Country Music Star Paisley made his debut as a solo artist after signing to Arista. He released his first album, Who Needs Pictures, in 1999. The record produced the No. 1 hit "He Didn't Have to Be," followed by the chart-topping single, "We Danced." The album sold more than 1 million copies, and catapulted Paisley to fame. The next year, the Academy of Country Music (ACM) named Paisley the year's Best New Male Vocalist, and the Country Music Association (CMA) granted him the prestigious Horizon Award.
In February 2001, Paisley was inducted into the Grand Ole Opry's Hall of Fame. Several months later, he received his first Grammy Award nomination for Best New Artist. He also released his second album, Part II (2001), which featured his cheeky and unforgettable No. 1 single "I'm Gonna Miss Her (The Fishing Song)." Three other songs on the album, "I Wish You'd Stay," "Wrapped Around" and "Two People Fell in Love," also made it into the Top 10 on the country charts.
His next album, Mud on the Tires (2003), was equally, if not more successful, hitting No. 1 on the Billboard chart, and featuring an acclaimed duet with Alison Krauss called "Whiskey Lullaby." The video for his collaboration with Krauss won several awards, and the single made it to No. 3 on the Hot Country charts.
Paisley's 2005 effort, Time Well Wasted, came on the heels of his sold-out Two Hats and Redhead Tour with Reba McEntire and Terri Clark. The album included another notable collaboration, "When I Get Where I'm Going" with Dolly Parton, which won the CMA Award for Musical Event of the Year in 2006. The album also scored Paisley both ACM and CMA Awards for Best Album. That same year, Paisley embarked on a successful tour, with rising country star Carrie Underwood serving as his opening act.
Teaming up to record together, Paisley and Underwood sang a duet, "Oh Love," on his next release, 5th Gear (2007). Reaching the top spot on the country album charts, the album featured several No. 1 hit singles, including "Online," "Letter to Me" and "I'm Still a Guy." Paisley also took home several major awards that same year, winning the ACM Award for Top Male Vocalist and the CMA Award for Male Vocalist of the Year. He also won his first Grammy Award for the instrumental track "Throttleneck."
His next album, Play: The Guitar Album, hit stores in November 2008, featuring collaborations with musicians such as Keith Urban, Vince Gill and B.B. King. Paisley and Urban received 2008 Entertainer of the Year nominations at the CMAs for their duet. Although their performance didn't snag the award, Paisley walked away from the ceremony with other honors—this time for Male Vocalist of the Year and Music Video of the Year.
In 2009, Paisley released his American Saturday Night album. The first single off the album, a song called "Then," became Paisley's 14th No. 1 hit. Thanks to his album, Paisley was nominated for seven CMA Awards that year, including Entertainer of the Year. He also co-hosted the event alongside Underwood. The duo would go on to have the honor of hosting the CMAs several times.
Paisley's next studio effort, This Is Country Music (2011), featured a duet with Underwood on "Remind Me." He also performed with the group Alabama for the track "Old Alabama." With 2013's Wheelhouse, Paisley found himself under fire for the song "Accidental Racist." The album debuted at the top of the Billboard country charts, but it quickly lost momentum. In 2014, Paisley returned to more lighthearted country fare with Moonshine in the Trunk.
The summer of 2015 brought the news that Paisley would serve as a mentor for Blake Shelton's team on Season 9 of The Voice. Paisley also performed in a concert to celebrate the 90th birthday of the Grand Ole Opry, with footage scheduled to be released in a documentary at the end of the year.