In an interview with The Boot, Chesney explained the reasoning behind the title of his new release, citing the influence of Guy Clark, saying "I was sitting in my truck and a friend had given me Guy's album, which had just come out. It's a song that talks about living life to its fullest, being a man about your responsibilities and not compromising. As soon as I heard it, I knew I had to cut it -- and call the album that -- because it says everything about the way you live your life, and what life can be if you refuse to buy into limits, which, as someone who's read all his books, is everything Hemingway's novels revolved around."
In a CMT blog, Chesney also commented saying that he wanted the album to be "something more " than its predecessor, Lucky Old Sun: "I came to town to write songs, to make records, to create something that spoke about how I lived, and the people who I knew who were just like me and my friends lived."
The album debuted at number one on the U.S. Billboard 200, selling 183,000 copies in its first week of release. The release is his sixth number one album, thus ranking him second among country acts with the most number one albums, only behind Garth Brooks. In its second week of release, the album dropped to number two on the Billboard 200, selling 65,000 copies. In its third week of release it fell to number six on the Billboard 200, selling 40,000 copies. In its fourth week of release, the album fell to number thirteen on the Billboard 200 selling 26,126 copies. As of the chart dated July 2, 2011, the album has sold 850,706 copies in the US. As of 9/23/2011 it has been certified platinum by the RIAA.
Upon its release, Hemingway’s Whiskey received generally positive reviews from most music critics. At Metacritic, which assigns a normalized rating out of 100 to reviews from mainstream critics, the album received an average score of 67, based on 6 reviews, which indicates "generally favorable reviews". Jon Caramanica with The New York Times referred to the album as "darker" than his previous work, saying "on Hemingway’s Whiskey, though, his voice sounds smoother and deeper than usual, and he’s using it to more potent effect." He also preferred Chesney's version of the title track over Guy Clark's, saying "His version of the title track is of course far cleaner than Guy Clark’s, whose original take on it was practically withering on the microphone, but Mr. Chesney sounds studious and earnest." Matt Bjorke with Roughstock gave it a four-star rating, saying "Hemingway’s Whiskey is a record that finds Kenny Chesney feeling recharged. It’s a record that runs the gamut of human emotion and paints stories the way Hemingway’s novels did."Stephen Thomas Erlewine with Allmusic referred to the album as "burnished and classy" and admired the amount of 'slow' material on the album.American Songwriter critic Rick Moore gave it a four star rating. Calling it "a solid effort", he commented on the songwriting of the album, saying it "pays homage to Nashville’s songwriting community". At Rolling Stone, Jody Rosen found that "Chesney serves up the usual carpe diem anthems", however he noted that "when the mood turns serious, he slips: He can't muster the gravitas to pull off the title track, a maudlin tribute to Ernest Hemingway." In addition, Rosen concluded with "as long as the weather's sunny and the blender's whirring, Chesney's fine company." Robert Silva of About.com called it a "solid effort". At USA Today, Brian Mansfield proclaimed the effort to be "finely aged country".
Bill Friskics-Warren with The Washington Post called it "his most stylistically wide-ranging [album] to date" and recommended the title track and "Small Y'all" as the best on the album. Blake Boldt with The 9513 gave it a 3½ out of 5 star rating; he called Chesney "the hillbilly king of the Caribbean" and said "with [the album] he maintains that image and proves that he can still let loose occasionally." Mario Tarradell with The Dallas Morning News called it his "first exceptionally good CD since 2002's No Shoes, No Shirt, No Problems. Greg Victor with Parcbench called it his "first extraordinary album since No Shoes, No Shirt, No Problems" He called the tracks "a little more grown-up than usual", and gave it a 3½ out of 5 star rating. Stuart Munro with The Boston Globe called it "another well-wrought articulation of Chesney’s musical world" but also noted that "it isn’t all that far from where he’s been since 2002’s No Shoes, No Shirt, No Problems." Jessica Phillips with Country Weekly gave it 3½ out of 5 stars, and noted that his decision to take the past year of touring off "paid off with a more cohesive collection of songs that are at once universal yet obviously personal." She also called his take on the track "Small Y’all" "easily the most traditionally country tune Kenny has recorded during the past few years."