- Wrote "You Had Me From Hello" after Renée Zellweger's famous line in Jerry Maguire (1996).
- Favorite TV show is Friends (1994).
- Is a huge Aerosmith and Bruce Springsteen fan.
- His wedding ceremony lasted 15 minutes
- Is a die hard fan of the Boston Red Sox and the Tennessee Titans.
- Married actress Renée Zellweger on the resort island St. John in the U.S. Virgin Islands, where he has maintained a home on the beach for many years, and where he often goes to escape and wind down in between tour dates.
- He was born to Dave Chesney and Karen Chandler (then Karen Chesney).
- Two of his albums "All I Want for Christmas is a Real Good Tan" and "Be As You Are: Songs from an Old Blue Chair" both went platinum without a radio single or promotion.
- 2002 ACM Award-winner for Best Male Vocalist.
- Favorite musicians are Conway Twitty, Keith Whitley, Ricky Skaggs, George Jones, Lynyrd Skynyrd and James Taylor.
- In 1990, he graduated with a degree in marketing from East Tennessee State University.
- Is a Board Member, along with actor Morgan Freeman, for PLANIT NOW, a hurricane relief and preparation non-profit.
- 2004 CMA Award-winner for Entertainer of the Year and Album of the Year.
- In April of 2005 his song "Anything but Mine" hit number 1 on the Country charts after spending 17 weeks on the charts.
- Won the Entertainer of the Year Award at the Academy of Country Music Awards on May 17, 2005
- He won the 2004 CMA Album of the Year for his record When the Sun Goes Down.
- On the CMT Top 20 Videos of 2005, he held the #8 (Who You'd Be Today) and #2 (Anything But Mine) slots.
- Good friend of Peyton Manning.
- Has a younger half-sister named Jennifer Chandler.
- Was raised in Luttrell, Tennessee, which is also the hometown of country star Chet Atkins.
- Met his ex-wife Renée Zellweger at a tsunami relief benefit in January 2005.
- Brother of the Lambda Chi Alpha Fraternity from East Tennessee State University
- Favorite book is "The Firm" by John Grisham.
- Has been in an on and off long-term relationship with model Jamie Hill Fuller since March 2008.
- Scored his first top 10 hit on Billboard magazine's country singles chart with 1995's "Fall in Love." However, it wasn't until 1996 when he made his breakthrough with the No. 2 hit "Me and You."
- Along with Keith Urban, Dierks Bentley, and other music stars who reside in Nashville, Tennessee, Kenny's home was engulfed in a flood in May, 2010.
- His first No. 1 hit came in August 1997 with "She's Got it All" (a three week No. 1 country smash), and the No. 1 hits kept coming: "That's Why I'm Here" (1998); "How Forever Feels" (a six-week No. 1) and "You Had Me From Hello" (both 1999); "Don't Happen Twice" (2001) and "The Good Stuff" (a seven-week No. 1 from 2002). "How Forever Feels" was Billboard's No. 2 country hit of 1999, while "The Good Stuff" was the magazine's No. 1 country song of 2002. Other major hits include "When I Close My Eyes" (1997); "A Chance" and "I Will Stand" (1998); "She Thinks My Tractor's Sexy" (1999); "What I Need to Do" (2000); "The Tin Man" (2001); and "Young" (2002). As 2003 dawned, he was on his way to another major country smash -- the Bill Anderson-Dean Dillon-penned "A Lot of Things Different."
- On his Poets and Pirates tour. (June 2008)
- Attended Gibbs High School.
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