Following the release of their fifth studio album How I Spent My Summer Vacation (2001), bassist Bryan Kienlen ended an intimate relationship and wrote new material as a result of it.

Recording took place at Lakeview Farms, North Brookfield, Massachusetts, and Water Music, Hoboken, New Jersey, with John Seymour as the main producer, and Kienlen and guitarist Pete Steinkopf as co-producers.

Anchors Aweigh is a pop-punk and punk-rock album that has a darker sound than its predecessor; the band experimented with melodies and rhythms during the writing stage.

[1] It was promoted with an extensive tour with Hot Water Music; in 2002, the band released the compilation album The Bad, the Worse, and the Out of Print and a split with Anti-Flag.

[7] Sessions occurred in January 2003, mainly at Lakeview Farms Studios in North Brookfield, Massachusetts, with assistant engineer Chris Evans.

[7] The music of Anchors Aweigh has been described as punk rock[10][11] and pop-punk;[12] it retains the atmosphere of How I Spent My Summer Vacation and moves it into darker territory.

[16] The album opens with the fast-tempo track "Apartment 5F" whose loud guitar work leads into the slow, mellow intro of "Kids and Heroes".

"Sing Along Forever" exemplifies the album's overall tone; according to Nick Madsen of IGN, it is "An energized, punk rock song at heart ...

[28] After appearing at Hellfest 2K3 in Syracuse, New York, and Krazy Fest 6 in Louisville, Kentucky, The Bouncing Souls embarked on the Punk-O-Rama tour in Canada with Hot Water Music, the Forgotten, and Worthless United.

[23] According to Derek Scancarelli of Forbes, the artwork, which was made by Kienlen, symbolizes "a ship sailing off into the dark distance, marking the end of a chapter".

[47] The Bouncing Souls toured the US East Coast in April 2005 with Let It Burn, The Loved Ones, and The Explosion, and appeared at The Bamboozle festival.

[13] AllMusic reviewer Robert L. Doerschuk wrote the band sound "tight; McDermott in particular earns his stripes as a punk virtuoso in the artful tempo manipulations" in tracks such as 'Apartment 5F' and 'Blind Date' ".

[50] According to Rolling Stone writer John D. Luerssen, the band were showing "more heart than ever", and when the fans "pick up this stellar disc, that very void will be filled".

[18] Punknews.org founder Aubin Paul said Anchors Aweigh displays a "new side of the Souls" though "at its core, it's still a bunch of friends who clearly play this music because it moves them".

[14] CMJ New Music Monthly's Chad Swiatecki wrote the album is a "surprise ... sport[ing] songs with sharp claws that dig in like never before".

[52] The Free Lance-Star writer Craig Graziano criticized the band for attempting to retread How I Spent My Summer Vacation, and added; "[n]ot much musical ground is broken".

[20] Grady Gadbow of Lollipop Magazine said the album's sole "melodic strength" is its "call and response vocals and ubiquitous whoa-oh-ohs", and added; "those skills alone do not make a record rock.