- Black Sheep Hit: He has three typical modes: beachy Jimmy Buffett-esque tunes, introspective acoustic ballads, or arena rock. His two biggest hits, "The Good Stuff" and "There Goes My Life", are none of the above. (They're still ballads, but in a markedly different and more mainstream style from his usual ballads such as "Down the Road" or "You and Tequila".)
- Breakthrough Hit: "She's Got It All" (1997) was his first #1 on Billboard and the song that helped kick-start his career. A couple years later, "How Forever Feels" pushed him from rapidly-ascending second-tier to A-lister.
- Chart Displacement: While many of his #1 hits have been forgotten, "She Thinks My Tractor's Sexy" and "I Go Back" remain among his most popular with peaks of #11 and #2. His version of Mac McAnally's 1990 hit "Back Where I Come From" appears to have eclipsed the original, even though Mac's version was a single (reaching #14 in 1990) and Kenny's was not. This is due to Chesney's being a longtime staple of his concerts, and a live version appearing on his first Greatest Hits Album.
- Follow Up Failure: Occurred with the singles off Songs for the Saints in 2018: lead single "Get Along" went to #1 with ease, but the followup "Better Boat" stalled at #24, snapping a 51-song streak of Top 20 hits and accounting for his worst-perfoming single since 1998.
- Production Posse: Since Everywhere We Go, he has been produced by Buddy Cannon. He has also included guitarist Kenny Greenberg on nearly every album released in the 21st century, and nearly all of his music videos since "Young" have been directed by Shaun Silva.
- What Could Have Been: He was scheduled to film the video for the re-release of "The Tin Man" at the World Trade Center on September 11, 2001, but the shoot was held up due to a delay in shipping the equipment.
- Working Title: Cosmic Hallelujah was originally supposed to be titled Some Town Somewhere.
Trivia / Kenny Chesney