| 100% | GNATSLIFE | 9 | Shortest song ever recorded by Sinatra? |
| 41% | FORNOONE | 8 | Song recorded by the Beatles |
| 41% | INMYLIFE | 8 | Song recorded by the Beatles |
| 41% | LOVEMEDO | 8 | Song recorded by the Beatles |
| 41% | ONEFOR | 6 | __ My Baby, song by Frank Sinatra |
| 40% | FROSTYTHESNOWMAN | 16 | Holiday song first recorded by Gene Autry |
| 40% | SEESEERIDER | 11 | Blues song first recorded by Ma Rainey |
| 39% | PUPPYLOVE | 9 | Song recorded by Paul Anka and Donny Osmond |
| 39% | MOONRIVER | 9 | Song recorded by Audrey Hepburn and Frank Ocean |
| 37% | DEEPCUTS | 8 | Songs by a recording artist that aren't well known |
| 37% | WHYBABYWHY | 10 | #1 country song once recorded by Charley Pride |
| 37% | IMEMINE | 7 | Last song recorded by the Beatles |
| 36% | TWICE | 5 | "You Only Live ___" (James Bond song sung by Nancy Sinatra) |
| 36% | HAVE | 4 | "___ You Ever Seen the Rain?" song by Creedence Clearwater Revival |
| 36% | HOUNDDOG | 8 | Canine song recorded by Elvis Presley in 1956 |
| 35% | MYWAY | 5 | 1969 song by Frank Sinatra, written by Paul Anka: 2 wds. |
| 35% | EVAH | 4 | "Well, Did You __?" song covered by Bing Crosby and Frank Sinatra |
| 35% | END | 3 | Last song recorded by all four Beatles, with "the" |
| 35% | IMEMINE | 7 | Last new song recorded by the Beatles |
| 34% | BESTOFMYLOVE | 12 | 1974 Eagles song also recorded by Rod Stewart in 2006: 4 wds. |
| 34% | TUESDAY | 7 | Ruby __, song recorded by The Rolling Stones |
| 34% | WINE | 4 | "Summer ___," 1966 song by Lee Hazlewood that was made famous by Nancy Sinatra |
| 33% | DITTY | 5 | Short song |
| 33% | ARIETTE | 7 | Short song |
| 33% | ISLE | 4 | "___ of Capri" (song covered by Sinatra) |
| 33% | HEART | 5 | "Mama's Broken ___," 2011 song by Miranda Lambert from the album "Four the Record" |
| 33% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 32% | HAVE | 4 | "___ You Ever Seen the Rain," question posed by Creedence Clearwater Revival in a 1971 song |
| 32% | CHEEKTOCHEEK | 12 | Irving Berlin song recorded as a duet by Louis Armstrong and 48-Across (3 wds.) |
| 32% | COVER | 5 | Recording of a song originally done by another band |