| Year | Song | US Hot 100 | US country | Album |
|---|
| 1994 | "Whatever It Takes" | - | 59 | In My Wildest Dreams |
| 1995 | "Fall In Love" | - | 6 | All I Need To Know |
| "All I Need To Know" | - | 8 | All I Need To Know |
| 1996 | "Grandpa Told Me So" | - | 23 | All I Need To Know |
| "Back In My Arms Again" | - | 41 | Me and You |
| "Me and You" | - | 2 | Me and You |
| 1997 | "When I Close My Eyes" | - | 2 | Me and You |
| "She's Got It All" | - | 1 | I Will Stand |
| 1998 | "A Chance" | - | 11 | I Will Stand |
| "That's Why I'm Here" | 79 | 2 | I Will Stand |
| "Touchdown Tennessee" | - | 64 | limited-edition single |
| 1999 | "Team Of Destiny" | - | 72 | original A-side of "How Forever Feels" |
| "How Forever Feels" | 27 | 1 | Everywhere We Go |
| "You Had Me From Hello" | 34 | 1 | Everywhere We Go |
| "She Thinks My Tractor's Sexy" | 66 | 11 | Everywhere We Go |
| 2000 | "Away In a Manger" | - | 67 | Country Christmas Classics (Various Artists) |
| "What I Need To Do" | 56 | 8 | Everywhere We Go |
| "I Lost It" | 34 | 3 | Greatest Hits |
| 2001 | "Don't Happen Twice" | 26 | 1 | Greatest Hits |
| "The Tin Man" | - | 19 | All I Need To Know |
| 2002 | "Young" | 35 | 2 | No Shoes, No Shirt, No Problems |
| "Live Those Songs" | - | 60 | No Shoes, No Shirt, No Problems |
| "The Good Stuff" | 22 | 1 | No Shoes, No Shirt, No Problems |
| 2003 | "A Lot Of Things Different" | 55 | 6 | No Shoes, No Shirt, No Problems |
| "Big Star" | 28 | 2 | No Shoes, No Shirt, No Problems |
| "No Shoes, No Shirt, No Problem" | 28 | 2 | No Shoes, No Shirt, No Problems |
| "There Goes My Life" | 29 | 1 | When the Sun Goes Down |
| "All I Want For Christmas Is a Real Good Tan" | - | 28 | All I Want For Christmas Is a Real Good Tan |
| "I'll Be Home For Christmas" | - | 60 | All I Want For Christmas Is a Real Good Tan |
"Pretty Paper"
(Kenny Chesney featuring Willie Nelson) | - | 45 | All I Want For Christmas Is a Real Good Tan |
| "Jingle Bells" | - | 49 | All I Want For Christmas Is a Real Good Tan |
| "Silver Bells" | - | 54 | All I Want For Christmas Is a Real Good Tan |
"Silent Night"
(Kenny Chesney featuring The Grisgby Twins) | - | 57 | All I Want For Christmas Is a Real Good Tan |
| "Thank God For Kids | - | 60 | All I Want For Christmas Is a Real Good Tan |
| 2004 | "When the Sun Goes Down"
(with Uncle Kracker) | 26 | 1 | When the Sun Goes Down |
"Hey Good Lookin'"
(Jimmy Buffett with Clint Black, Kenny Chesney, Alan Jackson, Toby Keith and George Strait) | 63 | 8 | Licence To Chill (Jimmy Buffet album) |
| "I Go Back" | 32 | 2 | When the Sun Goes Down |
| "The Woman With You" | 33 | 2 | When the Sun Goes Down |
| 2005 | "Guitars and Tiki Bars" | - | 53 | Be as You Are (Songs From an Old Blue Chair) |
| "Anything But Mine" | 48 | 1 | When the Sun Goes Down |
| "Keg In the Closet" | 64 | 6 | When the Sun Goes Down |
| "Who You'd Be Today" | 37 | 2 | The Road and the Radio |
| "Living In Fast Forward" 1 | 48 | 1 | The Road and the Radio |
| "The Road and the Radio" | - | 59 | The Road and the Radio |
| "Beer In Mexico" | - | 60 | The Road and the Radio |
| 2006 | "Summertime" 1 | 34 | 1 | The Road and the Radio |
| "You Save Me" | - | - | The Road and the Radio |
Male Celebrities 