Black Sails in the Sunset was released on May 18, 1999 through Nitro Records. It is the first album to feature guitarist Jade Puget as a permanent member, thus making it the first album the current line-up of the band truly collaborated. The album did not peak on any mainstream Billboard charts, however, it managed to peak at #6 on the Top Heatseekers (Pacific) chart.
Black Sails in the Sunset was received well by critics. Alternative Press gave the album four-and-a-half out of five stars, commenting that "with new guitarist Jade Puget adding a sense of brooding, thespian eloquence to the disc's shadowy post-hardcore, AFI all but reinvented themselves," and "With longer, deeper, richer, more complex compositions than they've ever attempted before, Black Sails tackles everything from brooding hardcore ... to shimmering balladry..." The publication also went as far as to say that Black Sails is "their first epic."
Decoy Music reviewer Aaron Yarborough praised Davey Havok's lyrical contribution to the album, commending his efforts to "find himself," saying "the way he expresses how he feels is pure poetry." Yarborough concluded by recommending the album to "anyone who likes heavy punk."
All tracks recorded during the Black Sails sessions unless otherwise noted.
"Lower It" is featured as track 7 on the vinyl edition of the album. It was eventually re-released on the AFI retrospective compilation.
"Who Knew?" is featured on the Black Sails EP. It is released as the hidden track in the place of "Midnight Sun" on the Japanese edition of the album.
"Transference" is featured on the No Time to Kill compilation. It is the only song by AFI to contain lead vocals by Hunter Burgan, which can be heard during the chorus of the song.
"The Chicken Song" is featured as a hidden track on the No Time to Kill compilation. It features Burgan playing the piano and Havok and Puget sharing lead vocal duties. The band often jokingly deny the existence of the song.
"Weight of Words" was known to be recorded during the Black Sails sessions, but has yet to be released. However, the AFI retrospective compilation is often called 'The Weight of Words' on online shopping sites.
On the side of the album is a hidden message, reading 'Beyond And To All Time I Stand'. This is a lyric from the album's hidden track, Midnight Sun.
The track "Midnight Sun" was inspired by the poem De Profundis Clamavi by Charles Baudelaire. Havok can be heard reciting parts of the poem in the song's bridge.
"Porphyria Cutanea Tarda" is listed as "Porphyria" on the back cover of the album, as it was listed on Black Sails EP.
Jade Puget has stated that "Malleus Maleficarum" was the first song he wrote as part of AFI.
The opening track, "Strength Through Wounding" contains a repeated chant, "Through our bleeding, we are one," which fans often chant during concerts while waiting for the band to come onstage, or between songs.
Dexter Holland, the vocalist for The Offspring, is featured in the tracks 'Clove Smoke Catharsis' and 'The Prayer Position'. Similarly, Davey Havok did backing vocals for The Offspring's Ixnay on the Hombre album two years prior.
"God Called In Sick Today" has been played at nearly every AFI show since its release, usually as the last song of the set. An exception is the I Heard a Voice – Live from Long Beach Arena show, in which they concluded with "Miss Murder" after performing "God Called In Sick Today".
Most of the lyrics are properly capitalized, but "Clove Smoke Catharsis" and "The Last Kiss" are printed completely lowercase for unknown reasons.