* BreakthroughHit: "Wild One" on the country charts, "This Kiss" on the pop charts.
* CreatorCouple: With Music/TimMcGraw since 1996.
* 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.
* 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...
* 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.
* FollowUpFailure: After her first two singles "Wild One" and "Piece of My Heart" both went to #1, "But I Will" fizzled out at #35.
* HideYourPregnancy: Attempted in the "This Kiss" video, but there are a few shots where her baby bump is at least somewhat noticeable.
* WhatCouldHaveBeen:
** 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...
** She recorded "What Hurts the Most" (itself already having been cut by Music/MarkWills) ''and'' "Why" for ''Fireflies'', but neither made the final cut. Both ended up being cut by Music/RascalFlatts instead, with their take on the former becoming one of their biggest hits.