2000s
In September 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 April 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 album also became his first to top both the Billboard 200 and the Top Country Albums Chart. In June 2002, the video for "Young" was honored by CMT with the Video of the Year and Male Video of the Year awards. A Lot of Things Different originally written by Bill Anderson, was the third single from the album and peaked at number 6. Big Star, released January 2003, was the fourth single released from the album and peaked at number 2 seven weeks later. In May 2003, ACM honored Chesney as Top Male Vocalist of the Year, while "The Good Stuff" received the award for Single Record of the Year. In April 2004, title track won the Hottest Video of the Year at the CMT awards, given to the fan-voted "sexiest" clip. No Shoes, No Shirt, No Problems has since been certified platinum 5x.
In October 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.
In February 2004, Chesney released When the Sun Goes Down. The album once again topped both the Billboard 200 and Top Country Albums charts. The record won album of the year at the 2004 Country Music Association Awards. 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 has since been certified platinum 5x.
In 2004, 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. "Hey Good Lookin' garnered Chesney his first Grammy nomination for Best Country Collaboration With Vocals at the 47th Annual Grammy Awards.
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 May 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.
Chesney's next album, The Road and the Radio, released in November 2005, 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. The album became his third straight to top both the Billboard 200 and the Top Country Albums Chart. It has since been certified platinum 4x by the RIAA.
In May 2006, Chesney was honored with his second Entertainer of the Year at the Academy of Country Music Awards.
Live: Live Those Songs Again, Chesney's first live album was released in September 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.
In 2006, 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, boosting 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.
In 2007, 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.
In 2007, Chesney also recorded a duet with Reba McEntire on her 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. He also embarked on his Flip-Flop Summer Tour.
In November 2007, Chesney was named the CMA Entertainer of the Year for the third time in four years. Also in November 2007, the compilation Super Hits album was released as part of Sony BMG's Super Hits series.
In September 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". It placed third in album sales that week, behind Graduation by Kanye West and Curtis by 50 Cent. The lead-off single from the album was "Never Wanted Nothing More", written by Ronnie Bowman and Chris Stapleton. It reached number one 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, although the record was broken the following week by "More Than a Memory" by Garth Brooks. The third single, "Shiftwork" (a duet with George Strait) peaked at No. 2 on the country charts. In June 2008, the fourth and final single, "Better as a Memory", became Chesney's fourteenth number one hit. The album topped the U.S. country charts, and also became his first to chart on the Billboard Canadian Albums peaking a number 7.
"Shiftwork" was later nominated for Best Country Collaboration With Vocals at the 51st Annual Grammy Awards.
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. Chesney did not cancel any shows due to the injury.
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 change in the awards process to awarding the honor based on fan votes and not determined by music industry professionals.
In August 2008, Chesney released a song titled "Everybody Wants to Go to Heaven", which reached number one Billboard Hot Country Songs chart. The album Lucky Old Sun was released on October 14, 2008. It was followed by a cover of Mac McAnally's 1990 single "Down the Road". The album once again topped both the Billboard 200 and the Top Country Albums Chart, and has since been certified platinum by the RIAA. Chesney's cover of "Down the Road" garnered him his 3rd Grammy nomination for Best Country Collaboration with Vocals on December 2, 2009.
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.
