| 1 | * BreakthroughHit: "Wild One" on the country charts, "This Kiss" on the pop charts. |
| 2 | * CreatorCouple: With Music/TimMcGraw since 1996. |
| 3 | * CreatorsOddball: ''Breathe'' was noticeably more pop than her previous efforts, but it was still rooted in country enough to get her hits there. ''Cry'' completed the transition from country-pop to outright pop. Although this sound won her a Grammy for the title track and gave her a third number one on the AC charts, the rest of the album did very little at country or pop radio ("Cry" zoomed to #12 then dropped like a rock), and led to many fans accusing her of selling out to the pop base. She pretty much returned to her mid-1990s sound with ''Fireflies'' in 2005. |
| 4 | * CutSong: She recorded "What Hurts the Most" for ''Fireflies'' in 2005 but axed it from the tracklist at the last second. Then Music/RascalFlatts recorded the song... |
| 5 | * DevelopmentHell: She has been trying to mount a comeback since 2011, but her only attempts have been two low-charting singles: a cover of Music/OneRepublic's "Come Home", and "American Heart". However, she had a one-time return to the Top 5 in 2014 backing her husband on "Meanwhile Back at Mama's", and finally released a duets album with him in 2017. |
| 6 | * FollowUpFailure: After her first two singles "Wild One" and "Piece of My Heart" both went to #1, "But I Will" fizzled out at #35. |
| 7 | * HideYourPregnancy: Attempted in the "This Kiss" video, but there are a few shots where her baby bump is at least somewhat noticeable. |
| 8 | * WhatCouldHaveBeen: |
| 9 | ** Hill was briefly engaged to her producer, Scott Hendricks, but broke it off to marry Music/TimMcGraw. Seeing as the duet "It's Your Love" kicked both singers' careers into high gear... |
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