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| | time | views | |
| Kenny Chesney - Trip Around the Sun | 2:56 | 1,398,993 | |
| Kenny Chesney - Boston (Live) | 6:46 | 1,414,383 | |
| Kenny Chesney - David Lee Murphy - Guest on Live in No Shoes Nation | 2:11 | 58,856 | |
| Kenny Chesney - Dave Matthews - Guest on Live in No Shoes Nation | 1:47 | 23,150 | |
| Kenny Chesney - Hemingway's Whiskey (Live) | 3:59 | 105,297 | |
| Kenny Chesney - Zac Brown Band - Guest on Live in No Shoes Nation | 2:24 | 25,693 | |
| Kenny Chesney - Save It for a Rainy Day (Live with Old Dominion) | 4:14 | 326,251 | |
| Kenny Chesney - Dust on the Bottle (Live with David Lee Murphy) | 3:45 | 895,848 | |
| Kenny Chesney - Medley: The Joker / Three Little Birds (Live With Dave Matthews) (Audio) | 5:16 | 51,109 | |
| Kenny Chesney - I'm Alive (Live) (Audio) | 3:55 | 25,040 | |
| Kenny Chesney - American Kids (Live) (Audio) | 5:31 | 38,517 | |
| Kenny Chesney - Coastal (Live) (Audio) | 3:14 | 24,872 | |
| Kenny Chesney - Everybody Wants to Go to Heaven (Live With Zac Brown Band) (Audio) | 3:20 | 37,938 | |
| Kenny Chesney - There Goes My Life (Live) | 4:23 | 966,187 | |
| Kenny Chesney - Noise (Live) (Audio) | 3:40 | 12,051 | |
| Kenny Chesney - Hemingway's Whiskey (Live) (Audio) | 4:70 | 7,702 | |
| Kenny Chesney - I Go Back (Live) (Audio) | 5:58 | 49,375 | |
| Kenny Chesney - Down the Road (Live With Mac McAnally) (Audio) | 3:11 | 34,975 | |
| Kenny Chesney - No Shoes, No Shirt, No Problems (Live) (Audio) | 3:35 | 25,892 | |
| Kenny Chesney - Save It for a Rainy Day (Live With Old Dominion) (Audio) | 4:18 | 11,535 | |
| Kenny Chesney - Dust on the Bottle (Live With David Lee Murphy) (Audio) | 3:43 | 25,564 | |
| Kenny Chesney - Big Star (Live With Taylor Swift) (Audio) | 5:90 | 85,315 | |
| Kenny Chesney - Old Dominion - Guest on Live in No Shoes Nation | 2:58 | 4,722 | |
| Kenny Chesney - Flora-Bama (Live) (Audio) | 4:34 | 43,469 | |
| Kenny Chesney - Pirate Flag (Live) (Audio) | 4:24 | 6,244 | |
| Kenny Chesney - Summertime (Live) (Audio) | 4:30 | 29,789 | |
| Kenny Chesney - Happy on the Hey Now (A Song for Kristi) (Live) (Audio) | 5:54 | 28,401 | |
| Kenny Chesney - One Step Up (Live) (Audio) | 6:32 | 56,179 | |
| Kenny Chesney - When I See This Bar (Live With Eric Church) (Audio) | 9:14 | 120,823 | |
| Kenny Chesney - Boston (Live) (Audio) | 6:47 | 19,167 | |
| Kenny Chesney - Guitars and Tiki Bars (Live) (Audio) | 4:21 | 9,141 | |
| Kenny Chesney - Anything but Mine (Live) (Audio) | 6:50 | 214 | |
| Kenny Chesney - Out Last Night (Live) (Audio) | 4:11 | 396 | |
| Kenny Chesney - Old Blue Chair (Live) (Audio) | 3:38 | 434 | |
| Kenny Chesney - There Goes My Life (Live) (Audio) | 4:35 | 233 | |
| Kenny Chesney - Somewhere with You (Live) (Audio) | 4:31 | 201 | |
| Kenny Chesney - The Boys of Fall (Live) (Audio) | 6:53 | 282 | |
| Kenny Chesney - You and Tequila (Live With Grace Potter) (Audio) | 4:48 | 471 | |
| Kenny Chesney - Pirate Flag (Live) | 4:16 | 4,822 | |
| Kenny Chesney - Mac McAnally - Guest on Live in No Shoes Nation | 2:00 | 5,939 | |
| Kenny Chesney - Young (Live) (Audio) | 4:33 | 19,007 | |
| Kenny Chesney - All the Pretty Girls | 3:29 | 6,556,842 | |
| Kenny Chesney - Rich and Miserable | 6:90 | 886,660 | |
| Kenny Chesney - Bar at the End of the World (Audio) | 3:29 | 2,373,889 | |
| Kenny Chesney - Trip Around the Sun (Audio) | 2:56 | 177,054 | |
| Kenny Chesney - Some Town Somewhere (Audio) | 2:52 | 109,030 | |
| Kenny Chesney - Bucket (Audio) | 3:16 | 145,035 | |
| Kenny Chesney - Jesus and Elvis (Audio) | 4:90 | 103,173 | |
| Kenny Chesney - Coach (Audio) | 4:48 | 343,770 | |
| Kenny Chesney - All the Pretty Girls (Audio) | 3:35 | 1,329,028 | |
| Kenny Chesney - Winnebago (Audio) | 3:00 | 100,572 | |
| Kenny Chesney - Rich and Miserable (Lyric Video) | 3:32 | 584,226 | |
| Kenny Chesney - Setting the World On Fire | 3:47 | 12,483,264 | |
| Kenny Chesney - Setting the World On Fire (Audio) | 3:42 | 10,190,407 | |
| Kenny Chesney - Noise | 3:34 | 5,692,282 | |
| Kenny Chesney - Noise (Lyric Video) | 3:25 | 1,181,458 | |
| Kenny Chesney - No Shoes TV // Episode 18: Foxboro, MA | 4:50 | 30,843 | |
| Kenny Chesney - No Shoes TV // Episode 17: Detroit, MI | 4:40 | 17,283 | |
| Kenny Chesney - No Shoes TV // Episode 16: East Rutherford, NJ | 3:14 | 12,863 | |
| Kenny Chesney - No Shoes TV // Episode 15: Denver, CO | 3:30 | 10,512 | |
| Kenny Chesney - No Shoes TV // Episode 14: Kansas City, MO | 3:58 | 11,966 | |
| Kenny Chesney - No Shoes TV // Episode 13: The Rose Bowl | 4:60 | 11,974 | |
| Kenny Chesney - No Shoes TV // Episode 12: Minneapolis, MN | 4:60 | 13,224 | |
| Kenny Chesney - No Shoes TV // Episode 11: Philadelphia, PA | 3:24 | 9,321 | |
| Kenny Chesney - Save It for a Rainy Day | 3:50 | 17,613,601 | |
| Kenny Chesney - No Shoes TV // Episode 10: Seattle, WA | 3:32 | 12,410 | |
| Kenny Chesney - No Shoes TV // Episode 9: Green Bay, WI | 6:30 | 13,426 | |
| Kenny Chesney - No Shoes TV // Episode 8: Atlanta, GA | 4:12 | 9,986 | |
| Kenny Chesney - No Shoes TV // Episode 7: Chicago, IL | 4:54 | 15,834 | |
| Kenny Chesney - No Shoes TV // Episode 6: Pittsburgh, PA | 4:30 | 19,535 | |
| Kenny Chesney - No Shoes TV // Episode 5: Arlington, TX | 4:43 | 16,906 | |
| Kenny Chesney - No Shoes TV // Episode 4: Indianapolis, IN | 4:10 | 10,254 | |
| Kenny Chesney - No Shoes TV // Episode 3: Santa Clara, CA | 4:40 | 10,479 | |
| Kenny Chesney - No Shoes TV // Episode 2: Tortuga | 4:27 | 15,892 | |
| Kenny Chesney - No Shoes TV // Episode 1: Nashville, TN | 3:59 | 27,962 | |
| Kenny Chesney - Wild Child | 3:40 | 9,910,945 | 1 list |
| Kenny Chesney - Groundbreaker Award (2014 American Country Countdown Awards) | 2:32 | 45,647 | |
| Kenny Chesney - Christmas in Blue Chair Bay | 4:48 | 384,029 | |
| Kenny Chesney - Flora-Bama | 5:16 | 1,279,692 | 1 list |
| Kenny Chesney - Til It's Gone | 4:47 | 927,495 | |
| Kenny Chesney - American Kids - About the Song | 2:29 | 63,282 | |
| Kenny Chesney - The Big Revival Creative Process | 2:30 | 31,128 | |
| Kenny Chesney - Kenny's Year Off | 2:45 | 46,594 | |
| Kenny Chesney - Beer Can Chicken (Audio) | 4:90 | 157,604 | |
| Kenny Chesney - Don't It (Audio) | 3:18 | 184,947 | |
| Kenny Chesney - Drink It Up (Audio) | 2:49 | 241,488 | |
| Kenny Chesney - Til It's Gone (Audio) | 4:12 | 951,989 | |
| Kenny Chesney - Save It for a Rainy Day (Audio) | 3:40 | 425,425 | |
| Kenny Chesney - If This Bus Could Talk (Audio) | 4:55 | 98,014 | |
| Kenny Chesney - Rock Bottom (Audio) | 3:42 | 124,659 | |
| Kenny Chesney - Flora-Bama - About the Song | 2:54 | 32,556 | |
| Kenny Chesney - Drink It Up - About the Song | 1:39 | 22,395 | |
| Kenny Chesney - The Big Revival - About the Song | 2:31 | 14,624 | |
| Kenny Chesney - The Big Revival (Audio) | 3:14 | 291,834 | |
| Kenny Chesney - Flora-Bama (Audio) | 4:34 | 1,073,586 | |
| Kenny Chesney - American Kids | 3:23 | 14,248,564 | |
| Kenny Chesney - American Kids - Music Video Teaser Trailer | 0:25 | 76,624 | |
| Kenny Chesney - Spread the Love ft. The Wailers, Elan | 4:52 | 197,271 | |
| Kenny Chesney - When I See This Bar | 6:10 | 1,980,892 | |
| Kenny Chesney - Pirate Flag | 3:46 | 8,147,741 | |
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