| Hint | Answer | % Correct |
|---|---|---|
| Third Album (2022) | Stick Season | 96%
|
| First Album (2019) | Busyhead | 84%
|
| State He's From | Vermont | 76%
|
| Northern Attitude ft. | Hozier | 72%
|
| Dial Drunk ft. | Post Malone | 67%
|
| Second Album (2021) | I Was/I Am | 62%
|
| Everywhere Everything ft. | Gracie Abrams | 60%
|
| "The Only Song Of His He'll Listen To" | Maine | 60%
|
| Second EP (2020) | Cape Elizabeth | 54%
|
| Collabed With Zach Bryan on | Sarah's Place | 54%
|
| This Pop Star Recently Covered Stick Season | Olivia Rodrigo | 52%
|
| She Calls Me Back ft. | Kacey Musgraves | 45%
|
| Call Your Mom ft. | Lizzy McAlpine | 44%
|
| What He Says His "Home Stadium" Is | Fenway Park | 43%
|
| Homesick ft. | Sam Fender | 36%
|
| Hurt Somebody ft. | Julia Michaels | 32%
|
| First EP (2018) | Hurt Somebody | 31%
|
| Platform He Wrote "Stick Season" on | TikTok | 31%
|
| State He Currently Lives In | Massachusetts | 21%
|
| First Song Released (2017) | Young Blood | 20%
|
| City He's From | Stratford | 18%
|
| Was Featured on This James Bay Song with The Lumineers | Up All Night | 18%
|
| "Album" He Just Released (2024) | Live From Fenway Park | 17%
|
| Second First Pitch MLB Team | Red Sox | 17%
|
| Paul Revere ft. | Gregory Alan Isakov | 14%
|
| You're Gonna Go Far ft. | Brandi Carlile | 13%
|
| Someone Like You ft. | Joy Oladokun | 11%
|
| His Fianceé | Brenna Nolan | 7%
|
| City He Currently Lives In | Watertown | 7%
|
| One of His Brothers | Simon | 6%
|
| First First Pitch MLB Team | Mariners | 5%
|
| Agency He's Signed To | Republic Records | 3%
|
| His Sister | Sasha | 2%
|
| The Other Brothers | Spencer | 1%
|