| 1989 Grammy winner for "Nick of Time" | 47 |
| 1989 Grammy Lifetime Achievement Award winner | 45 |
| 1989 French Open winner and others | 34 |
| 1989 film written as "Teenie Weenies" | 47 |
| 1989 film set in an inner-city high school | 42 |
| 1989 film "Milo & ___" | 36 |
| 1989 Ernest Borgnine movie set in Africa | 40 |
| 1989 comedy-mystery with Tom Selleck | 36 |
| 1989 comedy that takes place at Channel 62 | 42 |
| 1989 comedy "_____ -Devil" | 36 |
| 1989 best seller, with "The" | 38 |
| 1989 Best Original Song Oscar winner | 36 |
| 1989 B-52's hit song Love ____ | 37 |
| 1989 AP Female Athlete of the Year | 34 |
| 1989 "Weird Al" Yankovic movie | 40 |
| 1989 "Weird Al" Yankovic cult film | 44 |
| 1988's Best Picture Oscar winner | 36 |
| 1988's "Akira," e.g. | 34 |
| 1988 World Series M.V.P. Hershiser | 34 |
| 1988 World Series hero Hershiser | 32 |
| 1988 winner of seven Olympic swimming medals | 44 |
| 1988 vice-presidential candidate | 32 |
| 1988 triple gold winner, familiarly | 35 |
| 1988 Tony-winning play inspired by a Puccini work | 49 |
| 1988 Tony winner for "Speed-the-Plow" | 47 |
| 1988 thriller with Steven Seagal | 32 |
| 1988 swimming gold medalist Kristin | 35 |
| 1988 sequel costarring George Clooney | 37 |
| 1988 self-titled platinum country album | 39 |
| 1988 Sean Penn and Robert Duvall gang movie | 43 |
| 1988 Schwarzenegger action flick | 32 |
| 1988 Rob Lowe/Meg Tilly thriller | 32 |
| 1988 Radio Hall of Fame inductee | 32 |
| 1988 platinum-selling country album | 35 |
| 1988 Oscar nominee Edward James ___ | 35 |
| 1988 Olympics swimming sensation | 32 |
| 1988 Olympics superheavyweight gold medalist | 44 |
| 1988 Olympics sprinter, familiarly | 34 |
| 1988 Olympic track star, informally | 35 |
| 1988 Olympic track star nickname | 32 |
| 1988 Olympic sprinter, popularly | 32 |
| 1988 Olympic gold-medal swimmer Kristin | 39 |
| 1988 Olympic gold medalist Carolyn | 34 |
| 1988 National League Rookie of the Year Chris | 45 |
| 1988 N.L. Rookie of the Year Chris | 34 |
| 1988 movie, 'Without --' | 32 |
| 1988 Miss America winner Kaye Lani ___ Rafko | 44 |
| 1988 marathon gold medalist Rosa ___ | 36 |
| 1988 LL Cool J hit "Going Back to ___" | 48 |
| 1988 Kennedy Center Honors recipient | 36 |
| 1988 Johnny Unitas Golden Arm Award winner Rodney | 49 |
| 1988 John Cleese movie, with "A" | 42 |
| 1988 Japanese animated cyberpunk action movie | 45 |
| 1988 Heisman Trophy runner-up Rodney | 36 |
| 1988 Hanks film with a fortune-telling machine | 46 |
| 1988 Grammy winner for "Crying" | 41 |
| 1988 film remake starring Dennis Quaid | 38 |
| 1988 film about an optimistic broker? | 37 |
| 1988 Dick Francis thriller, with "The" | 48 |
| 1988 Dennis Quaid/Meg Ryan movie | 32 |
| 1988 Connery film, with "The" | 39 |
| 1988 Connery film (with "The") | 40 |
| 1988 comedy with Bette Midler and Lily Tomlin | 45 |
| 1988 comeback hit for the Beach Boys | 36 |
| 1988 Christopher Walken children's comedy | 45 |
| 1988 chart-topping country album | 32 |
| 1988 biopic about Dian Fossey, literally | 40 |
| 1988 Bette Midler/Lily Tomlin comedy | 36 |
| 1988 Best Play Tony winner inspired by Puccini | 46 |
| 1988 Belinda Carlisle hit "___ Weak" | 46 |
| 1988 animated action film set in 2019 Tokyo | 43 |
| 1988 and 2008 presidential candidate | 36 |
| 1988 and 1992 Olympic track gold medalist) | 42 |
| 1988 action hit that takes place on Christmas Eve | 49 |
| 1988 A.L. Rookie of the Year Weiss | 34 |
| 1988 A.L. Rookie of the Year Walt | 33 |
| 1988 #1 Michael Jackson hit "Dirty ___" | 49 |
| 1987-95 Senate Judiciary Committee head | 39 |
| 1987 world figure skating champion Brian | 40 |
| 1987 world figure skating champion | 34 |
| 1987 U2 album, with "The" | 35 |
| 1987 self-titled million-selling album | 38 |
| 1987 sci-fi film set in near-future Detroit | 43 |
| 1987 Rock and Roll Hall of Fame inductee | 40 |
| 1987 R.E.M. hit, with "The" | 37 |
| 1987 Pulitzer-winning critic Richard ___ | 40 |
| 1987 Peace Nobelist from Costa Rica | 35 |
| 1987 Oscar-nominated role for Denzel Washington | 47 |
| 1987 Oscar role for Michael Douglas | 35 |
| 1987 Nobel Peace Prize recipient | 32 |
| 1987 Nicolas Cage/Holly Hunter film | 35 |
| 1987 N.L. Rookie of the Year Santiago | 37 |
| 1987 movie with the hit "Hungry Eyes" | 47 |
| 1987 miniseries set in a Soviet-controlled U.S. | 47 |
| 1987 Michael Crichton best-seller | 33 |
| 1987 Luther Vandross #2 R&B album | 37 |
| 1987 Louis L'Amour bestseller | 33 |
| 1987 film about a mechanical crime-fighter | 42 |
| 1987 film about a cyborg policeman | 34 |
| 1987 duet by Eric Clapton and Tina Turner | 41 |