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The music was recorded at Toronto, Ontario's Church of the Holy Trinity on 27 November 1987, with the band circled around a single microphone. The album includes a mixture of original material by the band and covers of classic folk, rock and country songs, including the band's most famous single, a cover of The Velvet Underground's "Sweet Jane", based on the version found on 1969: The Velvet Underground Live, rather than the later studio version from Loaded. Also included is "Blue Moon Revisited (Song for Elvis)", which is both a cover and an original, combining a new song by the band with the pop standard "Blue Moon".
The album was released in early 1988 on Latent Records in Canada, and rereleased worldwide later in the year on RCA Records. "Working on a Building" and "Blue Moon Revisited (Song for Elvis)" did not appear on the Latent Records release. "Blue Moon Revisited" was originally released on It Came from Canada, Vol. 4, a compilation of Canadian independent bands.
In 2007 the album was performed live in its entirety as part of the All Tomorrow's Parties-curated Don't Look Back series. Also in that year, the band returned to The Church of the Holy Trinity to record a new version of the Trinity Session with guest musicians Natalie Merchant, Vic Chesnutt and Ryan Adams. This new set of recordings was released as Trinity Revisited, to commemorate the 20th anniversary of The Trinity Session.
According to website Acclaimed Music, the album is the 893rd most acclaimed album ever released. It was named the 42nd best album of the 1980s by Pitchfork Media in 2002 and the 36th best Canadian album by Chart in 2000. It was also ranked 62nd in Bob Mersereau's book The Top 100 Canadian Albums in 2007.
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