Originally "Enjoy the Struggle" was scheduled to be released as the lead single, however there was a change of mind and the band decided this song would be a better choice. Vocalist Andy Cairns told entertainnment.ie: "I think what originally happened was that one video company really loved 'Enjoy The Struggle', so that was going to be the single but then he buggered off to LA to work on something else. The new company that we were working with, a bunch of young lads from Manchester, really liked 'Crooked Timber.' We don't really mind, we're not trying to get into the top 40 with it. It's just something to have out there and to let people know what the band is about. I'd be happy with any of the tracks though, but maybe the 10 minute long 'Magic Mountain' might be pushing it a little!"
Cairns explained the album title to entertainnment.ie: "It's from Immanuel Kant, the (18th century German) philosopher. He said, 'from the crooked timber of humanity, no straight thing was ever made.' I found that quote indirectly from doing a little research on Samuel Beckett, because I like Samuel Beckett. We needed an album title and we didn't have anything at that point. We liked Crooked Timber but didn't know if we wanted to go with a title track. I like it though, I find [the quote] kind of life-affirming. It's almost like saying 'yeah, everyone is different but you make the most of what you're given.'"
The lyrics for "Mary, Did You Know?" were written by Christian singer and comedian Mark Lowry, after his pastor asked him to write a Christmas musical for their church. Southern gospel musician Buddy Greene later added music to his words.
Geffen Records made history on June 27, 1994 when Aerosmith's "Head First" became the first major label song made available for exclusive digital download. Download speeds at the time were so slow it took around 75 minutes to download the track.