2000 U.S. Open champion Marat | 29 |
| 2000 U.S. Open winner | 21 |
| 2000 U.S. Open winner Marat | 27 |
| 2000 US Open champ Marat __ | 27 |
| 2000 US Open winner Marat | 25 |
| 2000 Viacom acquisition | 23 |
| 2000 Viacom purchase | 20 |
| 2000 was its year | 17 |
| 2000 Woody Allen film | 21 |
| 2000 Woody Allen movie | 22 |
| 2000 World Series locale | 24 |
| 2000 World Series losers | 24 |
| 2000 World Series M.V.P. | 24 |
| 2000 World Series manager | 25 |
| 2000 World Series MVP | 21 |
| 2000 World Series MVP Derek | 27 |
| 2000 World Series participant | 29 |
| 2000 World Series site | 22 |
| 2000 World Series stadium | 25 |
| 2000 World Series team | 22 |
| 2000 World Series venue | 23 |
| 2000 Zellweger/Freeman flick | 28 |
| 2000, e.g. | 10 |
| 2000, e.g., in Spain | 20 |
| 2000, for one | 13 |
| 2000-01 Hart Memorial Trophy winner Joe | 39 |
| 2000-01 NBA MVP | 15 |
| 2000–02 WNBA franchise | 29 |
| 2000s Bengals running back Dorsey | 33 |
| 2000s caffeinated offshoot of 7 Up | 34 |
| 2000s caffeinated offshoot of 7 Up, based off an upside-down 7 Up logo | 70 |
| 2000s CBS sitcom | 16 |
| 2000s Chevy | 11 |
| 2000s documentary whose first episode was "From Pole to Pole" | 71 |
| 2000s drama set in Newport Beach | 32 |
| 2000s events in North Korea, for short | 38 |
| 2000s first lady Bush | 21 |
| 2000s Giants manager Felipe | 27 |
| 2000s GM compacts | 17 |
| 2000s HBO drama set in Utah | 27 |
| 2000s high school drama | 23 |
| 2000s Houston-based scandal subject | 35 |
| 2000s Iraq war subject, briefly | 31 |
| 2000s Korean compact | 20 |
| 2000s leadership nickname | 25 |
| 2000s National Book Festival host | 33 |
| 2000s New Hampshire senator John | 32 |
| 2000s scandal subject | 21 |
| 2000s Senate leader's turndown? | 35 |
| 2000s service site | 18 |
| 2000s sitcom set in Houston | 27 |
| 2000s sitcom set in Texas | 25 |
| 2000s sitcom single mom | 23 |