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Kenny Chesney's 10 Best Songs: Critic's Picks

Kenny Chesney photographed on Aug. 25, 2014 in Nashville.
Austin Hargrave

Kenny Chesney photographed on Aug. 25, 2014 in Nashville. 

When Kenny Chesney made his chart debut in 1993 with “Whatever It Takes,” few in the industry could have ever guessed that fans were witnessing the beginning of one of the most consistent careers in the history of Country Music. Along the way, he has also tallied multiple wins from the CMA and the ACM for Entertainer of the Year, as his concerts have become more events than merely a show.

When you look at the career-defining moments of Chesney’s career, one will find some of the biggest party songs in the format’s history – but there’s a lot more to Kenny Chesney than merely a good time. The East Tennessee native has given the genre some of the best ballad moments of the past two decades – many of which make this list of the 10 best Kenny Chesney songs to date.

Best Songs: Alabama | Alan Jackson | Blake Shelton | Brad Paisley | Carrie Underwood | Chris Stapleton | Dierks Bentley | Dixie Chicks | Dolly Parton | Eric Church | Garth Brooks | George Jones | George Strait | Jason Aldean | Johnny Cash | John Denver | Keith Urban | Kenny Rogers | Lady Antebellum | Miranda Lambert | Rascal Flatts | Reba McEntire | Shania Twain | Thomas Rhett | Tim McGraw | Toby Keith | Willie Nelson | Zac Brown Band

10. Kenny Chesney, "Somewhere With You"

One of the first major hits from Nashville tunesmith Shane McAnally, this was perhaps one of the singer’s more sensual tracks of his career. It was culled from his 2010 disc Hemingway’s Whiskey, which may very well be the best album of his two-decade plus career. The cut also was the only of Chesney’s hits to cross over to the Adult Contemporary chart, peaking at No. 15.

9. Kenny Chesney, "The Boys Of Fall"

Also a hit from Hemingway’s Whiskey, this one struck a chord with listeners in grass-roots America. Whether it be the Bulldogs of Hickman County High School in Centerville, TN or the Bacon County Raiders in Alma, Georgia, every town has a special love affair with the football games that take place on Friday nights in the Autumn. Chesney had his own gridiron memories to draw from in this ballad from Casey Beathard -- whose son C.J. was recently drafted by San Francisco -- and Dave Turnbull, making for one of his most varied number one hits.

8. Kenny Chesney, "Living In Fast Forward"

In interviews, the singer has talked about the fact that he definitely identified with these lyrics from David Lee Murphy and Rivers Rutherford, admitting that once he started to hit his stride as a performer, the pace was a lot faster than he could have ever imagined. The video for this song gave fans a rare behind-the-scenes look at life on the road for the four-time CMA Entertainer of the Year.

7. Kenny Chesney, "No Shoes, No Shirt, No Problems"

Who doesn’t dream of a place where there's no boss, no clock, no stress, and no dress code? The singer touched a nerve with listeners with this light-hearted tropical number, which remains a mainstay of his stage show.

6. Kenny Chesney, "Who You’d Be Today"

The story of the impact of losing someone close to you was felt by many listeners of this blockbuster hit from the fall of 2005. The singer balanced the obvious sadness of the situation with a hope that he would see that person again -- in another lifetime. Whether it be a spouse, a child, parent, or a friend, this song remains a special Kenny Chesney song in his catalog.

5. Kenny Chesney, "The Good Stuff"

The longest-lasting of Chesney’s chart-toppers, this song spent seven weeks at the pinnacle of Billboard's Country Songs chart in the summer of 2002. In this song, the singer meets a bartender who changes his life, as he shares memories of his late wife. Though Chesney was the performer in the song, he did a superb job in letting the bartender be the central character, talking about the truly "Good Stuff" in life.

4. Kenny Chesney, "A Lot Of Things Different"

Chesney turned to Country Music Hall of Fame member Bill Anderson and Dean Dillon for this sobering portrait of a man looking back on his life, and realizing that he had more regrets about his loved ones than not. It was perhaps the most brooding performance of his career, and one that struck a chord with many who had been in that situation at one time or another.

3. Kenny Chesney, "How Forever Feels"

This Kenny Chesney song almost became a hit by another artist: Chesney’s pal Tim McGraw originally cut the song, but decided not to release it. Though the song did speak of popping the question -- the ultimate commitment -- this song was light-hearted and fun, with its mention of beach balls, cruising down the interstate, and Jimmy Buffett. Who could resist a song like that? This one helped to move Chesney’s career into the fast lane upon its release back in the summer months of 1999.

2. Kenny Chesney, "There Goes My Life"

A brilliant composition from Wendell Mobley and Neil Thrasher about a man thrust into the role of fatherhood before he intended to be. Earlier in his career, the singer might not have been able to pull off the performance that he did in the fall of 2003, but by this time, he was one of the top interpreters in the format. The magic of this song is how the phrase 'T"here Goes My Life" changes significance with the passing of a few years. It seems that it wasn’t just the daughter in this song that grew up -- her father learned a few of life’s lessons, as well.

1. Kenny Chesney, "Don’t Blink"

Perhaps the biggest hit record ever in country music to center around an interview, Chesney worked his magic on this story of a man who becomes inspired by the story of a man celebrating his 102nd birthday. The title of the song comes when the interviewer asks the man his advice about the secret of life. Life does go by too fast, and this song captured that emotion -- and that speed -- in a thought-provoking manner.

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