Don’t be fooled by his crazy love life and history of heroin addiction — James Taylor was born a square, and he’ll die one. He first encountered music as child cellist and took up the guitar as a pre-teen, before attending boarding school at Milton Academy in Massachusetts (he dropped out and returned to public school midway through his junior year). He also summered — that squarest of all verbs — on Martha’s Vineyard. But what really makes Taylor uncool is his music, a tenderized version of folk-rock whose best example is the schlocky “You’ve Got a Friend.” Hell, even his attempt at darkness and depth, “Fire and Rain,” sounds hopelessly gentle.
California’s pre-punk ’70s music scene was a strange place — basically, everyone was snarfing up kilos of drugs and sleeping with everyone else, and the music that came out of this debauchery was… soft rock. Stevie Nicks’ eternal, dark-mystic badass status and the pleasantly bizarre Tusk save Fleetwood Mac from inclusion on this list, but The Eagles? They gifted us with the painfully sweet “Hotel California,” which spends six whole minutes reminding us how difficult it is to be a rock star staying at fancy resort (probably the Chateau Marmont).
Hall & Oates
There is soft rock, and then there’s Yacht Rock, the hilarious web series that cast some of the wimpiest rockers of the ’70s and ’80s as over-the-top characters. While Kenny Loggins, Toto, Steely Dan, and (of course) The Eagles are all featured, the show’s breakout stars were Hall & Oates, due largely to John Oates’s portrayal as an abusive tyrant, controlling Daryl Hall through violence. Yacht Rock‘s popularity catalyzed a strange, semi-ironic Hall & Oates comeback, earning them a whole new audience of hipsters — and reminding the rest of us that few rock hits are quite as square as “I Can’t Go for That (No Can Do)” or “Maneater.”
Sting’s career has gone something like this: First, he was a punk-ish 20-something who founded a New Wave band called The Police, who actually did some interesting fusing of reggae and rock. But the group got softer and softer with each new album, and Sting sung in an irritating-to-some, magnetic-to-others falsetto most of the time. In the mid-’80s, he went solo, embracing jazz and contributing vocals to fellow square act Dire Straits’ “Money for Nothing.” By the ’90s, he was giving us adult-contemporary crap like “Fields of Gold.” Now he is some kind of New Age yogi who may or may not be into Tantric sex.
Phil Collins is in the running for one of the squarest-looking dudes in rock — but that alone wouldn’t qualify for this list. Even his time in the long-running prog-rock ensemble Genesis (which is certainly pretty dorky) and history of Disney soundtrack work don’t clinch it. No, what earns Collins his spot is his solo career, full of often nonsensical, feel-good hits like “Sussudio,” “A Groovy Kind of Love,” and “Against All Odds (Take a Look at Me Now).” If pleated khaki pants had a soundtrack, it would be Phil Collins.
Huey Lewis and the News
Huey Lewis wouldn’t even think of arguing if you accused him of being square — he labeled himself with the epithet back in ’87, with the hit “Hip to Be Square.” The song is such a yuppie anthem that it earned a place of honor in Bret Easton Ellis’s American Psycho, with finance exec/serial killer Patrick Bateman pointing out that the song is “not just about the pleasures of conformity, and the importance of trends, it’s also a personal statement about the band itself.” We couldn’t agree more.
When one of your hardest songs is the wistful “Summer of ’69,” then you’re probably pretty square. We tend to think of Bryan Adams as a less-talented, latter-day Rod Stewart (whose early work and mod past saved him from inclusion on this list) — that raspy-voiced crooner whose entire purpose seems to be to soundtrack suburban, middle-aged lovemaking. Why else would anyone ever queue up “Have You Ever Really Loved a Woman?” or “(Everything I Do) I Do It for You”?
Hootie & the Blowfish
We have nothing against Hootie & the Blowfish — they seem like the kind of nice guys you might meet hanging out nervously at the edges of a frat party. Their sweet, lighthearted love songs (“Hold My Hand,” “Only Wanna Be with You,” and even the break-up ballad “Let Her Cry”) are just the kind of tunes we could see that guy strumming on the quad, acoustic guitar slung around his neck. Alas, that isn’t exactly the profile we tend to look for in our rock stars.
Remember how confused you were the first time you heard Matchbox 20’s Rob Thomas doing the vocals for that Santana song, “Smooth”? That cognitive dissonance is what happens when the truly cool and the seriously square come together. We always got the feeling that Thomas and his band desperately wanted us to think they were hip, posing moodily and constantly referring to their tumultuous emotional states in songs. And yet, what they end up with is stuff like “3 A.M.” — an anthem of angst that’s more at home in the mall than at the bar. Also? About a year ago, Thomas guested on none other than Daryl Hall’s internet concert series, where he played not only his own hits but also some Hall & Oates tracks.
You wrote “Yellow.” You married Gwyneth Paltrow. You will never be Radiohead. Conversation over.