| 1959 Gidget player | 18 |
| 1959 Glenn Ford film | 20 |
| 1959 Gregory Peck film | 22 |
| 1959 guest of Dwight | 20 |
| 1959 Henry Fonda comedy/drama | 29 |
| 1959 hit based on the traditional folk song "The Wreck of the Old 97" | 79 |
| 1959 hit by Ritchie Valens | 26 |
| 1959 hit by the Drifters | 24 |
| 1959 hit for Dodie Stevens | 26 |
| 1959 hit for The Fiestas | 24 |
| 1959 hit song about "a man named Charlie" | 51 |
| 1959 hit song set on "a tragic and fateful day" | 57 |
| 1959 hit that was a 1948 political campaign song | 48 |
| 1959 hit TV theme song | 22 |
| 1959 hit with a melody based on the folk song "The Wreck of the Old 97" | 81 |
| 1959 hit with the line "Charlie couldn't get off of that train" | 77 |
| 1959 hit with the line "Fight the fare increase!" | 59 |
| 1959 hit with the lyric "Did he ever return? No, he never returned" | 77 |
| 1959 hit with the lyric "Fight the fare increase!" | 60 |
| 1959 hit with the lyric "One day I feel so happy, next day I feel so sad" | 83 |
| 1959 Howard Hawks western | 25 |
| 1959 Hudson/Day film | 20 |
| 1959 Hudson/Day movie | 21 |
| 1959 Jackie Wilson hit | 22 |
| 1959 John Wayne classic | 23 |
| 1959 John Wayne film | 20 |
| 1959 John Wayne western | 23 |
| 1959 Johnny Mathis classic | 26 |
| 1959 Kingston Trio hit | 22 |
| 1959 Kingston Trio tune | 23 |
| 1959 Merman vehicle | 19 |
| 1959 Mickey Rooney movie | 24 |
| 1959 Monroe classic | 19 |
| 1959 movie remade in 2006 | 25 |
| 1959 movie starring Red as Randy Sherman (with "The") | 63 |
| 1959 musical by Jule Styne, featuring Ethel Merman as a domineering stage mother | 80 |
| 1959 Mystics song title word repeated before "Oh my darlin' don't you cry" | 92 |
| 1959 NBA MVP Bob | 16 |
| 1959 Neil Sedaka hit | 20 |
| 1959 Nobelist for Physiology Severo | 35 |
| 1959 Nobelist Severo | 20 |
| 1959 novella that begins "The first time I saw Brenda she asked me to hold her glasses" | 97 |
| 1959 Philip Roth book | 21 |
| 1959 play (with ''Once'') | 41 |
| 1959 play by Lorraine Hansberry | 31 |
| 1959 pop hit that asked "Why?" | 40 |
| 1959 pop hit, after "La" | 34 |
| 1959 pop idol | 13 |
| 1959 pop/folk hit | 17 |
| 1959 post-apocalyptic classic | 29 |
| 1959 Ricky Nelson hit | 21 |
| 1959 Ricky Nelson hit with the lyric "We gotta get on home" | 69 |
| 1959 Ritchie Valens hit | 23 |
| 1959 Rock Hudson/Doris Day romp | 31 |
| 1959 Rodgers and Hammerstein hit | 32 |
| 1959 romantic comedy appropriate for this puzzle? | 49 |
| 1959 Spanish-language Top 40 hit | 32 |
| 1959 spy novel | 14 |
| 1959 Steiger title role | 23 |
| 1959 Tony-nominated play whose 2014 Broadway production stars Denzel Washington | 79 |
| 1959 Tony-nominated play whose title is from a Langston Hughes poem | 67 |
| 1959 western directed by Howard Hawks | 37 |
| 1959 Wimbledon winner ___ Olmedo | 32 |
| 1959 winner of a record 11 Oscars | 33 |
| 1959-'60 heavyweight champ Johansson | 40 |
| 1959-60 heavyweight champion Johansson | 38 |
| 1960 #1 Brenda Lee hit | 22 |
| 1960 #1 hit | 11 |
| 1960 #1 hit "___ Angel" | 33 |
| 1960 #1 hit about a car accident | 32 |
| 1960 #1 hit from the album "Gunfighter Ballads and Trail Songs" | 73 |
| 1960 #1 Marty Robbins hit | 25 |
| 1960 Alfred Hitchcock thriller | 30 |
| 1960 and 1961 A.L. MVP | 22 |
| 1960 Bobby Rydell hit | 21 |
| 1960 Broadway musical | 21 |
| 1960 Cantinflas film | 20 |
| 1960 chart topper with the line "Are you somewhere up above" | 70 |
| 1960 chess champ | 16 |
| 1960 chess champion | 19 |
| 1960 chess champion Mikhail | 27 |
| 1960 crime comedy starring the Rat Pack | 39 |
| 1960 dance biography | 20 |
| 1960 debate monogram | 20 |
| 1960 debate participant | 23 |
| 1960 debater | 12 |
| 1960 Elia Kazan film | 20 |
| 1960 Elvis hit ____ Now or Never | 35 |
| 1960 Elvis Presley hit | 22 |
| 1960 Elvis western | 18 |
| 1960 European Championship winner | 33 |
| 1960 Everly Brothers hit | 24 |
| 1960 Everly Brothers tune | 25 |
| 1960 figure skating gold medalist | 33 |
| 1960 film based on a Robert Bloch novel | 39 |
| 1960 film set in Las Vegas | 26 |
| 1960 Glenn Ford western | 23 |
| 1960 gold-medal boxer | 21 |
| 1960 gold-winning pugilist | 26 |
| 1960 Grammy co-winner for the song "We've Got Us" | 63 |