Kenny Chesney

At 56 years old, Kenny Chesney has this physical status:

Kenneth Arnold Chesney (born March 26, 1968) is an American country music singer, songwriter, and record producer.

The RIAA has released 20 albums, 20 of which have been rated Gold or higher by the RIAA.

He has also released more than 40 Top 10 singles on the US Billboard Hot Country Songs and Country Airplay charts, 30 of which have reached number one.

Many of these artists have also charted within the top 40 of the US Billboard Hot 100, making him one of the most popular crossover artists.

He has recorded over 30 million albums worldwide, as well as producing the Boys of Fall, an ESPN film.

He has received six Academy of Country Music awards (including four consecutive Entertainer of the Year awards from 2005 to 2008), as well as nine awards from the Country Music Association.

He is one of country's most popular touring acts, with regular audiences outnumbering the venues in which he appears.

Chesney's 2007 Flip-Flop Summer Tour was the highest-grossing country road trip of the year, according to the Country Music Association.

He has received the Academy of Country Music's 1997 New Male Vocalist of the Year, 2002 Top Male Vocalist of the Year, and the Triple Crown Award in 2005.

On May 18, 2008, the Academy of Country Music announced his fourth consecutive Entertainer of the Year award.

Early life

Chesney was born in Knoxville, Tennessee, United States, on March 26, 1968, and was raised in Luttrell. He is of English and Irish descent. He is the son of David Chesney, a former elementary school teacher, and Karen Chandler, a hair stylist in the Knoxville area. Jennifer Chandler, Chesney's younger sister, has one sibling. Chesney graduated from Gibbs High School in 1986, where he played baseball and football. For Christmas, he received his first guitar, "The Terminator," and started teaching himself how to play it. Chesney studied advertising at East Tennessee State University in Johnson City, Tennessee, where he was a member of the ETSU Bluegrass Program and the Lambda Chi Alpha fraternity and graduated in 1990. He recorded a self-released demo album at the Classic Recording Studio in Bristol, Virginia, in 1989. While performing at local clubs in Johnson City, he sold 1,000 copies and used the funds from album sales to buy a new guitar. After graduating from East Tennessee State in 1990, he moved to Nashville and appeared at many local clubs, including The Bluebird Cafe. He became the resident performer at The Turf, a swanky tonk bar in the city's historic district.

Personal life

After Chesney attempted to ride a police horse in Buffalo, New York, in 2000, Chesney and Tim McGraw became embroiled in a confrontation with police officers. After police officers nearby discovered the horse was stolen, McGraw came to Chesney's assistance. Although both were arrested and convicted, Chesney and McGraw were charged with disorderly conduct and assault, but they were not convicted in 2001.

Chesney married actress Renée Zellweger on May 9, 2005, on the island of St. John. They had met in January at a tsunami relief conference. They announced their plans for an annulment on September 15 of this year, after just four months of marriage. Zellweger cited fraud as the reason for the published papers, and after media coverage of her use of the word "fraud," she defended the usage of the word "fraud" by claiming that it was "simply legal word and not a representation of Kenny's character." Later, Chesney explained that his marriage's breakdown was due to "the fact that I panicked." "The only fraud that was committed was me thinking that I knew what it was like, that I really understood what it was like to be married, and I really didn't." In late December 2005, the annulment was declared.

Forbes estimated Chesney's annual income at $42 million in 2015.

Chesney came to the rescue of the victims of Hurricane Irma, both in the United States and the British Virgin Islands, one of whom was given a free ride to the mainland United States. Chesney owns a mansion on St. John, one of the United States Virgin Islands, where many people stayed to survive the hurricane. Love for Love City, Chesney's charitable fund, has also been set up to assist victims of the storm victims. Chesney will donate all funds from "Songs for the Saints" to the fund.

Source

Career and awards

"I met this kid today from East Tennessee," Clay Bradley, BMI's head of writer relations, told Chesney. "I think you're going to really like him as a person," says the singer, a good songwriter, and more. During his Tomlinson audition, Chesney performed five songs. Tomlinson's reaction was ecstatic, and HitQuarters later told him: Tomlinson's reaction was enthusiastic.

Chesney left the audition with a songwriter's deal. A year later, an appearance at a songwriter's showcase culminated in a deal with Capricorn Records, which had just announced a country division.

In My Wildest Dreams, Chesney's debut album, was released on the independent Capricorn Records label in April 1994. "Whatever It Takes" and "The Tin Man" are two of the album's first two singles, which also reached the United States' lower regions. Billboard's Hot Country Singles & Tracks chart. The album's country music division was sold in Nashville until Capricorn Records' decision to Atlanta later this year.

Chesney's second studio album All I Need to Know was released in 1995. Three singles were released on the album. "Fall in Love" and the title track both made it to the top ten, while "Grandpa Told Me So" debuted at number 23. Chesney co-wrote "When He Was My Age" from their album When and Where, which was released in the United States that year. Chesney's album included fiddle and steel instruments in order to bring out the down-home sentiments and the distinctive Tennessee twang in his voice. This collection seemed to capture the traditional spirit that made country music famous.

Me and You, Chesney's third studio album and his second major-label one, which were released in 1996, was released. "Back In My Arms Again," Chesney's first single, debuted just outside the top 40 on the country charts, while "When I Close My Eyes" (which Chesney had on his previous record) and "When I Close My Eyes," which was later released by Keith Palmer on his 1991 debut album and later on his 1993 debut album Down the Road) debuted at number two. The Recording Industry Association of America's first album, Me and You, was Chesney's first album to be named gold (RIAA). On this album, Mac McAnally's 1990 single "Back Where I Come From" was also included. Despite the fact that Chesney's version was never released as a single, it has nevertheless been a hit at his concerts. Chesney was voted New Male Vocalist of the Year by the 1997 Academy of Country Music in honor of his his years.

I Will Stand, Chesney's fourth album and third from BNA Records, which was followed in 1997. "She's Got It All" was Chesney's first number one hit on the Billboard country charts and stayed at number one for three weeks. "A Chance," the album's second single, just shy of the top ten. In 1998, "That's Why I'm Here" was the third single on the charts.

We Go Where We Go, Chesney's fourth album from BNA, appeared in 1999. With "How Forever Feels" and "You Had Me From Hello," the former was two consecutive number one hits (the latter was influenced by a line in Jerry Maguire's film). "She Thinks My Tractor's Sexy" and "What I Need to Do" were two more singles on the country charts, respectively. Everywhere We Go was Chesney's first album to be named platinum. The album marked a change from his original neotraditional country sound to a more familiar country pop/tropic rock/Gulf and Western sound he's since become well-known for.

Chesney's compilation album titled "Greatest Hits" came out in 2000. It featured four new songs as well as updated versions of "Fall in Love," "The Tin Man," and "Back Where I Come From." The latest iteration of "The Tin Man" was one of the disc's top hits, as well as two of the new songs, "I Lost It" and "Don't Happen Twice." He appeared with Kid Rock at a Waylon Jennings tribute concert in 2001 that featured Waylon's song Luckenbach Texas.

In 2002, the album No Shoes, No Shirt, No Problems was first released. "Young," the lead-off single, debuted at number 2 on the charts, while the follower "The Good Stuff" spent seven weeks on the top of the charts and became Billboard's No. 1 country song of the year in 2002. The 2002 film "Young" was recognized by CMT with the Video of the Year and Male Video of the Year awards. ACM named Chesney as the best Male Vocalist of the Year in 2003, while "The Good Stuff" was named the Year's Top Vocalist of the Year in 2003. CMT later named the video for the album's title track as the year's Hottest Video of the Year.

Chesney's album All I Want for Christmas Is a Real Good Tan. The album's title track reached No. 1 on the charts. 30 on the country charts from holiday airplay. Chesney's other notable contribution to Kid Rock's single "Cold and Empty" from his self-titled 6th studio collection Kid Rock in 2003 is his co-writing of "Cold and Empty."

When the Sun Goes Down, the album was released in 2004. "There Goes My Life," the lead-off single, spent seven weeks at number one on the Billboard country charts. The accompanying music video for the song was recognized by CMT with the Male Video of the Year award on April 21, 2004. The album's title track, which was a duet with Uncle Kracker, debuted at number one. The album's third single, "I Go Back," was honoured on April 11, 2005, with Country Music Television's Male Video of the Year Award. This song, as well as the album's fourth single, "The Woman with You," reached the top of the charts. The fifth single, "Anything But Mine," debuted at number one, and "Keg in the Closet," the final single, debuted at number six.

When the Sun Goes Down was named as the Year's Best Album of the Year in 2004, Chesney was named Entertainer of the Year, while Chesney was named Entainer of the Year. He was also honoured with the 2004 Artist of the Year award from the United Auto Workers.

Chesney released Be as You Are (Songs from an Old Blue Chair) in January 2005, and he sold it as part of his More in the Sun tour. Be aware that the majority of ballads are made. The album was nominated for RIAA Platinum and debuted at the top of both mainstream and pop music.

The Academy of Country Music presented Chesney with the coveted Triple-Crown Award in spring 2005. This award was presented following Chesney's 2004 Academy of Country Music's Entertainer of the Year award, as well as 1997's New Male Vocalist of the Year award and 2003's Best Male Vocalist of the Year award. Chesney was named as the year's second Entertainer of the Year at the Academy of Country Music Awards on May 23, 2006.

The Road and the Radio, Chesney's next album, debuted at number one on the Billboard 200 and has five singles. "Live in a Fast Forward," "Summertime," and "Beer in Mexico" all made it to number one, while "Who You Should Be Today" and "You Save Me" both fell short of the Top 5. Chesney encourages his obsession with perfection, as it comes from having songs right in the studio and on radio.

Live: Those Songs Again Chesney's first live album was released on September 19, 2006, via BNA Records. Live recordings of 15 songs, 11 of which were singles, were included in this collection. "Live Those Songs," "Never Gonna Feel Like That Again," "On the Shore of Somewhere Beautiful" and "Back Where I Come From" were never released as singles by Chesney, but "Back Where I Come From" was released as a single from Mac McAnally's 1990 album Simple Life.

Chesney performed on a remake of Hank Williams' single "Hey Good Lookin" (with Clint Black, Alan Jackson, Toby Keith, and George Strait), as well as a second song "License To Chill" from "Mike Buffett). Both songs appear on Buffett's album License to Chill, which is released in 2004.

Chesney and Tim McGraw co-produced a version of Tracy Lawrence's "Find Out Who Your Friends Are," which can be found on his album "For the Love." The official single version, which only features Lawrence's vocals, was released in August 2006, but it did not make it to the top of the country charts until January 2007, when the album was first released. Since the album's debut, Chesney and McGraw's version became extremely popular, earning the single a lot of airtime. On the country charts, 1 is the highest. Lawrence's first No. 1 was released on the album. The first single in 11 years, as well as the second-slowest climber No. 6. Billboard's top single in history.

Chesney co-wrote Rascal Flatts' 2007 single "Take Me There," which was also the lead-off single to their album Still Feels Good, starring Neil Thrasher and Wendell Mobley.

On her No. 1, Chesney also performed a duet with Reba McEntire on her No. 6. Duets, 2007 album Reba. At No. 1, "Every Other Weekend" reached its high point. On the Billboard Hot Country Songs chart, 15 songs have risen to No. 1 and No. 1 respectively. On the Billboard Bubbling Under Hot 100 Singles chart, 104 is number 104. The album has been certified Platinum by the Royal Institute of British Agricultural Association for sales over 1 million units around the world, and is also certified Platinum by the RIAA for sales over 1 million. The album's last single, "Every Other Weekend," was released.

Chesney was named CMA Entertainer of the Year for the third time in four years on November 7, 2007. The compilation Super Hits album was released next week as part of Sony BMG's Super Hits collection.

Chesney released the album Just Who I Am: Poets & Pirates on September 11, 2007. With a number of "breezy, steel-drum island songs," the album represented a change toward a more gulf and western sound. Kanye West's albums Graduation and Curtis were released the same day. Those artists were caught in the midst of a bidding war, with the former predicting that if West sold more albums than he did (thoughts he later retracted as a result of his contract conflicted with the promise). Chesney, on the other hand, has decided that country music will have a place in the competition, claiming that country artists were just as popular as those in the rap genre. Chesney came in third place in terms of annual sales among the three musical artists.

"Never Wanted Nothing More" was Just Who I Am: Poets & Pirates' lead-off single. Chesney's twelfth number one hit on Billboard's country charts. The United States is a republic in the United States. The album's second single "Don't Blink" debuted at No. 1 in the week that ended on September 15, 2007. The 16th debut on the chart since the introduction of SoundScan electronic tabulation in 1990 set a new record on that chart. Garth Brooks' "More Than a Memory" (More Than a Memory) debuted at No. 1, a record that was broken one week later. It's the first song to do so on the same chart. "Shiftwork" (a duet with George Strait) was the third single to debut at No. 1 on the charts. 2 on the country charts. "Better as a Memory," Chesney's fourth and final single during the week of June 28, 2008, became Chesney's fourteenth top-one hit.

Chesney began his Poets and Pirates Tour on April 26, 2008 at Williams-Brice Stadium in Columbia, South Carolina. His boot became trapped between a hydraulic lift and the roof of the stage surface, resulting in a serious ankle swelling; the bulk of the injury was concentrated within his toes. Chesney had to loosen his foot while the band continued to perform a long introduction of the song. He erupted and took his hand on his knee as he began to perform.

During the early part of his career, Chesney did not disclose the injury. On the other hand, he was clearly limping and seemed to be resting near a drum riser while leaning over and holding his knee during his songs' instrumental breaks. When he walked offstage, a University of South Carolina physician cut Chesney's cowboy boot off the front of stage and began treating the foot injury right away. X-rays that were taken afterwards revealed several fractured bones in his right foot.

As said, "the doctor" told me it's going to hurt, but it won't hurt worse than Saturday, I don't think – and it would give me something to dull the pain when I get out there. If something gives, I'll still have a doctor to look at, but I'll tape it up and get out there."

Chesney sluggishly dismissed the producers' awarding the award based on fan votes on May 19, 2008, just a day after being voted as the ACM Entertainer of the Year at the 43rd Annual Academy of Country Music Awards. "The entertainer of the year award is supposed to reflect heart and passion, as well as a huge amount of sacrifice, dedication, and concentration," he said. "That's the way Garth [Brooks] won it four times, that's the way I won it, because that's the way [George] Strait won it, Reba [McEntire] Alabama all those years." It's supposed to be "ethical" in its image.

Chesney revealed on July 24, 2008 that he would debut Lucky Old Sun, a new song from his forthcoming album. The album was called "Everybody Wants to Go to Heaven" and it debuted at No. 62 in the United States' chart week, August 16, 2008. On the Billboard Hot Country Songs chart, 22 appear on the Billboard Hot Country Songs chart. The album was released on October 14, 2008. Everyone wants to go to Heaven" has become a No. 1. 1 of the 1st strikers was struck. It was followed by a look at Mac McAnally's 1990 single "Down the Road."

The Sun City Carnival Tour debuted in 2009 and featured both small and large venues in order to hold his ticket prices low. The tour included a visit to Gillette Stadium for the fifth year in a row, marking the fifth year in a row that he appeared in the Foxboro, Massachusetts football field.

Chesney produced The Boys of Fall (2010), an ESPN film set in this same time.

Chesney's second compilation album, Greatest Hits II, was released in May 2009. The No. ranked in this album was included. As the lead single, "Out Last Night" became the top hit. This album was re-released on February 9, 2010 with two new tracks, "This Is Our Time" and "Ain't Back Yet," the latter becoming the album's third single in February 2010. Willie Nelson's "I'm Alive" is also included on this album, as well as one from Chesney's before Chesney's. Chesney himself released a version of the song as a duet with Dave Matthews later this year. This version was released in August 2009 as the album's second single.

Chesney's "The Boys of Fall" was his first single from his album Hemingway's Whiskey, which was released in September 2010. The album debuted at No. 1. Chesney's eighth number one hit on the Hot Country Songs chart this week, number 1 on the Hot Country Songs chart for the week of October 9, 2010.

On November 10, 2010, he appeared at the 44th Annual Country Music Awards.

In November 2010, Hemingway's Whiskey's "Somewhere With You," was released as the second single. The album debuted at No. 1 in the United States. For the week of November 6, 2010, the country chart ranked 35 on the country chart. Both it and its sequel, "Live a Little," debuted on the country charts. "You and Tequila" was co-written and first performed by Deana Carter. Chesney's version, which featured Grace Potter on backing vocals, soared to number three. "Reality" debuted on the first page of the charts after it was released.

Chesney produced and narrated The Color Orange, his favorite football player growing up, University of Tennessee quarterback Drew Brees' greatest football player growing up, and Canadian Football League hall-of-fame Condredge Holloway. The film was produced for ESPN's "Year of the Quarterback" series and premiered on February 20, 2011.

On June 19, 2012, Chesney's Welcome to the Fishbowl, his fourteenth studio album, was released. "Feel Like a Rock Star," Tim McGraw's lead-off single, debuted at number 13 on the country charts, making it the second highest debuting country song since the Billboard charts were first tabulated via Nielsen SoundScan, as well as the highest-debuting duet on the chart. Despite its high debut, the album debuted at number 11 just six weeks before dropping.

In June 2012, BNA Records came to an end. Chesney was then moved to Columbia Nashville, Tennessee. "Come Over," the album's second single, debuted under Columbia, debuted at number one. "El Cerrito Place" was Keith Gattis' third and final single on the album and was first released by Charlie Robison. Chesney's version, which featured Grace Potter on backing vocals, ranked at number ten on the country charts.

On April 30, 2013, Chesney's Life on a Rock, his fifteenth studio album, was released. "Pirate Flag," the album's first single, was released on iTunes on February 5, 2013 and debuted at number three on the Country Airplay chart in May 2013. On Billboard's Top Country Songs chart, Pirate Flag debuted at number 7 on Billboard's Hot Country Songs chart, May 25, 2013. On June 10, 2013, the album's second single, "When I See This Bar," was released to country radio. When I saw This Bar on Billboard's Hot Country Songs chart, it ranked at number 25 on the Billboard Hot Country Songs chart, on September 14, 2013. This particular album was a drastic change from his normal country feel to an all beach and island touch.

Chesney first performed "American Kids" on radio in June 2014. This song was released on September 23, 2014 as the lead-off single from his sixteenth studio album The Big Revival. "Total It's Gone," the album's second single, was released in mid-October. The week of January 31, 2015, it debuted on the Country Airplay chart at number one. Two days later, Grace Potter's third single "Wild Child" was released. The week of June 27, 2015, it debuted at number one on the Country Airplay chart for the week. On June 29, 2015, the album's fourth single, "Save It for a Rainy Day," was introduced to country radio. The week of October 9, 2015, the country Airplay chart ranked it at number one on the country Airplay chart.

Chesney unveiled his 2015 tour, The Big Revival Tour, which began on March 26, 2015. Jason Aldean and his partner announced on October 27 that they would appear in ten joint stadium shows in the summer of that year. Brantley Gilbert announced that he would open the Chesney/Aldean stadium performances, as well as five additional shows on Chesney's solo tour.

Chesney revealed on March 7, 2016, that he was in the studio recording new music. "Noise" is the album's lead single, and it was unveiled on March 24, 2016. On October 28, the album, Cosmic Hallelujah, was released. On July 28, 2016, P.NK's second song on the album, "Setting the World on Fire," was released to country radio.

Kenny Chesney, a fan of No Shoes Nation, announced to his followers on August 25, 2012, in Foxborough, Massachusetts. The term "No Shoes Nation" appears in Chesney's hit song "No Shoes, No Shirt, No Issue." The symbol of No Shoes Nation is a black flag with a white skull and crossbones. Since its debut in late 2017, the name was accompanied by a live album called Live in No Shoes Nation, which topped the Billboard 200. The name of Chesney's Sirius XM channel, No Shoes Radio, was inspired by No Shoes Nation.

Chesney had ended his deal with Sony Music Nashville and signed to Warner Bros. Records Nashville in January 2018. Chesney's first album, Songs for the Saints, was released on July 27, 2018.

He announced a new album, Here and Now, which includes the title track and "Tip of My Tongue," a leadoff single that was released in mid-2019. Chesney's 16th top ten album on the US Billboard 200 gained 233,000 units on the first day, earning the album as Chesney's 16th top ten album on the US Billboard 200.

Source

Career and awards

In 1992, the head of writer relations at BMI, Clay Bradley, recommended Chesney to his friend, Troy Tomlinson, at Opryland Music Group by saying: "I met this kid today from East Tennessee. He's a good singer, a good songwriter, and more than anything, I think you're going to really like him as a person." Chesney performed five songs during his audition for Tomlinson. Tomlinson's reaction was enthusiastic, later telling HitQuarters:

Chesney left the audition with a songwriter's contract. A year later, an appearance at a songwriter's showcase led to a contract with Capricorn Records, which had recently started a country division.

Chesney's debut album, In My Wildest Dreams, was released on the independent Capricorn Records label in April 1994. The album's first two singles, "Whatever It Takes" and "The Tin Man", both reached the lower regions of the U.S. Billboard Hot Country Singles & Tracks chart. The album sold approximately 10,000 copies before Capricorn Records closed its country music division in Nashville later that year and moved to Atlanta.

Chesney then signed with BNA Records, and released his second studio album All I Need to Know in 1995. The album produced three singles. "Fall in Love" and the title track both reached the Top 10, while "Grandpa Told Me So" peaked at number 23. That same year, Chesney co-wrote Confederate Railroad's single "When He Was My Age" from their album When and Where. Chesney utilized fiddle and steel instrumentation within this album in order to highlight the down-home sentiments and the unique Tennessee twang in his voice. This album seemed to capture the traditional spirit that made country music popular.

Chesney's third studio album and his second major-label one, entitled Me and You, was released in 1996. Its first single, "Back In My Arms Again", peaked just outside the Top 40 on the country charts, while its title track (which Chesney had recorded on his previous album) and "When I Close My Eyes" (which was previously recorded by Keith Palmer on his 1991 debut album and then by Larry Stewart on his 1993 debut album Down the Road) both peaked at number 2. Me and You was Chesney's first album to be certified gold by the Recording Industry Association of America (RIAA). A cover of Mac McAnally's 1990 single "Back Where I Come From" was also included on this album. Even though Chesney's version was never released as a single, it has been regularly performed during his concerts. In recognition of his successful year, Chesney was honored with the 1997 Academy of Country Music's New Male Vocalist of the Year award.

I Will Stand, Chesney's fourth album and his third from BNA Records, followed in 1997. The album's first single, "She's Got It All", became Chesney's first number one hit on the Billboard country charts and spent three weeks at that position. The album's second single, "A Chance", peaked just shy of the Top 10. The third single, "That's Why I'm Here", peaked at number 2 in 1998.

Everywhere We Go, Chesney's fourth album from BNA, came in 1999. That album produced two consecutive number one hits with "How Forever Feels" and "You Had Me from Hello" (the latter inspired by a line in the movie Jerry Maguire). The album also produced two more singles with "She Thinks My Tractor's Sexy" and "What I Need to Do", which peaked at numbers 11 and 8 on the country charts, respectively. Everywhere We Go was Chesney's first album to be certified platinum. The album marked a departure from his original neotraditional country sound, to his more familiar country pop/trop rock/Gulf and Western sound he has since become known for.

By 2000, Chesney released his Greatest Hits compilation album. It included four new tracks, as well as updated versions of "Fall in Love", "The Tin Man", and "Back Where I Come From". The new version of "The Tin Man" was one of the disc's three singles, along with two of the new tracks, "I Lost It" and "Don't Happen Twice". In 2001 he performed with Kid Rock at a Waylon Jennings tribute concert covering Waylon's song Luckenbach Texas.

The album No Shoes, No Shirt, No Problems was released in 2002. Its lead-off single, "Young", peaked at number 2, while the follower "The Good Stuff" spent seven weeks at number 1 and became Billboard's number one country song of the year for 2002. The video for "Young" was honored by CMT with the Video of the Year and Male Video of the Year awards for 2002. In 2003, ACM honored Chesney as Top Male Vocalist of the Year, while "The Good Stuff" received the award for Single Record of the Year. CMT later recognized the video for the album's title track as the Hottest Video of the Year.

In 2003, Chesney recorded All I Want for Christmas Is a Real Good Tan. The album's title track peaked at No. 30 on the country charts from holiday airplay. Other notable work Chesney did in 2003 is that he co wrote Kid Rock's single "Cold and Empty" from his self-titled 6th studio album Kid Rock.

2004 saw the release of the album When the Sun Goes Down. Its lead-off single, "There Goes My Life", spent seven weeks at number one on the Billboard country charts. On April 21, 2004, the accompanying music video for that song was honored by CMT with the Male Video of the Year award. The album's title track, a duet with Uncle Kracker, also went to number one. The music video for the album's third single, "I Go Back", was honored on April 11, 2005, with Country Music Television's Male Video of the Year Award. This song, along with the album's fourth single, "The Woman with You", both peaked at number two. The fifth single, "Anything But Mine", reached number one, and the final single, "Keg in the Closet", peaked to number six.

When the Sun Goes Down was honored with the 2004 CMA award for Album of the Year while Chesney was honored as the Entertainer of the Year. He was also presented with AMA's 2004 Artist of the Year award.

In January 2005, Chesney released the album Be as You Are (Songs from an Old Blue Chair), supporting it with his Somewhere in the Sun Tour. Be as You Are is composed mostly of ballads. The album qualified for RIAA Platinum and entered the top of both mainstream country and pop music.

In spring 2005, Chesney was honored with the prestigious Triple-Crown Award presented by the Academy of Country Music. This award was presented after Chesney's 2004 Academy of Country Music's Entertainer of the Year award was combined with 1997's New Male Vocalist of the Year award and 2003's Top Male Vocalist of the Year award. The following year, on May 23, 2006, Chesney was honored with his second Entertainer of the Year at the Academy of Country Music Awards.

Chesney's next album, The Road and the Radio, debuted at number one the Billboard 200 and produced five singles. "Living in Fast Forward", "Summertime", and "Beer in Mexico" all reached number one, while "Who You'd Be Today" and "You Save Me" both broke the Top 5. Chesney promotes his beliefs of perfection, as getting songs right in the studio, ultimately leads to performing it right on the road and on the radio.

Live: Live Those Songs Again, Chesney's first live album was released on September 19, 2006, via BNA Records. This album includes live renditions of 15 songs, 11 of which were singles. "Live Those Songs", "Never Gonna Feel Like That Again", "On the Coast of Somewhere Beautiful", and "Back Where I Come From" were never released by Chesney as singles, although "Back Where I Come From" was released as a single from Mac McAnally's 1990 album Simple Life.

Chesney collaborated with one of his personal heroes, Jimmy Buffett, on a remake of Hank Williams' single "Hey Good Lookin' (with Clint Black, Alan Jackson, Toby Keith, and George Strait), and a second song "License To Chill". Both songs are on Buffett's 2004 album License To Chill.

Chesney, along with Tim McGraw, contributed to a version of Tracy Lawrence's single "Find Out Who Your Friends Are", which can be found on his album For the Love. The official single version, only featuring Lawrence's vocals, was released in August 2006 but did not reach the Top 40 on the country charts until January 2007, when 'the album was released. After the album's release, the version with him, Chesney, and McGraw began receiving significant airplay, helping to boost the single to No. 1 on the country charts. The song became Lawrence's first No. 1 single in 11 years, as well as the second-slowest climbing No. 1 single in the history of the Billboard music charts.

With Neil Thrasher and Wendell Mobley, Chesney also co-wrote Rascal Flatts' 2007 single Take Me There", which served as the lead-off single to their album Still Feels Good.

Chesney also recorded a duet with Reba McEntire on her No. 1 2007 album Reba: Duets. "Every Other Weekend" peaked at No. 15 on the Billboard Hot Country Songs chart and No. 104 on the Billboard Bubbling Under Hot 100 Singles chart. The album has sold 2.1 million copies world-wide and is certified Platinum by the RIAA for sales of over 1 million. "Every Other Weekend" was the final single from the album.

On November 7, 2007, Chesney was named the CMA Entertainer of the Year for the third time in four years. The following week, on November 15, 2007, the compilation Super Hits album was released as part of Sony BMG's Super Hits series.

On September 11, 2007, Chesney released the album Just Who I Am: Poets & Pirates. This album represented a move to a more gulf and western sound with a number of "breezy, steel-drum island songs". Kanye West and 50 Cent's albums Graduation and Curtis were both released that same day. Those artists were in the midst of a competitive sales war, with the latter claiming that he would end his solo rap career if West sold more albums than he did (remarks he later retracted as terms of his contract conflicted with the promise). Chesney, however, decided that he would give country music a place in the competition, claiming country artists were just as popular as those in the rap genre. Chesney came in third place in record sales among the three musical artists.

The lead-off single from Just Who I Am: Poets & Pirates was "Never Wanted Nothing More". That song became Chesney's twelfth number one hit on the Billboard country charts. On the U.S. Billboard Hot Country Songs chart dated for the week ending on September 15, 2007, the album's second single "Don't Blink" debuted at No. 16, setting a new record for the highest debut on that chart since the inception of SoundScan electronic tabulation in 1990. This record was broken one week later by Garth Brooks' "More Than a Memory", which debuted at No. 1 on the same chart, making it the first song ever to do so. The third single, "Shiftwork" (a duet with George Strait) peaked at No. 2 on the country charts. During the week of June 28, 2008, the fourth and final single, "Better as a Memory", became Chesney's fourteenth number one hit.

Chesney started his Poets and Pirates Tour on April 26, 2008, at Williams-Brice Stadium in Columbia, South Carolina. During the introduction of his set, his boot got caught between a hydraulic lift and the lip of the stage surface, which crushed his foot causing a severe hematoma in the ankle; most of the damage was centering within his toes. It took about 30 seconds for Chesney to pry his foot loose as he squatted down on the stage while the band continued to play an extended introduction of the song. When Chesney finally freed himself, he stood up and held his hand on his knee as he began singing.

Chesney did not acknowledge the injury during the early part of his performance. However, he was visibly limping and seemed to rest near a drum riser while leaning over and holding his knee during the instrumental breaks of his songs. As he came offstage, a doctor from the University of South Carolina cut off Chesney's cowboy boot and immediately began treating the foot injury. X-rays that were taken afterwards revealed several crushed bones in his right foot.

That injury did not have him cancel any shows, as saying "[the doctor] told me it's going to hurt – though nothing could hurt worse than Saturday, I don't think – and they can give me something to deaden the pain when I get out there. I also have to have a doctor standing by should something give, but I'm going to tape it up, and I'm going to get out there".

On May 19, 2008, just a day after being honored as the ACM Entertainer of the Year at the 43rd Annual Academy of Country Music Awards, Chesney criticized the lack of choice in the producers' awarding the honor based on fan votes. "The entertainer of the year trophy is supposed to represent heart and passion and an amazing amount of sacrifice, commitment and focus", he said. "That's the way Garth [Brooks] won it four times, that's the way I won it, that's the way [George] Strait won it, Reba [McEntire], Alabama all those years. That's what it's supposed to represent."

On July 24, 2008, Chesney announced that he would be releasing a new single from an upcoming album entitled Lucky Old Sun. The song was titled "Everybody Wants to Go to Heaven", and for the chart week of August 16, 2008, it debuted at No. 22 on the Billboard Hot Country Songs chart. The album was released on October 14, 2008. "Everybody Wants to Go to Heaven" became a No. 1 hit. It was followed by a cover of Mac McAnally's 1990 single "Down the Road".

Chesney's 2009 tour was titled the Sun City Carnival Tour and featured both small and large venues in order to keep his ticket prices down. The tour included a performance at Gillette Stadium again, marking the fifth year in a row that he played at the Foxboro, Massachusetts football field.

In this same period, Chesney produced a film for ESPN titled The Boys of Fall (2010).

In May 2009, Chesney released his second compilation album, Greatest Hits II. This album included the No. 1 hit, "Out Last Night", as the lead single. On February 9, 2010, this album was re-released with two new tracks "This Is Our Moment" and "Ain't Back Yet", with the latter becoming the album's third single in February 2010. Also included on this album is one that Willie Nelson recorded before Chesney did, "I'm Alive". Chesney himself later recorded a version of the song as a duet with Dave Matthews. This version was released in August 2009 as the album's second single.

In July 2010, Chesney released "The Boys of Fall" as the lead-off single from his album Hemingway's Whiskey, which was released in September 2010. The song hit No. 1 on the Hot Country Songs chart for the week of October 9, 2010, marking Chesney's eighteenth number one hit.

He then appeared at the 44th Annual Country Music Awards on November 10, 2010.

The second single from Hemingway's Whiskey, "Somewhere with You", was released in November 2010. The song debuted at No. 35 on the country chart for the week of November 6, 2010. Both it and its followup, "Live a Little", went to number 1 on the country charts. The next single was "You and Tequila", co-written and originally recorded by Deana Carter. Chesney's rendition, which featured Grace Potter on backing vocals, went to number 3. After it, "Reality" also went to number 1.

Chesney produced and narrated a biographical film, The Color Orange, on his favorite football player growing up, University of Tennessee quarterback and Canadian Football League hall-of-fame Condredge Holloway. The film was produced for ESPN's "Year of the Quarterback" series, and premiered on February 20, 2011.

Chesney released his fourteenth studio album, Welcome to the Fishbowl, on June 19, 2012. Its lead-off single, a Tim McGraw duet titled "Feel Like a Rock Star", debuted at number 13 on the country charts, making it the second-highest debuting country song since the Billboard charts were first tabulated via Nielsen SoundScan, and the highest-debuting duet on that chart. Despite its high debut, the song peaked at number 11 only six weeks later before falling.

BNA Records closed in June 2012. As a result, Chesney was transferred to Columbia Nashville. His first release under Columbia was the album's second single, "Come Over", which went to number 1. The album's third and final single was "El Cerrito Place", which was written by Keith Gattis and originally recorded by Charlie Robison. Chesney's rendition, which featured Grace Potter on backing vocals, went to number 10 on the country charts.

Chesney released his fifteenth studio album, Life on a Rock, on April 30, 2013. The first single from the album, "Pirate Flag", was released to iTunes on February 5, 2013, and peaked at number 3 on the Country Airplay chart in May 2013. Pirate Flag peaked at number 7 on Billboard's Hot Country Songs chart, May 25, 2013. The album's second single, "When I See This Bar", was released to country radio on June 10, 2013. When I see This Bar peaked at number 25 on Billboard's Hot Country Songs chart, September 14, 2013. This specific album was a drastic change from his regular country feel, to an all beach and island touch.

In June 2014, Chesney released the new song "American Kids" to radio. This song served as the lead-off single from his sixteenth studio album The Big Revival, which was released on September 23, 2014. The album's second single, "Til It's Gone", was released in mid-October. It reached number one on the Country Airplay chart the week of January 31, 2015. The third single "Wild Child", which is a duet with Grace Potter, was released two days later. It reached number one on the Country Airplay chart the week of June 27, 2015. The album's fourth single, "Save It for a Rainy Day", was released to country radio on June 29, 2015. It reached number one on the Country Airplay chart the week of October 9, 2015.

On October 24, Chesney announced his 2015 tour The Big Revival Tour, which began on March 26, 2015. On October 27, he and Jason Aldean announced that they would perform 10 joint stadium shows in the summer of that year. Two days later, Brantley Gilbert announced that he would be opening for the Chesney/Aldean stadium shows, as well as five additional shows on Chesney's solo tour.

On March 7, 2016, Chesney announced that he was in the studio working on new music. The lead single to the album is titled "Noise", which was released to country radio on March 24, 2016. The album, Cosmic Hallelujah, was released on October 28. The second song in the album, "Setting the World on Fire", featuring singer P!NK was released to country radio on July 28, 2016.

On August 25, 2012, at Gillette Stadium in Foxborough, Massachusetts, Kenny Chesney announced to his fans that he would call his fan following No Shoes Nation. The term No Shoes Nation originated from Chesney's hit song "No Shoes, No Shirt, No Problem". The symbol of No Shoes Nation is a black flag with a white skull and crossbones. The name was accompanied by a live album called Live in No Shoes Nation, which topped the Billboard 200 after its release in late 2017. No Shoes Nation inspired the name of Chesney's Sirius XM channel, No Shoes Radio.

In January 2018, it was announced that Chesney had ended his contract with Sony Music Nashville and signed to Warner Bros. Records Nashville. Chesney released his first album with Warner, entitled Songs for the Saints, on July 27, 2018.

In March 2020, he announced a new album called Here and Now, which features the title track and "Tip of My Tongue", a leadoff single that was released in mid-2019. The album debuted at number one and became Chesney's 16th top 10 album on the US Billboard 200, with 233,000 units.