Rise to Success: Career Highlights of Kenny Chesney

How Kenny Chesney built a successful career. Explore key moments that defined the journey.

Kenny Chesney is an American country music singer-songwriter, known for his successful career spanning several decades. Since his 1994 debut album, "In My Wildest Dreams", he has released 19 more albums and sold over 30 million records globally. Chesney has had 27 singles reach the top 40 of the Billboard Hot 100, solidifying his position as a prominent figure in contemporary country music.

Sections (3)

Full Timeline Career & Achievements Success & Recognition

1989: Self-Released Demo Album

In 1989, Kenny Chesney recorded and self-released a demo album, Good Old Boy At Heart, at the Classic Recording Studio in Bristol, Virginia. He sold 1,000 copies at local clubs to buy a new guitar.

1990: Moved to Nashville

In 1990, after graduating from East Tennessee State University, Kenny Chesney moved to Nashville, Tennessee to pursue his music career, performing at local clubs.

March 1991: Audition at The Bluebird Cafe

In March 1991, Kenny Chesney successfully auditioned to sing at The Bluebird Cafe in Nashville, Tennessee, marking an early milestone in his career.

1992: Songwriter's Contract

In 1992, Kenny Chesney secured a songwriter's contract with Opryland Music Group after being recommended by Clay Bradley and auditioning for Troy Tomlinson.

April 1994: Debut Album Release

In April 1994, Kenny Chesney's debut album, In My Wildest Dreams, was released on the independent Capricorn Records label.

1994: Debut Album Release

In 1994, Kenny Chesney released his debut album, In My Wildest Dreams. It was the start of his journey as a country music artist.

June 1995: Signed with BNA Records

In June 1995, Kenny Chesney signed with BNA Records and released his second studio album, All I Need to Know, marking a significant step in his career.

June 1996: Release of "Me and You" Album

In June 1996, Kenny Chesney released his third studio album, Me and You, which became his first album to be certified gold by the RIAA.

July 1997: Release of "I Will Stand" Album

In July 1997, Kenny Chesney released his fourth album, I Will Stand, which featured his first number one hit, "She's Got It All."

1997: Academy of Country Music Award

In 1997, Kenny Chesney was honored with the Academy of Country Music's New Male Vocalist of the Year award, marking an early recognition of his talent.

1997: Previous ACM New Male Vocalist of the Year Award

In 1997, Kenny Chesney won the Academy of Country Music's New Male Vocalist of the Year award, an achievement contributing to his Triple Crown Award in 2005.

1998: "That's Why I'm Here" Peaked at Number 2

In 1998, Kenny Chesney's song "That's Why I'm Here", from the album "I Will Stand", peaked at number 2 on the Billboard country charts.

March 1999: Release of "Everywhere We Go" Album

In March 1999, Kenny Chesney released his fourth album from BNA, Everywhere We Go, which produced two consecutive number one hits and marked a shift in his musical style.

September 2000: Release of Greatest Hits Compilation Album

In September 2000, Kenny Chesney released his Greatest Hits compilation album, which included four new tracks and updated versions of some of his previous songs.

2001: Performance at Waylon Jennings Tribute Concert

In 2001, Kenny Chesney performed with Kid Rock at a Waylon Jennings tribute concert, covering Waylon's song "Luckenbach Texas".

April 2002: Release of "No Shoes, No Shirt, No Problems" Album

In April 2002, Kenny Chesney released the album No Shoes, No Shirt, No Problems. The lead-off single, "Young", peaked at number 2, while "The Good Stuff" spent seven weeks at number 1.

June 2002: CMT Video of the Year Award

In June 2002, the video for "Young" by Kenny Chesney was honored by CMT with the Video of the Year and Male Video of the Year awards.

January 2003: Release of "Big Star" Single

In January 2003, Kenny Chesney released "Big Star" as the fourth single from the album "No Shoes, No Shirt, No Problems". It peaked at number 2 seven weeks later.

May 2003: ACM Awards for Kenny Chesney and "The Good Stuff"

In May 2003, Kenny Chesney was honored as Top Male Vocalist of the Year by the ACM, while his song "The Good Stuff" received the award for Single Record of the Year.

October 2003: Recording of "All I Want for Christmas Is a Real Good Tan"

In October 2003, Kenny 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.

2003: Previous ACM Top Male Vocalist of the Year Award

In 2003, Kenny Chesney won the Academy of Country Music's Top Male Vocalist of the Year award, which contributed to his Triple Crown Award in 2005.

February 2004: Release of "When the Sun Goes Down" Album

In February 2004, Kenny Chesney released When the Sun Goes Down. Its lead-off single, "There Goes My Life", spent seven weeks at number one on the Billboard country charts.

April 2004: CMT Award for Hottest Video of the Year

In April 2004, Kenny Chesney won the Hottest Video of the Year award at the CMT awards for the title track, "No Shoes, No Shirt, No Problems", given to the fan-voted "sexiest" clip.

April 21, 2004: CMT Male Video of the Year Award

On April 21, 2004, Kenny Chesney's music video for "There Goes My Life" was honored by CMT with the Male Video of the Year award.

2004: Collaborations with Jimmy Buffett

In 2004, Kenny Chesney collaborated with Jimmy Buffett on a remake of Hank Williams' single "Hey Good Lookin' (with Clint Black, Alan Jackson, Toby Keith, and George Strait), and the song "License To Chill".

2004: Previous ACM Entertainer of the Year Award

In 2004, Kenny Chesney won the Academy of Country Music's Entertainer of the Year award, contributing to his later Triple Crown Award in 2005.

2004: CMA Album of the Year and Entertainer of the Year

In 2004, Kenny Chesney's album When the Sun Goes Down was honored with the CMA award for Album of the Year. Chesney was also honored as the Entertainer of the Year.

January 2005: Release of "Be as You Are" Album

In January 2005, Kenny 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.

April 11, 2005: CMT Male Video of the Year Award

On April 11, 2005, Kenny Chesney's music video for "I Go Back" was honored with Country Music Television's Male Video of the Year Award.

May 2005: Triple Crown Award

In May 2005, Kenny Chesney was honored with the prestigious Triple-Crown Award presented by the Academy of Country Music, recognizing his achievements over the years.

November 2005: Release of "The Road and the Radio" Album

In November 2005, Kenny Chesney released The Road and the Radio, which debuted at number one on the Billboard 200 and produced five singles.

2005: Academy of Country Music Award

In 2005, Kenny Chesney won the Academy of Country Music Award for Entertainer of the Year, marking a significant achievement in his career.

May 2006: Entertainer of the Year Award

In May 2006, Kenny Chesney was honored with his second Entertainer of the Year award at the Academy of Country Music Awards.

September 2006: Release of Live Album

In September 2006, Kenny Chesney released his first live album, Live: Live Those Songs Again, featuring live renditions of 15 songs.

January 2007: "Find Out Who Your Friends Are" Reaches Top 40

In January 2007, Tracy Lawrence's single "Find Out Who Your Friends Are", featuring Kenny Chesney and Tim McGraw, finally reached the Top 40 on the country charts, boosting it to No. 1 after the album's release.

2007: Co-writing "Take Me There" for Rascal Flatts

In 2007, Kenny Chesney co-wrote Rascal Flatts' single "Take Me There" with Neil Thrasher and Wendell Mobley. The song served as the lead-off single to their album Still Feels Good.

2007: Duet with Reba McEntire

In 2007, Kenny Chesney recorded a duet with Reba McEntire on her album Reba: Duets. The song, "Every Other Weekend", peaked at No. 15 on the Billboard Hot Country Songs chart.

2008: Fourth Consecutive Academy of Country Music Award

In 2008, Kenny Chesney won his fourth consecutive Academy of Country Music Award for Entertainer of the Year, further solidifying his status in country music.