| Era | Song | Hints | Answer | % Correct |
|---|---|---|---|---|
| 1 | Tim McGraw | Musician | Tim McGraw | 100%
|
| 26 | Clara Bow | Actress | Clara Bow | 87%
|
| 17 | no body, no crime (feat. HAIM) | Musician | Este Haim | 87%
|
| 15 | betty | Celebrity's Children | James Reynolds, Betty Reynolds, Inez Reynolds | 87%
|
| 3 | Dear John | Musician | John Mayer | 87%
|
| 16 | marjorie | Opera Singer | Marjorie Finlay | 87%
|
| 4 | 22 | Singer/Songwriter | Taylor Swift | 87%
|
| 28 | Clara Bow | Singer/Songwriter | Taylor Swift | 87%
|
| 27 | Clara Bow | Musician | Stevie Nicks | 80%
|
| 6 | Style | Actor | James Dean | 73%
|
| 9 | I Forgot That You Existed | Musician | Drake | 67%
|
| 12 | the last great american dynasty | American socialite | Rebekah Harkness | 67%
|
| 14 | the last great american dynasty | Artist | Salvador Dali | 67%
|
| 10 | London Boy | Fashion Designer | Stella McCartney | 67%
|
| 13 | the last great american dynasty | Heir to "Standard Oil" | William "Bill" Harkness | 67%
|
| 24 | The Tortured Poets Department | Musician | Charlie Puth | 60%
|
| 20 | The Tortured Poets Department | Poet | Dylan Thomas | 60%
|
| 23 | The Tortured Poets Department | Musician | Jack Antonoff | 60%
|
| 5 | Begin Again | Musician | James Taylor | 60%
|
| 21 | The Tortured Poets Department | Poet | Patti Smith | 60%
|
| 29 | The Black Dog | Pop/Punk Band | The Starting Line | 60%
|
| 2 | Fifteen | Taylor's Best-friend | Abigail Anderson | 53%
|
| 8 | ...Ready for It? | Actor/Actress | Richard Burton & Elizabeth Taylor | 53%
|
| 19 | You're on Your Own, Kid | Writer | Daisy May | 47%
|
| 25 | Guilty As Sin? | Scottish Band | The Blue Nile | 47%
|
| 18 | Snow On The Beach (feat. Lana Del Rey) | Musician | Janet Jackson | 40%
|
| 22 | The Tortured Poets Department | Musician | Lucy Dacus | 40%
|
| 11 | London Boy | Musician | Bruce Springsteen | 33%
|
| 7 | Bad Blood (feat. Kendrick Lamar) | Rapper | The D.O.C | 13%
|