Kenny Chesney's stardom snuck up quietly. He had a string of modest successes during the late '90s, but he never made crossover waves until 2002's No Shoes, No Shirt, No Problems, when his steady touring and steady shift toward adult pop paid off with his first number one album, but that was nothing compared to the stunning first-week sales of its successor, When the Sun Goes Down, which also debuted at number one to the very healthy sales of over 550,000. Chesney had clearly filled a void, one left by the diminished presence of Garth Brooks -- a singer who blurred the lines between '70s mainstream pop/rock and contemporary country, a singer who made adult-oriented music about everyday things. At one point Chesney was aligned with neo-traditionalist country singers, but by When the Sun Goes Down, he had left that far behind, using country as mere flavoring on an album whose heart and soul is firmly within the tradition of '70s singer/songwriters. Where Garth Brooks merely covered Billy Joel (and a latter-day tune at that), Chesney drops references to Joel, James Taylor, and Steve Miller, while covering Dave Loggins' "Please Come to Boston." So, it's not an entire surprise that he favors ballads, usually the anthemic type designed to fill out arenas, and when he does turn the tempo up, it's still laid-back, in the fashion of Jimmy Buffett, as on the appealing duet with Uncle Kracker on the title track. Chesney often refers to living in the Islands (the Caribbean Islands, that is) in his nice song-by-song liner notes and every one of the many pictures in the disc's booklet features him on an island, but this is hardly a tropical album -- it's a record for middle America, for soccer moms and sentimental NASCAR dads, for those who opted out of the corporate rat race in favor of a loving relationship, as the character in "The Woman With You" did. It's for a generation raised on rock but living on country, people who like to reminiscence but are perfectly happy in their domestic life. If this sounds condescending, it's not meant that way; it's an apt description of an album that captures a time, place, and mindset, the way Sgt. Pepper provided the soundtrack to the Summer of Love. Peppered with references to Abercrombie & Fitch, American Express, dogs named Bocephus, old frat brothers, and forgotten sorority sisters, all set to a canny blend of state-of-the-art country, '70s sensibility, and '80s production (check out muted delayed rhythm guitar on "I Go Back"), it's a thoroughly modern mature-pop album. Like Shania Twain's Come On Over or Up!, this is music that's meant to have universal appeal, but it's far subtler in its approach, not least because it's delivered not by a diva, but a humble guy with a likeable, friendly voice. It may not be country, but that doesn't matter; When the Sun Goes Down is winning, sturdy mainstream pop, and after hearing it, it's easy to see why so many listeners now take Chesney to heart -- he's writing the soundtrack to their lives.
AllMusic Review by Stephen Thomas Erlewine