| 1989 Nancy Reagan book | 22 |
| 1989 National Radio Hall of Fame inductee | 41 |
| 1989 Neill/Kidman thriller | 26 |
| 1989 New Kids on the Block hit | 30 |
| 1989 Nobel Peace Prize winner | 29 |
| 1989 one-man Broadway drama | 27 |
| 1989 one-man show | 17 |
| 1989 Oscar winner | 17 |
| 1989 Oscar winner Jessica | 25 |
| 1989 Oscar-winning title role for Jessica Tandy | 47 |
| 1989 Paul McCartney song | 24 |
| 1989 Peace Nobelist | 19 |
| 1989 Peace Prize recipient | 26 |
| 1989 Peace Prize winner | 23 |
| 1989 play about Capote | 22 |
| 1989 protest site in China | 26 |
| 1989 R.E.M. hit | 15 |
| 1989 R.E.M. single | 18 |
| 1989 Radio Hall of Fame inductee | 32 |
| 1989 Richard Dreyfuss film shown on BET, appropriately? | 55 |
| 1989 Ricki Lake TV movie | 24 |
| 1989 Robin Williams film | 24 |
| 1989 Rock and Roll Hall of Fame inductee | 40 |
| 1989 Rod Stewart hit | 20 |
| 1989 Rolling Stones album | 25 |
| 1989 Roseanne Barr title role | 29 |
| 1989 Rush album | 15 |
| 1989 Rush album with a rabbit in a top hat on its cover | 55 |
| 1989 Sally Field/Dolly Parton/Shirley MacLaine movie | 52 |
| 1989 sci-fi film with The | 29 |
| 1989 sci-fi movie sequel, with "The" | 46 |
| 1989 sci-fi novel by William Shatner | 36 |
| 1989 Sean Penn film | 19 |
| 1989 skateboarding film | 23 |
| 1989 Spike Lee film | 19 |
| 1989 Steven Spielberg film | 26 |
| 1989 tennis retiree | 19 |
| 1989 They Might Be Giants jam | 29 |
| 1989 Tom Hanks comedy | 21 |
| 1989 Tom Hanks comedy, with "The" | 43 |
| 1989 Tom Hanks film | 19 |
| 1989 Tom Hanks film with The | 32 |
| 1989 Tom Hanks film, with "The" | 41 |
| 1989 Tom Hanks movie | 20 |
| 1989 Tom Petty hit | 18 |
| 1989 Tom Selleck movie | 22 |
| 1989 undersea thriller | 22 |
| 1989 underwater sci-fi film | 27 |
| 1989 underwater thriller, with "The" | 46 |
| 1989 war film | 13 |
| 1989 Wilbur Smith novel | 23 |
| 1989 Winona Ryder movie | 23 |
| 1989 World Champion figure skater | 33 |
| 1989 world champion skater | 26 |
| 1989 World Series site | 22 |
| 1989's "Thrash Zone" band | 39 |
| 1989's ___ Prieta earthquake | 32 |
| 1989-'90 Broadway biodrama | 30 |
| 1989-'90 Broadway one-man show | 34 |
| 1989-90 Broadway play | 21 |
| 1989-90 dance craze from Brazil | 31 |
| 1989-90 futuristic cop show on Fox | 34 |
| 1989-90 Indian P.M. | 19 |
| 1989-90 Indian PM | 17 |
| 1989-90 sitcom set in an orphanage | 34 |
| 199, in Old Rome | 16 |
| 1990 #1 rap hit | 15 |
| 1990 #1 rap hit that starts "Yo, V.I.P., let's kick it" | 69 |
| 1990 A.L. Rookie of the Year | 28 |
| 1990 Alan Alda film | 19 |
| 1990 autobiography subtitled "Baseball, the Wall and Me" | 66 |
| 1990 Barry Levinson film | 24 |
| 1990 Beatty role | 16 |
| 1990 Belinda Carlisle hit | 25 |
| 1990 Best Actress in a Musical Tony winner | 42 |
| 1990 Best New Artist Grammy winner | 34 |
| 1990 Best Supporting Actor winner | 33 |
| 1990 Best Supporting Actress | 28 |
| 1990 Bette Midler film | 22 |
| 1990 bill that increased wheelchair access: Abbr. | 49 |
| 1990 Broadway biographical play | 31 |
| 1990 Broadway one-man play | 26 |
| 1990 Broadway one-man show | 26 |
| 1990 Connery-Pfeiffer film | 26 |
| 1990 Connery/Pfeiffer spy film | 30 |
| 1990 Craig Lucas play | 21 |
| 1990 Cyrano portrayer | 21 |
| 1990 Demi Moore film | 20 |
| 1990 Depeche Mode album | 23 |
| 1990 Emmy-winning talk show host | 32 |
| 1990 film | 9 |
| 1990 film autobiography "___: My Story" | 49 |
| 1990 film directed by Barry Levinson | 36 |
| 1990 film featuring the "Wet Bandits" | 47 |
| 1990 film star autobiography subtitled "My Story" | 59 |
| 1990 film whose first sequel was subtitled "Lost in New York" | 71 |
| 1990 film with the tagline "The few. The proud. The totally insane." | 78 |
| 1990 French Open doubles champ Sergio | 37 |
| 1990 Gérard Depardieu film | 29 |
| 1990 Grammy winner for her album "Days of Open Hand" | 62 |