| 1987 Warren Beatty flop | 23 |
| 1987 Wimbledon champ | 20 |
| 1987 Wimbledon winner | 21 |
| 1987 Woody Allen film | 21 |
| 1987 Woody Allen movie | 22 |
| 1987 world figure skating champion | 34 |
| 1987 world figure skating champion Brian | 40 |
| 1987 Worst Actor winner | 23 |
| 1987-89 | 7 |
| 1987-91 Mideast hostage Terry | 29 |
| 1987-91 TV drama | 16 |
| 1987-95 Senate Judiciary Committee head | 39 |
| 1988 #1 country album | 21 |
| 1988 #1 Michael Jackson hit "Dirty ___" | 49 |
| 1988 #1 song with the lyrics "You make me feel so fine / You keep me rocking all of the time" | 103 |
| 1988 A.L. Cy Young Award winner | 31 |
| 1988 A.L. MVP | 13 |
| 1988 A.L. MVP Canseco | 21 |
| 1988 A.L. Rookie of the Year Walt | 33 |
| 1988 A.L. Rookie of the Year Weiss | 34 |
| 1988 action hit that takes place on Christmas Eve | 49 |
| 1988 and 1992 Olympic track gold medalist) | 42 |
| 1988 and 2008 presidential candidate | 36 |
| 1988 animated action film set in 2019 Tokyo | 43 |
| 1988 baseball flick | 19 |
| 1988 baseball movie | 19 |
| 1988 baseball scandal movie | 27 |
| 1988 Beach Boys hit | 19 |
| 1988 Belinda Carlisle hit "___ Weak" | 46 |
| 1988 Best Actress winner | 24 |
| 1988 Best Picture | 17 |
| 1988 Best Picture, with the repeated line "I'm an excellent driver" | 81 |
| 1988 Best Play Tony winner inspired by Puccini | 46 |
| 1988 Best Supporting Actor | 26 |
| 1988 Bette Midler/Lily Tomlin comedy | 36 |
| 1988 bicentennial city | 22 |
| 1988 Bill Murray movie | 22 |
| 1988 biopic about Dian Fossey, literally | 40 |
| 1988 Burt Reynolds film | 23 |
| 1988 Burt Reynolds flop | 23 |
| 1988 Bush campaign adviser | 26 |
| 1988 buyer of Motown | 20 |
| 1988 buyer of Motown Records | 28 |
| 1988 Carl Weathers title role | 29 |
| 1988 chart-topping country album | 32 |
| 1988 Christopher Walken children's comedy | 45 |
| 1988 comeback hit for the Beach Boys | 36 |
| 1988 comedy starring Richard Dreyfuss and Raul Julia | 52 |
| 1988 comedy with Bette Midler and Lily Tomlin | 45 |
| 1988 Connery film (with "The") | 40 |
| 1988 Connery film, with "The" | 39 |
| 1988 cop movie that Ice-T rapped the title track to | 51 |
| 1988 Costner/Sarandon film | 26 |
| 1988 country album | 18 |
| 1988 Cusack film | 16 |
| 1988 Cy Young winner Hershiser | 30 |
| 1988 Danzig single | 18 |
| 1988 Dennis Quaid film | 22 |
| 1988 Dennis Quaid remake | 24 |
| 1988 Dennis Quaid thriller | 26 |
| 1988 Dennis Quaid/Meg Ryan movie | 32 |
| 1988 Dick Francis thriller, with "The" | 48 |
| 1988 Don DeLillo novel | 22 |
| 1988 Dreyfuss-Julia comedy | 26 |
| 1988 earthquake site | 20 |
| 1988 Edward James Olmos film | 28 |
| 1988 Errol Morris documentary about the murder of a police officer, with "The" | 88 |
| 1988 fantasy film | 17 |
| 1988 film "Rent-___" | 30 |
| 1988 film about an optimistic broker? | 37 |
| 1988 film about Charlie Parker | 30 |
| 1988 film costarring Robert De Niro and Charles Grodin | 54 |
| 1988 film farce fish | 20 |
| 1988 film noir remake | 21 |
| 1988 film remake starring Dennis Quaid | 38 |
| 1988 film set in a New England pie maker's shop | 51 |
| 1988 film that precipitated the Buchwald v. Paramount lawsuit | 61 |
| 1988 film with the line "I'm an excellent driver" | 63 |
| 1988 Grammy winner for "Crying" | 41 |
| 1988 Grand Slam winner | 22 |
| 1988 Hanks film with a fortune-telling machine | 46 |
| 1988 Heisman Trophy runner-up Rodney | 36 |
| 1988 Heisman Trophy winner | 26 |
| 1988 Heisman winner Barry | 25 |
| 1988 hit for Breathe | 20 |
| 1988 hit for Pebbles | 20 |
| 1988 hit for the Beach Boys | 27 |
| 1988 inductees into the Rock and Roll Hall of Fame | 50 |
| 1988 Japanese animated cyberpunk action movie | 45 |
| 1988 Jean Claude Van Damme film, or where an L.A. gang docks their boats? | 73 |
| 1988 Joe Keenan novel (2,7) | 27 |
| 1988 John Cleese movie, with "A" | 42 |
| 1988 John Cusack film | 21 |
| 1988 John Sayles film, in Rome? | 31 |
| 1988 Johnny Unitas Golden Arm Award winner Rodney | 49 |
| 1988 Jonathan Demme film | 24 |
| 1988 Kennedy Center Honors recipient | 36 |
| 1988 Kevin Costner movie | 24 |
| 1988 LL Cool J hit "Going Back to ___" | 48 |
| 1988 marathon gold medalist Rosa ___ | 36 |