In the 1990s, Clint Black was a trendsetter in country music. When he released his freshman album, Killin' Time, in 1989, Black -- along with fellow then-rising stars Alan Jackson, Garth Brooks and Travis Tritt, among others -- ushered in a new style of music for the new decade. Together, they were known as the Class of '89.

Throughout his illustrious career, Black has released 10 studio albums and charted more than 30 Top 40 singles, including more than a dozen No. 1 hits. While Black's catalog is certainly extensive, a few of his songs rise above the rest; below, The Boot selects his Top 10.

  • 10

    "Been There"

    From: 'D'Lectrified' (1999)

    Black sings "Been There" as a duet with Steve Wariner, who also co-wrote the song with Black: "You suddenly discover there's a price you pay / For gettin' this far, it's the part of you / That you really didn't have to spend," they say in the track. "You know, I've been there, and I don't want to go back again." The song's cinematic music video, which also stars Wariner, helped propel "Been There" into the Top 5.

  • 9

    "When My Ship Comes In"

    From: 'The Hard Way' (1992)

    This final release from Black's third studio album, The Hard Way, is about the hope of better days ahead. Featuring lines such as, "No sun on the Rockies, not even the light of day / I feel that old cabin fever coming on / But I know where I'll be when Lady Luck finally blows my way / She'll put the wind in my sails, and I'll be gone," "When My Ship Comes In" was a bit prophetic for Black: The song became a multi-week No. 1 hit.

  • 8

    "Killin' Time"

    From: 'Killin' Time' (1989)

    Black's second single, the title track of his debut album, "Killin' Time" was a good indication of the music that fans could expect from the singer: This song is about a man so deep in grief over the end of a relationship that he keeps "a tight grip on the bottle" and says he "spent all my life just dying / For a love that passed away." "Killin' Time" became the No. 2 song of 1989 on Billboard's year-end country chart -- second only to Black's own "A Better Man."

  • 7

    "Nobody's Home"

    From: 'Killin' Time' (1989)

    There are certainly no silver linings in this sad song. "Nobody's Home" is about how much life has changed, for the worse, at the end of a relationship: "I still comb my hair the same / Still like the same cologne / And I still drive that pickup truck / That the same old bank still owns / But since you left, everybody says / I'm not the guy they've known / The lights are on, but nobody's home." "Nobody's Home" was the first song for which Black made a music video, which might have helped the song stay at the top of the charts for three consecutive weeks. The song also became the No. 1 country song on Billboard's year-end chart in 1990.

  • 6

    "Like the Rain"

    From: 'Greatest Hits' (1996)

    Written by Black and frequent collaborator Hayden Nicholas, "Like the Rain" became a hit because of both its lyrics -- "Like the rain, I have fallen for you, and I know just why you / Like the rain, always calling for you, I'm falling for you now / Just like the rain" -- and its melody. Rhythmic and moody, with actual sounds of rain on the album version, "Like the Rain" stayed at the top of the charts for three weeks.

  • 5

    "A Bad Goodbye"

    From: 'No Time to Kill' (1993)

    "A Bad Goodbye" is a duet with Wynonna Judd; she and Black recorded the song after touring together in 1993. Black says that the song -- which features lines such as "If I can't leave you with a smile / I don't know how far I'll have to go / Til I'm sure those eyes won't cry / And in my mind, I've left enough to know / That I can't leave you with a bad goodbye" -- was easy to write once he imagined himself being the one walking away.

    “When I started to think about it, I found the sadder meaning of a bad goodbye and started thinking, 'Okay, if we’re going to the sad part and somebody’s leaving with a bad goodbye or not wanting to leave, there must be still some love there,'" Black tells American Songwriter. "I started thinking about what I would be feeling, and then the song began writing itself, and things came out that were real.”

  • 4

    "Nothin' But the Taillights"

    From 'Nothin' But the Taillights' (1997)

    Also co-written with Wariner, "Nothin' But the Taillights" is an uptempo, humorous take on being left in the dust, literally and figuratively: "Now I'm walkin' in the moonlight / Seein' nothin' but the taillights," Black sings. "And that's a pair of taillights / I may never see again." The song stayed at the top of the charts for two weeks and is still a regular in Black's concert performances.

  • 3

    "Walkin' Away"

    From: 'Killin' Time' (1989)

    Written by Black and Nicholas, "Walkin' Away" begins with the lines "Walkin' away, I saw a side of you / That I knew was there all along / And that someday I'd say goodbye to you / 'Cause one right can still make two wrong." The song became Black's fourth consecutive No. 1 hit from his freshman album, Killin' Time, but it was the first time that Black had tried to infuse two of his favorite sounds into one song; the singer tells The Boot he wanted to write "a Cajun waltz, but with a real traditional country feel to it." Clearly, it worked: "Walkin' Away" stayed at the top of the charts for three weeks.

  • 2

    "When I Said I Do"

    From: 'D'Lectrified' (1999)

    Black sings "When I Said I Do" as a duet with his wife, actress Lisa Hartman Black. The song promises, "When I said I do, I meant that I will 'til the end of all time / Be faithful and true, devoted to you / That's what I had in mind when I said I do," so Black insisted on singing it with his wife, in spite of her initial reluctance.

    “It was four days from the deadline when I guilted her into it,” Black recalls. “Then she said she wasn’t going on The Tonight Show, but she did that. She said, ‘I’m not doing it live!’ But she did that, too."

  • 1

    "A Better Man"

    From: 'Killin' Time' (1989)

    "A Better Man" was the debut single from Black's freshman album, and the song became his first No. 1 hit. Co-written by Black and Nicholas, "A Better Man" was inspired by the end of a real-life romance, after seven years together; the song includes lines such as, "I know I'm leavin' here a better man / For knowin' you this way / Things I couldn't do before, now I think I can / And I'm leavin here a better man."

    The success of "A Better Man" undoubtedly helped heal Black's broken heart: The singer won an ACM for Single Record of the Year for "A Better Man," and the song became the No. 1 country song of 1989 on the Billboard charts.