- - '90s Country Music Star Celebrated First No. 1 Hit 26 Years Ago Today

Liz LindainDecember 12, 2025 at 2:05 AM

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A major country milestone just hit its 26-year mark.

On this day in 1999, Brad Paisley celebrated his first chart-topper when his second song, "He Didn’t Have to Be," reached No. 1 on the Billboard Hot Country Songs chart. The single marked a breakthrough moment in Paisley’s career and set the stage for the long run of hits that followed.

"He Didn't Have to Be" was the second single released before his debut album, Who Needs Pictures. Inspired by his collaborator and best friend, Kelley Lovelace, with whom he also co-wrote the song, the tune is written from the perspective of a son of a single mother. His mother begins dating a new man who almost immediately includes the child in activities like going to the movies. In the final verse, the son is about to become a father himself, standing in the hospital next to his stepfather and hoping that he can be "at least half the dad" that his stepfather "didn't have to be." It serves as a tribute to men who step into a father role without obligation.

"I was really lucky, it wasn't like we knew what we were doing," Paisley said in a 2010 interview with Boot. "I just happened [to write] that with my best friend from the bottom of my heart about his situation."

Released on Aug. 30, 1999, "He Didn't Have to Be" debuted at number 72 on the U.S. Billboard Hot Country Songs chart the week it was released. The song stayed on the chart for 30 weeks, peaking at No. 1 on Dec. 11, 1999, and holding that position for one week. These accomplishments led him to be nominated for Best New Artist at the Grammys and to win the Country Music Association's (CMA) Horizon Award and the Academy of Country Music's Best New Male Vocalist award in 2000.

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Born in West Virginia and graduated with a degree in music business from Belmont University, Paisley became a songwriter right after college, working for EMI Publishing and assisting in writing "Another You" by David Kersh and David Ball's "Watching My Baby Not Come Back." In 1998, he signed with Arista Nashville, where he released 12 studio albums with them before its closure in 2023. His most recent records, Song Still Sings (2024) was released through Sony Music Entertainment, while his latest Christmas album that he put out in November, Snow Globe Town, was released independently.

Throughout his almost 30-year-long career, Paisley has charted more than 50 singles on the Billboard country singles charts, including 19 number-one singles such as "When I Get Where I'm Going," "Perfect Storm" and "Then." The 53-year-old singer has also collaborated with other country artists such as Alison Krauss, Keith Urban, Dolly Parton, Carrie Underwood and Alabama.

Brad Paisley performs at Christmas in Rockefeller Center in New York City. Scott Gries/NBC via Getty Images

Currently, Paisley is on his Truck Still Works World Tour, which he started in mid-2025 and is extending into 2026 with international dates. He will be performing around Canada this week, and the tour will continue in California and Texas in January and February, then go to Europe over the summer. His next studio album, Son Of The Mountains, is expected to be released sometime next year, after he's done with his ongoing tour.

Related: Lainey Wilson Puts a Country Spin on '90s Rock Band's Newest Track

This story was originally published by Parade on Dec 12, 2025, where it first appeared in the Entertainment section. Add Parade as a Preferred Source by clicking here.

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Source: “AOL Entertainment”