Bentley's studio albums have accounted for 25 singles on the Hot Country Songs and Country Airplay charts, of which 15 have reached number one: his debut single "What Was I Thinkin'", "Come a Little Closer", "Settle for a Slowdown", "Every Mile a Memory", "Free and Easy (Down the Road I Go)", "Feel That Fire", "Sideways", "Am I the Only One", "Home", "5-1-5-0", "I Hold On", "Drunk on a Plane", "Say You Do", "Somewhere on a Beach" and "Different for Girls". Four more of his singles have reached the top 5.
Bentley was born on November 20, 1975 in Phoenix, Arizona as the son of Leon Fife Bentley (August 16, 1923 – June 1, 2012), a bank vice-president, and Catherine Childs. His father was born in Glasgow, Missouri, to Richard Thomas and Mary Cecile Fife Bentley, and was a First Lieutenant in World War II. His middle name, Dierks (which he now uses as his first name publicly), is also his maternal great-grandmother's surname. He attended Culver Academies and graduated from The Lawrenceville School in 1993. Afterward, he spent a year at the University of Vermont (UVM) before transferring to Vanderbilt University in Nashville, Tennessee, where he graduated in 1997.
Bentley worked at The Nashville Network (now Spike TV), researching old footage of country performances. In 2003, Capitol Nashville released Bentley's self-titled debut album. The album's first single, "What Was I Thinkin'," reached number one on the Billboard Hot Country Songs charts later that year. The next two singles from that album, "My Last Name" and "How Am I Doin'," reached No. 17 and No. 4, respectively.The album was certified Platinum by the RIAA.
Bentley's second Capitol album, Modern Day Drifter, was released in 2005. It spawned two number one singles, "Settle for a Slowdown" and "Come a Little Closer," and the top 5 hit, "Lot of Leavin' Left to Do." The album was also certified platinum.
In 2005, Bentley won the CMA Award for the Horizon Award (now Best New Artist) and was invited to be a member of the Grand Ole Opry. The induction took place on October 1, 2005. Bentley stands as the third youngest member after Carrie Underwood and Josh Turner.
On June 10, 2006, Bentley released his third album, Long Trip Alone. The album produced two No. 1 hits, "Every Mile a Memory" in 2006 and "Free and Easy (Down the Road I Go)" in 2007. The title track reached No. 10 on the country charts. The fourth single from the album, "Trying to Stop Your Leaving," peaked at No. 5.
In 2007, Bentley released a live DVD titled Live and Loud at the Fillmore, which was filmed in Denver, Colorado.
In a March 2008 interview, Bentley said he would let his fans be the executive producers of his first greatest hits album, Greatest Hits/Every Mile a Memory 2003–2008. The album was released on May 6, 2008. An album cut, "Sweet & Wild," reached No. 51 on the Hot Country Songs chart. The song was an uncredited duet with fellow country singer Sarah Buxton.
Bentley's fourth studio album, Feel That Fire, was released in February 2009. Its title track, co-written by Brett Beavers and The Warren Brothers, reached top 40 in October 2008 and became his sixth number one in February 2009. The second single from the album, "Sideways," was released on March 2, 2009 and went on to become his seventh number one in the summer of 2009. The album's third and final single, "I Wanna Make You Close Your Eyes," was released on September 13, and peaked at No. 2.
Bentley released his sixth studio album, Up on the Ridge, on June 8, 2010. The title track was released to iTunes on April 20, 2010. The song peaked at No. 21 on the Billboard Hot Country Songs chart and became Bentley's first single to miss the top 10 since "My Last Name." The album's second single, "Draw Me a Map," was released to radio on August 23, 2010 and peaked at No. 33.
Bentley's seventh album, Home, was released on February 7, 2012, led by the single, "Am I the Only One" which reached No. 1 on the Billboard Country Singles. The second single off the album is "Home", which was co-written by Bentley, Brett Beavers, and Dan Wilson (musician) also reached No. 1 on March 24, 2012. A third single, "5-1-5-0", was released shortly after "Home" fell from number one on the country chart. Dierks has been quoted by American Songwriter explaining “I wrote too many songs. I wrote 70. I wrote a lot. There’s 64 that are never going to see the light of day. That’s 64 days that I can’t get back.”
On August 21, 2012, Bentley released the Country & Cold Cans EP on iTunes. It includes five songs, including a radio edit of the track "Tip It On Back" from his album Home. Bentley paid for the studio time to record the EP himself. On October 23, Bentley and Miranda Lambert announced the co-headlined 33-show Locked and Reloaded Tour, that began on January 17, 2013.
Bentley's eighth album, Riser, was released on February 25, 2014. The album's first single, "Bourbon in Kentucky", was released to country radio on June 10, 2013. It peaked at number 45 on the Billboard Country Airplay chart, becoming Bentley's lowest charting single to date. The album's second single, "I Hold On", was released on August 26, 2013. It became his first number one on the Country Airplay chart in April 2014 and also his eleventh overall to do so. The third single, "Drunk on a Plane", followed that same month. It reached number one on Country Airplay in August 2014 and was also a strong commercial hit, reaching number 27 on the Billboard Hot 100. The album's fourth single, "Say You Do", was released on October 6, 2014. It reached at number one on Country Airplay in May 2015. The title track became the album's fifth single in June 2015.
Bentley along with Eric Paslay are featured on Charles Kelley's debut solo single, "The Driver" which was released on September 28, 2015. The song received a Grammy nomination for Best Country Duo/Group Performance for the 58th Annual Grammy Awards.
Bentley released his ninth album, Black, on May 27, 2016. The album's first single, "Somewhere on a Beach", was released on January 25, 2016.
Bentley co-hosted the 51st Academy of Country Music Awards on April 3, 2016, where he was also nominated for Male Vocalist of the Year and Video of the Year.
Bentley has begun releasing a series of four short films for songs from Black, with episode one being the song "I'll Be the Moon" featuring Maren Morris. The following episode serves as the video for "What the Hell Did I Say". The album's second single, "Different for Girls" featuring Elle King, was released to country radio on June 6, 2016. It reached at number one on Country Airplay in October 2016. The album's title track was released to country radio as the third single on November 14, 2016.
He was also selected as one of 30 artists to perform on "Forever Country", a mash-up track of Take Me Home, Country Roads, On the Road Again and I Will Always Love You which celebrates 50 years of the CMA Awards.
Bentley married Cassidy Black on December 17, 2005, in Mexico. They live in Nashville, with their dogs Jake (who has appeared in a few of Dierks' album covers and videos (died July 10, 2016)) and George. The couple have two daughters, born in 2008 and 2010, and a son born in 2013. The oldest child makes a vocal appearance on the song "Thinking of You." Their son Knox was born on October 9, 2013.
On June 2, 2012, Bentley announced his father had died the previous day.
Bentley holds a private pilot license and owns a Cirrus SR22.2006: High Times and Hangovers Tour
2007: Locked and Loaded Tour
2007: Free and Easy Summer Tour
2008: Throttle Wide Open Tour
2010: Up On The Ridge Tour
2011: Jägermeister Tour
2011: Country and Cold Cans
2012: Country and Cold Cans (Festivals)
2014: Riser Tour
2015: Sounds of Summer Tour
2016: Somewhere on a Beach Tour
2017: What The Hell World Tour
2013: Locked and Re-Loaded Tour – w/ Miranda Lambert
2004: Guitars, Tiki Bars and a Whole Lotta Love Tour – Kenny Chesney
2006: The Road and The Radio Tour – Kenny Chesney
2009: Paisley Party Tour – Brad Paisley
2009: American Saturday Night Tour – Brad Paisley
Don't Leave Me in Love (2001)
Dierks Bentley (2003)
Modern Day Drifter (2005)
Long Trip Alone (2006)
Greatest Hits/Every Mile a Memory 2003–2008 (2008)
Feel That Fire (2009)
Up on the Ridge (2010)