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     Faith Hill - Cry (2002) 
  • In the introduction Todd sounds legitimately perplexed as to how Faith Hill's career took such a nosedive thanks to this album, even though the album went platinum, hitting #1 right out of the gate. Even the lead single (the only song from the album he showed a clip of up until this point) didn't seem like much of a departure from her previous work.
    Todd: Isn't Faith Hill still the ideal woman, the wholesomely beautiful country pop balladeer we knew and loved?
    [cut to footage of Faith Hill performing the opening song of Cry, the very funky and not-at-all country-sounding "Free", signifying that this is yet another album that ended up on Trainwreckords because of a misguided change in direction]
    Faith Hill: [awkwardly holding the microphone] ♪Yeah, yeah, yeah, yeah, yeah, yeah!♪
    Todd: [visibly recoiling] Ugh!
    Faith Hill: ♪I'm free!♪ [proceeds to dance with all the awkward stage presence of a drunk at a party]
    Todd: Uh oh, mom's had a little too much chardonnay.
    • Once Todd starts discussing the album proper, he leads off with "Free" (despite not being any less horrified by the intro to the song, he does admit the rest of it is not as bad as that opening "Yeah yeah yeah"). He notes that Hill must have been particularly proud of this song, given how she not only made it the first song on the album, but performed it multiple times on national television.
      Todd: If it were buried in the album, maybe you could write it off. But like no, she definitely wants people to hear this song specifically. And to me, that's just an obvious sign that this whole album's gonna be a disaster.
  • Todd acknowledges the biggest reason why country music changed in 2001 after a few years of female country stars dominating the market, and spends over a minute describing the horrible tragic moment that brought America out of its isolated optimistic state and the violent and awful imagery that its people were suddenly subjected to against all expectations otherwise. He is, of course, talking about the Michael Bay film Pearl Harbor, released in the summer of 2001 and featuring a song by Faith Hill that Todd considers as clearly trying to emulate the success of Titanic's "My Heart Will Go On"
    Todd: Who the fuck let Michael Bay think that he could make a romance?! Jesus Christ, three full hours of this shit! Why would you do this, Michael Bay? Why would you do this to America?!
  • Todd describing the Country music charts as "More rigged than pro wrestling."
  • Todd suspects that radio stations used the excuse "Not country enough" to cover for the fact that they thought the album was just bad.
  • When discussing her awkward and stilted stage presence compared to Shania an even Celine, Todd throws up the title "Faith Hill having no stage presence for 1 minute" note .
  • When talking about the album track "Beautiful", Todd burst into laughter and almost chokes over the whispered line "like you're touching the wings of a butterfly".
    Todd: Is this what gets normie white women in the mood?
  • When going over the songwriters from the Adult Contemporary scene Faith Hill drew from for this album, one of those Todd calls attention to is Linda Perry (former frontwoman of 4 Non Blondes). But when showing a clip from their one hit "What's Up?" - a song he has publicly mentioned he loathes - he subtly dubs over the chorus with the infamous He-Man meme version.
    • The song "If You're Gonna Fly Away" is officially credited to Linda Perry and Alicia Moore. Todd mentions that Linda Perry did a lot of songwriting and producing for P!nk, and that Alicia Moore... well, is P!nk.note  He suspects that at the time, P!nk thought she couldn't handle a song "this mom-pop" and had to hand it over to someone else (before adding "not yet at least — check back in 10 years.")
  • Lampshading an appearance by Carlos Santana, because Carlos Santana will show up for anything.
  • A song from the album ended up on the Lilo & Stitch soundtrack...the Japanese version.
  • His profanity-laced paraphrase of Faith's manager wondering what they did to piss off country radio so badly.
  • Throughout the video, Todd seems torn between whether to go after Faith for a transparently misguided and obviously terrible change in direction or tight-fisted, insular power-players that control country music and country radio for destroying Faith's career as part of an overall attempt to remold country music into a rotten form Todd would spend the next twenty years groaning at. This culminates in the Kirk Summation, where Todd admits he's at odds about who exactly bears the blame between his distaste for the country music establishment jerking the wheel in a reactionary new direction and an artist he freely admits he was never much of a fan of putting out a pretty bad album and then winding her career down seemingly for good because she never got over audiences rejecting it.

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