| 1999 sitcom about a hockey player-turned-social worker | 54 |
| 1999 Richard Belzer book, "___, JFK, and Elvis" | 57 |
| 1999 recipient of the Mark Twain Prize for American Humor | 57 |
| 1999 Oscar winner for "Shakespeare in Love" | 53 |
| 1999 Oscar nominee for both direction and screenwriting | 55 |
| 1999 Keanu Reeves movie with two sequels, with "The" | 62 |
| 1999 film whose title is a hint to this puzzle's theme | 58 |
| 1999 film scripted by Lowell Ganz and Babaloo Mandel | 52 |
| 1999 commando rescue film subtitled "The Lost Patrol" | 63 |
| 1999 Brendan Fraser film based on a Hanna-Barbera toon | 54 |
| 1998 song by the Goo Goo Dolls that was #1 for 18 weeks | 55 |
| 1998 Leonardo DiCaprio adventure film, with 'The' | 57 |
| 1998 hit that begins "___, I do believe I failed you" | 63 |
| 1998 Grammy winner for narrating his book "Still Me" | 62 |
| 1998 film with the voice of Gene Hackman as General Mandible | 60 |
| 1998 film thriller based on a TV series, with "The" | 61 |
| 1998 film that won the Golden Raspberry for Worst Remake | 56 |
| 1998 film in which Woody Allen's character is a six-footer | 62 |
| 1998 film featuring the voices of Gene Hackman and Sharon Stone | 63 |
| 1998 film character called Ping when dressed as a man | 53 |
| 1998 De Niro film with a memorable wrong-way car chase | 54 |
| 1998 biography subtitled "Living in the Shadows" | 58 |
| 1998 Best Screenplay nominee for "Primary Colors" | 59 |
| 1998 animated movie featuring Woody Allen's voice | 53 |
| 1998 animated film with soldiers, workers and a queen | 53 |
| 1998 animated film featuring the voice of Sylvester Stallone | 60 |
| 1998 animated film featuring the voice of Pierce Brosnan | 56 |
| 1998 and 2007 Oscar-nominated role for Cate Blanchett | 53 |
| 1998 Alanis Morissette hit with a slangy misspelling | 52 |
| 1997-2003 game show host who put up his own money for prizes | 60 |
| 1997 Will Smith/Tommy Lee Jones blockbuster, for short | 54 |
| 1997 Roberto Benigni film that starts with a board game? | 56 |
| 1997 Radiohead album with the single "Paranoid Android" | 65 |
| 1997 Kevin Spacey film, and a hint to this puzzle's theme | 61 |
| 1997 John Scofield album featuring Medeski, Martin & Wood | 61 |
| 1997 identity-switch movie with John Travolta and Nicolas Cage | 62 |
| 1997 film with the tagline "Coming soon. Honest." | 59 |
| 1997 best seller subtitled "Her True Story" | 53 |
| 1997 Aaliyah hit "The One ___ My Heart To" | 52 |
| 1996 thriller starring Robert De Niro and Wesley Snipes | 55 |
| 1996 sci-fi movie that won the Oscar for Visual Effects | 55 |
| 1996 Robin Williams film, and a hint to this puzzle's theme | 63 |
| 1996 Olympian noted for performing on an injured ankle | 54 |
| 1996 nominee parodied as referring to himself in third-person | 61 |
| 1996 movie with the tagline "Someone is going to pay" | 63 |
| 1996 movie starring Robert De Niro and Wesley Snipes | 52 |
| 1996 movie adaptation of "The Phil Silvers Show" | 58 |
| 1996 Michael Jordan movie featuring product placement | 53 |
| 1996 Helen Fielding book made into a film starring Renée Zellweger | 69 |
| 1996 Grammy winner for the album "The Road to Ensenada" | 65 |
| 1996 Grammy winner for the album "Falling Into You" | 61 |
| 1996 film with the tagline "YIKES! They've Landed!" | 65 |
| 1996 film with the tagline "Cupid is armed and dangerous!" | 68 |
| 1996 film with 12 Oscar nominations (with "The") | 58 |
| 1995 movie flop dubbed "Fishtar" by some critics | 58 |
| 1995 Chris O'Donnell/Minnie Driver romance--refilmed in 3-D? | 64 |
| 1994 sci-fi TV movie starring Stephen Baldwin and Lisa Bonet | 60 |
| 1994 R.E.M. hit about a gut feeling toward CIA spy Valerie? | 59 |
| 1994 movie based on an androgynous "SNL" character | 60 |
| 1994 movie based on a "Saturday Night Live" character | 63 |
| 1994 Michael Keaton film in which real journalists have cameo roles | 67 |
| 1994 memoir with a chapter on "New Robot Novels" | 58 |
| 1994 Julia Sweeney film based on an "SNL" skit | 56 |
| 1994 Grammy co-winner for "Talking Timbuktu" | 54 |
| 1994 film with the tagline "Get ready for rush hour" | 62 |
| 1994 film taglined "An everyday adventure" | 52 |
| 1994 Emmy winner for "Dvorák in Prague" | 52 |
| 1994 Denis Leary film about a crook who acts as an arbiter | 58 |
| 1994 Catherine Zeta-Jones film (with "The") | 53 |
| 1994 “S.N.L.”-based bomb starring Julia Sweeney | 55 |
| 1994 animated character voiced by four different people | 55 |
| 1993 X album with a terrible Greek god pun in its title | 55 |
| 1993 TV western starring Kenny Rogers and Travis Tritt | 54 |
| 1993 series "The Adventures of ___ County Jr." | 56 |
| 1993 Radiohead single with the line "I wish I was special" | 68 |
| 1993 movie starring Lara Flynn Boyle, with "The" | 58 |
| 1993 Julia Roberts movie featuring product placement | 52 |
| 1993 film that won Best Actress and Best Supporting Actress Oscars | 66 |
| 1993 film loosely based on the Jamaican bobsled team | 52 |
| 1993 drama for which Stockard Channing got an Oscar nomination | 62 |
| 1993 Debra Winger drama based on a Mary McGarry Morris novel | 60 |
| 1993 dance hit, and a question answered seven times in this puzzle | 66 |
| 1993 Aerosmith hit with the lyric "Love is sweet misery" | 66 |
| 1992 Paula Abdul hit, with Stevie Wonder on harmonica | 53 |
| 1992 Oscar-nominated title role for Robert Downey Jr. | 53 |
| 1992 movie featuring a much-publicized twist, with "The" | 66 |
| 1992 Grammy winner for Best Female Pop Vocal Performance | 56 |
| 1992 film directed by and starring Edward James Olmos | 53 |
| 1992 Disney movie featuring "Arabian Nights" | 54 |
| 1992 country hit that catapulted line dancing into the mainstream | 65 |
| 1992 comedy in which Damon Wayans plays a con artist | 52 |
| 1992 Best Original Screenplay Oscar winner featuring cross-dressing | 67 |
| 1991-2001 president of the National Organization for Women | 58 |
| 1991 Swedish movie nominated for a Best Foreign Film Oscar | 58 |
| 1991 Phoebe Cates comedy often compared to "Beetlejuice" | 66 |
| 1991 novel subtitled "Tales for an Accelerated Culture" | 65 |
| 1991 movie sequel subtitled "The Awakening" | 53 |
| 1991 Jeff Daniels movie, or a 1976 hit song for Nazareth | 56 |
| 1991 film that earned John Singleton a Best Director nomination | 63 |
| 1991 film starring Dustin Hoffman as a one-handed captain | 57 |