25 Boys Do Cry
Beginning with the Cure’s first B-side, “10.15 Saturday Night,” which finds its narrator sitting home crying, waiting for a girl to call, Smith has made a fetish out of romantic disappointment and pioneered a vocal style in which he sounds on the verge of breaking into heaving sobs at any moment. His tent-like black sweaters, smeared lipstick and messy bird’s nest of dark hair have become the uniform of choice for generations of histrionic white kids convinced the world doesn’t understand their pain.
Wussiest Moment: “The Lovecats,” the Cure’s fluffball 1983 hit, which features Smith literally meowing over a tune best suited for preschoolers.
24 Cutesy Celt
If a unicorn could sing songs, it would sound like Donovan. His curly mop, Scottish accent and fanciful songs, inevitably full of cutesy rhymes and childish doggerel, so enraptured stoned hippies that in 1967 he compared his power to that of Hitler. The moony, mystical minstrel routinely performed in a white robe surrounded by flowers and incense, and even declared he’d “come to lead” a change in America, one that would initiate “the beginning of a soft, quiet time.” Yes, cloying ditties like “Mellow Yellow,” “Jennifer Juniper” and “Clara Clairvoyant” were certainly quiet. But quietly annoying.
Wussiest moment: Sang backing vocals on the Beatles’ “Yellow Submarine,” proving that wussiness is contagious.
23 Everyone in ’N Sync
Lance Bass achieves cosmonaut accreditation but can’t find anyone to launch him into space; Joey Fatone sings show tunes; Chris Kirkpatrick fronts a presumably Spinal Tap–inspired “rock” outfit called Nigels 11; and JC Chasez records “I’m Not Sleeping Alone,” in which he doth protest too much.
Wussiest moment: In “Without Me,” Eminem says Kirkpatrick should get his ass kicked “worse than them little limpbizkit bastards.” No one argues.
22 Sniffy Schoolmarm
There’s nothing wrong with dogooders; after all, they, uh, do good. So we don’t dislike the former 10,000 Maniacs singer for playing lots of benefits, or for posting gardening links and haikus on her website. But Merchant is like that goody-goody in the ninth grade who always reminded the teacher if she forgot to assign homework. It’s wrong for a parent to hit a child, but the main point of her song on that topic, “What’s the Matter Here?,” seems to be the illustration of Merchant’s own moral superiority to an angry parent. Plus, she declaims her own decorous folk-rock songs as if she’s reading Shakespeare on the stage of the goddamn Globe Theater.
Wussiest moment: Did we mention the haikus on her website?
21 The Father of Wuss
In 1955, Fats Domino, a black piano wizard from New Orleans, cut “Ain’t That a Shame,” a bouncy R&B number he’d written. Pat Boone, a clean-cut preppie crooner, re-recorded it, only without the soul, and released it the same year, selling far more copies. Thus was born a career in Caucasian dilution: Just as rock was turning dirty, Boone whitewashed raucous songs by Little Richard and others, selling sterile versions of black music and blooming into the decade’s second-biggest pop singer, behind Elvis Presley. In his later years, Boone became an apologist for President Bush’s war in Iraq.
Wussiest moment: Fathered Debby Boone, whose appalling 1977 smash, “You Light Up My Life,” is the worst song in the history of the world.
20 Crybaby Cowboy
Where earlier generations of country stars loved Cadillacs and whiskey, Brooks adored James Taylor and Dan Fogelberg, and even cried onstage while performing his sentimental ballads. He ushered in a generation of neutered country dudes, and sold more records than anyone but the Beatles, by embodying a cultural turn towards I-need-some-Kleenex confessions.
Wussiest moment: In a Barbara Walters TV interview, she asked about his children, and his eyes filled with tears.
19 Soft, White And Plain
As the Me Decade dawned, Bread helpfully unsaddled the 1960s’ groovy free-love ideals from any downer political agenda that could potentially ruin the mood. In doing so, mellow, mushy tunes like “Make It With You” and “Baby I’m-a Want You” created the oxymoronically named “soft rock” template from which a thousand Starland Vocal Bands would soon bloom.
Wussiest moment: In a catalogue filled with drippy odes to being hopelessly whipped, “It Don’t Matter to Me” deserves special mention for blithely accepting a lover banging other guys.
18 Hip-hop Hippie
Being a sensitive backpacker MC is one thing. But when you’re a teetotaling, incense-burning, crocheted-scarf-wearing vegetarian whose real name is Lonnie Lynn … well, let’s just say street cred isn’t an issue. Call him the hip-hop Stuart Smalley: “I just wanna be happy with being me,” Kanye’s boho homey once rapped. Awww …
Wussiest moment: Shortened his name from Common Sense in 1995 after being sued by a ska band with the same name. A ska band.
17 Enter Sadman
The haircuts were lame and the anti-Napster crusade lamer, but neither prepared fans for the soppy bitchfest that was Some Kind of Monster: The once-throttling metalheads dropped $40K a month on a touchy-feely life coach in a Cosby sweater who played master to Metallica’s puppets. Lars and James bicker and weep throughout, but neither has the decency to just go ahead and slug the other.
Wussiest moment: Lars’s ego is crushed by his gnomish father who, upon hearing a new song, sagely advises, “I would delete that.”
After the Beatles imploded, George went Eastern mystic, John became an art-damaged revolutionary, Ringo moved to L.A. and hoovered half of Columbia with Keith Moon, and Paul … wrote “Maybe I’m Amazed” and “Silly Love Songs” while insisting crew members go vegan. Only rock star ever to win Order of Merit of Chile for “services to music, peace and human understanding.”
Wussiest moment: After decades as a dedicated pot smoker, Macca quits in 2002 at the insistence of high-on-life new bride Heather Mills. His kowtowing is rewarded four years later with a potentially half-billion-dollar divorce suit.
15 Ride, Ride Like the Wimp
After selling more than four million copies of his 1979 self-titled debut, crafting the first-ballot Wussy Hall of Fame ballad “Sailing” and sweeping the Grammys in every major category, this doughy, falsetto-voiced Texan guarantees sophomore slumpage by appearing on the back cover of his 1983 follow-up wearing a pink suit. Two decades later, Seth MacFarlane names pudgy, hopelessly awkward son on Family Guy Christopher Cross Griffin.
Wussiest moment: “Think of Laura” becomes the unofficial love theme to General Hospital in 1983.
14 Mild World
After scoring his first hit with a song called “I Love My Dog,” Stevens spent the next decade whining about the sex-symbol status conferred upon him by his brooding good looks and über-sensitive folk-pop. Maudlin, self-righteous tunes like “Moonshadow” and “Father and Son” answer problems both personal and political with a smug, don’t-worry-be-happy shrug, as if Cat were willing to wallow in his misery but not do anything about it.
Wussiest Moment: He had his girlfriend, actress Patti D’Arbanville, snatched away by Mick Jagger, then wrote a song, “Lady D’Arbanville,” about his undying love for her. She didn’t come back.
13 Twee Are the World
Belle and Sebastian
Inspiring slavish devotion from cardigan-clad legions of poetry majors, this Scottish chamber-pop collective are like the Smiths but without all the macho posturing. Named after a French kiddie show, the painfully shy band refused to appear in publicity photos for years, instead using a picture of an anonymous girl.
Wussiest moment: Hypersensitive bandleader Stuart Murdoch tells biographer Paul Whitelaw, “Great words almost always reduce me to tears. It’s a relief to know that beauty can exist.”
12 The “Heidily-ho” Hippie
Even famous semi-wuss George Harrison called the neat-combed Nash’s music “soulless.” As leader of the Hollies, a squeaky rendition of the Beatles, he incited the hatred of his peers: Screaming Lord Sutch crowned them “diabolical.” He then joined David Crosby and Stephen Stills in a grandiose supergroup and turned hippie ideals into the Mommy & Me melody of “Our House” and the chicken-soup platitudes of “Teach Your Children.” Smug and sanctimonious, Nash is the Ned Flanders of rock & roll, mustache included.
Wussiest moment: The 53 consecutive “la-la-la’s” he trills halfway through “Our House.”
11 Schlock Horror
His debut album opened with a cutesy recording of the infant Manilow singing along with his grandpa. Remarkably, Manilow’s oeuvre got progressively less rocking from then on. His subsequent albums offer a torrential outpouring of gloopy ballads so sugary and unbearable that councilors in the Sydney suburb of Rockdale recently announced plans to play it through outdoor speakers in order to disperse gangs of antisocial teenagers from their streets.
Wussiest moment: “Her name was Lola/She was a showgirl …”
10 Fizzy McGuire
Duff was tween-pop’s Breck Girl — a sex- and drug-free sprite best summed up by the name of her next movie character: Sunshine Goodness. Then, when the whole Disney thing got old, she remade herself as a punk by donning black nail varnish and dating one of the Good Charlotte twins. Nancy Spungen she ain’t.
Wussiest moment: In 2004, smack in the middle of a nasty catfight with Lindsay Lohan, Duff told Blender, “I just want us to be friends.”
9 All Yellow
It’s not his posh background. It’s not that he went to college. It’s not that he played field hockey there. It’s not his teetotalling or the fact he was a virgin until 22. (Okay, it’s a little of that.) What really makes Chris Martin so drippy are those needy, apologetic tunes: He begs, he pleads, he crumbles, he crawls, he’s lost, he’s scared, he’s sorry and he misses you. Plus: He plays a girl’s instrument.
Wussiest Moment: Being derided as “a bit wimpy” by noted ruffian Charlotte Church.
8 Face the Muzak
Ever since his late-’80s ascendance, Kenneth “Babyface” Edmonds has sought to take the bump and grind out of R&B and replace it with gentle, easy-listening melodies and Dr. Phil–worthy affirmations. The Barry Manilow–loving songwriter-producer-performer writes about love with the soft-focus banality of a guy born to pen Hallmark cards and sings as if he’s trying not to wake his grandma in the next room.
Wussiest moment: Writing an album’s worth of tunes about the struggles of being a love-starved middle-aged woman for the Waiting to Exhale soundtrack.
7 Honky-Tonk Hokum
With their boy-band looks and lyrics saccharine enough to induce comas even in non-diabetics, this chartbusting country trio exemplify New Nashville at its most heavy-handed and least roughneck. “Anything that can be played at a wedding is probably going to be a hit,” justifies awesomely monikered lead singer Gary LeVox.
Wussiest moment: Their 2004 single “Skin,” the video for which features Cirque du Soleil, is about a cancer patient named Sarabeth who fears her chemotherapy-related hair loss will keep her from dancing at the prom. It does not.
6 Bad Sax
As the leading perpetrator of the crime against humanity commonly known as “smooth jazz,” this pube-headed soprano saxophonist/walking punchline may be the very poster boy of wussiness. Despite sagely preparing himself to spend a lifetime in nerdery by graduating with an accounting degree, this Albert Einstein of the bland instead chose to pursue music — and has since sold more than 45 million albums of dentist-friendly instrumental pap. Loathed even by other smooth-jazzbos such as purist Pat Metheny, his cover of “My Heart Will Go On” makes Celine Dion sound like Courtney Love.
Wussiest moment: The David Blaine of elevator music, G-Unit made the Guinness Book of World Records for holding an E-flat note for an agonizing 45+ minutes.
5 Along Comes a Woman
It’s not as though Chicago were exactly hardcore thugs before he became their focal point, but under Cetera’s dictatorship they purged their jazzier impulses to concentrate full-bore on self-pitying schmaltz like “If You Leave Me Now” and “Hard to Say I’m Sorry.” That was merely a warm-up for a solo career so flaccid that on his Amy Grant duet, “The Next Time I Fall,” the milquetoast Christian pop balladeer sounds tough by comparison.
Wussiest moment: His unconvincing stab at chivalry, “Glory of Love,” actually felt too mawkish for The Karate Kid Part II.
4 Boyz Next Door
Boyz II Men
Never mind the quasi-thuggish “z” in their name — these Philly melismaniacs are about as gangsta as crying in your pillow. Four early-’90s R&B heartthrobs with an image more wholesome than fortified milk, they crooned their way to more than 25 million in sales and set the stage for all the boy bands who followed.
Wussiest moment: The please-forgive-me-baby No. 1 smash “On Bended Knee,” which singlehandedly set men back at least 10 years.
3 Leader of the Bland
Through the ’70s and early ’80s, the weedy-voiced Fogelberg was the bard of choice for doe-eyed, turtlenecked white guys who were convinced that showing their sensitive side and/or growing a beard would increase their chances of getting laid. And while his sentimental tunes consistently sounded like Poco outtakes, he insisted he was more influenced by classical composers like Tchaikovsky.
Wussiest Moment: His tribute to his “papa,” “Leader of the Band.”
2 98° and Falling
Granted, if we’d been dumped by Jessica Simpson, we’d probably be pretty bummed, too. But Lachey’s new D-I-V-O-R-C-E album wallows in so much misery and self-pity it makes Morrissey sound like the Pussycat Dolls. “There’s only so many tears that you can cry,” the ex-Newlywed sobs on one track. Let’s hope he’s right—for everyone’s sake.
Wussiest moment: The whimpering piano ballad “What’s Left of Me.” Apparently, it’s not his manhood.
1 Mr. Sensitivity
Like pro wrestlers, some musicians have cool nicknames: Jerry Lee Lewis is “The Killer” and Jerry Butler was “The Iceman.” But James Taylor calls himself “Sweet Baby James.” And we know what babies do, right? They cry all the goddamn time. Setting morbid boo-hoo-hooing tales of suicidal friends (“Fire and Rain”) and visits to a mental institution (“Knockin’ Round the Zoo”) to lullaby melodies and soft-rocking acoustic guitar in a series of hits starting in 1970, this lanky, genial North Carolinian perfected what Elvis Costello once called “the ‘Fuck me, I’m sensitive’ school” of music. In the soft, caring, unruffled voice of a marriage counselor, he initiated an era of confessional, listen-to-my-troubles singer-songwriters and turned excessive self-examination into a hallmark of the baby-boom generation.
Wussiest moment: His cover of “Summertime Blues,” in which he takes on Eddie Cochran’s yawp of frustration as if he wants to be the white Bill Cosby.