100 Best Songs of the ’80s (#100-91)

These are the top 100 songs of the 1980s.

96: Lyle Lovett – If I Had a Boat (1987)

On its surface, the basic premise of the song reads as rather silly: Lovett wishes he had a boat and a pony, the latter of which he would ride on the former. There’s a bit about Roy Rogers and Trigger, Tonto and the Lone Ranger, and, in a strange twist, an impressionistic verse in which he becomes “like lightning.” In all, it’s a brief, sweet song built around Lovett’s delicately finger-picked guitar line and Paul Franklin’s intermittent pedal steel swells. By no means a hit—it reached number 66 on the singles chart—it did manage to spawn an equally minimalist black and white video in which Lovett merely paces in and out of frame in what appears to be an abandoned house, playing and singing the song in between stifling his laughter.

But the video itself offers another take on the lyrics, showing Lovett both alone and free to do as he chooses, not confined by the camera’s lens. This idea then lends the song greater depth, being one not of a childhood fantasy, so much as the struggle to hold on to said childhood fantasy in the face of increasingly less and less personal freedoms as one enters fully into adulthood. In the first verse, Lovett as seeking freedom from society (“I’d go out on the ocean”) with both his boat and pony. The move to Roy Rogers in the second projects the need to not be tied down to anyone or anything (“I couldn’t bring myself to marrying old Dale”). The third verse is perhaps the song’s most profound as Tonto, rather than exploring life’s what-ifs, takes matters into his own hands and ditches the Lone Ranger, by whom he had been knowingly used.

The simple fingerpicked guitar line remains largely unaccompanied throughout, the ghostly pedal steel swooping in and out occasionally before things pick up momentarily during the solo section. Yet even that is less an exercise in instrumental virtuosity or prowess and more of an understated disassembly of the track’s singsong melody. Ending as it does to allow Lovett to once again take control of the song with just his guitar and voice plays into the idea of personal freedoms and lack of social attachment or an existence predicated on a reliance on anyone or anything else but the trusty sidekick, in this case his guitar. – John Paul

95: Tears for Fears – Head Over Heels (1985)

Perhaps not quite as iconic or instantly recognizable as “Shout” or “Everybody Wants to Rule the World,” but “Head Over Heels” is nevertheless an indelible piece of ’80s pop. Newer audiences might know it as the simplistic love song director Richard Kelly perverted into a self-reflexive shorthand for teenage oddity in Donnie Darko, but there’s something enduring about a track this sweet and effective. Roland Orzabal’s vocal delivery, with its woeful lilt and soaring sense of yearning, sounds like a John Hughes screenplay compressed into a .wav file.

The first verse offers just the right bittersweet mixture of angst and nostalgia, functioning like the unintentional soundtrack to every adolescence ever. But the second verse gives way to something more abstract, something stranger and more nuanced. Orzabal’s lyrics transform from a diarist’s bad Valentine’s Day to a stream of consciousness screed about the environment, familial tethers and the prison of masculinity.

On Songs from the Big Chair, “Head Over Heels” is buttressed by the song “Broken,” first as a prolonged preamble, then as a live reprise at the tail end of the track. There’s a radio edit that trims the cut down without this parenthetical framing, but the more you listen to both versions, the track is stronger and more effective within the context of the album. It re-contextualizes this comparatively straightforward love song as a rose-colored lens interlude between two more chaotic pieces of synth-pop. It makes the segue into that big, halftime chorus just as sweeping as the initial sugar-rush high of falling for someone new before plunging back into the looser, more uncertain aftermath of unrequited love. – Dom Griffin

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