Twenty years ago, on Sept. 28, 1999, Garth Brooks released his most infamous album -- only, it wasn't a Garth Brooks album. It was a greatest hits album from a fictitious Australian rock 'n' roller, Chris Gaines.

Chris Gaines: Greatest Hits, also known as Garth Brooks in ... the Life of Chris Gaines, was initially intended to be a "pre-soundtrack" for a movie called The Lamb, in which Brooks was supposed to star as Gaines. Brooks wanted to use this record as a chance for fans to get to know the character -- but the movie project fell apart, and the only things that remain are a VH1 Behind the Music special, a hard-to-find album and a whole bunch of (some ironic, some sincere) nostalgia for this weird bit of Brooks history.

Chris Gaines: Greatest Hits is viewed as a weird experiment at best and a embarrassing flop at worst. If you consider it the latter, though, remember that it was a flop that hit No. 2 on the all-genre Billboard 200, earned Brooks his only Billboard Hot 100 Top 40 song and sold more than 2 million copies, which isn't bad as far as flops go.

Read on for a deep dive into Chris Gaines: Greatest Hits. Ahead of its 20th anniversary, we scrounged up a copy and are ranking its songs from worst to best.

  • 13

    "Driftin' Away"

    “Driftin’ Away” answers a question that no one was really asking: What do you get when you merge a late-‘90s boy band with country music? The answer might just be Gaines’ “Driftin’ Away,” a silky smooth song about a love slowly fading away. Gaines plays all the boy band parts in this solo song, with the exception of one of its highlights: the backing vocals in the chorus outro.

  • 12

    "Digging for Gold"

    Gaines’ work isn’t short on songs with a message, and “Digging for Gold” has a clear one: Be wary of materialistic people. “They married on a fancy yacht out on the water / He knew she was young enough to be his daughter,” he sings in the opening lines of this classic rock-infused song. The track features a strangely rushed chorus and opening guitars that would be at home in any country song.

  • 11

    "Right Now"

    There’s no clearer “message song” in Gaines’ oeuvre than “Right Now.” One of four official singles released from the album, it's is an ambitious, bombastic song about what’s wrong with America, and it samples the Youngbloods' 1960s hit “Get Together” to get its point across. The heavy-handed verses feature Gaines experimenting with spoken-word rapping, a style that, ironically enough, would make a resurgence in country music decades later.

  • 10

    "Maybe"

    Listeners can be forgiven for thinking that “Maybe,” with its background verse instrumentation that sounds straight out of “Lucy in the Sky with Diamonds," is a cover of a late-era Beatles song. Even the lyrical references in the chorus -- “Even though the bird has flown / Maybe she’ll fly on home” -- sound as though they might be lifted from a track by the Fab Four. But if you like layered vocals and psychedelic flutes, “Maybe” is definitely the song for you.

  • 9

    "White Flag"

    “White Flag” makes an honest attempt at bringing some funky blues rock to this album. The verses are driven by a catchy, repetitive guitar riff, which fades when Gaines rolls into the syncopated chorus lyrics: “Sendin’ up, sendin’ up, sendin’ up a white flag / Love won’t have a chance / If all we do is fight about it.”

  • 8

    "Snow in July"

    Now you’re talkin about your freedom / What is that you say? / You suddenly declared to me / Your independence Day,” Gaines sings in the pre-chorus of “Snow in July,” a song about being surprised by a sudden breakup. But the real surprise in “Snow in July” is what that pre-chorus leads to: a genuinely funky refrain with a fun guitar and bass groove to match.

  • 7

    "Way of the Girl"

    Gaines isn’t Prince, but “Way of the Girl” makes it seem as though he might want to be. Bolstered by cheesy synth and smooth guitars, this song doesn't quite reach the same level of funk as the Purple One, but kudos to Gaines for giving it a genuine go. Check out that fully committed, guttural, “Hey!” mid-first verse for proof.

  • 6

    "Unsigned Letter"

    If you didn’t know any better, you might hear “Unsigned Letter” and think you had just discovered your new favorite single by the Wallflowers -- but this ‘90s rock-infused little gem is all Gaines, even down to the uncharacteristically rough, whispery vocals and the driving, mid-tempo electric guitar. Just like a Wallflowers song, those rough vocals bloom into something bigger and smoother in the chorus, and the result is -- while maybe not wholly original -- quite pleasant.

  • 5

    "That's the Way I Remember It"

    One of the album’s official singles, “That’s the Way I Remember It” is the project's unplugged opener, a song that starts deceptively upbeat and, as it progresses, becomes genuinely emotional. It sounds a bit like early Jason Mraz: a sparkly, mid-tempo song that deals with nostalgia and memory. “Some of our stories fade as we get older,” the narrator explains, “Some get sweeter every time they’re told."

  • 4

    "My Love Tells Me So"

    Gaines signs off with “My Love Tells Me So,” the closing song on this album. As in many of his other song, he shape-shifts on this one: The choppy opening piano chords and vocals make him sound like a blend between Paul McCartney and Elton John. Songwriter Gordon Kennedy joins Gaines on vocals for this song, playing Tommy Levitz, Gaines' late friend and bandmate.

  • 3

    "It Don't Matter to the Sun"

    For all of the musical experimentation on this album, one of its standout tracks is still “It Don’t Matter to the Sun” -- a song that, if you added in some fiddles, could pass as a pretty standard Garth Brooks song. The song falls on the folksier side of country; it’s simply a down-the-middle ballad executed to perfection.

  • 2

    "Lost in You"

    With an opening that sounds like Extreme’s "More Than Words,��� Chris Gaines: Greatest Hits' lead single, “Lost in You,” is the album’s biggest commercial success, having risen to No. 5 on the Billboard Hot 100 chart. It's a stripped-down jam, an unplugged love song with producer Babyface’s influence all over it. Gaines pulls out his best (and it truly is good) falsetto to admit, “Heaven knows / I’m head over heels and it shows.”

  • 1

    "Main Street"

    Like many of Gaines’ songs, this one has clear musical influences. “Main Street” doesn’t just sound like a Bob Dylan song -- its verses are clearly inspired by “Knockin’ on Heaven’s Door,” which makes it the most purposeful musical tribute on the album. Despite that fact (or perhaps because of it) the ultra-rootsy “Main Street” is the strongest song on the album. The best thing about it? Trisha Yearwood is a co-writer. Who knows how Gaines and Yearwood met (hmmmm ...), but it’s a good thing they did.