Prior to working on their fifth album, Fountains of Wayne had done acoustic tours that would eventually influence the direction they took for the record. According to guitarist Jody Porter, "It’s a little bit more introspective and not as loud of a record as the last two. I think that came from the fact that we started last year doing acoustic-based tours because we didn’t have a record out. We wanted to get back out on tour and did it stripped-down. Overall it’s not as brash or guitar-heavy."^[2]

Having taken a back seat to bassist Adam Schlesinger during the writing and recording of previous album Traffic and Weather due to personal health issues, lead singer and co-songwriter Chris Collingwood became more involved this time around. Collingwood stated, "When we made the last record, I was not doing well in a lot of different ways, drunk a lot of the time. I didn’t contribute a whole lot to the last record, and I think we settled into a situation where Adam was taking control of a lot of things. I only wrote three songs on the previous Fountains of Wayne record, so when this one came along I had a lot more to bring. It was just a matter of bringing everything back into balance, and there was a lot of fighting about it."^[3]

During the making of the album, the relationship between Collingwood and Schlesinger had deteriorated to the point where they had to stop working and seek professional help. According to Collingwood in 2016, "Adam and I just fought constantly making that record. We stopped making that record in the middle of making that record to try to work out a whole bunch of things that were going on between us. We saw a psychiatrist and tried to work things out." In the end, they agreed to finish the album and tour behind it, before going their separate ways.^[4]

Jody Rosen, writing in Rolling Stone, had high praise for the album, and said the storytelling was "sharp" and the guitar hooks "crunchy," with the overall direction of the album darker than previous outings.^[6] Jill Menze of Billboard called the album "excellent", describing it as "a new minimal sound with a poppy, folk-leaning flair."^[7]

Spin gave the album a score of 7/10. Critic Stacey Anderson writes, "'Sky' eschews the occasional decade-hopscotching of 2007's Traffic and Weather, reaching a new, raw sincerity and cohesiveness: 'Hate to See You Like This' is an anxious entreaty to a depressed girlfriend exquisitely framed by a dramatic backdrop of electric and acoustic guitars."^[5]

Chris Willman of Reuters also strongly recommended the album, but cautioned listeners: "It may be a moot point that the new effort is FOW's least airplay-friendly, since neither radio nor MTV would likely play this kind of stuff anymore even if the group did manage to come up with a 'Stacy's Mom II.' But fans who prefer an abundance of power in their power-pop may worry about what the lopsided spunk-to-sadness ratio portends for the beloved band."^[8] He called "Action Hero" the best track on the album.^[8] Matt Diehl of the Los Angeles Times lauded the album. "Sky teems with immaculate power pop, spanning jangling Beatlesque rockers like “The Summer Place” through the bittersweet balladry of “I Hate to See You Like This”... It's a remarkably consistent album, full of snappy arrangements, surprising chord changes and tasteful instrumentation, but Collingwood's voice embodies its true appeal," he wrote. "That storytelling depth raises Fountains of Wayne to the apex of their genre, imparting a wry, cynical worldview that lingers well after the snap, crackle and fizz subsides."^[9]

Allison Stewart, reviewing the album for The Washington Post, was more mixed in her assessment. She said, "Sky, with its carefully detailed stories of suburban schlubs, feuding bar owners and luckless Acela riders, hits all the right notes, but something feels off. Slow and sentimental, more wistful than droll, Sky is as interested in loping, acoustic country-folk songs as it is in vigorous pop. If the band’s last album, 2007’s Traffic and Weather, was a Cars homage, Sky is an unofficial tribute to the Jayhawks. It’s not a misfire — one of its gentlest songs, “A Road Song,” is also one of the band's all-time finest — but those who expect the usual gimlet-eyed power pop (that is to say, most everyone) will be left wondering where it went."^[10]

In the United Kingdom, The Guardian critic Michael Hann described the album's music as "a more sedate sound, the dominant texture being acoustic guitar overlaid with muted electrics."^[11] But the sound was a good one for the band, he said, and named the final track, "Cemetery Guns," the album's best for being "beautifully arranged and written with calm understatement".^[11]

America covered "A Road Song" on their 2011 Back Pages album.^[12][13]

All songs written by Chris Collingwood and Adam Schlesinger, except where noted.

Fountains of Wayne

• Chris Collingwood - lead vocals, rhythm guitar, keyboards, production
• Jody Porter - lead guitar, backing vocals
• Adam Schlesinger - bass, rhythm guitar, keyboards, backing vocals, production
• Brian Young - drums, percussion

Additional Musicians

• Ronnie Buttacavoli - trumpet
• Garo Yellin - cello

Technical Personnel

• Arjun Agerwala - engineer
• Violeta Alvarez - photography
• Rudyard Lee Cullers - engineer
• George Marino - mastering
• Atsuo Matsumoto - assistant engineer
• Mike Nesci - assistant engineer
• Geoff Sanoff - engineer
• Adam Tilzer - assistant engineer

• Sky Full of Holes (deluxe) at YouTube (streamed copy where licensed)
• Sky Full of Holes at Metacritic