If the lyrics of any song perfectly match the circumstances surrounding that song's place in pop history, that song would have to be If We Never Meet Again, written by Jules Shear, who may perhaps be best known for writing If She Knew What She Wants, which was a hit for the Bangles. In 1988, his band Reckless Sleepers released the album "Big Boss Sounds", which included If We Never Meet Again, an unabashedly pretty (and witty and wise) song about a lost love. Despite its pop perfection, the song was relegated to college radio playlists, and never broke the U.S. top 100 (it hit #89 in Canada according to the wikiwakiwoo). The song was subsequently covered by Philly band Tommy Conway and the Young Rumblers, and hit #48 on the Billboard charts). Perhaps the best known version of the song is Roger McGuinn's cover, on his 1990 "Back from Rio" album.
Youtube has a tragically incomplete video of the original version of the song. The complete video of the Young Rumblers' version (which I had never heard until researching this post) is available on Youtube:
The Roger McGuinn version is also available on Youtube, accompanied by a fan video:
It's hard to conceive how this song failed to be a major hit, which passed into "Standards" status. Yep, this is the one that got away- as wistful as a lost love, and as wise as an older, more mature individual contemplating what might have been.
Note: This post wasn't inspired by a fit of melancholy... it was ultimately inspired by hearing the Byrds' cover of Chimes of Freedom on a local radio station's fantastic "Ten at Ten" feature (tagline: Ten great songs from one great year), which had me busting out the Roger McGuinn.