| | Kenny Chesney songs | | | |
| 121 | Sherry's Living In Paradise [from the "Be as You Are"] | | 03:20 | |
| 122 | She's Got It All [from the "I Will Stand"] | | 03:25 | |
| 123 | Shiftwork (with George Strait) [from the "Just Who I Am: Poets & Pirates"] | | 04:30 | |
| 124 | Sing 'Em Good My Friend [from the "Welcome to the Fishbowl"] | | 04:38 | |
| 125 | Small Y'all (ft. George Jones) [from the "Hemingway's Whiskey"] | | 02:54 | |
| 126 | Some People Change [from the "When the Sun Goes Down"] | | 03:27 | |
| 127 | Somebody Take Me Home [from the "The Road and the Radio"] | | 03:33 | |
| 128 | Somebody's Callin' [from the "In My Wildest Dreams"] | | 02:36 | |
| 129 | Someone Else's Hog [from the "All I Need to Know"] | | 02:36 | |
| 130 | Something Sexy About The Rain [from the "Be as You Are"] | | 05:24 | |
| 131 | Somewhere In The Sun [from the "Be as You Are"] | | 04:45 | |
| 132 | Somewhere With You [from the "Hemingway's Whiskey"] | | 04:05 | |
| 133 | Soul Of A Sailor [from the "Be as You Are"] | | 04:14 | |
| 134 | Soul Of A Sailor (Live) [from the "Lucky Old Sun"] | | 05:40 | |
| 135 | Spirit Of A Storm [from the "Lucky Old Sun"] | | 03:36 | |
| 136 | Spread The Love (feat. The Wailers with Elan) [from the "Life on a Rock"] | | 04:16 | |
| 137 | Steamy Windows [from the "I Will Stand"] | | 04:28 | |
| 138 | Summertime [from the "The Road and the Radio"] | | 03:28 | |
| 139 | Ten With A Two [from the "Lucky Old Sun"] | | 03:11 | |
| 140 | Tequila Loves Me [from the "The Road and the Radio"] | | 04:09 | |
| 141 | That Lucky Old Sun (with Willie Nelson) [from the "Lucky Old Sun"] | | 04:16 | |
| 142 | That's Why I'm Here [from the "I Will Stand"] | | 04:02 | |
| 143 | The Big Revival [from the "The Big Revival"] | | 03:11 | |
| 144 | The Bigger The Fool (The Harder They Fall) [from the "All I Need to Know"] | | 02:46 | |
| 145 | The Boys of Fall [from the "Hemingway's Whiskey"] | | 06:32 | |
| 146 | The Good Stuff [from the "No Shoes, No Shirt, No Problems"] | | 03:22 | |
| 147 | The Life [from the "Lucky Old Sun"] | | 04:26 | |
| 148 | The Road And The Radio [from the "The Road and the Radio"] | | 05:10 | |
| 149 | The Tin Man [from the "In My Wildest Dreams"] | | 03:29 | |
| 150 | The Tin Man [from the "All I Need to Know"] | | 03:26 | |
| 151 | The Woman With You [from the "When the Sun Goes Down"] | | 04:31 | |
| 152 | There Goes My Life [from the "When the Sun Goes Down"] | | 05:02 | |
| 153 | Til It's Gone [from the "The Big Revival"] | | 04:10 | |
| 154 | Time Flies [from the "Welcome to the Fishbowl"] | | 03:37 | |
| 155 | To Get to You (55th and 3rd) [from the "Welcome to the Fishbowl"] | | 05:41 | |
| 156 | Turn for the Worse [from the "Me and You"] | | 02:38 | |
| 157 | Way Down Here [from the "Lucky Old Sun"] | | 05:53 | |
| 158 | Welcome to the Fishbowl [from the "Welcome to the Fishbowl"] | | 03:30 | |
| 159 | What I Need To Do [from the "Everywhere We Go"] | | 04:04 | |
| 160 | What I Need To Do (Live) [from the "When the Sun Goes Down"] | | 04:39 | |
| 161 | Whatever It Takes [from the "In My Wildest Dreams"] | | 03:01 | |
| 162 | When I Close My Eyes [from the "Me and You"] | | 03:30 | |
| 163 | When I Close My Eyes (Acoustic Version) [from the "I Will Stand"] | | 03:38 | |
| 164 | When I See This Bar [from the "Life on a Rock"] | | 06:02 | |
| 165 | When I Think About Leaving [from the "When the Sun Goes Down"] | | 04:39 | |
| 166 | When She Calls Me Baby [from the "In My Wildest Dreams"] | | 03:34 | |
| 167 | When the Sun Goes Down (duet with Uncle Kracker) [from the "When the Sun Goes Down"] | | 04:50 | |
| 168 | Where I Grew Up [from the "Hemingway's Whiskey"] | | 03:39 | |
| 169 | While He Still Knows Who I Am [from the "Welcome to the Fishbowl"] | | 04:15 | |
| 170 | Who You'd Be Today [from the "The Road and the Radio"] | | 04:16 | |
| 171 | Wife and Kids [from the "Just Who I Am: Poets & Pirates"] | | 04:23 | |
| 172 | Wild Child (with Grace Potter) [from the "The Big Revival"] | | 03:09 | |
| 173 | Wild Ride (with Joe Walsh) [from the "Just Who I Am: Poets & Pirates"] | | 04:20 | |
| 174 | You and Tequila (ft. Grace Potter) [from the "Hemingway's Whiskey"] | | 04:02 | |
| 175 | You and Tequila (Live at Red Rocks Amphitheatre) [from the "Welcome to the Fishbowl"] | | 04:49 | |
| 176 | You Had Me From Hello [from the "Everywhere We Go"] | | 03:50 | |
| 177 | You Save Me [from the "The Road and the Radio"] | | 03:57 | |
| 178 | You Win, I Win, We Lose [from the "I Will Stand"] | | 03:24 | |
| 179 | Young [from the "No Shoes, No Shirt, No Problems"] | | 03:58 | |