Unlike his peers Tim McGraw, Kenny Chesney and Faith Hill, who offered a more traditional sound on their early recordings, Keith Urban started out as a soft rock- and R&B-loving pop-country pace-setter. Fans could hear it all the way back in 1999, on his self-titled American debut (not to be confused with his lesser-known Australian debut from 1991), released 20 years ago, on Oct. 19 of that year.

Many artists can (and often should) change over time, but there’s a charm to Urban’s decision to stick with what works for him. After all, he's ridden his truth to 18 No. 1 singles and his current status as the defending ACM and CMA Entertainer of the Year.

In honor of America’s earliest tastes of a tenderhearted crooner and lightning-fast guitar picker turning two decades old, The Boot went back and rated all 12 songs off Urban's groundbreaking self-titled album. Read on to see how they stack up.

  • 12

    "I Thought You Knew"

    Songs like this one make it sound as though Urban would just as well be part of Boyz II Men rather than Brooks & Dunn. That R&B admiration has kept Urban a relevant touring and recording artist in a swiftly changing and fickle business.

  • 11

    "You're the Only One"

    On some of his slower-tempo songs, Urban sounds like a reverse Dan Seals. That’s to say that he could transition from country singer to soft rock revivalist and yacht rock god — not that the reigning Entertainer of the Year needs a side gig.

  • 10

    “A Little Luck of Our Own”

    Urban sings this one for every couple or family that, if they didn’t know any better, might think they’re cursed with bad luck. It mirrors Brad Paisley's delightful glass-half-full mindset that, even when things don’t seem ideal, everything will be okay.

  • 9

    “If You Wanna Stay”

    Although this song ranks relatively low on the list, it includes this album’s best vocal performance. After all, when Urban sings, “Go if you wanna go, stay if you wanna stay,” it’s clear that he fears such a compromise might leave him broken and lonely.

  • 8

    “Out on My Own”

    For a few seconds, that opening guitar work sounds like a modern country nod to Elvis Presley's “Suspicious Minds,” which is awesome. It sets the tone for a song that at its crescendo represents the pop-country sound of 1999 in all its radio-friendly glory.

  • 7

    “It’s a Love Thing”

    The upbeat opener on Urban’s debut album straddles the line between a peppy '90s fiddle tune and the sort of snap-along pop crossover hits that’d become more prominent in the well-rounded entertainer’s songbook in the coming century.

  • 6

    “Don’t Shut Me Out”

    This one crosses the streams of traditional country’s studio magic and Urban’s poptimism. The traditional half of the equation comes from fiddler Stuart Duncan’s finest work on the album. It guides along a song built on one of modern country’s strong suits: lyrics about being a decent human being.

  • 5

    "Rollercoaster"

    This one’s too weird to not make the Top 5. It’s basically Urban trying to be the 1999 equivalent of Roy Clark, which can’t possibly be a bad thing.

  • 4

    “I Wanna Be Your Man (Forever)”

    Not even Urban’s earliest hits were more fun than this raucous tune, which belongs on either your workout or line-dancing playlist (or, really, why not both?). Come to think of it, nothing from Urban’s stacked catalog surpasses this one when it comes to being a guaranteed party-starter.

  • 3

    "Your Everything"

    This song made history when it introduced Urban as country music’s next great love song crooner. It peaked at No. 4, making it the first Top 10 hit in America by a man born in New Zealand.

  • 2

    “But for the Grace of God”

    Urban wasted no time earning pop-rock cred, co-writing this single with Go-Gos members Jane Wiedlin and Charlotte Caffey. It became Urban’s first-ever No. 1 hit in America in February of 2001.

  • 1

    "Where the Blacktop Ends"

    Rural party-starting themes go down well with the tight harmonies and country sunshine of this Top 3 single. It might be the first example of Urban picking wisely from great songwriters’ work, considering it was co-written by Allen Shamblin (“The House that Built Me”) and Steve Wariner.